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Topical›Chemistry 9701›Carbonyl compounds›Aldehydes and ketones›Paper 1

Aldehydes and ketones — Paper 1 · A Level Chemistry 9701

17.1· 336 questions · 336 marks · 403 min · 2005–2025· Multiple choice

Every Cambridge A Level Chemistry Paper 1 question on aldehydes and ketones, laid out as 90 A4 pages with the mark scheme below. Nothing is left out. Free to read, no account.

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Question 1: Compounds X, Y and Z all react with PCl5 to release hydrogen chloride, but only one of them reacts with 2,4-dinitrophenylhydrazine reagent.…Question 2: What is formed when propanone is refluxed with an anhydrous solution of NaBH4? A propanal B propan-1-ol C propan-2-ol D propaneQuestion 3: Which alcohol may be oxidised to a product which reacts with 2,4-dinitrophenylhydrazine reagent but not with Fehling’s reagent? A butan-1-o…1 / 90
Question 4: The first stage in the synthesis of antipyrine, a drug used in reducing fever, is the reaction between compound P and phenylhydrazine. CH3C…Question 5: Aldehydes and ketones are carbonyl compounds. Which of them react both with NaBH4 and with Tollens’ reagent? A both aldehydes and ketones B…Question 6: Which compound • is unaffected by hot alkaline potassium manganate(VII); • gives hydrogen when treated with sodium? A (CH3)2CHCOCH3 B (CH3)…2 / 90
Question 7: A common industrial solvent is a mixture of propanone, CH3COCH3, and pentyl ethanoate CH3CO2(CH2)4CH3. Which reagent would have no effect o…Question 8: The following three hydrocarbons all occur naturally. Which of these will be split into two organic compounds, both containing a ketone gro…Question 9: Rofecoxib, an efficient drug against arthritis, has the following structure. R is an inert group. R CH2 C O * C C O Which reactions are pos…Question 10: Compound X on refluxing with aqueous sodium hydroxide gave mixture Y which on distillation with acidified potassium dichromate(VI) produced…3 / 90
Question 11: Which reaction will distinguish between a primary and a secondary alcohol? A warming with H+ / MnO − 4 B warming with H+ / Cr2O 2 − 7 C deh…Question 12: Hept-4-enal is present in cow’s milk. CH3CH2CH=CHCH2CH2CHO hept-4-enal What is formed when hept-4-enal is reduced with either hydrogen and …Question 13: Which of these reactions is shown by butanone, CH3COCH2CH3? A On warming with acidified potassium dichromate(VI) the solution turns green. …Question 14: An alcohol of molecular formula C4H10O2 contains two OH groups and has an unbranched carbon atom chain. On reaction with an excess of hot M…Question 15: Ethanal, CH3CHO, can be reduced using an aqueous methanolic solution of NaBH4 as the reducing agent. This is a nucleophilic addition reacti…4 / 90
Question 16: The structure of the antioxidant vitamin C is shown in the diagram. HO OH C C O C CHCH(OH)CH2OH O On the basis of this structure, which pro…Question 17: Carvone gives the characteristic flavour to caraway and spearmint. O CH3 H3C C CH2 carvone Prolonged heating of carvone with hot concentrat…Question 18: The naturally-occurring molecule civetone is found in a gland of the African civet cat and has been used in perfumery. CH2 CH2 CH2 H2C CH2 …5 / 90
Question 19: Cyanohydrins can be made from carbonyl compounds by generating CN– ions from HCN in the presence of a weak base. R R OH CN– C O + HCN C R′ …Question 20: A compound has a relative molecular mass of 88 and its molecule contains only four carbon atoms. What could this compound be? 1 a saturated…Question 21: What will react differently with the two isomeric alcohols, (CH3)3CCH2OH and (CH3)2CHCH2CH2OH? A acidified aqueous potassium manganate(VII)…Question 22: Which reagent will give similar results with both butanone and butanal? A acidified aqueous potassium dichromate(VI) B an alkaline solution…Question 23: What is formed when propanone is refluxed with a solution of NaBH4? A propanal B propan-1-ol C propan-2-ol D propane6 / 90
Question 24: The diagram shows some laboratory apparatus. water heat Which preparations could this apparatus be used for? 1 bromoethane, from ethanol, s…Question 25: Which reagent will give similar results with both butanone and butanal? A acidified aqueous potassium dichromate(VI) B an alkaline solution…Question 26: What is formed when propanone is refluxed with a solution of NaBH4? A propanal B propan-1-ol C propan-2-ol D propaneQuestion 27: What is formed when propanone is refluxed with a solution of NaBH4? A propanal B propan-1-ol C propan-2-ol D propaneQuestion 28: Which reagent will give similar results with both butanone and butanal? A acidified aqueous potassium dichromate(VI) B an alkaline solution…7 / 90
Question 29: The diagram shows some laboratory apparatus. water heat Which preparations could this apparatus be used for? 1 bromoethane, from ethanol, s…Question 30: Which alcohol gives only one possible oxidation product when warmed with dilute acidified potassium dichromate(VI)? A butan-1-ol B butan-2-…Question 31: Which compound would undergo nucleophilic addition? A bromoethane, C2H5Br B ethanal, CH3CHO C ethane, C2H6 D ethene, C2H4Question 32: Glyceraldehyde, HOCH2CH(OH)CHO, is formed during photosynthesis, and contains a chiral carbon atom. Which reagents will react with glyceral…8 / 90
Question 33: When ethanal, CH3CHO, reacts with HCN and the organic product is hydrolysed by aqueous acid, organic compound Y is formed. When propanal, C…Question 34: Many, but not all, organic reactions need to be heated before reaction occurs. Which reaction occurs at a good rate at room temperature (20…Question 35: Which pair of reagents will take part in a redox reaction? A CH3CH2OH + concentrated H2SO4 B CH3CHO + Tollens’ reagent C CH3CO2C2H5 + dilut…Question 36: The diagram shows a compound present in smoke from burning garden waste. H H H C C C O H Which reagents would undergo a colour change on re…Question 37: Which alcohol gives only one possible oxidation product when warmed with dilute acidified potassium dichromate(VI)? A butan-1-ol B butan-2-…9 / 90
Question 38: Which compound would undergo nucleophilic addition? A bromoethane, C2H5Br B ethanal, CH3CHO C ethane, C2H6 D ethene, C2H4Question 39: Glyceraldehyde, HOCH2CH(OH)CHO, is formed during photosynthesis, and contains a chiral carbon atom. Which reagents will react with glyceral…Question 40: Acrylic acid is produced from propene, a gaseous product of oil refineries. O x y OH acrylic acid Which statement about acrylic acid is not…Question 41: Compound X changes the colour of warm acidified sodium dichromate(VI) from orange to green. 1 mol of X reacts with 2 mol of HCN in the pres…Question 42: A compound Y is treated with warm acidified potassium dichromate(VI). The resulting organic product gives an orange precipitate with 2,4-di…10 / 90
Question 43: Aldehydes and ketones are carbonyl compounds. Which of them react with NaBH4 and react with Fehling’s reagent? A both aldehydes and ketones…Question 44: Sorbitol is an artificial sweetener used to sweeten chocolate which is suitable for diabetics. OH H C H H C OH HO C H H C OH H C OH H C H O…Question 45: Which reaction would not give ethanoic acid as a product? A heating ethanenitrile under reflux with dilute sodium hydroxide B heating ethan…Question 46: A compound Y is treated with warm acidified potassium dichromate(VI). The resulting organic product gives an orange precipitate with 2,4-di…11 / 90
Question 47: Compound X changes the colour of warm acidified sodium dichromate(VI) from orange to green. 1 mol of X reacts with 2 mol of HCN in the pres…Question 48: Aldehydes and ketones are carbonyl compounds. Which of them react with NaBH4 and react with Fehling’s reagent? A both aldehydes and ketones…Question 49: Sorbitol is an artificial sweetener used to sweeten chocolate which is suitable for diabetics. OH H C H H C OH HO C H H C OH H C OH H C H O…12 / 90
Question 50: Disaccharides, C12H22O11, are important in the human diet. For example, sucrose is found in pastries and lactose occurs in milk products. B…Question 51: DHA is a colourless liquid which reacts with protein in skin to cause it to darken. It has the structure shown. O HOCH2CCH2OH DHA Which obs…Question 52: Ethanal, CH3CHO, can be reduced using NaBH4 in aqueous ethanol. This is a nucleophilic addition reaction. What could be the first step of t…13 / 90
Question 53: In a sequence of reactions, ethanal is converted into a compound H. HCN, NaCN hot dilute H2SO4 CH3OH, heat CH3CHO F G H trace of conc. H2SO…Question 54: Compound X has molecular formula C4H10O. Separate samples of X are tested with three different reagents. Which results could not be obtaine…Question 55: Which pairs of homologous series have the same C:H ratio in their general formulae? 1 aldehydes and ketones 2 carboxylic acids and esters 3…Question 56: Disaccharides, C12H22O11, are important in the human diet. For example, sucrose is found in pastries and lactose occurs in milk products. B…14 / 90
Question 57: DHA is a colourless liquid which reacts with protein in skin to cause it to darken. It has the structure shown. O HOCH2CCH2OH DHA Which obs…Question 58: Fumaric acid can be converted into oxaloacetic acid by a two-step process involving the intermediate Q. step 1 step 2 HO2CCH=CHCO2H Q HO2CC…Question 59: Which compound, on reaction with hydrogen cyanide, produces a compound with a chiral centre? A CH3CHO B CH3CH2COCH2CH3 C CH3CO2CH3 D HCHOQuestion 60: CH3COCH2CH2OH CH3COCH2CHO CH3CH(OH)CH2CH3 CH3CH2CH2CHO W X Y Z Which of these compounds can be oxidised by acidified dichromate(VI) solutio…15 / 90
Question 61: A reaction pathway diagram is shown. energy reaction pathway Which reaction does not have such a profile? NaCN A CH3CHO + HCN CH3CH(OH)CN B…Question 62: The compound cis-hex-3-enal is responsible for the characteristic smell of cut grass. The human nose is particularly sensitive to this comp…Question 63: A common industrial solvent is a mixture of propanone, CH3COCH3, and pentyl ethanoate CH3CO2(CH2)4CH3. Which reagent would have no reaction…16 / 90
Question 64: The compound shown is a hormone produced during pregnancy to suppress ovulation. CH3 C O CH3 CH3 HO Which reagents would give positive resu…Question 65: CH3COCH2CH2OH CH3COCH2CHO CH3CH(OH)CH2CH3 CH3CH2CH2CHO W X Y Z Which of these compounds can be oxidised by acidified dichromate(VI) solutio…Question 66: The compound cis-hex-3-enal is responsible for the characteristic smell of cut grass. The human nose is particularly sensitive to this comp…Question 67: In 1903 Arthur Lapworth became the first chemist to investigate a reaction mechanism. The reaction he investigated was that of hydrogen cya…17 / 90
Question 68: Compound X, C6H12O, is oxidised by acidified sodium dichromate(VI) to compound Y. Compound Y reacts with ethanol in the presence of a littl…Question 69: Which reagents react with butanone, C2H5COCH3? 1 Tollens’ reagent 2 sodium borohydride 3 2,4-dinitrophenylhydrazine reagentQuestion 70: But-2-ene-1,4-diol is converted in two steps through an intermediate X into ketobutanedioic acid. hot acidified KMnO4 HOCH2CH=CHCH2OH X HO2…Question 71: In 1903 Arthur Lapworth became the first chemist to investigate a reaction mechanism. The reaction he investigated was that of hydrogen cya…18 / 90
Question 72: Compound X, C6H12O, is oxidised by acidified sodium dichromate(VI) to compound Y. Compound Y reacts with ethanol in the presence of a littl…Question 73: Which reagents react with butanone, C2H5COCH3? 1 Tollens’ reagent 2 sodium borohydride 3 2,4-dinitrophenylhydrazine reagentQuestion 74: An organic compound X ● is unaffected by hot acidified potassium manganate(VII), ● reacts with ethanoic acid in the presence of concentrate…Question 75: Complete combustion of compound X produces carbon dioxide and water only. X produces steamy fumes with PCl5. X does not give any visible pr…Question 76: Which compound is optically active and could also be oxidised to a ketone? A 2-methylbutan-1-ol B 3-methylhexan-3-ol C 3-methylpentan-2-ol …19 / 90
Question 77: Which pairs of reagents will react together in a redox reaction? 1 CH3CHO + Fehling’s reagent 2 CH4 + Cl 2 3 CH3COCH3 + Tollens’ reagentQuestion 78: Use of the Data Booklet is relevant to this question. 2.30 g of ethanol were mixed with an excess of aqueous acidified potassium dichromate…Question 79: Burnt sugar has a characteristic smell caused partly by the following compound. O CH3 C CHO This compound contains two functional groups. W…Question 80: In which reactions is the organic compound oxidised by the given reagent? 1 CH3CH2CHO + Fehling’s reagent 2 CH3CH2CH2CHO + Tollens’ rea…Question 81: Which carbonyl compound reacts with hydrogen cyanide to form a product that has no chiral carbon atom? A butanone B ethanal C propanal D pr…20 / 90
Question 82: How many of the following compounds produce a carboxylic acid on heating under reflux with hot acidified K2Cr2O7? CH3CH2CHO CH3COCH3 CH3CH2…Question 83: What can be produced when an aqueous solution of butan-2-ol is oxidised under suitable conditions? 1 butanone 2 butanoic acid 3 butanalQuestion 84: The Mr of compound X is 72. The composition by mass of X is 66.7 % carbon, 11.1 % hydrogen and 22.2 % oxygen. X gives an orange precipitate…Question 85: Burnt sugar has a characteristic smell caused partly by the following compound. O CH3 C CHO This compound contains two functional groups. W…Question 86: Which compound gives an organic product with a lower boiling point when it is heated under reflux with an excess of acidified potassium dic…21 / 90
Question 87: A liquid X is known to be either a single organic compound or a mixture of organic compounds. When treated with sodium, X gives off hydroge…Question 88: A new industrial preparation of ethyl ethanoate has been developed using cheap sources of ethanol. Cu catalyst Cu catalyst CH3CH2OH CH3CHO …Question 89: The compound ‘leaf alcohol’ is partly responsible for the smell of new-mown grass. CH3CH2CH=CHCH2CH2OH leaf alcohol What will be formed whe…Question 90: In which reaction is the organic compound oxidised? A CH3CH2OH + concentrated H3PO4 B CH3CH2CH2CHO + Tollens’ reagent C CH3COCH3 + 2,…22 / 90
Question 91: A new industrial preparation of ethyl ethanoate has been developed using cheap sources of ethanol. Cu catalyst Cu catalyst CH3CH2OH CH3CHO …Question 92: In which reaction is the organic compound oxidised? A CH3CH2OH + concentrated H3PO4 B CH3CH2CH2CHO + Tollens’ reagent C CH3COCH3 + 2,…Question 93: Pent-2-ene, CH3CH2CH=CHCH3, reacts in a similar way to ethene. Pent-2-ene is reacted with cold, dilute, acidified manganate(VII) ions. What…Question 94: How many hydrogen atoms are added to each molecule of ethanal when it is reacted with NaBH4 in water? A 1 B 2 C 4 D 6Question 95: A series of tests was carried out on the compound shown below. O O CH3CCH2CH CHCH2C H Which pairs of reagents would both give a positive re…23 / 90
Question 96: Hydroxyethanal, HOCH2CHO, is heated under reflux with an excess of acidified potassium dichromate(VI) until no further oxidation takes plac…Question 97: Compound X has the molecular formula C4H10O2. X has an unbranched carbon chain and contains two OH groups. On reaction with an excess of ho…Question 98: Which pairs of reagents will take part in a redox reaction? 1 CH3COCH3 + Tollens’ reagent 2 CH3CH2CHO + Fehling’s reagent 3 CH3CH=CH2 …Question 99: The compound pentan-1,4-diol has two OH groups per molecule and can be oxidised. Which statements about pentan-1,4-diol or its oxidation pr…Question 100: Compound X, C4H8O, produces an orange precipitate when it is reacted with 2,4-dinitrophenylhydrazine reagent. Compound X produces a carboxy…24 / 90
Question 101: Which pairs of reagents will take part in a redox reaction under suitable conditions? 1 CH3(CH2)4CHO + Tollens’ reagent 2 CH3(CH2)4CH3 +…Question 102: Compound X produces a carboxylic acid when heated under reflux with acidified potassium dichromate(VI). Compound X has no reaction with sod…Question 103: Hept-4-enal is present in cow’s milk. CH3CH2CH=CHCH2CH2CHO hept-4-enal Which row correctly shows the product formed when hept-4-enal is tre…Question 104: Which reactions must be warmed to form a solid product? 1 CH3CH2CHO + 2,4-dinitrophenylhydrazine reagent 2 CH3CH2CHO + Fehling’s reagen…25 / 90
Question 105: β-carotene is responsible for the orange colour of carrots. CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 β-carotene β-carotene is oxidised by ho…Question 106: For which mixtures of reagents are the colour changes described correctly? reagents colour change 1 pentanal + hot, acidified potassium dic…Question 107: β-carotene is responsible for the orange colour of carrots. CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 β-carotene β-carotene is oxidised by ho…Question 108: For which mixtures of reagents are the colour changes described correctly? reagents colour change 1 pentanal + hot, acidified potassium dic…26 / 90
Question 109: In this question, structural isomerism and stereoisomerism should be considered. How many isomeric aldehydes have the formula C5H10O? A 3 B…Question 110: Aldehydes and ketones are carbonyl compounds. Which of them react with both LiAl H4 and Tollens’ reagent? A aldehydes only B both aldehydes…Question 111: Which reactions have a coloured organic product? 1 ethanal + 2,4-dinitrophenylhydrazine reagent 2 ethanol + acidified potassium dichrom…Question 112: Which reagent will give a different observation with compounds P and Q? HOCH2CH(OH)CHO HOCH2COCH2OH P Q A Br2(aq) B hot acidified KMnO4 C s…Question 113: Which alcohol will react with an acidified solution of potassium dichromate(VI) to produce a ketone containing six carbon atoms? A 2,2-dime…Question 114: Use of the Data Booklet is relevant to this question. 2.40 g of propan-2-ol were mixed with excess acidified potassium dichromate(VI). The …27 / 90
Question 115: The diagram shows the structure of compound X. O O X What is the product of the reaction between compound X and an excess of NaBH4? A B C D…Question 116: Methanoic acid, HCO2H, has acidic properties similar to those of other carboxylic acids. In addition it can be oxidised by the same oxidisi…Question 117: Compound Q can be made from propanone. O Q Which types of reaction will Q undergo? A nucleophilic addition and electrophilic addition B nuc…Question 118: The compounds below are all produced by plants. Each compound is warmed with acidified potassium dichromate(VI). Which compound will give a…28 / 90
Question 119: What is the mechanism for the reaction of ethanal, CH3CHO, with hydrogen cyanide, HCN, in the presence of a base? O O– O A CH3 C H CH3 C H …Question 120: Menthol and menthone are both found in peppermint oil. OH O menthol menthone Which statement about these compounds is correct? A Both compo…29 / 90
Question 121: Compound Z is heated with concentrated acidified potassium manganate(VII). This produces an equimolar mixture of CO2 and CH3COCH2CH2CH(COCH…Question 122: People who take statin drugs to control their blood cholesterol may also take ‘coenzyme Q10’. The diagram shows a simplified structure of o…Question 123: But-2-ene-1,4-diol is converted in two steps through an intermediate X into oxobutanedioic acid. step 1 step 2 HOCH2CH=CHCH2OH X HO2CCOCH2C…Question 124: Compound X has the molecular formula C3H6O3. Heating X under reflux with acidified K2Cr2O7 forms HO2CCOCO2H. Reacting X with NaBH4 forms HO…30 / 90
Question 125: Alcohol Y gives product Z after mild oxidation. Z gives a positive result with Tollens’ reagent and with 2,4-dinitrophenylhydrazine reagent…Question 126: Which reagent cannot be used to distinguish between ethanal and propanone? A acidified sodium dichromate(VI) solution B alkaline aqueous io…Question 127: A cycloalkene with the molecular formula C7H12 was oxidised by hot concentrated acidified MnO4 –. The only organic product was 2-methylhexa…Question 128: Which organic compound would not give either a yellow precipitate when treated with alkaline aqueous iodine or an orange precipitate when t…Question 129: In which reaction is the organic compound oxidised? A CH3CH2CH2CHO + Tollens’ reagent B CH3CH2CH2CHO + LiAl H4 C CH3CH2CH2OH + concen…31 / 90
Question 130: Propanal reacts with hydrogen cyanide to form 2-hydroxybutanenitrile. A suitable catalyst for this reaction is sodium cyanide. NaCN CH3CH2C…Question 131: Vitamin A contains retinol. OH retinol Under appropriate conditions, acidified KMnO4(aq) can be used to break apart C=C bonds. After these …Question 132: An unknown organic compound reacts with sodium to give a combustible gas as one product but does not give a yellow precipitate with alkalin…32 / 90
Question 133: Which compounds will give an orange precipitate with 2,4-dinitrophenylhydrazine reagent? CH3 O H HO O 1 O HO [R is an inert group] HO O OR …Question 134: Propanone reacts with an aqueous mixture of HCN and NaCN by a nucleophilic addition mechanism. The first stage of the mechanism involves at…33 / 90
Question 135: P, Q and R are carbonyl compounds. CH2 CH2 CH2 O C C O O C C O O C C O H3C H H H H3C CH3 P Q R Fehling’s solution can be used to help ident…Question 136: Which compounds would produce a carboxylic acid and a ketone when treated with hot, concentrated, acidified KMnO4? 1 2 3Question 137: When onions are peeled in air, the reaction shown is thought to occur. H 2CH3CH2C + 2H2O + 2[O] → H2SO4 + H2S + 2CH3CH2CHO S O Whi…Question 138: P, Q and R are carbonyl compounds. CH2 CH2 CH2 O C C O O C C O O C C O H3C H H H H3C CH3 P Q R Fehling’s solution can be used to help ident…34 / 90
Question 139: Which compounds would produce a carboxylic acid and a ketone when treated with hot, concentrated, acidified KMnO4? 1 2 3Question 140: When onions are peeled in air, the reaction shown is thought to occur. H 2CH3CH2C + 2H2O + 2[O] → H2SO4 + H2S + 2CH3CH2CHO S O Whi…Question 141: A carbonyl compound X will react with HCN in the presence of NaCN to make a compound with Mr 85. Compound X does not react with Fehling’s r…Question 142: H2NNHC6H3(NO2)2 is the structural formula of 2,4-DNPH. Many, but not all, organic reactions need to be heated before reaction occurs. Which…Question 143: 2,2,4-trimethylpentanal is used in the manufacture of adhesives. Which reagents would 2,2,4-trimethylpentanal react with? 1 2,4-dinitrophen…35 / 90
Question 144: The formulae of three compounds are shown. C3H7CHO C2H5COCH3 CH2CHCH2CH2OH Only one of these compounds will decolourise…Question 145: Which statement about butan-1-ol, butan-2-ol, and 2-methylbutan-2-ol is not correct? A They all react with methanoic acid to form an ester.…Question 146: Which compound will react with acidified potassium dichromate(VI) and with alkaline aqueous iodine? A CH3COCH2CH3 B CH3CH(OH)CH2CH3 C CH3CH…Question 147: Substance M is refluxed with aqueous sodium hydroxide. One of the products of this reaction reacts with alkaline aqueous iodine to give a p…36 / 90
Question 148: Glucose can be used to prepare sorbitol, a compound used as a sugar substitute. H OH OH OH OH OH OH O HO OH OH OH OH glucose sorbitol Which…Question 149: 3-methylbutanone is treated with alkaline aqueous iodine. The mixture of products is then acidified. Which compound is present in the final…Question 150: Ethene is reacted with steam in the presence of concentrated H3PO4. The product of this reaction is added to acidified potassium dichromate…Question 151: A sample of the ester CH3CH2CH2CO2CH2CH3 is hydrolysed. The product mixture is then treated with hot, acidified KMnO4. What are the final c…37 / 90
Question 152: The compounds below are used to make perfumes. Which compounds will produce a yellow precipitate with alkaline aqueous iodine? 1 2 3 OH OH …Question 153: Which compound would produce two different carboxylic acids when treated with hot, concentrated, acidified manganate(VII) ions? A B C DQuestion 154: When compound X is warmed with dilute, acidified potassium dichromate(VI) there is no colour change. X does not give an orange precipitate …Question 155: Compound G ● has a chiral centre, ● gives a positive result with alkaline aqueous iodine, ● does not give a silver mirror with Tollens’ rea…38 / 90
Question 156: Compound M is an important ingredient in perfume. O O O compound M M reacts with HCN. Which statements about this reaction are correct? 1 A…Question 157: Glucose can be used to prepare sorbitol, a compound used as a sugar substitute. H OH OH OH OH OH OH O HO OH OH OH OH glucose sorbitol Which…Question 158: 3-methylbutanone is treated with alkaline aqueous iodine. The mixture of products is then acidified. Which compound is present in the final…39 / 90
Question 159: Ethene is reacted with steam in the presence of concentrated H3PO4. The product of this reaction is added to acidified potassium dichromate…Question 160: A sample of the ester CH3CH2CH2CO2CH2CH3 is hydrolysed. The product mixture is then treated with hot, acidified KMnO4. What are the final c…Question 161: Compound X can be converted into compound Y in a single step. OH X O O Y What could be the identity of X? A B C DQuestion 162: Which compound reacts with 2,4-dinitrophenylhydrazine reagent but does not react with Tollens’ reagent? A CH3COCO2H B CH3CH(OH)CHO C CH3COC…40 / 90
Question 163: Compound X produces a carboxylic acid when heated under reflux with acidified potassium dichromate(VI). Compound X does not react with sodi…Question 164: Compound Q ● contains a chiral centre, ● gives a positive result with Fehling’s reagent, ● gives a positive result with alkaline aqueous io…41 / 90
Question 165: What is the mechanism for the reaction of ethanal, CH3CHO, with hydrogen cyanide, HCN, in the presence of NaCN? O O– O A CH3 C H CH3 C H CH…Question 166: Which reagent could be used to carry out the following reaction? O O OH A a solution containing acidified dichromate(VI) ions B a solution …42 / 90
