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Topical›Chemistry 9701›Hydrocarbons›Alkenes›Paper 1

Alkenes — Paper 1 · A Level Chemistry 9701

14.2· 272 questions · 272 marks · 326 min · 2005–2025· Multiple choice

Every Cambridge A Level Chemistry Paper 1 question on alkenes, laid out as 77 A4 pages with the mark scheme below. Nothing is left out. Free to read, no account.

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Question 1: Which hydrocarbon, on treatment with hot acidified potassium manganate(VII), would give ethanoic acid only? A CH3CH CH2 B CH3CH CHCH3 CH3 C…Question 2: The sex-attractant of the house-fly is muscalure, with the following formula. CH3(CH2)7CH = CH(CH2)12CH3 Which statements about muscalure a…Question 3: The structures below show isomers of C6H12. 1 2 3 4 CH3 CH3 CH3 C2H5 C2H5 H C2H5 CH3 C C C C C C C C H C2H5 H CH3 CH3 CH3 H CH3 In which pa…Question 4: Which reagent could detect the presence of alcohol in a petrol consisting mainly of a mixture of alkanes and alkenes? A Na B Br2 (in CCl4) …1 / 77
Question 5: Deuterium, D, is the H 2 isotope of hydrogen. DBr has the same chemical properties as HBr. 1 Which compounds could be made by the reaction …Question 6: Which alkene could exist in cis and trans forms? A CH3CH2CH2CH CH2 B CH3CH2CH CHCH3 C CH3CH2C CH2 CH3 D CH3CH CCH3 CH3Question 7: The following three hydrocarbons all occur naturally. Which of these will be split into two organic compounds, both containing a ketone gro…Question 8: Which compounds are able to react with concentrated sulphuric acid to give a product that will decolourise acidic potassium manganate(VII)?…2 / 77
Question 9: Limonene is an oil formed in the peel of citrus fruits. CH3 CH2 C CH3 limonene Which product is formed when molecular bromine reacts with l…Question 10: Which pair of reaction types is illustrated by the reaction sequence below? HI in CH3CO2H NaOH(aq) CH3CH=CHCH3 CH3CH2CHICH3 CH3CH2CH(OH)CH3…Question 11: Trichloroethene is widely used as a dry-cleaning agent. H Cl \ 4 C=C Ve C Cl With which of the following does trichloroethene react to give…3 / 77
Question 12: Compound X • has the molecular formula C10H14O; • is unreactive towards mild oxidising agents. What is the structure of the compound formed…Question 13: Ferulic acid is an antioxidant that occurs widely in plants. HO CH=CHCO2H CH3O ferulic acid Which reagents can react with the –CH=CHCO2H pa…Question 14: The compound ‘leaf alcohol’ is partly responsible for the smell of new-mown grass. CH3CH2CH=CHCH2CH2OH leaf alcohol Which two compounds wil…Question 15: Which hydrocarbon can form a monochloro-substitution derivative which shows both chirality and cis-trans isomerism? A CH3CH=CH2 B (CH3)2C=C…4 / 77
Question 16: Which statements about alkenes are correct? 1 They are formed when higher alkanes are cracked. 2 They are used as monomers for polymerisati…Question 17: In which reaction does the carbon-containing product have a smaller bond angle than the organic reactant? A bromoethane refluxed with ethan…Question 18: Carvone gives the characteristic flavour to caraway and spearmint. O CH3 H3C C CH2 carvone Prolonged heating of carvone with hot concentrat…Question 19: A fraction of distilled crude oil contains molecules with between 15 and 19 carbon atoms. This fraction is cracked by strong heating. Why i…5 / 77
Question 20: Geraniol is one of several compounds produced by the scent glands of honey bees to help them mark nectar-bearing flowers and locate the ent…Question 21: The presence of 11-cis retinal, C20H28O, in cells in the eye is important for vision. The structure of retinal includes an aldehyde group, …6 / 77
Question 22: Sorbic acid is used as a food preservative because it kills fungi and moulds. H H O C C C H3C C C OH H H sorbic acid Sorbic acid will react…Question 23: Bromine reacts with ethene to form 1,2-dibromoethane. What is the correct description of the organic intermediate in this reaction? A It ha…Question 24: Which compound exhibits both cis-trans and optical isomerism? A CH3CH=CHCH2CH3 B CH3CHBrCH=CH2 C CH3CBr=CBrCH3 D CH3CH2CHBrCH=CHBrQuestion 25: Which isomer of C4H10O forms three alkenes on dehydration? A butan-1-ol B butan-2-ol C 2-methylpropan-1-ol D 2-methylpropan-2-ol7 / 77
Question 26: Limonene is an oil formed in the peel of citrus fruits. CH3 CH2 C CH3 limonene Which product is formed when an excess of bromine, Br2(l), r…Question 27: The compound 2-methylpropene, C4H8, is a monomer used in the production of synthetic rubber. H CH3 C C H CH3 In addition to 2-methylpropene…Question 28: An organic compound decolourises aqueous bromine and reacts with sodium to produce hydrogen. Which molecular formula could represent this c…Question 29: Nine compounds have molecular formula C4H8Br2. Which compound may be synthesised from an alkene by an addition reaction? A 1,1-dibromobutan…8 / 77
Question 30: Part of the structure of strobilurin, a fungicide, is shown. R and R' are inert groups. O OCH3 R' R If strobilurin is first warmed with aqu…Question 31: Fluoroalkenes are used to make polymers such as poly(vinyl)fluoride (PVF). PVF is used to make non-flammable interiors for aircraft. The di…Question 32: One of the characteristics of addition polymerisation is that the empirical formulae of the polymer and of its monomer are the same. The ab…9 / 77
Question 33: Limonene is an oil formed in the peel of citrus fruits. CH3 CH2 C CH3 limonene Which product is formed when an excess of bromine, Br2(l), r…Question 34: The compound 2-methylpropene, C4H8, is a monomer used in the production of synthetic rubber. H CH3 C C H CH3 In addition to 2-methylpropene…Question 35: An organic compound decolourises aqueous bromine and reacts with sodium to produce hydrogen. Which molecular formula could represent this c…10 / 77
Question 36: In the reaction pathway below, an alkane is converted into a carboxylic acid through several stages. stage 1 stage 2 stage 3 C10H22 C2H4 C2…Question 37: 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 38: Which alkenes, on reaction with steam at 600 K and 6 x 106 Pa pressure in the presence of a phosphoric acid catalyst, could produce an alco…Question 39: The products obtained by cracking an alkane, X, are methane, ethene and propene. The mole fraction of ethene in the products is 0.5. What i…Question 40: Which compound does not show cis-trans isomerism? A 2-methylpent-2-ene B 3-methylpent-2-ene C 3,4-dimethylhex-3-ene D pent-2-ene11 / 77
Question 41: Which compounds can be obtained from ethene in a single reaction? 1 CH3CH3 2 ( CH2CH2 )n 3 HOCH2CH2OHQuestion 42: 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 43: Which isomer of C6H13OH gives the greatest number of different alkenes when it is dehydrated? A B CH3 