Question 167: Compound X contains three carbon atoms. Part of a simplified infra-red spectrum of compound X is shown. 100 transmittance 50 0 4000 3000 20…Question 168: Limonene is found in lemons. limonene Limonene is heated with concentrated acidified potassium manganate(VII). Which compounds are produced…Question 169: The Mr of compound X is 72. The composition by mass of X is 66.7% carbon, 11.1% hydrogen and 22.2% oxygen. X gives an orange precipitate wi…43 / 90
Question 170: Which alcohol will react with an acidified solution of potassium dichromate(VI) to produce a ketone containing six carbon atoms? A 2,2-dime…Question 171: Which statement about butanone is correct? A Butanone can be dehydrated by concentrated sulfuric acid to give CH2=CHCH=CH2. B Butanone give…Question 172: Which pairs of compounds may be distinguished from each other by testing with alkaline aqueous iodine? 1 ethane-1,2-diol and ethanol 2 prop…Question 173: Compound S can be extracted from natural compounds. Reacting S with hot, concentrated KMnO4 produces the organic product, T. Some of the ab…44 / 90
Question 174: Which compounds, on reaction with NaBH4, form a compound with a chiral carbon atom? 1 CH3CH2CH2COCH3 2 CH2CHCOCH2CH3 3 CH3CH2COCH2CH3Question 175: Acrolein is an organic compound with the molecular formula C3H4O. It is used in water treatment and as a herbicide. When acrolein reacts wi…Question 176: Which compound shows optical isomerism and gives a positive test with alkaline aqueous iodine? A CH3COCH(OH)CH3 B CH3COCH2CH2OH C HOCH2CH(C…Question 177: J is a branched-chain alcohol, C5H12O. J is heated under reflux with an excess of Cr2O7 2– / H+ until no further reaction occurs. An organi…45 / 90
Question 178: Ethanal reacts with HCN in the presence of KCN. Which changes in bonding occur during this reaction? 1 A carbon-carbon bond is formed. 2 A …Question 179: Compound X has the empirical formula C2H3O. Compound X reacts with 2,4-dinitrophenylhydrazine reagent to give an orange precipitate and als…Question 180: The compound cis-hex-3-enal is responsible for the characteristic smell of cut grass. O cis-hex-3-enal Which reagents will react with cis-h…Question 181: Which compound shows optical isomerism and gives a positive test with alkaline aqueous iodine? A CH3COCH(OH)CH3 B CH3COCH2CH2OH C HOCH2CH(C…46 / 90
Question 182: J is a branched-chain alcohol, C5H12O. J is heated under reflux with an excess of Cr2O7 2– / H+ until no further reaction occurs. An organi…Question 183: Compound L has the molecular formula C10H16. A sample of L reacted with an excess of hot, concentrated, acidified potassium manganate(VII).…47 / 90
Question 184: Which product is formed when 3-methylpentane-1,3,4-triol is heated under reflux with an excess of acidified potassium dichromate(VI)? A HO2…Question 185: Structural isomerism only should be considered when answering this question. All the isomeric alcohols with the molecular formula C5H12O ar…Question 186: When compound X is heated with Cr2O7 2– / H+, a colour change from orange to green is observed. Two tests are carried out on the organic pr…Question 187: An organic compound T undergoes the following reactions. ● T is oxidised by hot, acidified potassium manganate(VII). ● T reacts with sodium…48 / 90
Question 188: Compound X is treated with two reagents successively, forming compound Z. X CHO a mild oxidising agent NaBH4 Y Z COCH3 What could be Z? A B…Question 189: Which reagent may be used to distinguish between propanone and ethanol? A 2,4-dinitrophenylhydrazine B bromine water C Fehling’s reagent D …Question 190: Compound Y ● reacts with alkaline aqueous iodine to form a yellow precipitate ● changes the colour of warm, acidified potassium dichromate(…49 / 90
Question 191: A molecule of geraniol is shown. geraniol OH What is formed when geraniol is reacted with an excess of cold, dilute, acidified manganate(VI…Question 192: Which reagent could be used to distinguish between ethanal and propanal? A 2,4-dinitrophenylhydrazine B I2 / NaOH(aq) C K2Cr2O7 / H2SO4(aq)…Question 193: An oxidising agent that can oxidise ethanal to ethanoic acid or ethanoate ions will also oxidise methanoic acid, HCO2H, to carbon dioxide a…Question 194: Which compound would produce a carboxylic acid and a ketone when treated with hot, concentrated acidified manganate(VII) ions? A B C D50 / 90
Question 195: Compound Q reacts with 2,4-dinitrophenylhydrazine to give a precipitate. Compound Q does not produce a precipitate when warmed with Fehling…Question 196: An alkene reacts with hot, concentrated, acidified potassium manganate(VII) to produce a single organic product as shown. hot, concentrated…Question 197: The diagram shows the structure of compound Z. Z O O What is the product of the reaction between compound Z and an excess of NaBH4? A B C D…51 / 90
Question 198: Compound Q shows the following reactions. ● It gives an orange precipitate with 2,4-dinitrophenylhydrazine. ● It gives a red-brown precipit…Question 199: An organic compound X reacts with hot, concentrated acidified potassium manganate(VII) solution to give a single carbon-containing product.…Question 200: Propan-1-ol can be reacted with acidified potassium dichromate(VI) to form propanoic acid, reaction 1, or propanal, reaction 2. O O reactio…Question 201: Compound X has stereoisomers and forms a precipitate when warmed with Fehling’s reagent. What could be the structure of compound X? A B C D…52 / 90
Question 202: The diagram shows the structure of Y. H H H H C C C C C H H O H O H Two suggestions are made about Y. 1 Y can be oxidised by hot, acidified…Question 203: Each of the compounds below is treated separately with an excess of NaBH4. The product of each reaction is then heated with an excess of co…Question 204: An alkene reacts with hot, concentrated, acidified potassium manganate(VII) to produce a single organic product as shown. hot, concentrated…53 / 90
Question 205: The diagram shows the structure of compound Z. Z O O What is the product of the reaction between compound Z and an excess of NaBH4? A B C D…Question 206: Compound Q shows the following reactions. ● It gives an orange precipitate with 2,4-dinitrophenylhydrazine. ● It gives a red-brown precipit…Question 207: The infrared spectrum shown was obtained from a compound J. 100 transmittance 50 0 4000 3000 2000 1500 1000 500 wavenumber / cm–1 Which sta…54 / 90
Question 208: Compound X is treated with an excess of lithium aluminium hydride. The reaction is allowed to go to completion. X O O OH What is the struct…Question 209: What is the skeletal formula of the compound formed when CH3CH=CHCH2OH is heated, under reflux, with K2Cr2O7 / H+? A B C D O O OH O OH O OH…Question 210: Ethanal and hydrogen cyanide react together. The reaction mechanism involves cyanide ions. CH3 H3C O – H3C OH C O C H CN C + CN– H CN– H CN…55 / 90
Question 211: Which compounds will produce a yellow precipitate with alkaline aqueous iodine? 1 2 3 OH OH HO O OH OHQuestion 212: The skeletal formula of compound X is shown. O Which row is correct? observation on molecular addition of X to formula of X Fehling’s reage…Question 213: In which of the reactions is the organic compound oxidised by the given reagent? 1 CH3CHO + HCN reagent 2 CH3CH2CH2CHO + Tollens’ reage…56 / 90
Question 214: When the apparatus is set up as shown, an orange precipitate forms in test-tube Z. Y Z air compound Q + acidified potassium 2,4-dinitrophen…Question 215: The table shows the molecular formulae of three molecules P, Q and R. None of the molecules are cyclic. molecule molecular formula P CH4O Q…Question 216: Which reagent could be used to distinguish between propane-1,2-diol and ethane-1,2-diol? A alkaline aqueous iodine B aqueous acidified dich…57 / 90
Question 217: Compound X has the structure shown. compound X OH O Which statements about compound X are correct? 1 X will decolourise cold, acidified KMn…Question 218: Which statement about compound T and compound U is correct? compound T compound U O O H3C C H C CH2CH2CH3 CH(CH3)CH2CH3 A T and U are stere…Question 219: Compound X has the structure shown. compound X O Which type of carbonyl group is present and how many chiral centres are there in one molec…58 / 90
Question 220: Propanal reacts with hydrogen cyanide to form 2-hydroxybutanenitrile. A suitable catalyst for this reaction is sodium cyanide. NaCN CH3CH2C…Question 221: An alcohol with the molecular formula C5H12O decolourises warm acidified potassium manganate(VII). The alcohol also gives a yellow precipit…Question 222: Which pair of test results would prove that a substance, X, is a ketone? A X has no reaction with Tollens’ reagent. X reacts with alkaline …Question 223: Carvone is found in spearmint oil. carvone O Which product is formed when carvone is reacted with NaBH4? A B C D OH O O OH59 / 90
Question 224: Compound X contains two functional groups. compound X O CH3 C CHO Which reagent will react with only one of the functional groups? A acidif…Question 225: Diols in which both hydroxy groups are bonded to the same carbon atom can spontaneously eliminate a molecule of water to produce a carbonyl…Question 226: How many structural isomers are there of molecular formula C5H10O that give a red precipitate with Fehling’s solution? A 1 B 2 C 3 D 4Question 227: The infra-red spectrum shown was obtained from compound G. 100 transmittance / % 50 0 4000 3000 2000 1500 1000 500 wavenumber / cm–1 What c…60 / 90
Question 228: Which reagents could be used, under suitable conditions, to oxidise CH3CH2CH2OH to CH3CH2CHO? 1 acidified potassium manganate(VII) 2 acidif…Question 229: Which substances have molecular formula C4H8O? 1 O 2 O OH 3Question 230: An alcohol with the molecular formula C5H12O decolourises warm acidified potassium manganate(VII). The alcohol also gives a yellow precipit…Question 231: Which pair of test results would prove that a substance, X, is a ketone? A X has no reaction with Tollens’ reagent. X reacts with alkaline …Question 232: Carvone is found in spearmint oil. carvone O Which product is formed when carvone is reacted with NaBH4? A B C D OH O O OH61 / 90
Question 233: Which compound produces a ketone when refluxed with an acidified solution of potassium dichromate(VI)? A pentan-1-ol B 2-methylbutan-1-ol C…Question 234: In this question you can assume that 1H and 3H have the same chemical properties. A sample of ethanal contains only one isotope of hydrogen…62 / 90
Question 235: When reactant X is treated with a suitable reagent, products Y and Z are formed. Infrared spectra of X, Y and Z are shown. reactant X 100 t…Question 236: Two carbonyl compounds have the molecular formula C3H6O. Which reagents give different observations with these two compounds? 1 acidified a…63 / 90
Question 237: An organic compound, T, does not fizz when aqueous sodium carbonate is added to it. Compound T contains 27.6% by mass of oxygen. What could…Question 238: Which compound would produce two different carboxylic acids when treated with hot, concentrated, acidified manganate(VII) ions? A B C DQuestion 239: Compound X has the empirical formula C2H4O. Its infra-red spectrum is shown. 100 transmittance / % 50 0 4000 3000 2000 1500 1000 500 wavenu…Question 240: Which pairs of compounds may be distinguished by testing with alkaline aqueous iodine? 1 butanal and butanone 2 pentan-2-one and pentan-3-o…64 / 90
Question 241: Which reactions have a coloured organic product? 1 ethanal + 2,4-dinitrophenylhydrazine reagent 2 ethanol + acidified potassium dichrom…Question 242: The molecular formula of Z is C4H8O. The infra-red spectrum of Z is shown. 100 transmittance / % 50 0 4000 3000 2000 1500 1000 500 wavenumb…Question 243: Which alcohols can be oxidised to form an organic compound which will give coloured precipitates with both 2,4-dinitrophenylhydrazine reage…65 / 90
Question 244: Two carbon-containing products result from the reaction of alkene Z with a hot, concentrated, acidified solution of potassium manganate(VII…Question 245: The skeletal formulae of three compounds are shown. R S T OH O O O O Which compounds will give a positive test with 2,4-dinitrophenylhydraz…Question 246: Three compounds, X, Y and Z, are shown. X Y Z C2H5COCH3 C2H5CHO CH3CO2H Which statements about X, Y and Z are correct? 1 X reacts with alka…Question 247: Alcohol Y gives a yellow precipitate with alkaline aqueous iodine. It can be oxidised to give a mixture of products including substance Z. …66 / 90
Question 248: Compound P is heated under reflux with an excess of acidified potassium dichromate(VI) to form compound Q. Compound Q has a lower boiling p…Question 249: Which compound produces a precipitate with 2,4-dinitrophenylhydrazine reagent and also with alkaline aqueous iodine? A butan-2-ol B butanal…Question 250: When an organic compound, Q, is treated with phosphorus pentachloride, fumes of hydrogen chloride are evolved. When Q is warmed with acidif…Question 251: Alcohol Y gives a yellow precipitate with alkaline aqueous iodine. It can be oxidised to give a mixture of products including substance Z. …Question 252: Reduction of compound R with LiAl H4 gives the compound 4-methylpentane-2,3-diol. What could be the identity of compound R? A B C D O O O O…67 / 90
Question 253: Which compound will react with LiAl H4 to form two optical isomers? A CH3CH2COCH3 B CH3CH2CH2CHO C CH3CH2COCH2CH3 D CH3CH(CH3)CH2CO2HQuestion 254: The skeletal formulae of two organic compounds are shown. Which reagents can be used to distinguish these two compounds? 1 alkaline I2(aq) …Question 255: A carbonyl compound, X, reacts with HCN in the presence of NaCN to make a compound with Mr 85. Compound X does not react with Fehling’s rea…Question 256: Primary alcohols can be oxidised to aldehydes using either acidified potassium dichromate(VI) or acidified potassium manganate(VII). The re…68 / 90
Question 257: Which reaction has a product that gives a yellow precipitate when treated with alkaline I2(aq)? A 2-chloropropane is warmed with a dilute a…Question 258: Which compound forms a precipitate when mixed with 2,4-DNPH reagent and also forms a precipitate when mixed with Fehling’s reagent? A B C D…Question 259: Structural isomerism only should be considered when answering this question. Several compounds with molecular formula C4H8O2 have one carbo…Question 260: Which reaction has a nucleophilic addition mechanism and gives a good yield of product under the stated conditions? A 1-bromopropane reacti…Question 261: A carbonyl compound has the structural formula CH3COCHO. Which row is correct for the observations made when this compound is treated with …69 / 90
Question 262: Compound R can be formed from 1-bromopropane using a nucleophilic substitution reaction followed by an oxidation reaction. What is the iden…Question 263: Three colourless liquids with the following formulae are contained in separate unlabelled bottles. CH3CH2CO2H CH3CH(OH)CO2H CH3COCO2H Which…Question 264: W reacts with alkaline I2(aq) to form a yellow precipitate and CH3CH2CO2 – ions. Which row identifies W and the yellow precipitate? identit…Question 265: 1.0 mol of an organic compound, J, requires 6.0 mol of oxygen for complete combustion. 1.0 mol of J reacts with sodium, producing 0.50 mol …70 / 90
Question 266: The table shows a student’s predictions for the reactions of three compounds. alkaline Fehling’s Tollens’ compound I,(aq) reagent reagent …Question 267: Which mechanism describes the reaction of aldehydes and ketones with HCN + NaCN? A electrophilic addition B electrophilic substitution C …Question 268: Three colourless liquids with the following formulae are contained in separate unlabelled bottles. CH3CH2CO2H CH3CH(OH)CO2H CH3COCO2H Which…Question 269: W reacts with alkaline I2(aq) to form a yellow precipitate and CH3CH2CO2 – ions. Which row identifies W and the yellow precipitate? identit…71 / 90
Question 270: When illudin S is heated under reflux with an excess of acidified potassium dichromate(VI), compound M is formed. illudin S OH compound M O…Question 271: Structural and stereoisomerism should be considered when answering this question. P has molecular formula C5H10O. P produces an orange prec…Question 272: Two isomeric alcohols, W and X, have molecular formula C4H9OH. W is oxidised to carbonyl compound Y which gives a red precipitate with Fehl…Question 273: 2-methylbut-2-ene is reacted with hot, concentrated, acidified potassium manganate(VII) solution. What are the products of this reaction? A…72 / 90
Question 274: T is an organic compound which contains 66.7% by mass of carbon. T also contains one atom of oxygen per molecule. T reacts with alkaline I2…Question 275: Which statement about butanone is correct? A Butanone can be dehydrated by concentrated sulfuric acid to give CH2=CHCH=CH2. B Butanone give…Question 276: β-carotene is responsible for the orange colour of carrots. β-carotene CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 β-carotene is oxidised by ho…Question 277: Which compound will produce a yellow-orange precipitate when added to 2,4-dinitrophenylhydrazine? A B C D O O O OH O Ethanal, CH3CHO, under…73 / 90
Question 278: Which row identifies the type of reaction and the name of the product formed? type of reaction name of product A electrophilic addition 2-h…Question 279: In the mass spectrum of compound J, the ratio of the height of the M +1 ion peak to the height of the M + ion peak is 4:91. Compound J form…Question 280: The formulae of three compounds are shown. C3H7CHO C2H5COCH3 CH2CHCH2CH2OH Only one of these compounds will decolourise bromine water. Only…Question 281: Which alcohol reacts with alkaline I2(aq) to produce ethanoate ions? A ethanol B methylpropan-2-ol C propan-2-ol D butan-2-ol74 / 90
Question 282: Heating compound X, C7H,,0,, under reflux with an excess of acidified potassium dichromate(VI) produces compound Y. Compound Y produces hy…Question 283: Which reaction takes place by a nucleophilic addition mechanism? A propene reacting with hydrogen bromide B 2-bromopropane reacting with so…Question 284: β-carotene is responsible for the orange colour of carrots. β-carotene CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 β-carotene is oxidised by ho…Question 285: Which compound will produce a yellow-orange precipitate when added to 2,4-dinitrophenylhydrazine? A B C D O O O OH O Ethanal, CH3CHO, under…75 / 90
Question 286: But-2-ene reacts with cold dilute acidified KMnO4 to give product X. But-2-ene reacts with hot concentrated acidified KMnO4 to give product…Question 287: In which pair will each compound give a different visible result with alkaline I2(aq)? A CH3CH2OH and CH3CHO B CH3CHO and CH3COCH3 C CH3COO…Question 288: Which reagent gives a positive result with propanone? A alkaline I2(aq) B aqueous bromine C Fehling’s reagent D Tollens’ reagentQuestion 289: Hydroxyethanal, HOCH2CHO, is heated under reflux with an excess of acidified K2Cr2O7 until no further oxidation takes place. What is the sk…Question 290: X is a non-cyclic ketone with a single carbonyl group and no other functional groups. Ketone X has the following properties. ● When ketone …76 / 90
Question 291: Compound Y: ● changes the colour of acidified K2Cr2O7 from orange to green ● has no effect on Fehling’s reagent ● produces an orange precip…Question 292: Z is a gaseous hydrocarbon which has a density of 3.50  10–3 g cm–3 under room conditions. Z reacts with an excess of hot concentrated aci…Question 293: Compound X can be oxidised to compound Y. Compound Y gives a yellow precipitate with alkaline I2(aq). What is compound X? A butan-1-ol B bu…Question 294: In which reaction is the organic compound oxidised? A CH3CH2CH2CHO + Tollens’ reagent B CH3CH2CH2CHO + LiAl H4 C CH3CH2CH2OH + concen…Question 295: Which reaction will distinguish between propan-1-ol and propan-2-ol? A warming with acidified KMnO4 B warming with acidified K2Cr2O7 C dehy…77 / 90
Question 296: The diagram shows a simplified structure of coenzyme Q10. coenzyme Q10 O CH3O CH3O H O n Which row describes the structure of coenzyme Q10 …Question 297: But-2-ene reacts with cold dilute acidified KMnO4 to give product X. But-2-ene reacts with an excess of hot concentrated acidified KMnO4 to…Question 298: Four different alcohols are treated with alkaline I2(aq). Which row is correct? name of alcohol formulae of products A butan-2-ol CH3COO– a…78 / 90
Question 299: Butanedione, CH3COCOCH3, is a yellow liquid. How does butanedione react with 2,4-dinitrophenylhydrazine reagent and Fehling’s reagent? 2,4-…Question 300: Compound Q reacts separately with HCN and NaBH4 under suitable conditions. Both reactions produce an organic product with a chiral centre. …Question 301: Compound X has the following properties. ● When 0.20 mol of X undergoes complete combustion, 14.4 dm3 of carbon dioxide is produced, measur…79 / 90
Question 302: Vitamin A contains retinol. retinol OH Under appropriate conditions, acidified KMnO4(aq) can be used to break C=C bonds. After these bonds …Question 303: Compound Y reacts with alkaline I2(aq). When the products of this reaction are acidified, a dicarboxylic acid is produced. The formula of t…Question 304: Which alcohol gives only one possible oxidation product when warmed with dilute acidified potassium dichromate(VI)? A butan-1-ol B butan-2-…80 / 90
Question 305: The diagram shows three reactions of ethanal. In each case, an excess of ethanal is used. solid 2 alkaline I2(aq) heat acidified K2Cr2O7 et…Question 306: The compound ‘leaf alcohol’ is partly responsible for the smell of new-mown grass. leaf alcohol CH3CH2CH=CHCH2CH2OH What will be formed whe…Question 307: Compound X: ● does not react with Tollens’ reagent ● forms a yellow precipitate with alkaline I2(aq) ● does not react with sodium. What cou…81 / 90
Question 308: Which compound can undergo nucleophilic addition? A bromoethane, C2H5Br B ethanal, CH3CHO C ethane, C2H6 D ethene, C2H4Question 309: Which statement about H2C=C(CH3)CH2CO2CH3 is correct? A It can be hydrolysed to a secondary alcohol. B It can be made using ethanoic acid a…Question 310: Vitamin A contains retinol. retinol OH Under appropriate conditions, acidified KMnO4(aq) can be used to break C=C bonds. After these bonds …Question 311: Compound Y reacts with alkaline I2(aq). When the products of this reaction are acidified, a dicarboxylic acid is produced. The formula of t…82 / 90
Question 312: Which alcohol gives only one possible oxidation product when warmed with dilute acidified potassium dichromate(VI)? A butan-1-ol B butan-2-…Question 313: Which compound, on reaction with hydrogen cyanide, produces a compound with a chiral centre? A CH3CHO B CH3CH2COCH2CH3 C CH3CO2CH3 D HCHOQuestion 314: The diagram shows three reactions of ethanal. In each case, an excess of ethanal is used. solid 2 alkaline I2(aq) heat acidified K2Cr2O7 et…Question 315: Organic compound X has the empirical formula C2H4O. Compound X is reduced by LiAl H4, but not by NaBH4. What is compound X? A ethanoic acid…83 / 90
Question 316: Compound T is tested with three reagents and gives the results shown. reagent result 2,4-DNPH orange precipitate Fehling’s solution no reac…Question 317: Complete combustion of compound T produces carbon dioxide and water only. Compound T produces steamy fumes with PCl5. Compound T does not g…Question 318: Information about carbonyl compound X is given. ● Compound X reacts with LiAlH4 to produce a secondary alcohol. ● Compound X reacts with al…Question 319: An alkene P reacts with an excess of hot concentrated acidified KMnO4(aq). Methylpropanoic acid is the only organic product. What is alkene…84 / 90
Question 320: Methanoic acid, HCO2H, has acidic properties similar to those of other carboxylic acids. In addition, it can be oxidised by the same oxidis…Question 321: Butan-2-one reacts with alkaline I2(aq). An excess of dilute sulfuric acid is then added to the reaction mixture. The organic products of t…Question 322: What is formed when propanone is heated under reflux with a solution of NaBH4? A propan-2-ol B propan-1-ol C propanal D propaneQuestion 323: Compound P displays cis/trans isomerism and gives a red-brown precipitate with Fehling’s solution. What is P? C C H CH3 H CH2CHO A C C H CH…Question 324: An alcohol, U, is reacted with hot acidified K2Cr2O7 solution. The organic product of the reaction contains 58.8% C, 9.8% H and 31.4% O by …85 / 90
Question 325: An alkene reacts with hot concentrated acidified KMnO4 to produce a single organic product as shown. hot concentrated O O acidified KMnO4(a…Question 326: Acidified potassium dichromate(VI), K2Cr2O7, is added to propan-1-ol and the mixture is immediately distilled. The distillate is treated wi…Question 327: Compound Q gives positive results when tested separately with alkaline I2(aq) and with Tollens’ reagent. What is compound Q? A CHOCH2CH2CHO…86 / 90
Question 328: The balanced equation for the reaction of X with an excess of acidified K2Cr2O7 is shown. X + 3[O]  Y + H2O Compound Y is the only o…Question 329: Compound Q reacts when heated with HCN in the presence of a catalyst to produce compound R. Molecules of compound R each contain four carbo…Question 330: Seven aldehydes and ketones ● contain only one oxygen atom per molecule ● have four or fewer carbon atoms in their structures. Alkaline I2(…87 / 90
Question 331: An organometallic lithium compound, RLi, contains the nucleophile R–. CH3CH2Li reacts with pentan-2-one. The mechanism is nucleophilic addi…Question 332: The structure of a naturally occurring compound, Q, is shown. compound Q O O OH HO O Compound Q is heated under reflux with an excess of ac…88 / 90
Question 333: The skeletal formulas of two compounds are shown. progesterone O O testosterone OH O Which statements about progesterone and testosterone a…Question 334: The balanced equation for the reaction of X with an excess of acidified K2Cr2O7 is shown. X + 3[O]  Y + H2O Compound Y is the only o…89 / 90
Question 335: Compound Q reacts when heated with HCN in the presence of a catalyst to produce compound R. Molecules of compound R each contain four carbo…Question 336: Seven aldehydes and ketones ● contain only one oxygen atom per molecule ● have four or fewer carbon atoms in their structures. Alkaline I2(…90 / 90

Mark scheme336 answers

Answers below. Sit the paper first if you are practising.

Pastlit

Chemistry 9701 · Aldehydes and ketones — Paper 1

A Level · topical answer key — answer key (teacher use)

Question

Answer

Marks

1D1
2C1
3B1
4D1
5B1
6B1
7A1
8D1
9B1
10A1
11D1
12A1
13C1
14C1
15C1
16B1
17C1
18B1
19C1
20C1
21B1
22D1
23C1
24B1
25D1
26C1
27C1
28D1
29B1
30B1
31B1
32B1
33C1
34D1
35B1
36A1
37B1
38B1
39B1
40C1
41D1
42B1
43B1
44A1
45A1
46B1
47D1
48B1
49A1
1 / 7

Pastlit

Chemistry 9701 · Aldehydes and ketones — Paper 1

A Level · topical answer key — answer key (teacher use)

Question

Answer

Marks

50B1
51B1
52—1
53—1
54—1
55—1
56B1
57B1
58D1
59A1
60C1
61B1
62C1
63C1
64B1
65C1
66C1
67C1
68B1
69C1
70C1
71C1
72B1
73C1
74C1
75D1
76C1
77B1
78C1
79A1
80B1
81D1
82B1
83D1
84A1
85C1
86D1
87D1
88B1
89C1
90B1
91B1
92B1
93A1
94B1
95B1
96B1
97C1
98C1
2 / 7

Pastlit

Chemistry 9701 · Aldehydes and ketones — Paper 1

A Level · topical answer key — answer key (teacher use)

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Answer

Marks

99A1
100A1
101B1
102A1
103A1
104C1
105B1
106B1
107B1
108B1
109C1
110A1
111D1
112C1
113B1
114A1
115A1
116—1
117—1
118—1
119—1
120—1
121—1
122D1
123C1
124C1
125A1
126B1
127A1
128B1
129A1
130D1
131D1
132B1
133D1
134D1
135B1
136A1
137B1
138B1
139A1
140B1
141D1
142D1
143B1
144D1
145D1
146B1
147C1
3 / 7

Pastlit

Chemistry 9701 · Aldehydes and ketones — Paper 1

A Level · topical answer key — answer key (teacher use)

Question

Answer

Marks

148B1
149C1
150D1
151C1
152C1
153B1
154C1
155D1
156D1
157B1
158C1
159D1
160C1
161A1
162A1
163A1
164C1
165B1
166A1
167C1
168C1
169A1
170B1
171D1
172B1
173B1
174B1
175C1
176A1
177C1
178B1
179A1
180C1
181A1
182C1
183A1
184A1
185C1
186D1
187A1
188A1
189A1
190B1
191A1
192B1
193C1
194D1
195A1
196D1
4 / 7

Pastlit

Chemistry 9701 · Aldehydes and ketones — Paper 1

A Level · topical answer key — answer key (teacher use)

Question

Answer

Marks

197A1
198A1
199B1
200C1
201D1
202D1
203C1
204D1
205A1
206A1
207C1
208D1
209B1
210A1
211C1
212A1
213C1
214B1
215C1
216A1
217C1
218B1
219D1
220D1
221B1
222C1
223A1
224A1
225A1
226D1
227C1
228B1
229A1
230B1
231C1
232A1
233D1
234A1
235B1
236A1
237B1
238B1
239A1
240B1
241D1
242D1
243C1
244B1
245A1
5 / 7

Pastlit

Chemistry 9701 · Aldehydes and ketones — Paper 1

A Level · topical answer key — answer key (teacher use)

Question

Answer

Marks

246A1
247A1
248D1
249C1
250C1
251A1
252A1
253A1
254B1
255D1
256C1
257A1
258B1
259B1
260C1
261D1
262A1
263C1
264A1
265B1
266A1
267C1
268C1
269A1
270B1
271D1
272C1
273B1
274D1
275D1
276B1
277D1
278C1
279A1
280D1
281C1
282A1
283C1
284B1
285D1
286B1
287D1
288A1
289B1
290B1
291C1
292D1
293B1
294A1
6 / 7

Pastlit

Chemistry 9701 · Aldehydes and ketones — Paper 1

A Level · topical answer key — answer key (teacher use)

Question

Answer

Marks

295D1
296D1
297C1
298C1
299B1
300A1
301B1
302D1
303D1
304B1
305B1
306C1
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Another paper, or another topic

Paper
Paper 1336 questionsPaper 2questions comingPaper 4questions coming

All of Carbonyl compounds →

Questions as text

Q1 · Compounds X, Y and Z all react with PCl5 to release hydrogen chloride, but only one of… 9701/11 Oct/Nov 2005

25 Compounds X, Y and Z all react with PCl5 to release hydrogen chloride, but only one of them reacts with 2,4-dinitrophenylhydrazine reagent. Which one of the following combinations could be X, Y and Z ? X Y Z CH2OH CHO CO2H A CH2OH CHO CO2H CH2OH CH2OH CHO B CH2OH CHO CO2H CH2OH CH2OH CHO C CHO CO2H CO2H CH2OH CHO CO2H D CO2H CO2H CO2H

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2005

Q2 · What is formed when propanone is refluxed with an anhydrous solution of NaBH4? 9701/11 Oct/Nov 2005

27 What is formed when propanone is refluxed with an anhydrous solution of NaBH4? A propanal B propan-1-ol C propan-2-ol D propane

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2005

Q3 · Which alcohol may be oxidised to a product which reacts with 2,4-dinitrophenylhydrazine… 9701/11 May/June 2006

27 Which alcohol may be oxidised to a product which reacts with 2,4-dinitrophenylhydrazine reagent but not with Fehling’s reagent? A butan-1-ol B butan-2-ol C 2-methylpropan-1-ol D 2-methylpropan-2-ol

1 marks

Answer: B

This question in 9701/11 May/June 2006

Q4 · The first stage in the synthesis of antipyrine, a drug used in reducing fever, is the… 9701/11 May/June 2006

28 The first stage in the synthesis of antipyrine, a drug used in reducing fever, is the reaction between compound P and phenylhydrazine. CH3COCH2CO2CH2CH3 + NHNH2 Q P phenylhydrazine What is the product Q of this first stage? A CH3COCH2CONH B NHCH2CO2CH2CH3 C CH3COCH2CO NHNH2 D NHN CH3CCH2CO2CH2CH3

1 marks

Answer: D

This question in 9701/11 May/June 2006

Q5 · Aldehydes and ketones are carbonyl compounds 9701/11 May/June 2006

29 Aldehydes and ketones are carbonyl compounds. Which of them react both with NaBH4 and with Tollens’ reagent? A both aldehydes and ketones B aldehydes only C ketones only D neither aldehydes nor ketones

1 marks

Answer: B

This question in 9701/11 May/June 2006

Q6 · Which compound • is unaffected by hot alkaline potassium manganate(VII); • gives hydrogen… 9701/11 Oct/Nov 2006

27 Which compound • is unaffected by hot alkaline potassium manganate(VII); • gives hydrogen when treated with sodium? A (CH3)2CHCOCH3 B (CH3)3COH C CH3CH2CH(OH)CH3 D CH3CO2CH(CH3)2

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2006

Q7 · A common industrial solvent is a mixture of propanone, CH3COCH3, and pentyl ethanoate… 9701/11 Oct/Nov 2006

28 A common industrial solvent is a mixture of propanone, CH3COCH3, and pentyl ethanoate CH3CO2(CH2)4CH3. Which reagent would have no effect on this solvent? A Na(s) B NaBH4 C NaOH(aq) D 2,4-dinitrophenylhydrazine reagent

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2006

Q8 · The following three hydrocarbons all occur naturally 9701/11 Oct/Nov 2006

37 The following three hydrocarbons all occur naturally. Which of these will be split into two organic compounds, both containing a ketone group, when treated with hot acidified potassium manganate(VII)? 1 2 3

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2006

Q9 · Rofecoxib, an efficient drug against arthritis, has the following structure 9701/11 Oct/Nov 2006

40 Rofecoxib, an efficient drug against arthritis, has the following structure. R is an inert group. R CH2 C O * C C O Which reactions are possible with this structure? 1 The bond marked is hydrolysed by heating with aqueous sodium hydroxide. 2 Aqueous bromine is decolourised. 3 An orange precipitate is formed with 2,4-dinitrophenylhydrazine reagent.

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2006

Q10 · Compound X on refluxing with aqueous sodium hydroxide gave mixture Y which on… 9701/11 Oct/Nov 2007

16 Compound X on refluxing with aqueous sodium hydroxide gave mixture Y which on distillation with acidified potassium dichromate(VI) produced propanone. Mixing Y with dilute nitric acid and aqueous silver nitrate gave a cream precipitate. What could compound X be? A CH3CHBrCH3 B CH3CHICH3 C CH3CH2CH2Br D CH3CH2CH2I

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2007

Q11 · Which reaction will distinguish between a primary and a secondary alcohol? 9701/11 Oct/Nov 2007

27 Which reaction will distinguish between a primary and a secondary alcohol? A warming with H+ / MnO − 4 B warming with H+ / Cr2O 2 − 7 C dehydration, followed by reaction with Br2(aq) D oxidation, followed by reaction with Fehling’s (or Tollens’) reagent

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2007

Q12 · Hept-4-enal is present in cow’s milk 9701/11 Oct/Nov 2007

28 Hept-4-enal is present in cow’s milk. CH3CH2CH=CHCH2CH2CHO hept-4-enal What is formed when hept-4-enal is reduced with either hydrogen and a nickel catalyst or sodium borohydride? A with H2 / Ni CH3(CH2)5CH2OH B with H2 / Ni CH3(CH2)5CH3 C with NaBH4 CH3(CH2)5CH2OH D with NaBH4 CH3(CH2)5CHO

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2007

Q13 · Which of these reactions is shown by butanone, CH3COCH2CH3? 9701/11 Oct/Nov 2007

29 Which of these reactions is shown by butanone, CH3COCH2CH3? A On warming with acidified potassium dichromate(VI) the solution turns green. B On heating with Fehling’s reagent a red precipitate is formed. C With 2,4-dinitrophenylhydrazine reagent an orange precipitate is formed. D With hydrogen cyanide an aldehyde is formed.

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2007

Q14 · An alcohol of molecular formula C4H10O2 contains two OH groups and has an unbranched… 9701/11 May/June 2008

26 An alcohol of molecular formula C4H10O2 contains two OH groups and has an unbranched carbon atom chain. On reaction with an excess of hot MnO / H+ this alcohol is converted into a compound of − 4 molecular formula C4H6O4. To which two carbon atoms in the chain of the alcohol are the two OH groups attached? A 1st and 2nd B 1st and 3rd C 1st and 4th D 2nd and 3rd

1 marks

Answer: C

This question in 9701/11 May/June 2008

Q15 · Ethanal, CH3CHO, can be reduced using an aqueous methanolic solution of NaBH4 as the… 9701/11 May/June 2008

28 Ethanal, CH3CHO, can be reduced using an aqueous methanolic solution of NaBH4 as the reducing agent. This is a nucleophilic addition reaction. What could be the first step of this mechanism? A attack of an H+ ion at the carbon atom of the carbonyl group B attack of an H+ ion at the oxygen atom of the carbonyl group C attack of an H– ion at the carbon atom of the carbonyl group D attack of an H– ion at the oxygen atom of the carbonyl group

1 marks

Answer: C

This question in 9701/11 May/June 2008

Q16 · The structure of the antioxidant vitamin C is shown in the diagram 9701/11 Oct/Nov 2008

40 The structure of the antioxidant vitamin C is shown in the diagram. HO OH C C O C CHCH(OH)CH2OH O On the basis of this structure, which properties is vitamin C likely to have? 1 It is soluble in water. 2 It decolourises aqueous bromine rapidly. 3 It reduces Fehling’s reagent.

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2008

Q17 · Carvone gives the characteristic flavour to caraway and spearmint 9701/11 May/June 2009

28 Carvone gives the characteristic flavour to caraway and spearmint. O CH3 H3C C CH2 carvone Prolonged heating of carvone with hot concentrated acidified potassium manganate(VII) produces carbon dioxide and a compound X. X contains nine carbon atoms and reacts with 2,4-dinitrophenylhydrazine reagent. What is the maximum number of molecules of 2,4-dinitrophenylhydrazine that will react with one molecule of X? A 1 B 2 C 3 D 4

1 marks

Answer: C

This question in 9701/11 May/June 2009

Q18 · The naturally-occurring molecule civetone is found in a gland of the African civet cat… 9701/11 Oct/Nov 2009

27 The naturally-occurring molecule civetone is found in a gland of the African civet cat and has been used in perfumery. CH2 CH2 CH2 H2C CH2 CH2 C O H2C CH CH2 HC CH2 CH2 H2C H2C CH2 CH2 civetone With which reagent will civetone not react? A 2,4-dinitrophenylhydrazine reagent B Fehling’s reagent C hydrogen bromide D sodium tetrahydridoborate(III) (sodium borohydride)

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2009

Q19 · Cyanohydrins can be made from carbonyl compounds by generating CN– ions from HCN in the… 9701/11 Oct/Nov 2009

28 Cyanohydrins can be made from carbonyl compounds by generating CN– ions from HCN in the presence of a weak base. R R OH CN– C O + HCN C R′ R′ CN In a similar reaction, –CH2CO2CH3 ions are generated from CH3CO2CH3 by strong bases. Which compound can be made from an aldehyde and CH3CO2CH3 in the presence of a strong base? A CH3CH(OH)CO2CH3 B CH3CO2CH2CH(OH)CH3 C CH3CH2CH(OH)CH2CO2CH3 D (CH3)2C(OH)CH2CO2CH3

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2009

Q20 · A compound has a relative molecular mass of 88 and its molecule contains only four carbon… 9701/11 Oct/Nov 2009

40 A compound has a relative molecular mass of 88 and its molecule contains only four carbon atoms. What could this compound be? 1 a saturated non-cyclic diol 2 a secondary alcohol containing an aldehyde group 3 a primary alcohol containing a ketone group

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2009

Q21 · What will react differently with the two isomeric alcohols, (CH3)3CCH2OH and… 9701/11 May/June 2010

22 What will react differently with the two isomeric alcohols, (CH3)3CCH2OH and (CH3)2CHCH2CH2OH? A acidified aqueous potassium manganate(VII) B concentrated sulfuric acid C phosphorus pentachloride D sodium

1 marks

Answer: B

This question in 9701/11 May/June 2010

Q22 · Which reagent will give similar results with both butanone and butanal? 9701/11 May/June 2010

23 Which reagent will give similar results with both butanone and butanal? A acidified aqueous potassium dichromate(VI) B an alkaline solution containing complexed Cu2+ ions (Fehling’s solution) C an aqueous solution containing [Ag(NH3)2]+ (Tollens’ reagent) D 2,4-dinitrophenylhydrazine reagent

1 marks

Answer: D

This question in 9701/11 May/June 2010

Q23 · What is formed when propanone is refluxed with a solution of NaBH4? 9701/11 May/June 2010

24 What is formed when propanone is refluxed with a solution of NaBH4? A propanal B propan-1-ol C propan-2-ol D propane

1 marks

Answer: C

This question in 9701/11 May/June 2010

Q24 · The diagram shows some laboratory apparatus 9701/11 May/June 2010

40 The diagram shows some laboratory apparatus. water heat Which preparations could this apparatus be used for? 1 bromoethane, from ethanol, sodium bromide and concentrated sulfuric acid 2 ethanal, from ethanol, sodium dichromate(VI) and sulfuric acid 3 1,2-dibromoethane, from bromine and ethene

1 marks

Answer: B

This question in 9701/11 May/June 2010

Q25 · Which reagent will give similar results with both butanone and butanal? 9701/12 May/June 2010

22 Which reagent will give similar results with both butanone and butanal? A acidified aqueous potassium dichromate(VI) B an alkaline solution containing complexed Cu2+ ions (Fehling’s solution) C an aqueous solution containing [Ag(NH3)2]+ (Tollens’ reagent) D 2,4-dinitrophenylhydrazine reagent

1 marks

Answer: D

This question in 9701/12 May/June 2010

Q26 · What is formed when propanone is refluxed with a solution of NaBH4? 9701/12 May/June 2010

23 What is formed when propanone is refluxed with a solution of NaBH4? A propanal B propan-1-ol C propan-2-ol D propane

1 marks

Answer: C

This question in 9701/12 May/June 2010

Q27 · What is formed when propanone is refluxed with a solution of NaBH4? 9701/13 May/June 2010

22 What is formed when propanone is refluxed with a solution of NaBH4? A propanal B propan-1-ol C propan-2-ol D propane

1 marks

Answer: C

This question in 9701/13 May/June 2010

Q28 · Which reagent will give similar results with both butanone and butanal? 9701/13 May/June 2010

24 Which reagent will give similar results with both butanone and butanal? A acidified aqueous potassium dichromate(VI) B an alkaline solution containing complexed Cu2+ ions (Fehling’s solution) C an aqueous solution containing [Ag(NH3)2]+ (Tollens’ reagent) D 2,4-dinitrophenylhydrazine reagent

1 marks

Answer: D

This question in 9701/13 May/June 2010

Q29 · The diagram shows some laboratory apparatus 9701/13 May/June 2010

40 The diagram shows some laboratory apparatus. water heat Which preparations could this apparatus be used for? 1 bromoethane, from ethanol, sodium bromide and concentrated sulfuric acid 2 ethanal, from ethanol, sodium dichromate(VI) and sulfuric acid 3 1,2-dibromoethane, from bromine and ethene

1 marks

Answer: B

This question in 9701/13 May/June 2010

Q30 · Which alcohol gives only one possible oxidation product when warmed with dilute acidified… 9701/11 Oct/Nov 2010

24 Which alcohol gives only one possible oxidation product when warmed with dilute acidified potassium dichromate(VI)? A butan-1-ol B butan-2-ol C 2-methylpropan-1-ol D 2-methylpropan-2-ol

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2010

Q31 · Which compound would undergo nucleophilic addition? 9701/11 Oct/Nov 2010

27 Which compound would undergo nucleophilic addition? A bromoethane, C2H5Br B ethanal, CH3CHO C ethane, C2H6 D ethene, C2H4

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2010

Q32 · Glyceraldehyde, HOCH2CH(OH)CHO, is formed during photosynthesis, and contains a chiral… 9701/11 Oct/Nov 2010

38 Glyceraldehyde, HOCH2CH(OH)CHO, is formed during photosynthesis, and contains a chiral carbon atom. Which reagents will react with glyceraldehyde to produce an organic product without a chiral carbon atom? 1 warmed acidified K2Cr2O7 2 NaBH4 3 Tollens’ reagent

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2010

Q33 · When ethanal, CH3CHO, reacts with HCN and the organic product is hydrolysed by aqueous… 9701/12 Oct/Nov 2010

22 When ethanal, CH3CHO, reacts with HCN and the organic product is hydrolysed by aqueous acid, organic compound Y is formed. When propanal, C2H5CHO, is heated under reflux with acidified potassium dichromate(VI), organic compound Z is formed. What is the difference in relative molecular mass of compounds Y and Z? A 12 B 14 C 16 D 17

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2010

Q34 · Many, but not all, organic reactions need to be heated before reaction occurs 9701/12 Oct/Nov 2010

25 Many, but not all, organic reactions need to be heated before reaction occurs. Which reaction occurs at a good rate at room temperature (20 °C)? A C10H22 → C8H18 + C2H4 B CH3CH2CH2Br + NH3 → CH3CH2CH2NH2 + HBr C CH3CH2OH + KBr → CH3CH2Br + KOH D (CH3)2CO + H2NNHC6H3(NO2)2 → (CH3)2C=NNHC6H3(NO2)2 + H2O

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2010

Q35 · Which pair of reagents will take part in a redox reaction? 9701/12 Oct/Nov 2010

26 Which pair of reagents will take part in a redox reaction? A CH3CH2OH + concentrated H2SO4 B CH3CHO + Tollens’ reagent C CH3CO2C2H5 + dilute H2SO4 D CH3COCH3 + Fehling’s solution

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2010

Q36 · The diagram shows a compound present in smoke from burning garden waste 9701/12 Oct/Nov 2010

37 The diagram shows a compound present in smoke from burning garden waste. H H H C C C O H Which reagents would undergo a colour change on reaction with this compound? 1 aqueous bromine 2 Fehling’s reagent 3 warm acidified K2Cr2O7

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2010

Q37 · Which alcohol gives only one possible oxidation product when warmed with dilute acidified… 9701/13 Oct/Nov 2010

25 Which alcohol gives only one possible oxidation product when warmed with dilute acidified potassium dichromate(VI)? A butan-1-ol B butan-2-ol C 2-methylpropan-1-ol D 2-methylpropan-2-ol

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2010

Q38 · Which compound would undergo nucleophilic addition? 9701/13 Oct/Nov 2010

27 Which compound would undergo nucleophilic addition? A bromoethane, C2H5Br B ethanal, CH3CHO C ethane, C2H6 D ethene, C2H4

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2010

Q39 · Glyceraldehyde, HOCH2CH(OH)CHO, is formed during photosynthesis, and contains a chiral… 9701/13 Oct/Nov 2010

40 Glyceraldehyde, HOCH2CH(OH)CHO, is formed during photosynthesis, and contains a chiral carbon atom. Which reagents will react with glyceraldehyde to produce an organic product without a chiral carbon atom? 1 warmed acidified K2Cr2O7 2 NaBH4 3 Tollens’ reagent

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2010

Q40 · Acrylic acid is produced from propene, a gaseous product of oil refineries 9701/11 May/June 2011

20 Acrylic acid is produced from propene, a gaseous product of oil refineries. O x y OH acrylic acid Which statement about acrylic acid is not correct? A Both bond angles x and y are approximately 120°. B It decolourises aqueous bromine. C It gives an orange precipitate with 2,4-dinitrophenylhydrazine reagent. D It reacts with an alcohol to give an ester.

1 marks

Answer: C

This question in 9701/11 May/June 2011

Q41 · Compound X changes the colour of warm acidified sodium dichromate(VI) from orange to green 9701/11 May/June 2011

26 Compound X changes the colour of warm acidified sodium dichromate(VI) from orange to green. 1 mol of X reacts with 2 mol of HCN in the presence of KCN. What could X be? A CH3CH2CH2CHO B CH3COCH2COCH3 C H2C=CHCH2CHO D OHCCH2CH2CHO

1 marks

Answer: D

This question in 9701/11 May/June 2011

Q42 · A compound Y is treated with warm acidified potassium dichromate(VI) 9701/11 May/June 2011

28 A compound Y is treated with warm acidified potassium dichromate(VI). The resulting organic product gives an orange precipitate with 2,4-dinitrophenylhydrazine reagent but does not give a silver mirror with Tollens’ reagent. What is Y? A butan-1-ol B butan-2-ol C butanal D 2-methylpropan-2-ol

1 marks

Answer: B

This question in 9701/11 May/June 2011

Q43 · Aldehydes and ketones are carbonyl compounds 9701/11 May/June 2011

29 Aldehydes and ketones are carbonyl compounds. Which of them react with NaBH4 and react with Fehling’s reagent? A both aldehydes and ketones B aldehydes only C ketones only D neither aldehydes nor ketones

1 marks

Answer: B

This question in 9701/11 May/June 2011

Q44 · Sorbitol is an artificial sweetener used to sweeten chocolate which is suitable for… 9701/11 May/June 2011

40 Sorbitol is an artificial sweetener used to sweeten chocolate which is suitable for diabetics. OH H C H H C OH HO C H H C OH H C OH H C H OH sorbitol Which functional groups can be produced when this molecule is subjected to oxidation under suitable conditions? 1 aldehyde 2 carboxylic acid 3 ketone

1 marks

Answer: A

This question in 9701/11 May/June 2011

Q45 · Which reaction would not give ethanoic acid as a product? 9701/12 May/June 2011

30 Which reaction would not give ethanoic acid as a product? A heating ethanenitrile under reflux with dilute sodium hydroxide B heating ethanenitrile under reflux with dilute sulfuric acid C heating ethanal under reflux with acidified sodium dichromate(VI) D heating ethanol under reflux with acidified sodium dichromate(VI)

1 marks

Answer: A

This question in 9701/12 May/June 2011

Q46 · A compound Y is treated with warm acidified potassium dichromate(VI) 9701/13 May/June 2011

23 A compound Y is treated with warm acidified potassium dichromate(VI). The resulting organic product gives an orange precipitate with 2,4-dinitrophenylhydrazine reagent but does not give a silver mirror with Tollens’ reagent. What is Y? A butan-1-ol B butan-2-ol C butanal D 2-methylpropan-2-ol

1 marks

Answer: B

This question in 9701/13 May/June 2011

Q47 · Compound X changes the colour of warm acidified sodium dichromate(VI) from orange to green 9701/13 May/June 2011

24 Compound X changes the colour of warm acidified sodium dichromate(VI) from orange to green. 1 mol of X reacts with 2 mol of HCN in the presence of KCN. What could X be? A CH3CH2CH2CHO B CH3COCH2COCH3 C H2C=CHCH2CHO D OHCCH2CH2CHO

1 marks

Answer: D

This question in 9701/13 May/June 2011

Q48 · Aldehydes and ketones are carbonyl compounds 9701/13 May/June 2011

30 Aldehydes and ketones are carbonyl compounds. Which of them react with NaBH4 and react with Fehling’s reagent? A both aldehydes and ketones B aldehydes only C ketones only D neither aldehydes nor ketones

1 marks

Answer: B

This question in 9701/13 May/June 2011

Q49 · Sorbitol is an artificial sweetener used to sweeten chocolate which is suitable for… 9701/13 May/June 2011

39 Sorbitol is an artificial sweetener used to sweeten chocolate which is suitable for diabetics. OH H C H H C OH HO C H H C OH H C OH H C H OH sorbitol Which functional groups can be produced when this molecule is subjected to oxidation under suitable conditions? 1 aldehyde 2 carboxylic acid 3 ketone

1 marks

Answer: A

This question in 9701/13 May/June 2011

Q50 · Disaccharides, C12H22O11, are important in the human diet 9701/11 Oct/Nov 2011

37 Disaccharides, C12H22O11, are important in the human diet. For example, sucrose is found in pastries and lactose occurs in milk products. Both of these compounds can be hydrolysed. sucrose + H2O → CH2OH(CHOH)4CHO + CH2OH(CHOH)3COCH2OH glucose fructose lactose + H2O → CH2OH(CHOH)4CHO + CH2OH(CHOH)4CHO glucose galactose Which statements about these hydrolysis products are correct? 1 Glucose and fructose have structural isomers. 2 Glucose and galactose are optical isomers. 3 Glucose and galactose are ketones.

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2011

Q51 · DHA is a colourless liquid which reacts with protein in skin to cause it to darken 9701/11 Oct/Nov 2011

38 DHA is a colourless liquid which reacts with protein in skin to cause it to darken. It has the structure shown. O HOCH2CCH2OH DHA Which observations would be made when testing this substance? 1 Hydrogen is produced when sodium is added. 2 A coloured precipitate is produced when 2,4-dinitrophenylhydrazine reagent is added. 3 A silver precipitate is produced when Tollens’ reagent is added.

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2011

Q52 · Ethanal, CH3CHO, can be reduced using NaBH4 in aqueous ethanol 9701/12 Oct/Nov 2011

23 Ethanal, CH3CHO, can be reduced using NaBH4 in aqueous ethanol. This is a nucleophilic addition reaction. What could be the first step of this mechanism? A attack of an H– ion at the carbon atom of the carbonyl group B attack of an H– ion at the oxygen atom of the carbonyl group C attack of an H+ ion at the carbon atom of the carbonyl group D attack of an H+ ion at the oxygen atom of the carbonyl group

1 marks

This question in 9701/12 Oct/Nov 2011

Q53 · In a sequence of reactions, ethanal is converted into a compound H 9701/12 Oct/Nov 2011

24 In a sequence of reactions, ethanal is converted into a compound H. HCN, NaCN hot dilute H2SO4 CH3OH, heat CH3CHO F G H trace of conc. H2SO4 What could H be? A CH3CH2COOCH3 B CH3CH(OH)COOCH3 C CH3CH(OH)OCOCH3 D CH3CH(OCH3)COOH

1 marks

This question in 9701/12 Oct/Nov 2011

Q54 · Compound X has molecular formula C4H10O 9701/12 Oct/Nov 2011

37 Compound X has molecular formula C4H10O. Separate samples of X are tested with three different reagents. Which results could not be obtained? 2,4-dinitrophenylhydrazine warm acidified potassium Tollens’ reagent reagent dichromate(VI) solution 1 silver mirror forms orange precipitate forms colour changes from orange to green 2 no change no change no change 3 no change no change colour changes from orange to green

1 marks

This question in 9701/12 Oct/Nov 2011

Q55 · Which pairs of homologous series have the same C:H ratio in their general formulae? 9701/12 Oct/Nov 2011

40 Which pairs of homologous series have the same C:H ratio in their general formulae? 1 aldehydes and ketones 2 carboxylic acids and esters 3 alkenes and ketones

1 marks

This question in 9701/12 Oct/Nov 2011

Q56 · Disaccharides, C12H22O11, are important in the human diet 9701/13 Oct/Nov 2011

39 Disaccharides, C12H22O11, are important in the human diet. For example, sucrose is found in pastries and lactose occurs in milk products. Both of these compounds can be hydrolysed. sucrose + H2O → CH2OH(CHOH)4CHO + CH2OH(CHOH)3COCH2OH glucose fructose lactose + H2O → CH2OH(CHOH)4CHO + CH2OH(CHOH)4CHO glucose galactose Which statements about these hydrolysis products are correct? 1 Glucose and fructose have structural isomers. 2 Glucose and galactose are optical isomers. 3 Glucose and galactose are ketones.

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2011

Q57 · DHA is a colourless liquid which reacts with protein in skin to cause it to darken 9701/13 Oct/Nov 2011

40 DHA is a colourless liquid which reacts with protein in skin to cause it to darken. It has the structure shown. O HOCH2CCH2OH DHA Which observations would be made when testing this substance? 1 Hydrogen is produced when sodium is added. 2 A coloured precipitate is produced when 2,4-dinitrophenylhydrazine reagent is added. 3 A silver precipitate is produced when Tollens’ reagent is added.

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2011

Q58 · Fumaric acid can be converted into oxaloacetic acid by a two-step process involving the… 9701/11 May/June 2012

20 Fumaric acid can be converted into oxaloacetic acid by a two-step process involving the intermediate Q. step 1 step 2 HO2CCH=CHCO2H Q HO2CCOCH2CO2H fumaric acid oxaloacetic acid Each of these steps can be achieved in the laboratory by a single reagent. What could be the intermediate Q and the reagent for step 2? Q reagent for step 2 A HO2CCHBrCH2CO2H warm acidified KMnO4 B HO2CCHBrCH(OH)CO2H warm NaOH(aq) C HO2CCH(OH)CH2CO2H Fehling’s solution D HO2CCH(OH)CH2CO2H warm acidified K2Cr2O7

1 marks

Answer: D

This question in 9701/11 May/June 2012

Q59 · Which compound, on reaction with hydrogen cyanide, produces a compound with a chiral… 9701/11 May/June 2012

25 Which compound, on reaction with hydrogen cyanide, produces a compound with a chiral centre? A CH3CHO B CH3CH2COCH2CH3 C CH3CO2CH3 D HCHO

1 marks

Answer: A

This question in 9701/11 May/June 2012

Q60 · CH3COCH2CH2OH CH3COCH2CHO CH3CH(OH)CH2CH3 CH3CH2CH2CHO W X Y Z Which of these compounds… 9701/11 May/June 2012

26 CH3COCH2CH2OH CH3COCH2CHO CH3CH(OH)CH2CH3 CH3CH2CH2CHO W X Y Z Which of these compounds can be oxidised by acidified dichromate(VI) solution and also gives a positive response to Tollens’ reagent? A W and X only B W and Y only C X and Z only D Y and Z only

1 marks

Answer: C

This question in 9701/11 May/June 2012

Q61 · A reaction pathway diagram is shown 9701/11 May/June 2012

28 A reaction pathway diagram is shown. energy reaction pathway Which reaction does not have such a profile? NaCN A CH3CHO + HCN CH3CH(OH)CN B C2H5Br + NaOH → C2H5OH + NaBr C (CH3)3CBr + NaOH → (CH3)3 COH + NaBr Br D + Br2 Br

1 marks

Answer: B

This question in 9701/11 May/June 2012

Q62 · The compound cis-hex-3-enal is responsible for the characteristic smell of cut grass 9701/11 May/June 2012

39 The compound cis-hex-3-enal is responsible for the characteristic smell of cut grass. The human nose is particularly sensitive to this compound, being able to detect 0.25 parts per billion in air. O cis-hex-3-enal Which reagents will react with cis-hex-3-enal? 1 sodium 2 sodium borohydride 3 Fehling’s reagent

1 marks

Answer: C

This question in 9701/11 May/June 2012

Q63 · A common industrial solvent is a mixture of propanone, CH3COCH3, and pentyl ethanoate… 9701/12 May/June 2012

29 A common industrial solvent is a mixture of propanone, CH3COCH3, and pentyl ethanoate CH3CO2(CH2)4CH3. Which reagent would have no reaction with this industrial solvent? A HCl (aq) B HCN(aq) with a little KCN C Na(s) D NaBH4

1 marks

Answer: C

This question in 9701/12 May/June 2012

Q64 · The compound shown is a hormone produced during pregnancy to suppress ovulation 9701/12 May/June 2012

40 The compound shown is a hormone produced during pregnancy to suppress ovulation. CH3 C O CH3 CH3 HO Which reagents would give positive results with this compound? 1 aqueous bromine 2 2,4-dinitrophenylhydrazine 3 Fehling’s reagent

1 marks

Answer: B

This question in 9701/12 May/June 2012

Q65 · CH3COCH2CH2OH CH3COCH2CHO CH3CH(OH)CH2CH3 CH3CH2CH2CHO W X Y Z Which of these compounds… 9701/13 May/June 2012

25 CH3COCH2CH2OH CH3COCH2CHO CH3CH(OH)CH2CH3 CH3CH2CH2CHO W X Y Z Which of these compounds can be oxidised by acidified dichromate(VI) solution and also gives a positive response to Tollens’ reagent? A W and X only B W and Y only C X and Z only D Y and Z only

1 marks

Answer: C

This question in 9701/13 May/June 2012

Q66 · The compound cis-hex-3-enal is responsible for the characteristic smell of cut grass 9701/13 May/June 2012

40 The compound cis-hex-3-enal is responsible for the characteristic smell of cut grass. The human nose is particularly sensitive to this compound, being able to detect 0.25 parts per billion in air. O cis-hex-3-enal Which reagents will react with cis-hex-3-enal? 1 sodium 2 sodium borohydride 3 Fehling’s reagent

1 marks

Answer: C

This question in 9701/13 May/June 2012

Q67 · In 1903 Arthur Lapworth became the first chemist to investigate a reaction mechanism 9701/11 Oct/Nov 2012

28 In 1903 Arthur Lapworth became the first chemist to investigate a reaction mechanism. The reaction he investigated was that of hydrogen cyanide with propanone. What do we now call the mechanism of this reaction? A electrophilic addition B electrophilic substitution C nucleophilic addition D nucleophilic substitution

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2012

Q68 · Compound X, C6H12O, is oxidised by acidified sodium dichromate(VI) to compound Y 9701/11 Oct/Nov 2012

30 Compound X, C6H12O, is oxidised by acidified sodium dichromate(VI) to compound Y. Compound Y reacts with ethanol in the presence of a little concentrated sulfuric acid to give liquid Z. What is the formula of Z? A CH3(CH2)4COCH2CH3 B CH3(CH2)4CO2CH2CH3 C CH3CH2CO2(CH2)4CH3 D CH3CO2(CH2)5CH3

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2012

Q69 · Which reagents react with butanone, C2H5COCH3? 9701/11 Oct/Nov 2012

39 Which reagents react with butanone, C2H5COCH3? 1 Tollens’ reagent 2 sodium borohydride 3 2,4-dinitrophenylhydrazine reagent

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2012

Q70 · But-2-ene-1,4-diol is converted in two steps through an intermediate X into… 9701/12 Oct/Nov 2012

24 But-2-ene-1,4-diol is converted in two steps through an intermediate X into ketobutanedioic acid. hot acidified KMnO4 HOCH2CH=CHCH2OH X HO2CCOCH2CO2H step 1 step 2 but-2-ene-1,4-diol ketobutanedioic acid What could be the reagent for step 1 and the intermediate X? reagent for step 1 X A cold acidified KMnO4 HOCH2CH2CH(OH)CH2OH B hot acidified KMnO4 OHCCH(OH)CH2CHO C steam and concentrated H2SO4 HOCH2CH(OH)CH2CH2OH D warm acidified K2Cr2O7 HO2CCH=CHCO2H

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2012

Q71 · In 1903 Arthur Lapworth became the first chemist to investigate a reaction mechanism 9701/12 Oct/Nov 2012

28 In 1903 Arthur Lapworth became the first chemist to investigate a reaction mechanism. The reaction he investigated was that of hydrogen cyanide with propanone. What do we now call the mechanism of this reaction? A electrophilic addition B electrophilic substitution C nucleophilic addition D nucleophilic substitution

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2012

Q72 · Compound X, C6H12O, is oxidised by acidified sodium dichromate(VI) to compound Y 9701/12 Oct/Nov 2012

30 Compound X, C6H12O, is oxidised by acidified sodium dichromate(VI) to compound Y. Compound Y reacts with ethanol in the presence of a little concentrated sulfuric acid to give liquid Z. What is the formula of Z? A CH3(CH2)4COCH2CH3 B CH3(CH2)4CO2CH2CH3 C CH3CH2CO2(CH2)4CH3 D CH3CO2(CH2)5CH3

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2012

Q73 · Which reagents react with butanone, C2H5COCH3? 9701/12 Oct/Nov 2012

39 Which reagents react with butanone, C2H5COCH3? 1 Tollens’ reagent 2 sodium borohydride 3 2,4-dinitrophenylhydrazine reagent

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2012

Q74 · An organic compound X ● is unaffected by hot acidified potassium manganate(VII), ● reacts… 9701/13 Oct/Nov 2012

20 An organic compound X ● is unaffected by hot acidified potassium manganate(VII), ● reacts with ethanoic acid in the presence of concentrated sulfuric acid. What is compound X? A CH3CO2C2H5 B CH3CH2COCH3 C (CH3)3COH D CH3CH2CHOHCH3

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2012

Q75 · Complete combustion of compound X produces carbon dioxide and water only 9701/13 Oct/Nov 2012

24 Complete combustion of compound X produces carbon dioxide and water only. X produces steamy fumes with PCl5. X does not give any visible product with 2,4-dinitrophenylhydrazine reagent. What can be deduced with certainty from this information? A X is a carboxylic acid. B X is a hydrocarbon. C X is an alcohol. D X is not an aldehyde.

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2012

Q76 · Which compound is optically active and could also be oxidised to a ketone? 9701/13 Oct/Nov 2012

28 Which compound is optically active and could also be oxidised to a ketone? A 2-methylbutan-1-ol B 3-methylhexan-3-ol C 3-methylpentan-2-ol D propan-2-ol

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2012

Q77 · Which pairs of reagents will react together in a redox reaction? 9701/13 Oct/Nov 2012

38 Which pairs of reagents will react together in a redox reaction? 1 CH3CHO + Fehling’s reagent 2 CH4 + Cl 2 3 CH3COCH3 + Tollens’ reagent

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2012

Q78 · Use of the Data Booklet is relevant to this question 9701/11 May/June 2013

26 Use of the Data Booklet is relevant to this question. 2.30 g of ethanol were mixed with an excess of aqueous acidified potassium dichromate(VI). The reaction mixture was then boiled under reflux for one hour. The desired organic product was then collected by distillation. The yield of product was 60.0 %. What mass of product was collected? A 1.32 g B 1.38 g C 1.80 g D 3.20 g

1 marks

Answer: C

This question in 9701/11 May/June 2013

Q79 · Burnt sugar has a characteristic smell caused partly by the following compound 9701/11 May/June 2013

27 Burnt sugar has a characteristic smell caused partly by the following compound. O CH3 C CHO This compound contains two functional groups. Which reagent will react with only one of the functional groups? A acidified potassium dichromate(VI) B 2,4-dinitrophenylhydrazine C hydrogen cyanide D sodium hydroxide

1 marks

Answer: A

This question in 9701/11 May/June 2013

Q80 · In which reactions is the organic compound oxidised by the given reagent? 9701/11 May/June 2013

38 In which reactions is the organic compound oxidised by the given reagent? 1 CH3CH2CHO + Fehling’s reagent 2 CH3CH2CH2CHO + Tollens’ reagent 3 CH3CHO + 2,4-dinitrophenylhydrazine reagent

1 marks

Answer: B

This question in 9701/11 May/June 2013

Q81 · Which carbonyl compound reacts with hydrogen cyanide to form a product that has no chiral… 9701/12 May/June 2013

27 Which carbonyl compound reacts with hydrogen cyanide to form a product that has no chiral carbon atom? A butanone B ethanal C propanal D propanone

1 marks

Answer: D

This question in 9701/12 May/June 2013

Q82 · How many of the following compounds produce a carboxylic acid on heating under reflux… 9701/12 May/June 2013

28 How many of the following compounds produce a carboxylic acid on heating under reflux with hot acidified K2Cr2O7? CH3CH2CHO CH3COCH3 CH3CH2CH2OH CH3CHOHCH3 A 1 B 2 C 3 D 4

1 marks

Answer: B

This question in 9701/12 May/June 2013

Q83 · What can be produced when an aqueous solution of butan-2-ol is oxidised under suitable… 9701/12 May/June 2013

38 What can be produced when an aqueous solution of butan-2-ol is oxidised under suitable conditions? 1 butanone 2 butanoic acid 3 butanal

1 marks

Answer: D

This question in 9701/12 May/June 2013

Q84 · The Mr of compound X is 72 9701/12 May/June 2013

39 The Mr of compound X is 72. The composition by mass of X is 66.7 % carbon, 11.1 % hydrogen and 22.2 % oxygen. X gives an orange precipitate with 2,4-dinitrophenylhydrazine reagent. X does not react with Fehling’s reagent. What can be deduced from this information? 1 X is a carbonyl compound. 2 X is a ketone. 3 X is butanone.

1 marks

Answer: A

This question in 9701/12 May/June 2013

Q85 · Burnt sugar has a characteristic smell caused partly by the following compound 9701/13 May/June 2013

23 Burnt sugar has a characteristic smell caused partly by the following compound. O CH3 C CHO This compound contains two functional groups. Which reagent will react with both functional groups? A acidified potassium dichromate(VI) B Fehling’s solution C hydrogen cyanide D sodium hydroxide

1 marks

Answer: C

This question in 9701/13 May/June 2013

Q86 · Which compound gives an organic product with a lower boiling point when it is heated… 9701/13 May/June 2013

26 Which compound gives an organic product with a lower boiling point when it is heated under reflux with an excess of acidified potassium dichromate(VI)? A 2-methylbutan-1-ol B 2-methylbutan-2-ol C pentan-1-ol D pentan-2-ol

1 marks

Answer: D

This question in 9701/13 May/June 2013

Q87 · A liquid X is known to be either a single organic compound or a mixture of organic… 9701/13 May/June 2013

39 A liquid X is known to be either a single organic compound or a mixture of organic compounds. When treated with sodium, X gives off hydrogen gas. When treated with 2,4-dinitrophenylhydrazine reagent, X gives orange crystals. Which deductions about X can definitely be made? 1 At least one component of X is a carbonyl compound. 2 Only one of the components of X is a carbonyl compound. 3 At least one component of X is an alcohol.

1 marks

Answer: D

This question in 9701/13 May/June 2013

Q88 · A new industrial preparation of ethyl ethanoate has been developed using cheap sources of… 9701/11 Oct/Nov 2013

20 A new industrial preparation of ethyl ethanoate has been developed using cheap sources of ethanol. Cu catalyst Cu catalyst CH3CH2OH CH3CHO CH3CH(OH)OCH2CH3 –2[H] + CH3CH2OH Cu catalyst –2[H] CH3CO2CH2CH3 Which process is involved at some stage in this reaction sequence? A electrophilic addition B nucleophilic addition C nucleophilic substitution D reduction

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2013

Q89 · The compound ‘leaf alcohol’ is partly responsible for the smell of new-mown grass 9701/11 Oct/Nov 2013

22 The compound ‘leaf alcohol’ is partly responsible for the smell of new-mown grass. CH3CH2CH=CHCH2CH2OH leaf alcohol What will be formed when ‘leaf alcohol’ is oxidised using an excess of hot, acidified K2Cr2O7(aq)? A CH3CH2CH(OH)CH(OH)CH2CO2H B CH3CH2COCOCH2CO2H C CH3CH2CH=CHCH2CO2H D CH3CH2CO2H and HO2CCH2CO2H

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2013

Q90 · In which reaction is the organic compound oxidised? 9701/11 Oct/Nov 2013

28 In which reaction is the organic compound oxidised? A CH3CH2OH + concentrated H3PO4 B CH3CH2CH2CHO + Tollens’ reagent C CH3COCH3 + 2,4-dinitrophenylhydrazine reagent D CH3CN + dilute H2SO4

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2013

Q91 · A new industrial preparation of ethyl ethanoate has been developed using cheap sources of… 9701/12 Oct/Nov 2013

20 A new industrial preparation of ethyl ethanoate has been developed using cheap sources of ethanol. Cu catalyst Cu catalyst CH3CH2OH CH3CHO CH3CH(OH)OCH2CH3 –2[H] + CH3CH2OH Cu catalyst –2[H] CH3CO2CH2CH3 Which process is involved at some stage in this reaction sequence? A electrophilic addition B nucleophilic addition C nucleophilic substitution D reduction

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2013

Q92 · In which reaction is the organic compound oxidised? 9701/12 Oct/Nov 2013

28 In which reaction is the organic compound oxidised? A CH3CH2OH + concentrated H3PO4 B CH3CH2CH2CHO + Tollens’ reagent C CH3COCH3 + 2,4-dinitrophenylhydrazine reagent D CH3CN + dilute H2SO4

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2013

Q93 · Pent-2-ene, CH3CH2CH=CHCH3, reacts in a similar way to ethene 9701/13 Oct/Nov 2013

23 Pent-2-ene, CH3CH2CH=CHCH3, reacts in a similar way to ethene. Pent-2-ene is reacted with cold, dilute, acidified manganate(VII) ions. What will be produced in the greatest amount? A CH3CH2CH(OH)CH(OH)CH3 B CH3CH2COCOCH3 C a mixture of CH3CH2CH(OH)CH2CH3 and CH3CH2CH2CH(OH)CH3 D CH3CH2COOH and CH3COOH

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2013

Q94 · How many hydrogen atoms are added to each molecule of ethanal when it is reacted with… 9701/13 Oct/Nov 2013

29 How many hydrogen atoms are added to each molecule of ethanal when it is reacted with NaBH4 in water? A 1 B 2 C 4 D 6

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2013

Q95 · A series of tests was carried out on the compound shown below 9701/13 Oct/Nov 2013

37 A series of tests was carried out on the compound shown below. O O CH3CCH2CH CHCH2C H Which pairs of reagents would both give a positive result for this compound? 1 Tollens’ reagent and a solution containing acidified dichromate(VI) ions 2 aqueous bromine and Fehling’s reagent 3 2,4-dinitrophenylhydrazine reagent and sodium carbonate

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2013

Q96 · Hydroxyethanal, HOCH2CHO, is heated under reflux with an excess of acidified potassium… 9701/11 May/June 2014

21 Hydroxyethanal, HOCH2CHO, is heated under reflux with an excess of acidified potassium dichromate(VI) until no further oxidation takes place. What is the skeletal formula of the organic product? A B C D O O OH O HO HO OH OH OH OH O O O O

1 marks

Answer: B

This question in 9701/11 May/June 2014

Q97 · Compound X has the molecular formula C4H10O2 9701/11 May/June 2014

28 Compound X has the molecular formula C4H10O2. X has an unbranched carbon chain and contains two OH groups. On reaction with an excess of hot, acidified, aqueous manganate(VII) ions, X is converted into a compound of molecular formula C4H6O4. To which two carbon atoms in the chain of X are the two OH groups attached? A 1st and 2nd B 1st and 3rd C 1st and 4th D 2nd and 3rd

1 marks

Answer: C

This question in 9701/11 May/June 2014

Q98 · Which pairs of reagents will take part in a redox reaction? 9701/11 May/June 2014

37 Which pairs of reagents will take part in a redox reaction? 1 CH3COCH3 + Tollens’ reagent 2 CH3CH2CHO + Fehling’s reagent 3 CH3CH=CH2 + Br2

1 marks

Answer: C

This question in 9701/11 May/June 2014

Q99 · The compound pentan-1,4-diol has two OH groups per molecule and can be oxidised 9701/11 May/June 2014

39 The compound pentan-1,4-diol has two OH groups per molecule and can be oxidised. Which statements about pentan-1,4-diol or its oxidation products are correct? 1 When one mole of pentan-1,4-diol reacts with an excess of sodium metal, one mole of hydrogen molecules is produced. 2 At least one of the possible oxidation products of pentan-1,4-diol will react with 2,4-dinitrophenylhydrazine reagent. 3 Dehydration of pentan-1,4-diol could produce a compound with empirical formula C5H8.

1 marks

Answer: A

This question in 9701/11 May/June 2014

Q100 · Compound X, C4H8O, produces an orange precipitate when it is reacted with… 9701/12 May/June 2014

26 Compound X, C4H8O, produces an orange precipitate when it is reacted with 2,4-dinitrophenylhydrazine reagent. Compound X produces a carboxylic acid when heated under reflux with an acidified solution of potassium dichromate(VI). What could be compound X? A butanal B butanone C 2-methylbutanal D 4-hydroxybut-1-ene

1 marks

Answer: A

This question in 9701/12 May/June 2014

Q101 · Which pairs of reagents will take part in a redox reaction under suitable conditions? 9701/12 May/June 2014

39 Which pairs of reagents will take part in a redox reaction under suitable conditions? 1 CH3(CH2)4CHO + Tollens’ reagent 2 CH3(CH2)4CH3 + Br2 3 CH3CO(CH2)4CH3 + Fehling’s reagent

1 marks

Answer: B

This question in 9701/12 May/June 2014

Q102 · Compound X produces a carboxylic acid when heated under reflux with acidified potassium… 9701/13 May/June 2014

22 Compound X produces a carboxylic acid when heated under reflux with acidified potassium dichromate(VI). Compound X has no reaction with sodium metal. What could be the identity of compound X? A propanal B propanone C propan-1-ol D propan-2-ol

1 marks

Answer: A

This question in 9701/13 May/June 2014

Q103 · Hept-4-enal is present in cow’s milk 9701/13 May/June 2014

26 Hept-4-enal is present in cow’s milk. CH3CH2CH=CHCH2CH2CHO hept-4-enal Which row correctly shows the product formed when hept-4-enal is treated with the given reducing agent? reducing agent product A H2 + Ni CH3(CH2)5CH2OH B H2 + Ni CH3(CH2)5CH3 C NaBH4 CH3(CH2)5CH2OH D NaBH4 CH3(CH2)5CHO

1 marks

Answer: A

This question in 9701/13 May/June 2014

Q104 · Which reactions must be warmed to form a solid product? 9701/13 May/June 2014

37 Which reactions must be warmed to form a solid product? 1 CH3CH2CHO + 2,4-dinitrophenylhydrazine reagent 2 CH3CH2CHO + Fehling’s reagent 3 CH3CH2CHO + Tollens’ reagent

1 marks

Answer: C

This question in 9701/13 May/June 2014

Q105 · Β-carotene is responsible for the orange colour of carrots 9701/11 Oct/Nov 2014

30 β-carotene is responsible for the orange colour of carrots. CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 β-carotene β-carotene is oxidised by hot, concentrated, acidified KMnO4. When an individual molecule of β-carotene is oxidised in this way, many product molecules are formed. How many of these product molecules contain a ketone functional group? A 4 B 6 C 9 D 11

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2014

Q106 · For which mixtures of reagents are the colour changes described correctly? 9701/11 Oct/Nov 2014

39 For which mixtures of reagents are the colour changes described correctly? reagents colour change 1 pentanal + hot, acidified potassium dichromate(VI) orange to green 2 pentan-2-one + warm Fehling’s reagent no change 3 cyclohexane + cold, acidified potassium manganate(VII) purple to colourless

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2014

Q107 · Β-carotene is responsible for the orange colour of carrots 9701/12 Oct/Nov 2014

30 β-carotene is responsible for the orange colour of carrots. CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 β-carotene β-carotene is oxidised by hot, concentrated, acidified KMnO4. When an individual molecule of β-carotene is oxidised in this way, many product molecules are formed. How many of these product molecules contain a ketone functional group? A 4 B 6 C 9 D 11

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2014

Q108 · For which mixtures of reagents are the colour changes described correctly? 9701/12 Oct/Nov 2014

39 For which mixtures of reagents are the colour changes described correctly? reagents colour change 1 pentanal + hot, acidified potassium dichromate(VI) orange to green 2 pentan-2-one + warm Fehling’s reagent no change 3 cyclohexane + cold, acidified potassium manganate(VII) purple to colourless

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2014

Q109 · In this question, structural isomerism and stereoisomerism should be considered 9701/13 Oct/Nov 2014

20 In this question, structural isomerism and stereoisomerism should be considered. How many isomeric aldehydes have the formula C5H10O? A 3 B 4 C 5 D 6

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2014

Q110 · Aldehydes and ketones are carbonyl compounds 9701/13 Oct/Nov 2014

21 Aldehydes and ketones are carbonyl compounds. Which of them react with both LiAl H4 and Tollens’ reagent? A aldehydes only B both aldehydes and ketones C ketones only D neither aldehydes nor ketones

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2014

Q111 · Which reactions have a coloured organic product? 9701/13 Oct/Nov 2014

39 Which reactions have a coloured organic product? 1 ethanal + 2,4-dinitrophenylhydrazine reagent 2 ethanol + acidified potassium dichromate(VI) 3 ethene + cold dilute acidified potassium manganate(VII)

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2014

Q112 · Which reagent will give a different observation with compounds P and Q? 9701/11 May/June 2015

20 Which reagent will give a different observation with compounds P and Q? HOCH2CH(OH)CHO HOCH2COCH2OH P Q A Br2(aq) B hot acidified KMnO4 C silver nitrate in ammonia solution D warm acidified K2Cr2O7

1 marks

Answer: C

This question in 9701/11 May/June 2015

Q113 · Which alcohol will react with an acidified solution of potassium dichromate(VI) to… 9701/12 May/June 2015

20 Which alcohol will react with an acidified solution of potassium dichromate(VI) to produce a ketone containing six carbon atoms? A 2,2-dimethylbutan-1-ol B 2-methylpentan-3-ol C 3,3-dimethylpentan-2-ol D 3-methylpentan-3-ol

1 marks

Answer: B

This question in 9701/12 May/June 2015

Q114 · Use of the Data Booklet is relevant to this question 9701/12 May/June 2015

26 Use of the Data Booklet is relevant to this question. 2.40 g of propan-2-ol were mixed with excess acidified potassium dichromate(VI). The reaction mixture was then boiled under reflux for twenty minutes. The organic product was then collected by distillation. The yield of product was 75.0%. What mass of product was collected? A 1.74 g B 1.80 g C 2.22 g D 2.32 g

1 marks

Answer: A

This question in 9701/12 May/June 2015

Q115 · The diagram shows the structure of compound X 9701/12 May/June 2015

27 The diagram shows the structure of compound X. O O X What is the product of the reaction between compound X and an excess of NaBH4? A B C D OH OH OH OH O O O OH

1 marks

Answer: A

This question in 9701/12 May/June 2015

Q116 · Methanoic acid, HCO2H, has acidic properties similar to those of other carboxylic acids 9701/12 Oct/Nov 2015

22 Methanoic acid, HCO2H, has acidic properties similar to those of other carboxylic acids. In addition it can be oxidised by the same oxidising agents that are capable of oxidising aldehydes. Which pair consists of two compounds that will give the same observations with Fehling’s reagent? A HCO2H and CH3CO2H B HCO2H and CH3CO2CH3 C HCO2H and CH3CH2COCH3 D HCO2H and CH3CH2CHO

1 marks

This question in 9701/12 Oct/Nov 2015

Q117 · Compound Q can be made from propanone 9701/12 Oct/Nov 2015

23 Compound Q can be made from propanone. O Q Which types of reaction will Q undergo? A nucleophilic addition and electrophilic addition B nucleophilic addition and nucleophilic substitution C nucleophilic addition only D nucleophilic substitution and electrophilic addition

1 marks

This question in 9701/12 Oct/Nov 2015

Q118 · The compounds below are all produced by plants 9701/12 Oct/Nov 2015

26 The compounds below are all produced by plants. Each compound is warmed with acidified potassium dichromate(VI). Which compound will give a different observation to the other three? A B C D OH OH OH OH

1 marks

This question in 9701/12 Oct/Nov 2015

Q119 · What is the mechanism for the reaction of ethanal, CH3CHO, with hydrogen cyanide, HCN, in… 9701/12 Oct/Nov 2015

27 What is the mechanism for the reaction of ethanal, CH3CHO, with hydrogen cyanide, HCN, in the presence of a base? O O– O A CH3 C H CH3 C H CH3 C + H– CN– CN CN O –O H C N OH B CH3 C H CH3 C H CH3 C H + CN– CN– CN CN O H C N OH OH + C CH3 C H CH3 C H CH3 C H CN– CN D initiation HCN H • + • CN O O • propagation CH3C + • CN CH3C H H CN O • OH CH3C H + H CN CH3C H + • CN CN CN O • OH termination CH3C H + H • CH3C H CN CN

1 marks

This question in 9701/12 Oct/Nov 2015

Q120 · Menthol and menthone are both found in peppermint oil 9701/12 Oct/Nov 2015

28 Menthol and menthone are both found in peppermint oil. OH O menthol menthone Which statement about these compounds is correct? A Both compounds can undergo mild oxidation. B Both compounds will give an orange precipitate with 2,4-dinitrophenylhydrazine reagent. C Menthol can be formed from menthone by reaction with NaBH4. D Menthone gives a positive test when warmed with Tollens’ reagent.

1 marks

This question in 9701/12 Oct/Nov 2015

Q121 · Compound Z is heated with concentrated acidified potassium manganate(VII) 9701/12 Oct/Nov 2015

40 Compound Z is heated with concentrated acidified potassium manganate(VII). This produces an equimolar mixture of CO2 and CH3COCH2CH2CH(COCH3)CH2CO2H. What could be the structural formula of Z?

1 marks

This question in 9701/12 Oct/Nov 2015

Q122 · People who take statin drugs to control their blood cholesterol may also take ‘coenzyme… 9701/12 Feb/March 2016

20 People who take statin drugs to control their blood cholesterol may also take ‘coenzyme Q10’. The diagram shows a simplified structure of one form of this coenzyme. O CH3O CH3O H O n coenzyme Q10 Which row describes this structure correctly? number of π bonds the coenzyme is in one molecule A an aldehyde n + 2 B an aldehyde n + 4 C a ketone n + 2 D a ketone n + 4

1 marks

Answer: D

This question in 9701/12 Feb/March 2016

Q123 · But-2-ene-1,4-diol is converted in two steps through an intermediate X into… 9701/12 Feb/March 2016

23 But-2-ene-1,4-diol is converted in two steps through an intermediate X into oxobutanedioic acid. step 1 step 2 HOCH2CH=CHCH2OH X HO2CCOCH2CO2H hot, acidified KMnO4 but-2-ene-1,4-diol oxobutanedioic acid What could be the reagent for step 1 and what is the intermediate X? reagent for step 1 X A cold, acidified KMnO4 HOCH2CH2CH(OH)CH2OH B hot, acidified K2Cr2O7 HO2CCH=CHCO2H C steam and concentrated H2SO4 HOCH2CH(OH)CH2CH2OH D warm, acidified K2Cr2O7 OHCCH(OH)CH2CHO

1 marks

Answer: C

This question in 9701/12 Feb/March 2016

Q124 · Compound X has the molecular formula C3H6O3 9701/12 Feb/March 2016

40 Compound X has the molecular formula C3H6O3. Heating X under reflux with acidified K2Cr2O7 forms HO2CCOCO2H. Reacting X with NaBH4 forms HOCH2CH(OH)CH2OH. What is a possible structural formula for X? 1 HOCH2CH2CO2H 2 HOCH2CH(OH)CHO 3 HOCH2COCH2OH

1 marks

Answer: C

This question in 9701/12 Feb/March 2016

Q125 · Alcohol Y gives product Z after mild oxidation 9701/11 May/June 2016

24 Alcohol Y gives product Z after mild oxidation. Z gives a positive result with Tollens’ reagent and with 2,4-dinitrophenylhydrazine reagent. What could be the identity of alcohol Y? A butan-1-ol B butan-2-ol C butan-2,3-diol D 2-methylbutan-2-ol

1 marks

Answer: A

This question in 9701/11 May/June 2016

Q126 · Which reagent cannot be used to distinguish between ethanal and propanone? 9701/11 May/June 2016

28 Which reagent cannot be used to distinguish between ethanal and propanone? A acidified sodium dichromate(VI) solution B alkaline aqueous iodine C cold acidified potassium manganate(VII) solution D Fehling’s reagent

1 marks

Answer: B

This question in 9701/11 May/June 2016

Q127 · A cycloalkene with the molecular formula C7H12 was oxidised by hot concentrated acidified… 9701/12 May/June 2016

23 A cycloalkene with the molecular formula C7H12 was oxidised by hot concentrated acidified MnO4 –. The only organic product was 2-methylhexane-1,6-dioic acid. What is the identity of the cycloalkene? CH3 CH3 CH3 CH3 A B C D CH3

1 marks

Answer: A

This question in 9701/12 May/June 2016

Q128 · Which organic compound would not give either a yellow precipitate when treated with… 9701/12 May/June 2016

26 Which organic compound would not give either a yellow precipitate when treated with alkaline aqueous iodine or an orange precipitate when treated with 2,4-dinitrophenylhydrazine reagent? A propanal B propan-1-ol C propan-2-ol D propanone

1 marks

Answer: B

This question in 9701/12 May/June 2016

Q129 · In which reaction is the organic compound oxidised? 9701/12 May/June 2016

27 In which reaction is the organic compound oxidised? A CH3CH2CH2CHO + Tollens’ reagent B CH3CH2CH2CHO + LiAl H4 C CH3CH2CH2OH + concentrated H3PO4 D CH3CO2C2H5 + dilute H2SO4

1 marks

Answer: A

This question in 9701/12 May/June 2016

Q130 · Propanal reacts with hydrogen cyanide to form 2-hydroxybutanenitrile 9701/12 May/June 2016

39 Propanal reacts with hydrogen cyanide to form 2-hydroxybutanenitrile. A suitable catalyst for this reaction is sodium cyanide. NaCN CH3CH2CHO + HCN CH3CH2CH(OH)CN Which statements about the reaction of propanal with hydrogen cyanide are correct? 1 The sodium cyanide provides a stronger nucleophile than HCN. 2 The reaction can be classified as nucleophilic substitution. 3 The hydrogen cyanide molecule attacks the propanal molecule to form an intermediate ion.

1 marks

Answer: D

This question in 9701/12 May/June 2016

Q131 · Vitamin A contains retinol 9701/13 May/June 2016

24 Vitamin A contains retinol. OH retinol Under appropriate conditions, acidified KMnO4(aq) can be used to break apart C=C bonds. After these bonds have been broken, further oxidation of the fragments may occur. Under which conditions is the acidified KMnO4(aq) used and what do the final oxidation products include? conditions final oxidation products A cold, dilute aldehydes and carboxylic acids B cold, dilute ketones and carboxylic acids C hot, concentrated aldehydes and carboxylic acids D hot, concentrated ketones and carboxylic acids

1 marks

Answer: D

This question in 9701/13 May/June 2016

Q132 · An unknown organic compound reacts with sodium to give a combustible gas as one product… 9701/13 May/June 2016

27 An unknown organic compound reacts with sodium to give a combustible gas as one product but does not give a yellow precipitate with alkaline aqueous iodine. What is a possible identity of the unknown organic compound? A propanal B propan-1-ol C propan-2-ol D propanone

1 marks

Answer: B

This question in 9701/13 May/June 2016

Q133 · Which compounds will give an orange precipitate with 2,4-dinitrophenylhydrazine reagent? 9701/13 May/June 2016

39 Which compounds will give an orange precipitate with 2,4-dinitrophenylhydrazine reagent? CH3 O H HO O 1 O HO [R is an inert group] HO O OR HO NHCH3 streptomycin CH3 CH3 CH3 CH3 O RO O [R is an inert group] 2 CH3 O O OH O CH3 OH avermectin B1b O H3C N OCH3 [R is an inert group] 3 O O R cocaine

1 marks

Answer: D

This question in 9701/13 May/June 2016

Q134 · Propanone reacts with an aqueous mixture of HCN and NaCN by a nucleophilic addition… 9701/11 Oct/Nov 2016

26 Propanone reacts with an aqueous mixture of HCN and NaCN by a nucleophilic addition mechanism. The first stage of the mechanism involves attack by cyanide ions. Which diagram correctly represents this? A B CH3 CH3 – δ+ δ– – δ+ δ– N C C O N C C O CH3 CH3 C D CH3 CH3 – δ+ δ– – δ+ δ– C N C O N C C O CH3 CH3

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2016

Q135 · P, Q and R are carbonyl compounds 9701/11 Oct/Nov 2016

27 P, Q and R are carbonyl compounds. CH2 CH2 CH2 O C C O O C C O O C C O H3C H H H H3C CH3 P Q R Fehling’s solution can be used to help identify these compounds. Which compounds form a red-brown precipitate on warming with Fehling’s solution? A P, Q and R B P and Q only C P only D Q only

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2016

Q136 · Which compounds would produce a carboxylic acid and a ketone when treated with hot… 9701/11 Oct/Nov 2016

37 Which compounds would produce a carboxylic acid and a ketone when treated with hot, concentrated, acidified KMnO4? 1 2 3

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2016

Q137 · When onions are peeled in air, the reaction shown is thought to occur 9701/11 Oct/Nov 2016

40 When onions are peeled in air, the reaction shown is thought to occur. H 2CH3CH2C + 2H2O + 2[O] → H2SO4 + H2S + 2CH3CH2CHO S O Which tests would give a positive reaction with the organic product? 1 warming with Tollens’ reagent 2 warming with acidified potassium manganate(VII) 3 warming with alkaline aqueous iodine

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2016

Q138 · P, Q and R are carbonyl compounds 9701/13 Oct/Nov 2016

27 P, Q and R are carbonyl compounds. CH2 CH2 CH2 O C C O O C C O O C C O H3C H H H H3C CH3 P Q R Fehling’s solution can be used to help identify these compounds. Which compounds form a red-brown precipitate on warming with Fehling’s solution? A P, Q and R B P and Q only C P only D Q only

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2016

Q139 · Which compounds would produce a carboxylic acid and a ketone when treated with hot… 9701/13 Oct/Nov 2016

37 Which compounds would produce a carboxylic acid and a ketone when treated with hot, concentrated, acidified KMnO4? 1 2 3

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2016

Q140 · When onions are peeled in air, the reaction shown is thought to occur 9701/13 Oct/Nov 2016

40 When onions are peeled in air, the reaction shown is thought to occur. H 2CH3CH2C + 2H2O + 2[O] → H2SO4 + H2S + 2CH3CH2CHO S O Which tests would give a positive reaction with the organic product? 1 warming with Tollens’ reagent 2 warming with acidified potassium manganate(VII) 3 warming with alkaline aqueous iodine

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2016

Q141 · A carbonyl compound X will react with HCN in the presence of NaCN to make a compound with… 9701/12 May/June 2017

20 A carbonyl compound X will react with HCN in the presence of NaCN to make a compound with Mr 85. Compound X does not react with Fehling’s reagent. What is X? A butanal B butanone C propanal D propanone

1 marks

Answer: D

This question in 9701/12 May/June 2017

Q142 · H2NNHC6H3(NO2)2 is the structural formula of 2,4-DNPH 9701/12 May/June 2017

27 H2NNHC6H3(NO2)2 is the structural formula of 2,4-DNPH. Many, but not all, organic reactions need to be heated before reaction occurs. Which reaction occurs at a good rate at room temperature (20 °C)? A C10H22 → C8H18 + C2H4 B CH3CH2CH2Br + NH3 → CH3CH2CH2NH2 + HBr C CH3CH2OH + KBr → CH3CH2Br + KOH D (CH3)2CO + H2NNHC6H3(NO2)2 → (CH3)2C=NNHC6H3(NO2)2 + H2O

1 marks

Answer: D

This question in 9701/12 May/June 2017

Q143 · 2,2,4-trimethylpentanal is used in the manufacture of adhesives 9701/12 May/June 2017

40 2,2,4-trimethylpentanal is used in the manufacture of adhesives. Which reagents would 2,2,4-trimethylpentanal react with? 1 2,4-dinitrophenylhydrazine reagent 2 Tollens' reagent 3 alkaline aqueous iodine

1 marks

Answer: B

This question in 9701/12 May/June 2017

Q144 · The formulae of three compounds are shown 9701/13 May/June 2017

22 The formulae of three compounds are shown. C3H7CHO C2H5COCH3 CH2CHCH2CH2OH Only one of these compounds will decolourise bromine water. Only one of these compounds will produce a silver mirror with Tollens’ reagent. Which row shows the correct results? decolourises forms a silver mirror bromine water with Tollens’ reagent A C3H7CHO C2H5COCH3 B C2H5COCH3 C3H7CHO C CH2CHCH2CH2OH C2H5COCH3 D CH2CHCH2CH2OH C3H7CHO

1 marks

Answer: D

This question in 9701/13 May/June 2017

Q145 · Which statement about butan-1-ol, butan-2-ol, and 2-methylbutan-2-ol is not correct? 9701/13 May/June 2017

26 Which statement about butan-1-ol, butan-2-ol, and 2-methylbutan-2-ol is not correct? A They all react with methanoic acid to form an ester. B They all react with sodium. C They can all be dehydrated to form an alkene. D They can all be oxidised to a carbonyl compound.

1 marks

Answer: D

This question in 9701/13 May/June 2017

Q146 · Which compound will react with acidified potassium dichromate(VI) and with alkaline… 9701/13 May/June 2017

27 Which compound will react with acidified potassium dichromate(VI) and with alkaline aqueous iodine? A CH3COCH2CH3 B CH3CH(OH)CH2CH3 C CH3CH2CH2CHO D CH3CH2CH2CH2OH

1 marks

Answer: B

This question in 9701/13 May/June 2017

Q147 · Substance M is refluxed with aqueous sodium hydroxide 9701/13 May/June 2017

39 Substance M is refluxed with aqueous sodium hydroxide. One of the products of this reaction reacts with alkaline aqueous iodine to give a pale yellow precipitate. Which compounds could be substance M? 1 CH3CO2CH3 2 CH3CO2CH2CH3 3 HCO2CH(CH3)2

1 marks

Answer: C

This question in 9701/13 May/June 2017

Q148 · Glucose can be used to prepare sorbitol, a compound used as a sugar substitute 9701/11 Oct/Nov 2017

26 Glucose can be used to prepare sorbitol, a compound used as a sugar substitute. H OH OH OH OH OH OH O HO OH OH OH OH glucose sorbitol Which reagent may be used for this conversion? A acidified potassium dichromate(VI) B sodium borohydride C sodium hydroxide D Tollens’ reagent

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2017

Q149 · 3-methylbutanone is treated with alkaline aqueous iodine 9701/11 Oct/Nov 2017

27 3-methylbutanone is treated with alkaline aqueous iodine. The mixture of products is then acidified. Which compound is present in the final mixture of products? A 3-methylbutanoic acid B butanoic acid C methylpropanoic acid D propanoic acid

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2017

Q150 · Ethene is reacted with steam in the presence of concentrated H3PO4 9701/11 Oct/Nov 2017

29 Ethene is reacted with steam in the presence of concentrated H3PO4. The product of this reaction is added to acidified potassium dichromate(VI) and heated under reflux for one hour. The final organic product is collected and labelled X. But-2-ene is treated with hot, concentrated, acidified potassium manganate(VII). The final organic product is collected and labelled Y. Which statement is correct? A One molecule of X has more carbon atoms than one molecule of Y. B One molecule of Y has more carbon atoms than one molecule of X. C X and Y have different functional groups. D X is the same compound as Y.

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2017

Q151 · A sample of the ester CH3CH2CH2CO2CH2CH3 is hydrolysed 9701/11 Oct/Nov 2017

30 A sample of the ester CH3CH2CH2CO2CH2CH3 is hydrolysed. The product mixture is then treated with hot, acidified KMnO4. What are the final carbon-containing products? A CH3CH2CO2H only B CH3CO2H + CH3CH2CO2H C CH3CO2H + CH3CH2CH2CO2H D CH3CH2OH + CH3CH2CH2CO2H

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2017

Q152 · The compounds below are used to make perfumes 9701/11 Oct/Nov 2017

39 The compounds below are used to make perfumes. Which compounds will produce a yellow precipitate with alkaline aqueous iodine? 1 2 3 OH OH HO O OH OH

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2017

Q153 · Which compound would produce two different carboxylic acids when treated with hot… 9701/12 Oct/Nov 2017

22 Which compound would produce two different carboxylic acids when treated with hot, concentrated, acidified manganate(VII) ions? A B C D

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2017

Q154 · When compound X is warmed with dilute, acidified potassium dichromate(VI) there is no… 9701/12 Oct/Nov 2017

27 When compound X is warmed with dilute, acidified potassium dichromate(VI) there is no colour change. X does not give an orange precipitate with 2,4-dinitrophenylhydrazine reagent. What could X be? A butan-2-ol B ethanal C methylpropan-2-ol D propanone

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2017

Q155 · Compound G ● has a chiral centre, ● gives a positive result with alkaline aqueous iodine… 9701/12 Oct/Nov 2017

29 Compound G ● has a chiral centre, ● gives a positive result with alkaline aqueous iodine, ● does not give a silver mirror with Tollens’ reagent. What could compound G be? A 1-hydroxybutan-2-one B 2-hydroxybutanal C 3-hydroxybutanal D 3-hydroxybutan-2-one

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2017

Q156 · Compound M is an important ingredient in perfume 9701/12 Oct/Nov 2017

39 Compound M is an important ingredient in perfume. O O O compound M M reacts with HCN. Which statements about this reaction are correct? 1 A small amount of NaOH will speed up the reaction. 2 The reaction is initiated by the transfer of a proton to one of the C=O groups. 3 Both of the C=O groups react with HCN.

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2017

Q157 · Glucose can be used to prepare sorbitol, a compound used as a sugar substitute 9701/13 Oct/Nov 2017

26 Glucose can be used to prepare sorbitol, a compound used as a sugar substitute. H OH OH OH OH OH OH O HO OH OH OH OH glucose sorbitol Which reagent may be used for this conversion? A acidified potassium dichromate(VI) B sodium borohydride C sodium hydroxide D Tollens’ reagent

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2017

Q158 · 3-methylbutanone is treated with alkaline aqueous iodine 9701/13 Oct/Nov 2017

27 3-methylbutanone is treated with alkaline aqueous iodine. The mixture of products is then acidified. Which compound is present in the final mixture of products? A 3-methylbutanoic acid B butanoic acid C methylpropanoic acid D propanoic acid

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2017

Q159 · Ethene is reacted with steam in the presence of concentrated H3PO4 9701/13 Oct/Nov 2017

29 Ethene is reacted with steam in the presence of concentrated H3PO4. The product of this reaction is added to acidified potassium dichromate(VI) and heated under reflux for one hour. The final organic product is collected and labelled X. But-2-ene is treated with hot, concentrated, acidified potassium manganate(VII). The final organic product is collected and labelled Y. Which statement is correct? A One molecule of X has more carbon atoms than one molecule of Y. B One molecule of Y has more carbon atoms than one molecule of X. C X and Y have different functional groups. D X is the same compound as Y.

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2017

Q160 · A sample of the ester CH3CH2CH2CO2CH2CH3 is hydrolysed 9701/13 Oct/Nov 2017

30 A sample of the ester CH3CH2CH2CO2CH2CH3 is hydrolysed. The product mixture is then treated with hot, acidified KMnO4. What are the final carbon-containing products? A CH3CH2CO2H only B CH3CO2H + CH3CH2CO2H C CH3CO2H + CH3CH2CH2CO2H D CH3CH2OH + CH3CH2CH2CO2H

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2017

Q161 · Compound X can be converted into compound Y in a single step 9701/12 Feb/March 2018

22 Compound X can be converted into compound Y in a single step. OH X O O Y What could be the identity of X? A B C D

1 marks

Answer: A

This question in 9701/12 Feb/March 2018

Q162 · Which compound reacts with 2,4-dinitrophenylhydrazine reagent but does not react with… 9701/12 Feb/March 2018

23 Which compound reacts with 2,4-dinitrophenylhydrazine reagent but does not react with Tollens’ reagent? A CH3COCO2H B CH3CH(OH)CHO C CH3COCHO D CH3CH(OH)CH3

1 marks

Answer: A

This question in 9701/12 Feb/March 2018

Q163 · Compound X produces a carboxylic acid when heated under reflux with acidified potassium… 9701/12 Feb/March 2018

26 Compound X produces a carboxylic acid when heated under reflux with acidified potassium dichromate(VI). Compound X does not react with sodium metal. What could be the identity of compound X? A propanal B propanone C propan-1-ol D propan-2-ol

1 marks

Answer: A

This question in 9701/12 Feb/March 2018

Q164 · Compound Q ● contains a chiral centre, ● gives a positive result with Fehling’s reagent… 9701/11 May/June 2018

25 Compound Q ● contains a chiral centre, ● gives a positive result with Fehling’s reagent, ● gives a positive result with alkaline aqueous iodine. What could compound Q be? A 1-hydroxybutanone B 2-hydroxybutanal C 3-hydroxybutanal D 3-hydroxybutanone

1 marks

Answer: C

This question in 9701/11 May/June 2018

Q165 · What is the mechanism for the reaction of ethanal, CH3CHO, with hydrogen cyanide, HCN, in… 9701/11 May/June 2018

26 What is the mechanism for the reaction of ethanal, CH3CHO, with hydrogen cyanide, HCN, in the presence of NaCN? O O– O A CH3 C H CH3 C H CH3 C + H– CN– CN CN O –O H C N OH B CH3 C H CH3 C H CH3 C H + CN– CN– CN CN O H C N OH OH C CH3 C H CH3 + C H CH3 C H CN– CN D initiation HCN H • + • CN O O • propagation CH3 C + • CN CH3 C H H CN O • OH CH3 C H + H CN CH3 C H + • CN CN CN O • OH termination CH3 C H + H • CH3 C H CN CN

1 marks

Answer: B

This question in 9701/11 May/June 2018

Q166 · Which reagent could be used to carry out the following reaction? 9701/11 May/June 2018

28 Which reagent could be used to carry out the following reaction? O O OH A a solution containing acidified dichromate(VI) ions B a solution containing dilute, acidified manganate(VII) ions C a solution containing hot, concentrated, acidified manganate(VII) ions D concentrated sulfuric acid

1 marks

Answer: A

This question in 9701/11 May/June 2018

Q167 · Compound X contains three carbon atoms 9701/11 May/June 2018

30 Compound X contains three carbon atoms. Part of a simplified infra-red spectrum of compound X is shown. 100 transmittance 50 0 4000 3000 2000 1500 1000 500 wavenumber / cm–1 Which compound could be X? A CH3CH2CHO B CH3CH2CO2H C CH3CH2CH2OH D CH3CO2CH3

1 marks

Answer: C

This question in 9701/11 May/June 2018

Q168 · Limonene is found in lemons 9701/11 May/June 2018

38 Limonene is found in lemons. limonene Limonene is heated with concentrated acidified potassium manganate(VII). Which compounds are produced? 1 CH3COCH2CH2CH(CH2CO2H)2 2 CO2 3 CH3COCH2CH2CH(COCH3)CH2CO2H

1 marks

Answer: C

This question in 9701/11 May/June 2018

Q169 · The Mr of compound X is 72 9701/11 May/June 2018

40 The Mr of compound X is 72. The composition by mass of X is 66.7% carbon, 11.1% hydrogen and 22.2% oxygen. X gives an orange precipitate with 2,4-dinitrophenylhydrazine reagent. X does not react with Fehling’s reagent. What can be deduced from this information? 1 X is a carbonyl compound. 2 X is a ketone. 3 X is butanone.

1 marks

Answer: A

This question in 9701/11 May/June 2018

Q170 · Which alcohol will react with an acidified solution of potassium dichromate(VI) to… 9701/12 May/June 2018

26 Which alcohol will react with an acidified solution of potassium dichromate(VI) to produce a ketone containing six carbon atoms? A 2,2-dimethylbutan-1-ol B 2-methylpentan-3-ol C 3,3-dimethylpentan-2-ol D 3-methylpentan-3-ol

1 marks

Answer: B

This question in 9701/12 May/June 2018

Q171 · Which statement about butanone is correct? 9701/12 May/June 2018

27 Which statement about butanone is correct? A Butanone can be dehydrated by concentrated sulfuric acid to give CH2=CHCH=CH2. B Butanone gives a positive result with Tollens’ reagent. C Butanone reacts with HCN by an electrophilic addition mechanism. D Butanone reacts with NaBH4 to give a chiral product.

1 marks

Answer: D

This question in 9701/12 May/June 2018

Q172 · Which pairs of compounds may be distinguished from each other by testing with alkaline… 9701/12 May/June 2018

38 Which pairs of compounds may be distinguished from each other by testing with alkaline aqueous iodine? 1 ethane-1,2-diol and ethanol 2 propan-2-ol and methylpropan-2-ol 3 ethanol and butan-2-ol

1 marks

Answer: B

This question in 9701/12 May/June 2018

Q173 · Compound S can be extracted from natural compounds 9701/13 May/June 2018

30 Compound S can be extracted from natural compounds. Reacting S with hot, concentrated KMnO4 produces the organic product, T. Some of the absorptions found in the infra-red spectra of S and T are described. S has no strong absorption between 1670 and 1740 cm–1. T has a strong absorption at 1720 cm–1 but has no strong, broad absorption between 2500 and 3000 cm–1. From this information, what could be the formulae of S and T? S T A CH3(CH2)5CH=CH2 CH3(CH2)5CO2H B CH3COCH2CH2COCH(CH3)2 CH3CO C CH3COCH(COCH3)CH2CH2CH(COCH3)CH3 D HO2CCH2CH2COCH2COCH3

1 marks

Answer: B

This question in 9701/13 May/June 2018

Q174 · Which compounds, on reaction with NaBH4, form a compound with a chiral carbon atom? 9701/13 May/June 2018

37 Which compounds, on reaction with NaBH4, form a compound with a chiral carbon atom? 1 CH3CH2CH2COCH3 2 CH2CHCOCH2CH3 3 CH3CH2COCH2CH3

1 marks

Answer: B

This question in 9701/13 May/June 2018

Q175 · Acrolein is an organic compound with the molecular formula C3H4O 9701/13 May/June 2018

40 Acrolein is an organic compound with the molecular formula C3H4O. It is used in water treatment and as a herbicide. When acrolein reacts with 2,4-dinitrophenylhydrazine an orange precipitate is obtained. Reaction of acrolein with Tollens’ reagent produces a silver mirror. Which statements are correct? 1 Acrolein reacts with alkaline aqueous iodine to produce a yellow precipitate. 2 Acrolein can be reduced to a primary alcohol. 3 Acrolein decolourises bromine water.

1 marks

Answer: C

This question in 9701/13 May/June 2018

Q176 · Which compound shows optical isomerism and gives a positive test with alkaline aqueous… 9701/11 Oct/Nov 2018

27 Which compound shows optical isomerism and gives a positive test with alkaline aqueous iodine? A CH3COCH(OH)CH3 B CH3COCH2CH2OH C HOCH2CH(CH3)CHO D (CH3)2C(OH)CHO

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2018

Q177 · J is a branched-chain alcohol, C5H12O 9701/11 Oct/Nov 2018

30 J is a branched-chain alcohol, C5H12O. J is heated under reflux with an excess of Cr2O7 2– / H+ until no further reaction occurs. An organic compound K is formed in good yield. The infra-red spectrum of K is shown. 100 transmittance % 50 0 4000 3000 2000 1500 1000 500 wavenumber / cm–1 What are the structures of the branched-chain alcohol J and compound K? J K A CH3CH(CH3)CH2CH2OH CH3CH(CH3)CH2CHO B CH3CH2CH(OH)CH2CH3 CH3CH2COCH2CH3 C CH3CH(CH3)CH(OH)CH3 CH3CH(CH3)COCH3 D CH3CH(CH3)CH2CH2OH CH3CH(CH3)CH2COOH

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2018

Q178 · Ethanal reacts with HCN in the presence of KCN 9701/11 Oct/Nov 2018

40 Ethanal reacts with HCN in the presence of KCN. Which changes in bonding occur during this reaction? 1 A carbon-carbon bond is formed. 2 A carbon-hydrogen bond is broken. 3 A carbon-nitrogen bond is broken.

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2018

Q179 · Compound X has the empirical formula C2H3O 9701/12 Oct/Nov 2018

27 Compound X has the empirical formula C2H3O. Compound X reacts with 2,4-dinitrophenylhydrazine reagent to give an orange precipitate and also decolourises warmed acidified potassium manganate(VII) solution. What could be the identity of X? A B O H H O H O H C C C C H C C C C H H H H H H O H C D HO O O H H H H O H C H C C C C C C H C C C HO H H H H H H H

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2018

Q180 · The compound cis-hex-3-enal is responsible for the characteristic smell of cut grass 9701/12 Oct/Nov 2018

40 The compound cis-hex-3-enal is responsible for the characteristic smell of cut grass. O cis-hex-3-enal Which reagents will react with cis-hex-3-enal? 1 sodium 2 sodium borohydride 3 Fehling’s reagent

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2018

Q181 · Which compound shows optical isomerism and gives a positive test with alkaline aqueous… 9701/13 Oct/Nov 2018

27 Which compound shows optical isomerism and gives a positive test with alkaline aqueous iodine? A CH3COCH(OH)CH3 B CH3COCH2CH2OH C HOCH2CH(CH3)CHO D (CH3)2C(OH)CHO

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2018

Q182 · J is a branched-chain alcohol, C5H12O 9701/13 Oct/Nov 2018

30 J is a branched-chain alcohol, C5H12O. J is heated under reflux with an excess of Cr2O7 2– / H+ until no further reaction occurs. An organic compound K is formed in good yield. The infra-red spectrum of K is shown. 100 transmittance % 50 0 4000 3000 2000 1500 1000 500 wavenumber / cm–1 What are the structures of the branched-chain alcohol J and compound K? J K A CH3CH(CH3)CH2CH2OH CH3CH(CH3)CH2CHO B CH3CH2CH(OH)CH2CH3 CH3CH2COCH2CH3 C CH3CH(CH3)CH(OH)CH3 CH3CH(CH3)COCH3 D CH3CH(CH3)CH2CH2OH CH3CH(CH3)CH2COOH

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2018

Q183 · Compound L has the molecular formula C10H16 9701/12 Feb/March 2019

21 Compound L has the molecular formula C10H16. A sample of L reacted with an excess of hot, concentrated, acidified potassium manganate(VII). Compound M is produced. M O O OH O What could be the structure of compound L? A B C D

1 marks

Answer: A

This question in 9701/12 Feb/March 2019

Q184 · Which product is formed when 3-methylpentane-1,3,4-triol is heated under reflux with an… 9701/12 Feb/March 2019

25 Which product is formed when 3-methylpentane-1,3,4-triol is heated under reflux with an excess of acidified potassium dichromate(VI)? A HO2CCH2C(CH3)(OH)COCH3 B HO2CCH2COC(OH)(CH3)2 C OHCCH2C(CH3)(OH)COCH3 D HO2CCH2CO(CH3)COCH3

1 marks

Answer: A

This question in 9701/12 Feb/March 2019

Q185 · Structural isomerism only should be considered when answering this question 9701/12 Feb/March 2019

27 Structural isomerism only should be considered when answering this question. All the isomeric alcohols with the molecular formula C5H12O are added separately to warm alkaline aqueous iodine. How many of the isomers give a yellow precipitate? A 0 B 1 C 2 D 3

1 marks

Answer: C

This question in 9701/12 Feb/March 2019

Q186 · When compound X is heated with Cr2O7 2– / H+, a colour change from orange to green is… 9701/12 Feb/March 2019

28 When compound X is heated with Cr2O7 2– / H+, a colour change from orange to green is observed. Two tests are carried out on the organic product of this reaction. test result Tollens’ reagent no change 2,4-dinitrophenylhydrazine orange precipitate What could be compound X? A B C D O O OH OH H O

1 marks

Answer: D

This question in 9701/12 Feb/March 2019

Q187 · An organic compound T undergoes the following reactions 9701/11 May/June 2019

27 An organic compound T undergoes the following reactions. ● T is oxidised by hot, acidified potassium manganate(VII). ● T reacts with sodium to give hydrogen. What could be compound T? A CH3CH2CH(OH)CH3 B CH3CH2CH2CHO C (CH3)3COH D CH3CH2COCH3

1 marks

Answer: A

This question in 9701/11 May/June 2019

Q188 · Compound X is treated with two reagents successively, forming compound Z 9701/11 May/June 2019

28 Compound X is treated with two reagents successively, forming compound Z. X CHO a mild oxidising agent NaBH4 Y Z COCH3 What could be Z? A B C D CO2H CH2OH CH2OH CO2H CH(OH)CH3 CH(OH)CH3 CH(OH)CH3 CH(OH)CH3

1 marks

Answer: A

This question in 9701/11 May/June 2019

Q189 · Which reagent may be used to distinguish between propanone and ethanol? 9701/11 May/June 2019

29 Which reagent may be used to distinguish between propanone and ethanol? A 2,4-dinitrophenylhydrazine B bromine water C Fehling’s reagent D Tollens’ reagent

1 marks

Answer: A

This question in 9701/11 May/June 2019

Q190 · Compound Y ● reacts with alkaline aqueous iodine to form a yellow precipitate ● changes… 9701/11 May/June 2019

38 Compound Y ● reacts with alkaline aqueous iodine to form a yellow precipitate ● changes the colour of warm, acidified potassium dichromate(VI) solution. What could be compound Y? OH 1 O 2 H 3 O

1 marks

Answer: B

This question in 9701/11 May/June 2019

Q191 · A molecule of geraniol is shown 9701/12 May/June 2019

23 A molecule of geraniol is shown. geraniol OH What is formed when geraniol is reacted with an excess of cold, dilute, acidified manganate(VII) ions? A B O OH OH HO HO HO HO OH OH O O C D O + O + O O OH OH O OH OH

1 marks

Answer: A

This question in 9701/12 May/June 2019

Q192 · Which reagent could be used to distinguish between ethanal and propanal? 9701/12 May/June 2019

27 Which reagent could be used to distinguish between ethanal and propanal? A 2,4-dinitrophenylhydrazine B I2 / NaOH(aq) C K2Cr2O7 / H2SO4(aq) D Tollens’ reagent

1 marks

Answer: B

This question in 9701/12 May/June 2019

Q193 · An oxidising agent that can oxidise ethanal to ethanoic acid or ethanoate ions will also… 9701/12 May/June 2019

40 An oxidising agent that can oxidise ethanal to ethanoic acid or ethanoate ions will also oxidise methanoic acid, HCO2H, to carbon dioxide and water. Which reagents, on heating, will react differently with HCO2H and CH3CO2H? 1 Na2CO3(aq) 2 Fehling’s reagent 3 dilute acidified KMnO4

1 marks

Answer: C

This question in 9701/12 May/June 2019

Q194 · Which compound would produce a carboxylic acid and a ketone when treated with hot… 9701/13 May/June 2019

23 Which compound would produce a carboxylic acid and a ketone when treated with hot, concentrated acidified manganate(VII) ions? A B C D

1 marks

Answer: D

This question in 9701/13 May/June 2019

Q195 · Compound Q reacts with 2,4-dinitrophenylhydrazine to give a precipitate 9701/13 May/June 2019

27 Compound Q reacts with 2,4-dinitrophenylhydrazine to give a precipitate. Compound Q does not produce a precipitate when warmed with Fehling’s solution. What could be the identity of compound Q? A CH3COCH3 B CH2(OH)CH2CH3 C CH3CH2CO2H D CH3CH2CHO

1 marks

Answer: A

This question in 9701/13 May/June 2019

Q196 · An alkene reacts with hot, concentrated, acidified potassium manganate(VII) to produce a… 9701/11 Oct/Nov 2019

22 An alkene reacts with hot, concentrated, acidified potassium manganate(VII) to produce a single organic product as shown. hot, concentrated, O O acidified KMnO4(aq) alkene OH What is the structure of the alkene? A B C D

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2019

Q197 · The diagram shows the structure of compound Z 9701/11 Oct/Nov 2019

26 The diagram shows the structure of compound Z. Z O O What is the product of the reaction between compound Z and an excess of NaBH4? A B C D OH OH OH OH O O O OH

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2019

Q198 · Compound Q shows the following reactions 9701/11 Oct/Nov 2019

27 Compound Q shows the following reactions. ● It gives an orange precipitate with 2,4-dinitrophenylhydrazine. ● It gives a red-brown precipitate with Fehling’s reagent. ● It gives a pale yellow precipitate with alkaline aqueous iodine. What could be the identity of Q? A ethanal B propan-2-ol C propanal D propanone

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2019

Q199 · An organic compound X reacts with hot, concentrated acidified potassium manganate(VII)… 9701/12 Oct/Nov 2019

22 An organic compound X reacts with hot, concentrated acidified potassium manganate(VII) solution to give a single carbon-containing product. What could be X? A CH2C(CH3)2 B CH3CHCHCH3 C CH2CHCH2CH3 D CH3CH2CH2CH3

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2019

Q200 · Propan-1-ol can be reacted with acidified potassium dichromate(VI) to form propanoic… 9701/12 Oct/Nov 2019

24 Propan-1-ol can be reacted with acidified potassium dichromate(VI) to form propanoic acid, reaction 1, or propanal, reaction 2. O O reaction 1 reaction 2 CH3CH2COH CH3CH2CH2OH CH3CH2CH propan-1-ol How can the reaction be carried out to ensure that reaction 2 occurs rather than reaction 1? A An excess of acidified potassium dichromate(VI) is used. B An excess of concentrated sulfuric acid is added. C The reaction mixture is distilled immediately after mixing. D The reaction mixture is heated under reflux.

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2019

Q201 · Compound X has stereoisomers and forms a precipitate when warmed with Fehling’s reagent 9701/12 Oct/Nov 2019

26 Compound X has stereoisomers and forms a precipitate when warmed with Fehling’s reagent. What could be the structure of compound X? A B C D O O O O

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2019

Q202 · The diagram shows the structure of Y 9701/12 Oct/Nov 2019

27 The diagram shows the structure of Y. H H H H C C C C C H H O H O H Two suggestions are made about Y. 1 Y can be oxidised by hot, acidified dichromate(VI) ions. 2 One mole of Y gives one mole of tri-iodomethane when it reacts with an excess of alkaline aqueous iodine. Which suggestions are correct? A both 1 and 2 B 1 only C 2 only D neither 1 nor 2

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2019

Q203 · Each of the compounds below is treated separately with an excess of NaBH4 9701/12 Oct/Nov 2019

40 Each of the compounds below is treated separately with an excess of NaBH4. The product of each reaction is then heated with an excess of concentrated H2SO4. Which compounds give only one final product with the molecular formula C7H10? 1 2 3 O O O O H O H O H

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2019

Q204 · An alkene reacts with hot, concentrated, acidified potassium manganate(VII) to produce a… 9701/13 Oct/Nov 2019

22 An alkene reacts with hot, concentrated, acidified potassium manganate(VII) to produce a single organic product as shown. hot, concentrated, O O acidified KMnO4(aq) alkene OH What is the structure of the alkene? A B C D

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2019

Q205 · The diagram shows the structure of compound Z 9701/13 Oct/Nov 2019

26 The diagram shows the structure of compound Z. Z O O What is the product of the reaction between compound Z and an excess of NaBH4? A B C D OH OH OH OH O O O OH

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2019

Q206 · Compound Q shows the following reactions 9701/13 Oct/Nov 2019

27 Compound Q shows the following reactions. ● It gives an orange precipitate with 2,4-dinitrophenylhydrazine. ● It gives a red-brown precipitate with Fehling’s reagent. ● It gives a pale yellow precipitate with alkaline aqueous iodine. What could be the identity of Q? A ethanal B propan-2-ol C propanal D propanone

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2019

Q207 · The infrared spectrum shown was obtained from a compound J 9701/12 Feb/March 2020

23 The infrared spectrum shown was obtained from a compound J. 100 transmittance 50 0 4000 3000 2000 1500 1000 500 wavenumber / cm–1 Which statement about J is correct? A Both C=O and C≡N are present. B Neither C=O nor C≡N are present. C C=O is present but not C≡N. D C≡N is present but not C=O.

1 marks

Answer: C

This question in 9701/12 Feb/March 2020

Q208 · Compound X is treated with an excess of lithium aluminium hydride 9701/12 Feb/March 2020

28 Compound X is treated with an excess of lithium aluminium hydride. The reaction is allowed to go to completion. X O O OH What is the structure of the organic product? A B O O O H OH C D HO HO O OH OH

1 marks

Answer: D

This question in 9701/12 Feb/March 2020

Q209 · What is the skeletal formula of the compound formed when CH3CH=CHCH2OH is heated, under… 9701/12 Feb/March 2020

29 What is the skeletal formula of the compound formed when CH3CH=CHCH2OH is heated, under reflux, with K2Cr2O7 / H+? A B C D O O OH O OH O OH OH OH OH

1 marks

Answer: B

This question in 9701/12 Feb/March 2020

Q210 · Ethanal and hydrogen cyanide react together 9701/12 Feb/March 2020

37 Ethanal and hydrogen cyanide react together. The reaction mechanism involves cyanide ions. CH3 H3C O – H3C OH C O C H CN C + CN– H CN– H CN H CN Which statements about this mechanism are correct? 1 CN– acts as a catalyst. 2 CN– is a nucleophile. 3 It is an addition reaction.

1 marks

Answer: A

This question in 9701/12 Feb/March 2020

Q211 · Which compounds will produce a yellow precipitate with alkaline aqueous iodine? 9701/12 Feb/March 2020

38 Which compounds will produce a yellow precipitate with alkaline aqueous iodine? 1 2 3 OH OH HO O OH OH

1 marks

Answer: C

This question in 9701/12 Feb/March 2020

Q212 · The skeletal formula of compound X is shown 9701/11 May/June 2020

20 The skeletal formula of compound X is shown. O Which row is correct? observation on molecular addition of X to formula of X Fehling’s reagent A C7H14O no change B C7H14O red precipitate forms C C7H16O no change D C7H16O red precipitate forms

1 marks

Answer: A

This question in 9701/11 May/June 2020

Q213 · In which of the reactions is the organic compound oxidised by the given reagent? 9701/11 May/June 2020

37 In which of the reactions is the organic compound oxidised by the given reagent? 1 CH3CHO + HCN reagent 2 CH3CH2CH2CHO + Tollens’ reagent 3 CH3CH2CHO + Fehling’s reagent

1 marks

Answer: C

This question in 9701/11 May/June 2020

Q214 · When the apparatus is set up as shown, an orange precipitate forms in test-tube Z 9701/11 May/June 2020

38 When the apparatus is set up as shown, an orange precipitate forms in test-tube Z. Y Z air compound Q + acidified potassium 2,4-dinitrophenylhydrazine dichromate(VI) reagent warm What could compound Q be? 1 CH3CH2CH2OH 2 CH3CH(OH)CH3 3 (CH3)3COH

1 marks

Answer: B

This question in 9701/11 May/June 2020

Q215 · The table shows the molecular formulae of three molecules P, Q and R 9701/12 May/June 2020

21 The table shows the molecular formulae of three molecules P, Q and R. None of the molecules are cyclic. molecule molecular formula P CH4O Q CH2O2 R CH2O Which molecules show a strong absorption between 1610 cm–1 and 1750 cm–1 in their infra-red spectra? A Q only B R only C Q and R only D P, Q and R

1 marks

Answer: C

This question in 9701/12 May/June 2020

Q216 · Which reagent could be used to distinguish between propane-1,2-diol and ethane-1,2-diol? 9701/12 May/June 2020

24 Which reagent could be used to distinguish between propane-1,2-diol and ethane-1,2-diol? A alkaline aqueous iodine B aqueous acidified dichromate(VI) C ethanol and a few drops of concentrated sulfuric acid D sodium metal

1 marks

Answer: A

This question in 9701/12 May/June 2020

Q217 · Compound X has the structure shown 9701/12 May/June 2020

37 Compound X has the structure shown. compound X OH O Which statements about compound X are correct? 1 X will decolourise cold, acidified KMnO4(aq). 2 X gives an orange precipitate with 2,4-DNPH reagent. 3 X does not react with Tollens’ reagent.

1 marks

Answer: C

This question in 9701/12 May/June 2020

Q218 · Which statement about compound T and compound U is correct? 9701/13 May/June 2020

24 Which statement about compound T and compound U is correct? compound T compound U O O H3C C H C CH2CH2CH3 CH(CH3)CH2CH3 A T and U are stereoisomers. B T can be distinguished from U by the use of alkaline aqueous iodine. C T can be reduced by LiAl H4 but not by NaBH4. D U can be formed by the oxidation of 3-methylbutan-1-ol.

1 marks

Answer: B

This question in 9701/13 May/June 2020

Q219 · Compound X has the structure shown 9701/13 May/June 2020

30 Compound X has the structure shown. compound X O Which type of carbonyl group is present and how many chiral centres are there in one molecule of X? carbonyl chiral group centres A aldehyde 0 B aldehyde 1 C ketone 0 D ketone 1

1 marks

Answer: D

This question in 9701/13 May/June 2020

Q220 · Propanal reacts with hydrogen cyanide to form 2-hydroxybutanenitrile 9701/13 May/June 2020

37 Propanal reacts with hydrogen cyanide to form 2-hydroxybutanenitrile. A suitable catalyst for this reaction is sodium cyanide. NaCN CH3CH2CHO + HCN CH3CH2CH(OH)CN Which statements about this catalysed reaction of propanal with hydrogen cyanide are correct? 1 The sodium cyanide provides a stronger nucleophile than HCN. 2 The reaction can be classified as nucleophilic substitution. 3 The hydrogen cyanide molecule attacks the propanal molecule to form an intermediate ion.

1 marks

Answer: D

This question in 9701/13 May/June 2020

Q221 · An alcohol with the molecular formula C5H12O decolourises warm acidified potassium… 9701/11 Oct/Nov 2020

26 An alcohol with the molecular formula C5H12O decolourises warm acidified potassium manganate(VII). The alcohol also gives a yellow precipitate with alkaline aqueous iodine. What could be the identity of the alcohol? A 2-methylbutan-2-ol B 3-methylbutan-2-ol C pentan-1-ol D pentan-3-ol

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2020

Q222 · Which pair of test results would prove that a substance, X, is a ketone? 9701/11 Oct/Nov 2020

27 Which pair of test results would prove that a substance, X, is a ketone? A X has no reaction with Tollens’ reagent. X reacts with alkaline aqueous iodine. B X is reduced by lithium aluminium hydride. X is oxidised by acidified dichromate(VI). C X reacts with 2,4-DNPH reagent. X has no reaction with Fehling’s reagent. D X reacts with hydrogen cyanide. X is reduced by lithium aluminium hydride.

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2020

Q223 · Carvone is found in spearmint oil 9701/11 Oct/Nov 2020

28 Carvone is found in spearmint oil. carvone O Which product is formed when carvone is reacted with NaBH4? A B C D OH O O OH

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2020

Q224 · Compound X contains two functional groups 9701/12 Oct/Nov 2020

23 Compound X contains two functional groups. compound X O CH3 C CHO Which reagent will react with only one of the functional groups? A acidified potassium dichromate(VI) B 2,4-DNPH reagent C hydrogen cyanide D NaBH4

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2020

Q225 · Diols in which both hydroxy groups are bonded to the same carbon atom can spontaneously… 9701/12 Oct/Nov 2020

25 Diols in which both hydroxy groups are bonded to the same carbon atom can spontaneously eliminate a molecule of water to produce a carbonyl compound. Which compound, after complete hydrolysis, gives a silver mirror with Tollens’ reagent? A 1,1-dibromobutane B 1,2-dibromobutane C 1,3-dibromobutane D 2,2-dibromobutane

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2020

Q226 · How many structural isomers are there of molecular formula C5H10O that give a red… 9701/12 Oct/Nov 2020

27 How many structural isomers are there of molecular formula C5H10O that give a red precipitate with Fehling’s solution? A 1 B 2 C 3 D 4

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2020

Q227 · The infra-red spectrum shown was obtained from compound G 9701/12 Oct/Nov 2020

30 The infra-red spectrum shown was obtained from compound G. 100 transmittance / % 50 0 4000 3000 2000 1500 1000 500 wavenumber / cm–1 What could be compound G? A CH3COCH2OH B CH3CH2CO2H C CH3CO2CH3 D CH3CHCHCH3

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2020

Q228 · Which reagents could be used, under suitable conditions, to oxidise CH3CH2CH2OH to… 9701/12 Oct/Nov 2020

37 Which reagents could be used, under suitable conditions, to oxidise CH3CH2CH2OH to CH3CH2CHO? 1 acidified potassium manganate(VII) 2 acidified potassium dichromate(VI) 3 Tollens’ reagent

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2020

Q229 · Which substances have molecular formula C4H8O? 9701/12 Oct/Nov 2020

39 Which substances have molecular formula C4H8O? 1 O 2 O OH 3

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2020

Q230 · An alcohol with the molecular formula C5H12O decolourises warm acidified potassium… 9701/13 Oct/Nov 2020

26 An alcohol with the molecular formula C5H12O decolourises warm acidified potassium manganate(VII). The alcohol also gives a yellow precipitate with alkaline aqueous iodine. What could be the identity of the alcohol? A 2-methylbutan-2-ol B 3-methylbutan-2-ol C pentan-1-ol D pentan-3-ol

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2020

Q231 · Which pair of test results would prove that a substance, X, is a ketone? 9701/13 Oct/Nov 2020

27 Which pair of test results would prove that a substance, X, is a ketone? A X has no reaction with Tollens’ reagent. X reacts with alkaline aqueous iodine. B X is reduced by lithium aluminium hydride. X is oxidised by acidified dichromate(VI). C X reacts with 2,4-DNPH reagent. X has no reaction with Fehling’s reagent. D X reacts with hydrogen cyanide. X is reduced by lithium aluminium hydride.

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2020

Q232 · Carvone is found in spearmint oil 9701/13 Oct/Nov 2020

28 Carvone is found in spearmint oil. carvone O Which product is formed when carvone is reacted with NaBH4? A B C D OH O O OH

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2020

Q233 · Which compound produces a ketone when refluxed with an acidified solution of potassium… 9701/12 Feb/March 2021

24 Which compound produces a ketone when refluxed with an acidified solution of potassium dichromate(VI)? A pentan-1-ol B 2-methylbutan-1-ol C 2-methylbutan-2-ol D 3-methylbutan-2-ol

1 marks

Answer: D

This question in 9701/12 Feb/March 2021

Q234 · In this question you can assume that 1H and 3H have the same chemical properties 9701/12 Feb/March 2021

27 In this question you can assume that 1H and 3H have the same chemical properties. A sample of ethanal contains only one isotope of hydrogen, 1H. It is reduced to compound Z, C2H6O, in a nucleophilic addition reaction using NaBH4. All the hydrogen atoms in the NaBH4 are the 3H isotope. NaBH4 CH3CHO C2H6O compound Z Compound Z is then oxidised back to ethanal and water. C2H6O + [O]  CH3CHO + H2O Which statement about the final mixture of products is correct? A Both ethanal and water contain 3H atoms. B Ethanal is the only product containing 3H atoms. C Neither ethanal nor water contain 3H atoms. D Water is the only product containing 3H atoms.

1 marks

Answer: A

This question in 9701/12 Feb/March 2021

Q235 · When reactant X is treated with a suitable reagent, products Y and Z are formed 9701/12 Feb/March 2021

30 When reactant X is treated with a suitable reagent, products Y and Z are formed. Infrared spectra of X, Y and Z are shown. reactant X 100 transmittance 50 0 4000 3000 2000 1000 wavenumber / cm–1 product Y product Z 100 100 transmittance transmittance 50 50 0 0 4000 3000 2000 1000 4000 3000 2000 1500 1000 500 wavenumber / cm–1 wavenumber / cm–1 Which row could be correct? X Y Z A 2,3-dimethylpent-2-ene propanone butanone B 2-methylpent-2-ene propanone propanoic acid C pent-2-ene ethanoic acid propanoic acid D propyl propanoate propan-1-ol propanoic acid

1 marks

Answer: B

This question in 9701/12 Feb/March 2021

Q236 · Two carbonyl compounds have the molecular formula C3H6O 9701/12 Feb/March 2021

39 Two carbonyl compounds have the molecular formula C3H6O. Which reagents give different observations with these two compounds? 1 acidified aqueous potassium manganate(VII) 2 Fehling’s reagent 3 alkaline aqueous iodine

1 marks

Answer: A

This question in 9701/12 Feb/March 2021

Q237 · An organic compound, T, does not fizz when aqueous sodium carbonate is added to it 9701/12 Feb/March 2021

40 An organic compound, T, does not fizz when aqueous sodium carbonate is added to it. Compound T contains 27.6% by mass of oxygen. What could be the identity of T? 1 propanal 2 ethyl butanoate 3 3-methylpentanoic acid

1 marks

Answer: B

This question in 9701/12 Feb/March 2021

Q238 · Which compound would produce two different carboxylic acids when treated with hot… 9701/11 May/June 2021

21 Which compound would produce two different carboxylic acids when treated with hot, concentrated, acidified manganate(VII) ions? A B C D

1 marks

Answer: B

This question in 9701/11 May/June 2021

Q239 · Compound X has the empirical formula C2H4O 9701/11 May/June 2021

26 Compound X has the empirical formula C2H4O. Its infra-red spectrum is shown. 100 transmittance / % 50 0 4000 3000 2000 1500 1000 500 wavenumber / cm–1 What could be the skeletal formula of compound X? A B C D OH O O O O O O H OH

1 marks

Answer: A

This question in 9701/11 May/June 2021

Q240 · Which pairs of compounds may be distinguished by testing with alkaline aqueous iodine? 9701/11 May/June 2021

38 Which pairs of compounds may be distinguished by testing with alkaline aqueous iodine? 1 butanal and butanone 2 pentan-2-one and pentan-3-ol 3 propanone and propan-2-ol

1 marks

Answer: B

This question in 9701/11 May/June 2021

Q241 · Which reactions have a coloured organic product? 9701/11 May/June 2021

39 Which reactions have a coloured organic product? 1 ethanal + 2,4-dinitrophenylhydrazine reagent 2 ethanol + acidified potassium dichromate(VI) 3 ethene + cold dilute acidified potassium manganate(VII)

1 marks

Answer: D

This question in 9701/11 May/June 2021

Q242 · The molecular formula of Z is C4H8O 9701/12 May/June 2021

30 The molecular formula of Z is C4H8O. The infra-red spectrum of Z is shown. 100 transmittance / % 50 0 4000 3000 2000 1500 1000 500 wavenumber / cm–1 What could be Z? A B C D OH O O OH OH

1 marks

Answer: D

This question in 9701/12 May/June 2021

Q243 · Which alcohols can be oxidised to form an organic compound which will give coloured… 9701/12 May/June 2021

39 Which alcohols can be oxidised to form an organic compound which will give coloured precipitates with both 2,4-dinitrophenylhydrazine reagent and alkaline aqueous iodine? OH 1 OH O 2 3 OH

1 marks

Answer: C

This question in 9701/12 May/June 2021

Q244 · Two carbon-containing products result from the reaction of alkene Z with a hot… 9701/13 May/June 2021

21 Two carbon-containing products result from the reaction of alkene Z with a hot, concentrated, acidified solution of potassium manganate(VII). One product forms an orange precipitate with 2,4-dinitrophenylhydrazine reagent. The other product is a gas which gives a white precipitate with aqueous calcium hydroxide. Which alkene could be alkene Z? A but-2-ene B 2-methylpropene C 2-methylbut-2-ene D propene

1 marks

Answer: B

This question in 9701/13 May/June 2021

Q245 · The skeletal formulae of three compounds are shown 9701/13 May/June 2021

26 The skeletal formulae of three compounds are shown. R S T OH O O O O Which compounds will give a positive test with 2,4-dinitrophenylhydrazine reagent? A R only B R and S only C S and T only D R, S and T

1 marks

Answer: A

This question in 9701/13 May/June 2021

Q246 · Three compounds, X, Y and Z, are shown 9701/13 May/June 2021

39 Three compounds, X, Y and Z, are shown. X Y Z C2H5COCH3 C2H5CHO CH3CO2H Which statements about X, Y and Z are correct? 1 X reacts with alkaline aqueous iodine. 2 Y reacts with Tollens’ reagent. 3 Z does not react with alkaline aqueous iodine.

1 marks

Answer: A

This question in 9701/13 May/June 2021

Q247 · Alcohol Y gives a yellow precipitate with alkaline aqueous iodine 9701/11 Oct/Nov 2021

25 Alcohol Y gives a yellow precipitate with alkaline aqueous iodine. It can be oxidised to give a mixture of products including substance Z. Substance Z gives a red-brown precipitate with Fehling’s solution. Which alcohol could be Y? A CH3CH(OH)CH(CH3)CH2OH B CH3C(OH)(CH3)CH2CH2OH C CH3CH(OH)CH2CH(OH)CH3 D CH2(OH)CH2CH(OH)CH2CH3

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2021

Q248 · Compound P is heated under reflux with an excess of acidified potassium dichromate(VI) to… 9701/12 Oct/Nov 2021

26 Compound P is heated under reflux with an excess of acidified potassium dichromate(VI) to form compound Q. Compound Q has a lower boiling point than compound P. What could be compound P? A 2-methylbutan-1-ol B 2-methylbutan-2-ol C pentan-1-ol D pentan-2-ol

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2021

Q249 · Which compound produces a precipitate with 2,4-dinitrophenylhydrazine reagent and also… 9701/12 Oct/Nov 2021

28 Which compound produces a precipitate with 2,4-dinitrophenylhydrazine reagent and also with alkaline aqueous iodine? A butan-2-ol B butanal C butanone D pentan-3-one

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2021

Q250 · When an organic compound, Q, is treated with phosphorus pentachloride, fumes of hydrogen… 9701/13 Oct/Nov 2021

24 When an organic compound, Q, is treated with phosphorus pentachloride, fumes of hydrogen chloride are evolved. When Q is warmed with acidified aqueous potassium dichromate(VI), the solution turns green. What is Q? A CH3CH2CHO B CH3CH2CO2H C CH3CH(OH)CH3 D (CH3)3COH

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2021

Q251 · Alcohol Y gives a yellow precipitate with alkaline aqueous iodine 9701/13 Oct/Nov 2021

25 Alcohol Y gives a yellow precipitate with alkaline aqueous iodine. It can be oxidised to give a mixture of products including substance Z. Substance Z gives a red-brown precipitate with Fehling’s solution. Which alcohol could be Y? A CH3CH(OH)CH(CH3)CH2OH B CH3C(OH)(CH3)CH2CH2OH C CH3CH(OH)CH2CH(OH)CH3 D CH2(OH)CH2CH(OH)CH2CH3

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2021

Q252 · Reduction of compound R with LiAl H4 gives the compound 4-methylpentane-2,3-diol 9701/13 Oct/Nov 2021

27 Reduction of compound R with LiAl H4 gives the compound 4-methylpentane-2,3-diol. What could be the identity of compound R? A B C D O O O O O O O O

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2021

Q253 · Which compound will react with LiAl H4 to form two optical isomers? 9701/11 May/June 2022

27 Which compound will react with LiAl H4 to form two optical isomers? A CH3CH2COCH3 B CH3CH2CH2CHO C CH3CH2COCH2CH3 D CH3CH(CH3)CH2CO2H

1 marks

Answer: A

This question in 9701/11 May/June 2022

Q254 · The skeletal formulae of two organic compounds are shown 9701/11 May/June 2022

35 The skeletal formulae of two organic compounds are shown. Which reagents can be used to distinguish these two compounds? 1 alkaline I2(aq) 2 acidified K2Cr2O7 3 2,4-dinitrophenylhydrazine (2,4-DNPH reagent) A 1, 2 and 3 B 1 and 3 only C 2 and 3 only D 2 only

1 marks

Answer: B

This question in 9701/11 May/June 2022

Q255 · A carbonyl compound, X, reacts with HCN in the presence of NaCN to make a compound with… 9701/11 May/June 2022

36 A carbonyl compound, X, reacts with HCN in the presence of NaCN to make a compound with Mr 85. Compound X does not react with Fehling’s reagent. What is compound X? A butanal B butanone C propanal D propanone

1 marks

Answer: D

This question in 9701/11 May/June 2022

Q256 · Primary alcohols can be oxidised to aldehydes using either acidified potassium… 9701/12 May/June 2022

33 Primary alcohols can be oxidised to aldehydes using either acidified potassium dichromate(VI) or acidified potassium manganate(VII). The reaction mixtures change colour as the oxidising agent is reduced. What are the colour changes seen? acidified potassium dichromate(VI) acidified potassium manganate(VII) before after before after A green orange purple colourless B orange green colourless purple C orange green purple colourless D purple colourless orange green

1 marks

Answer: C

This question in 9701/12 May/June 2022

Q257 · Which reaction has a product that gives a yellow precipitate when treated with alkaline… 9701/12 May/June 2022

34 Which reaction has a product that gives a yellow precipitate when treated with alkaline I2(aq)? A 2-chloropropane is warmed with a dilute aqueous solution of sodium hydroxide. B Ethanal is heated under reflux with acidified potassium dichromate(VI). C Methyl ethanoate is heated under reflux with dilute sulfuric acid. D Propanal is reacted with NaBH4, followed by dilute sulfuric acid.

1 marks

Answer: A

This question in 9701/12 May/June 2022

Q258 · Which compound forms a precipitate when mixed with 2,4-DNPH reagent and also forms a… 9701/12 May/June 2022

36 Which compound forms a precipitate when mixed with 2,4-DNPH reagent and also forms a precipitate when mixed with Fehling’s reagent? A B C D O O O O O O OH O

1 marks

Answer: B

This question in 9701/12 May/June 2022

Q259 · Structural isomerism only should be considered when answering this question 9701/13 May/June 2022

33 Structural isomerism only should be considered when answering this question. Several compounds with molecular formula C4H8O2 have one carbonyl group and one OH group. How many of these compounds produce yellow crystals with alkaline I2(aq) at room temperature? A 2 B 3 C 4 D 5

1 marks

Answer: B

This question in 9701/13 May/June 2022

Q260 · Which reaction has a nucleophilic addition mechanism and gives a good yield of product… 9701/13 May/June 2022

35 Which reaction has a nucleophilic addition mechanism and gives a good yield of product under the stated conditions? A 1-bromopropane reacting with hot ethanolic sodium hydroxide B 2-iodopropane reacting with hot aqueous sodium hydroxide C propanal reacting with hydrogen cyanide under alkaline conditions D propanal reacting with hydrogen cyanide under acidic conditions

1 marks

Answer: C

This question in 9701/13 May/June 2022

Q261 · A carbonyl compound has the structural formula CH3COCHO 9701/13 May/June 2022

36 A carbonyl compound has the structural formula CH3COCHO. Which row is correct for the observations made when this compound is treated with the given reagents? 2,4-DNPH reagent Fehling’s reagent A silver mirror red precipitate B silver mirror orange precipitate C orange precipitate silver mirror D orange precipitate red precipitate

1 marks

Answer: D

This question in 9701/13 May/June 2022

Q262 · Compound R can be formed from 1-bromopropane using a nucleophilic substitution reaction… 9701/11 Oct/Nov 2022

30 Compound R can be formed from 1-bromopropane using a nucleophilic substitution reaction followed by an oxidation reaction. What is the identity of R? A propanoic acid B propanone C propylamine D propyl ethanoate

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2022

Q263 · Three colourless liquids with the following formulae are contained in separate unlabelled… 9701/11 Oct/Nov 2022

31 Three colourless liquids with the following formulae are contained in separate unlabelled bottles. CH3CH2CO2H CH3CH(OH)CO2H CH3COCO2H Which two tests, carried out on separate samples of each liquid, will successfully identify each liquid? test 1 test 2 A NaHCO3 2,4-DNPH reagent B NaHCO3 Tollens’ reagent C warm acidified dichromate 2,4-DNPH reagent D warm acidified dichromate Tollens’ reagent

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2022

Q264 · W reacts with alkaline I2(aq) to form a yellow precipitate and CH3CH2CO2 – ions 9701/11 Oct/Nov 2022

33 W reacts with alkaline I2(aq) to form a yellow precipitate and CH3CH2CO2 – ions. Which row identifies W and the yellow precipitate? identity of identity of W yellow precipitate A butanone CHI3 B butanone CH3I C propanone CHI3 D propanone CH3I

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2022

Q265 · 1.0 mol of an organic compound, J, requires 6.0 mol of oxygen for complete combustion 9701/12 Oct/Nov 2022

33 1.0 mol of an organic compound, J, requires 6.0 mol of oxygen for complete combustion. 1.0 mol of J reacts with sodium, producing 0.50 mol of a gas that gives a ‘pop’ with a lighted splint. J reacts with an excess of hot acidified potassium manganate(VII) to produce an organic compound which gives an orange-red precipitate with 2,4-DNPH reagent. Which compound is J? A but-1-ene B butan-2-ol C propan-2-ol D 2-methylpropan-2-ol

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2022

Q266 · The table shows a student’s predictions for the reactions of three compounds 9701/12 Oct/Nov 2022

35 The table shows a student’s predictions for the reactions of three compounds. alkaline Fehling’s Tollens’ compound I,(aq) reagent reagent key 1 \Z J J J / = reaction occurs X = no reaction 2 3 Which rows show the correct predictions? A 1,2and 3 B 1tand2only C 1and3only D = 2and3only

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2022

Q267 · Which mechanism describes the reaction of aldehydes and ketones with HCN + NaCN? 9701/12 Oct/Nov 2022

36 Which mechanism describes the reaction of aldehydes and ketones with HCN + NaCN? A electrophilic addition B electrophilic substitution C nucleophilic addition D nucleophilic substitution

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2022

Q268 · Three colourless liquids with the following formulae are contained in separate unlabelled… 9701/13 Oct/Nov 2022

31 Three colourless liquids with the following formulae are contained in separate unlabelled bottles. CH3CH2CO2H CH3CH(OH)CO2H CH3COCO2H Which two tests, carried out on separate samples of each liquid, will successfully identify each liquid? test 1 test 2 A NaHCO3 2,4-DNPH reagent B NaHCO3 Tollens’ reagent C warm acidified dichromate 2,4-DNPH reagent D warm acidified dichromate Tollens’ reagent

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2022

Q269 · W reacts with alkaline I2(aq) to form a yellow precipitate and CH3CH2CO2 – ions 9701/13 Oct/Nov 2022

33 W reacts with alkaline I2(aq) to form a yellow precipitate and CH3CH2CO2 – ions. Which row identifies W and the yellow precipitate? identity of identity of W yellow precipitate A butanone CHI3 B butanone CH3I C propanone CHI3 D propanone CH3I

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2022

Q270 · When illudin S is heated under reflux with an excess of acidified potassium… 9701/12 Feb/March 2023

28 When illudin S is heated under reflux with an excess of acidified potassium dichromate(VI), compound M is formed. illudin S OH compound M OH HO O What is the molecular formula of compound M? A C15H16O4 B C15H16O5 C C15H18O4 D C15H18O5

1 marks

Answer: B

This question in 9701/12 Feb/March 2023

Q271 · Structural and stereoisomerism should be considered when answering this question 9701/12 Feb/March 2023

34 Structural and stereoisomerism should be considered when answering this question. P has molecular formula C5H10O. P produces an orange precipitate with 2,4-dinitrophenylhydrazine (2,4-DNPH reagent). How many isomeric structures does P have? A 5 B 6 C 7 D 8

1 marks

Answer: D

This question in 9701/12 Feb/March 2023

Q272 · Two isomeric alcohols, W and X, have molecular formula C4H9OH 9701/12 Feb/March 2023

35 Two isomeric alcohols, W and X, have molecular formula C4H9OH. W is oxidised to carbonyl compound Y which gives a red precipitate with Fehling’s solution. X is oxidised to carbonyl compound Z which does not give a red precipitate with Fehling’s solution. Which of W and X gives a yellow precipitate with alkaline I2(aq)? A insufficient data is given to answer this question B W only C X only D neither W nor X

1 marks

Answer: C

This question in 9701/12 Feb/March 2023

Q273 · 2-methylbut-2-ene is reacted with hot, concentrated, acidified potassium manganate(VII)… 9701/12 Feb/March 2023

40 2-methylbut-2-ene is reacted with hot, concentrated, acidified potassium manganate(VII) solution. What are the products of this reaction? A ethanal and propanone B ethanoic acid and propanone C ethanoic acid and propan-2-ol D ethanol and propan-2-ol

1 marks

Answer: B

This question in 9701/12 Feb/March 2023

Q274 · T is an organic compound which contains 66.7% by mass of carbon 9701/13 May/June 2023

33 T is an organic compound which contains 66.7% by mass of carbon. T also contains one atom of oxygen per molecule. T reacts with alkaline I2(aq) to produce a yellow precipitate. What is T? A methylpropan-2-ol B butan-2-ol C butanal D butanone

1 marks

Answer: D

This question in 9701/13 May/June 2023

Q275 · Which statement about butanone is correct? 9701/13 May/June 2023

34 Which statement about butanone is correct? A Butanone can be dehydrated by concentrated sulfuric acid to give CH2=CHCH=CH2. B Butanone gives a positive result with Tollens’ reagent. C Butanone reacts with HCN by an electrophilic addition mechanism. D Butanone reacts with NaBH4 to give a chiral product.

1 marks

Answer: D

This question in 9701/13 May/June 2023

Q276 · Β-carotene is responsible for the orange colour of carrots 9701/11 Oct/Nov 2023

30 β-carotene is responsible for the orange colour of carrots. β-carotene CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 β-carotene is oxidised by hot, concentrated, acidified KMnO4. When an individual molecule of β-carotene is oxidised in this way, many product molecules are formed. How many of these product molecules contain a ketone functional group? A 4 B 6 C 9 D 11

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2023

Q277 · Which compound will produce a yellow-orange precipitate when added to… 9701/11 Oct/Nov 2023

36 Which compound will produce a yellow-orange precipitate when added to 2,4-dinitrophenylhydrazine? A B C D O O O OH O Ethanal, CH3CHO, undergoes an addition reaction with HCN in the presence of CN– ions.

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2023

Q278 · Which row identifies the type of reaction and the name of the product formed? 9701/11 Oct/Nov 2023

37 Which row identifies the type of reaction and the name of the product formed? type of reaction name of product A electrophilic addition 2-hydroxypropanenitrile B electrophilic addition 2-hydroxyethanenitrile C nucleophilic addition 2-hydroxypropanenitrile D nucleophilic addition 2-hydroxyethanenitrile

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2023

Q279 · In the mass spectrum of compound J, the ratio of the height of the M +1 ion peak to the… 9701/11 Oct/Nov 2023

40 In the mass spectrum of compound J, the ratio of the height of the M +1 ion peak to the height of the M + ion peak is 4:91. Compound J forms a carboxylic acid when heated with acidified K2Cr2O7. What is compound J? A butanal B butanone C propan-1-ol D propanenitrile

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2023

Q280 · The formulae of three compounds are shown 9701/12 Oct/Nov 2023

31 The formulae of three compounds are shown. C3H7CHO C2H5COCH3 CH2CHCH2CH2OH Only one of these compounds will decolourise bromine water. Only one of these compounds will produce a silver mirror with Tollens’ reagent. Which row shows the correct results? forms a silver mirror with decolourises bromine water Tollens’ reagent A C3H7CHO C2H5COCH3 B C2H5COCH3 C3H7CHO C CH2CHCH2CH2OH C2H5COCH3 D CH2CHCH2CH2OH C3H7CHO

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2023

Q281 · Which alcohol reacts with alkaline I2(aq) to produce ethanoate ions? 9701/12 Oct/Nov 2023

34 Which alcohol reacts with alkaline I2(aq) to produce ethanoate ions? A ethanol B methylpropan-2-ol C propan-2-ol D butan-2-ol

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2023

Q282 · Heating compound X, C7H,,0,, under reflux with an excess of acidified potassium… 9701/12 Oct/Nov 2023

35 Heating compound X, C7H,,0,, under reflux with an excess of acidified potassium dichromate(VI) produces compound Y. Compound Y produces hydrogen gas with sodium metal and forms orange crystals with 2,4-DNPH reagent. What could X be? A B Cc D CH,OH OH CH, OH (CH,),C(OH)CH,CH,CH,CHO CH, CH,OH OH OH

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2023

Q283 · Which reaction takes place by a nucleophilic addition mechanism? 9701/12 Oct/Nov 2023

36 Which reaction takes place by a nucleophilic addition mechanism? A propene reacting with hydrogen bromide B 2-bromopropane reacting with sodium hydroxide in ethanol C propanone reacting with hydrogen cyanide D methane reacting with chlorine

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2023

Q284 · Β-carotene is responsible for the orange colour of carrots 9701/13 Oct/Nov 2023

30 β-carotene is responsible for the orange colour of carrots. β-carotene CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 β-carotene is oxidised by hot, concentrated, acidified KMnO4. When an individual molecule of β-carotene is oxidised in this way, many product molecules are formed. How many of these product molecules contain a ketone functional group? A 4 B 6 C 9 D 11

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2023

Q285 · Which compound will produce a yellow-orange precipitate when added to… 9701/13 Oct/Nov 2023

36 Which compound will produce a yellow-orange precipitate when added to 2,4-dinitrophenylhydrazine? A B C D O O O OH O Ethanal, CH3CHO, undergoes an addition reaction with HCN in the presence of CN– ions.

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2023

Q286 · But-2-ene reacts with cold dilute acidified KMnO4 to give product X 9701/12 Feb/March 2024

27 But-2-ene reacts with cold dilute acidified KMnO4 to give product X. But-2-ene reacts with hot concentrated acidified KMnO4 to give product Y. Which statement about product X and product Y is correct? A Both product X and product Y will react with 2,4-dinitrophenylhydrazine. B Neither product X nor product Y will react with 2,4-dinitrophenylhydrazine. C Product X will react with 2,4-dinitrophenylhydrazine, product Y will not. D Product Y will react with 2,4-dinitrophenylhydrazine, product X will not.

1 marks

Answer: B

This question in 9701/12 Feb/March 2024

Q287 · In which pair will each compound give a different visible result with alkaline I2(aq)? 9701/12 Feb/March 2024

33 In which pair will each compound give a different visible result with alkaline I2(aq)? A CH3CH2OH and CH3CHO B CH3CHO and CH3COCH3 C CH3COOH and C2H5COC2H5 D CH3CH2OH and C2H5CHO

1 marks

Answer: D

This question in 9701/12 Feb/March 2024

Q288 · Which reagent gives a positive result with propanone? 9701/12 Feb/March 2024

34 Which reagent gives a positive result with propanone? A alkaline I2(aq) B aqueous bromine C Fehling’s reagent D Tollens’ reagent

1 marks

Answer: A

This question in 9701/12 Feb/March 2024

Q289 · Hydroxyethanal, HOCH2CHO, is heated under reflux with an excess of acidified K2Cr2O7… 9701/12 Feb/March 2024

38 Hydroxyethanal, HOCH2CHO, is heated under reflux with an excess of acidified K2Cr2O7 until no further oxidation takes place. What is the skeletal formula of the organic product? A B C D O O OH O HO HO OH OH OH OH O O O O

1 marks

Answer: B

This question in 9701/12 Feb/March 2024

Q290 · X is a non-cyclic ketone with a single carbonyl group and no other functional groups 9701/11 May/June 2024

34 X is a non-cyclic ketone with a single carbonyl group and no other functional groups. Ketone X has the following properties. ● When ketone X is treated with NaBH4, the organic product has a Mr 2.3256% greater than the Mr of ketone X. ● Ketone X gives a yellow precipitate with alkaline I2(aq). How many isomeric ketones could be ketone X? A 1 B 2 C 3 D 4

1 marks

Answer: B

This question in 9701/11 May/June 2024

Q291 · Compound Y: ● changes the colour of acidified K2Cr2O7 from orange to green ● has no… 9701/11 May/June 2024

35 Compound Y: ● changes the colour of acidified K2Cr2O7 from orange to green ● has no effect on Fehling’s reagent ● produces an orange precipitate with 2,4-dinitrophenylhydrazine reagent. What is compound Y? A B C D CH3CCH2C H CH3CCH2CCH3 CH3CCH2CH2OH HOCH2CH2CH2CH2OH O O O O O

1 marks

Answer: C

This question in 9701/11 May/June 2024

Q292 · Z is a gaseous hydrocarbon which has a density of 3.50  10–3 g cm–3 under room conditions 9701/12 May/June 2024

26 Z is a gaseous hydrocarbon which has a density of 3.50  10–3 g cm–3 under room conditions. Z reacts with an excess of hot concentrated acidified KMnO4. Only one type of carboxylic acid is formed in this reaction. What is Z? A but-2-ene B 2,3-dimethylbut-2-ene C hex-2-ene D hex-3-ene

1 marks

Answer: D

This question in 9701/12 May/June 2024

Q293 · Compound X can be oxidised to compound Y 9701/12 May/June 2024

27 Compound X can be oxidised to compound Y. Compound Y gives a yellow precipitate with alkaline I2(aq). What is compound X? A butan-1-ol B butan-2-ol C methylpropan-1-ol D methylpropan-2-ol

1 marks

Answer: B

This question in 9701/12 May/June 2024

Q294 · In which reaction is the organic compound oxidised? 9701/12 May/June 2024

29 In which reaction is the organic compound oxidised? A CH3CH2CH2CHO + Tollens’ reagent B CH3CH2CH2CHO + LiAl H4 C CH3CH2CH2OH + concentrated H3PO4 D CH3CO2C2H5 + dilute H2SO4

1 marks

Answer: A

This question in 9701/12 May/June 2024

Q295 · Which reaction will distinguish between propan-1-ol and propan-2-ol? 9701/12 May/June 2024

31 Which reaction will distinguish between propan-1-ol and propan-2-ol? A warming with acidified KMnO4 B warming with acidified K2Cr2O7 C dehydration, followed by reaction with Br2(aq) D mild oxidation, followed by reaction with Fehling’s reagent

1 marks

Answer: D

This question in 9701/12 May/June 2024

Q296 · The diagram shows a simplified structure of coenzyme Q10 9701/12 May/June 2024

33 The diagram shows a simplified structure of coenzyme Q10. coenzyme Q10 O CH3O CH3O H O n Which row describes the structure of coenzyme Q10 correctly? number of  bonds the coenzyme is in one molecule A an aldehyde n + 2 B an aldehyde n + 4 C a ketone n + 2 D a ketone n + 4

1 marks

Answer: D

This question in 9701/12 May/June 2024

Q297 · But-2-ene reacts with cold dilute acidified KMnO4 to give product X 9701/13 May/June 2024

29 But-2-ene reacts with cold dilute acidified KMnO4 to give product X. But-2-ene reacts with an excess of hot concentrated acidified KMnO4 to give product Y. Which statement about X and Y is correct? A Only one of X and Y reacts with 2,4-dinitrophenylhydrazine. B X and Y both react with sodium hydroxide. C X and Y both react with sodium metal. D Y reacts with LiAl H4 to give X.

1 marks

Answer: C

This question in 9701/13 May/June 2024

Q298 · Four different alcohols are treated with alkaline I2(aq) 9701/13 May/June 2024

32 Four different alcohols are treated with alkaline I2(aq). Which row is correct? name of alcohol formulae of products A butan-2-ol CH3COO– and CH3CI3 B propan-1-ol CH3COO– and CHI3 C propan-2-ol CH3COO– and CHI3 D butan-2-ol CH3CH2COO– and CH3I

1 marks

Answer: C

This question in 9701/13 May/June 2024

Q299 · Butanedione, CH3COCOCH3, is a yellow liquid 9701/13 May/June 2024

34 Butanedione, CH3COCOCH3, is a yellow liquid. How does butanedione react with 2,4-dinitrophenylhydrazine reagent and Fehling’s reagent? 2,4-dinitrophenylhydrazine Fehling’s A positive positive B positive negative C negative positive D negative negative

1 marks

Answer: B

This question in 9701/13 May/June 2024

Q300 · Compound Q reacts separately with HCN and NaBH4 under suitable conditions 9701/13 May/June 2024

38 Compound Q reacts separately with HCN and NaBH4 under suitable conditions. Both reactions produce an organic product with a chiral centre. What is compound Q? A butanone B ethanal C propanal D propanone

1 marks

Answer: A

This question in 9701/13 May/June 2024

Q301 · Compound X has the following properties 9701/13 May/June 2024

39 Compound X has the following properties. ● When 0.20 mol of X undergoes complete combustion, 14.4 dm3 of carbon dioxide is produced, measured under room conditions. ● X reacts with 2,4-dinitrophenylhydrazine reagent to give an orange crystalline product. ● X does not give a yellow precipitate with alkaline I2(aq). What could be X? A hexan-3-one B propanal C propan-1-ol D propanone

1 marks

Answer: B

This question in 9701/13 May/June 2024

Q302 · Vitamin A contains retinol 9701/11 Oct/Nov 2024

29 Vitamin A contains retinol. retinol OH Under appropriate conditions, acidified KMnO4(aq) can be used to break C=C bonds. After these bonds have been broken, further oxidation of the fragments may occur. Under which conditions is the acidified KMnO4(aq) used and what do the final oxidation products include? conditions final oxidation products A cold, dilute aldehydes and carboxylic acids B cold, dilute ketones and carboxylic acids C hot, concentrated aldehydes and carboxylic acids D hot, concentrated ketones and carboxylic acids

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2024

Q303 · Compound Y reacts with alkaline I2(aq) 9701/11 Oct/Nov 2024

34 Compound Y reacts with alkaline I2(aq). When the products of this reaction are acidified, a dicarboxylic acid is produced. The formula of the dicarboxylic acid is HOOC–R–COOH where R consists of one or more CH2 groups. Which compound is Y? A pentan-1,4-diol B pentan-1,5-diol C pentan-2,3-diol D pentan-2,4-diol

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2024

Q304 · Which alcohol gives only one possible oxidation product when warmed with dilute acidified… 9701/11 Oct/Nov 2024

35 Which alcohol gives only one possible oxidation product when warmed with dilute acidified potassium dichromate(VI)? A butan-1-ol B butan-2-ol C 2-methylpropan-1-ol D 2-methylpropan-2-ol

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2024

Q305 · The diagram shows three reactions of ethanal 9701/11 Oct/Nov 2024

37 The diagram shows three reactions of ethanal. In each case, an excess of ethanal is used. solid 2 alkaline I2(aq) heat acidified K2Cr2O7 ethanal Fehling’s solution solution 1 solid 3 heat CH3CHO boil Observations are made after each of the three reactions. What are the colours of solution 1 and solids 2 and 3? solution 1 solid 2 solid 3 A green yellow silver mirror B green yellow red C orange red silver mirror D orange red red

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2024

Q306 · The compound ‘leaf alcohol’ is partly responsible for the smell of new-mown grass 9701/12 Oct/Nov 2024

33 The compound ‘leaf alcohol’ is partly responsible for the smell of new-mown grass. leaf alcohol CH3CH2CH=CHCH2CH2OH What will be formed when ‘leaf alcohol’ is oxidised using an excess of hot acidified K2Cr2O7(aq)? A CH3CH2CH(OH)CH(OH)CH2CO2H B CH3CH2COCOCH2CO2H C CH3CH2CH=CHCH2CO2H D CH3CH2CO2H and HO2CCH2CO2H

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2024

Q307 · Compound X: ● does not react with Tollens’ reagent ● forms a yellow precipitate with… 9701/12 Oct/Nov 2024

34 Compound X: ● does not react with Tollens’ reagent ● forms a yellow precipitate with alkaline I2(aq) ● does not react with sodium. What could be the identity of X? A CH3CHO B C2H5COCH3 C CH3COOC2H5 D CH3CHOHCH3

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2024

Q308 · Which compound can undergo nucleophilic addition? 9701/12 Oct/Nov 2024

35 Which compound can undergo nucleophilic addition? A bromoethane, C2H5Br B ethanal, CH3CHO C ethane, C2H6 D ethene, C2H4

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2024

Q309 · Which statement about H2C=C(CH3)CH2CO2CH3 is correct? 9701/12 Oct/Nov 2024

38 Which statement about H2C=C(CH3)CH2CO2CH3 is correct? A It can be hydrolysed to a secondary alcohol. B It can be made using ethanoic acid and a suitable alcohol. C It gives a positive test with alkaline I2(aq). D When treated with hot concentrated acidified KMnO4 it gives CH3COCH2COOH as one product.

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2024

Q310 · Vitamin A contains retinol 9701/13 Oct/Nov 2024

29 Vitamin A contains retinol. retinol OH Under appropriate conditions, acidified KMnO4(aq) can be used to break C=C bonds. After these bonds have been broken, further oxidation of the fragments may occur. Under which conditions is the acidified KMnO4(aq) used and what do the final oxidation products include? conditions final oxidation products A cold, dilute aldehydes and carboxylic acids B cold, dilute ketones and carboxylic acids C hot, concentrated aldehydes and carboxylic acids D hot, concentrated ketones and carboxylic acids

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2024

Q311 · Compound Y reacts with alkaline I2(aq) 9701/13 Oct/Nov 2024

34 Compound Y reacts with alkaline I2(aq). When the products of this reaction are acidified, a dicarboxylic acid is produced. The formula of the dicarboxylic acid is HOOC–R–COOH where R consists of one or more CH2 groups. Which compound is Y? A pentan-1,4-diol B pentan-1,5-diol C pentan-2,3-diol D pentan-2,4-diol

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2024

Q312 · Which alcohol gives only one possible oxidation product when warmed with dilute acidified… 9701/13 Oct/Nov 2024

35 Which alcohol gives only one possible oxidation product when warmed with dilute acidified potassium dichromate(VI)? A butan-1-ol B butan-2-ol C 2-methylpropan-1-ol D 2-methylpropan-2-ol

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2024

Q313 · Which compound, on reaction with hydrogen cyanide, produces a compound with a chiral… 9701/13 Oct/Nov 2024

36 Which compound, on reaction with hydrogen cyanide, produces a compound with a chiral centre? A CH3CHO B CH3CH2COCH2CH3 C CH3CO2CH3 D HCHO

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2024

Q314 · The diagram shows three reactions of ethanal 9701/13 Oct/Nov 2024

37 The diagram shows three reactions of ethanal. In each case, an excess of ethanal is used. solid 2 alkaline I2(aq) heat acidified K2Cr2O7 ethanal Fehling’s solution solution 1 solid 3 heat CH3CHO boil Observations are made after each of the three reactions. What are the colours of solution 1 and solids 2 and 3? solution 1 solid 2 solid 3 A green yellow silver mirror B green yellow red C orange red silver mirror D orange red red

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2024

Q315 · Organic compound X has the empirical formula C2H4O 9701/12 Feb/March 2025

26 Organic compound X has the empirical formula C2H4O. Compound X is reduced by LiAl H4, but not by NaBH4. What is compound X? A ethanoic acid B ethanal C butan-1-ol D butanoic acid

1 marks

Answer: D

This question in 9701/12 Feb/March 2025

Q316 · Compound T is tested with three reagents and gives the results shown 9701/12 Feb/March 2025

30 Compound T is tested with three reagents and gives the results shown. reagent result 2,4-DNPH orange precipitate Fehling’s solution no reaction acidified K2Cr2O7 no reaction What is compound T? A (CH3)2CHCHO B (CH3)2CHCH2OH C CH3CH(OH)COCH3 D (CH3)2CHCOCH3

1 marks

Answer: D

This question in 9701/12 Feb/March 2025

Q317 · Complete combustion of compound T produces carbon dioxide and water only 9701/11 May/June 2025

26 Complete combustion of compound T produces carbon dioxide and water only. Compound T produces steamy fumes with PCl5. Compound T does not give any visible product with 2,4-dinitrophenylhydrazine reagent. What can be deduced with certainty from this information? A Compound T is a carboxylic acid. B Compound T is a hydrocarbon. C Compound T is an alcohol. D Compound T is not an aldehyde.

1 marks

Answer: D

This question in 9701/11 May/June 2025

Q318 · Information about carbonyl compound X is given 9701/11 May/June 2025

27 Information about carbonyl compound X is given. ● Compound X reacts with LiAlH4 to produce a secondary alcohol. ● Compound X reacts with alkaline I2(aq) to give a yellow precipitate. What is compound X? A butanal B butanone C ethanal D pentan-3-one

1 marks

Answer: B

This question in 9701/11 May/June 2025

Q319 · An alkene P reacts with an excess of hot concentrated acidified KMnO4(aq) 9701/11 May/June 2025

36 An alkene P reacts with an excess of hot concentrated acidified KMnO4(aq). Methylpropanoic acid is the only organic product. What is alkene P? A 2,5-dimethylhex-3-ene B 2-methylbut-2-ene C methylpropene D oct-4-ene, C8H16

1 marks

Answer: A

This question in 9701/11 May/June 2025

Q320 · Methanoic acid, HCO2H, has acidic properties similar to those of other carboxylic acids 9701/12 May/June 2025

27 Methanoic acid, HCO2H, has acidic properties similar to those of other carboxylic acids. In addition, it can be oxidised by the same oxidising agents that are capable of oxidising aldehydes. Which pair consists of two compounds that will give the same observations with Fehling’s reagent? A HCO2H and CH3CO2H B HCO2H and CH3CO2CH3 C HCO2H and CH3CH2COCH3 D HCO2H and CH3CH2CHO

1 marks

Answer: D

This question in 9701/12 May/June 2025

Q321 · Butan-2-one reacts with alkaline I2(aq) 9701/12 May/June 2025

31 Butan-2-one reacts with alkaline I2(aq). An excess of dilute sulfuric acid is then added to the reaction mixture. The organic products of this reaction sequence are triiodomethane and product M. What is product M? A ethanoate ion B ethanoic acid C propanoate ion D propanoic acid

1 marks

Answer: D

This question in 9701/12 May/June 2025

Q322 · What is formed when propanone is heated under reflux with a solution of NaBH4? 9701/13 May/June 2025

30 What is formed when propanone is heated under reflux with a solution of NaBH4? A propan-2-ol B propan-1-ol C propanal D propane

1 marks

Answer: A

This question in 9701/13 May/June 2025

Q323 · Compound P displays cis/trans isomerism and gives a red-brown precipitate with Fehling’s… 9701/13 May/June 2025

37 Compound P displays cis/trans isomerism and gives a red-brown precipitate with Fehling’s solution. What is P? C C H CH3 H CH2CHO A C C H CH3 H COCH3 B C C H CHO H CH3 C C C CHO CH3 H H D

1 marks

Answer: D

This question in 9701/13 May/June 2025

Q324 · An alcohol, U, is reacted with hot acidified K2Cr2O7 solution 9701/14 May/June 2025

26 An alcohol, U, is reacted with hot acidified K2Cr2O7 solution. The organic product of the reaction contains 58.8% C, 9.8% H and 31.4% O by mass. What is the identity of alcohol U? A 2-methylbutan-2-ol B 3-methylbutan-2-ol C pentan-1-ol D propan-1-ol

1 marks

Answer: C

This question in 9701/14 May/June 2025

Q325 · An alkene reacts with hot concentrated acidified KMnO4 to produce a single organic… 9701/14 May/June 2025

30 An alkene reacts with hot concentrated acidified KMnO4 to produce a single organic product as shown. hot concentrated O O acidified KMnO4(aq) alkene OH What is the structure of the alkene? A B C D

1 marks

Answer: D

This question in 9701/14 May/June 2025

Q326 · Acidified potassium dichromate(VI), K2Cr2O7, is added to propan-1-ol and the mixture is… 9701/14 May/June 2025

34 Acidified potassium dichromate(VI), K2Cr2O7, is added to propan-1-ol and the mixture is immediately distilled. The distillate is treated with HCN in the presence of KCN. What is the organic product? A CH3C(CN)(OH)CH3 B CH3CH2CH2CO2H C CH3CH2CH(OH)CN D CH3CH2CH2CN

1 marks

Answer: C

This question in 9701/14 May/June 2025

Q327 · Compound Q gives positive results when tested separately with alkaline I2(aq) and with… 9701/14 May/June 2025

35 Compound Q gives positive results when tested separately with alkaline I2(aq) and with Tollens’ reagent. What is compound Q? A CHOCH2CH2CHO B CH3CH2COCHO C CH3COCH2CHO D CH3COCOCH3

1 marks

Answer: C

This question in 9701/14 May/June 2025

Q328 · The balanced equation for the reaction of X with an excess of acidified K2Cr2O7 is shown 9701/11 Oct/Nov 2025

33 The balanced equation for the reaction of X with an excess of acidified K2Cr2O7 is shown. X + 3[O]  Y + H2O Compound Y is the only organic product of the reaction. Which compound is X? HO C H H C H A OH C OH H H HO C H H C H B H2C C OH OH H H O C H C H C CH CH3 C O H O O HO C H C H D C C O H H

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2025

Q329 · Compound Q reacts when heated with HCN in the presence of a catalyst to produce compound R 9701/11 Oct/Nov 2025

36 Compound Q reacts when heated with HCN in the presence of a catalyst to produce compound R. Molecules of compound R each contain four carbon atoms. What is compound Q? O B O OH A O H D Cl C

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2025

Q330 · Seven aldehydes and ketones ● contain only one oxygen atom per molecule ● have four or… 9701/11 Oct/Nov 2025

38 Seven aldehydes and ketones ● contain only one oxygen atom per molecule ● have four or fewer carbon atoms in their structures. Alkaline I2(aq) is added to each of these carbonyl compounds separately. How many of these carbonyl compounds produce a yellow precipitate with alkaline I2(aq)? A 1 B 2 C 3 D 4

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2025

Q331 · An organometallic lithium compound, RLi, contains the nucleophile R– 9701/12 Oct/Nov 2025

34 An organometallic lithium compound, RLi, contains the nucleophile R–. CH3CH2Li reacts with pentan-2-one. The mechanism is nucleophilic addition. The first step produces an anion which is then protonated to form the final product. Which organic product is formed? A B C D OH OH OH OH

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2025

Q332 · The structure of a naturally occurring compound, Q, is shown 9701/12 Oct/Nov 2025

35 The structure of a naturally occurring compound, Q, is shown. compound Q O O OH HO O Compound Q is heated under reflux with an excess of acidified KMnO4. Organic product R is formed. Which row is correct? results of tests with compound Q results of tests with organic product R A orange precipitate with 2,4-DNPH yellow precipitate with alkaline I2(aq) and no reaction with alkaline I2(aq) and no reaction with Fehling’s reagent B red precipitate with Fehling’s reagent orange precipitate with 2,4-DNPH and no reaction with alkaline I2(aq) and no reaction with alkaline I2(aq) C yellow precipitate with alkaline I2(aq) no reaction with alkaline I2(aq) and orange precipitate with 2,4-DNPH and no reaction with Fehling’s reagent D yellow precipitate with alkaline I2(aq) yellow precipitate with alkaline I2(aq) and red precipitate with Fehling’s reagent and orange precipitate with 2,4-DNPH

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2025

Q333 · The skeletal formulas of two compounds are shown 9701/13 Oct/Nov 2025

26 The skeletal formulas of two compounds are shown. progesterone O O testosterone OH O Which statements about progesterone and testosterone are correct? A They both contain a ketone group, and they both have geometrical isomers due to the C=C bond. B They have the same molecular formula, and they both have geometrical isomers. C They have the same number of chiral carbons, and they have the same molecular formula. D They have the same number of chiral carbons, and they both contain a ketone group.

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2025

Q334 · The balanced equation for the reaction of X with an excess of acidified K2Cr2O7 is shown 9701/13 Oct/Nov 2025

33 The balanced equation for the reaction of X with an excess of acidified K2Cr2O7 is shown. X + 3[O]  Y + H2O Compound Y is the only organic product of the reaction. Which compound is X? HO C H H C H A OH C OH H H HO C H H C H B H2C C OH OH H H O C H C H C CH CH3 C O H O O HO C H C H D C C O H H

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2025

Q335 · Compound Q reacts when heated with HCN in the presence of a catalyst to produce compound R 9701/13 Oct/Nov 2025

36 Compound Q reacts when heated with HCN in the presence of a catalyst to produce compound R. Molecules of compound R each contain four carbon atoms. What is compound Q? O B O OH A O H D Cl C

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2025

Q336 · Seven aldehydes and ketones ● contain only one oxygen atom per molecule ● have four or… 9701/13 Oct/Nov 2025

38 Seven aldehydes and ketones ● contain only one oxygen atom per molecule ● have four or fewer carbon atoms in their structures. Alkaline I2(aq) is added to each of these carbonyl compounds separately. How many of these carbonyl compounds produce a yellow precipitate with alkaline I2(aq)? A 1 B 2 C 3 D 4

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2025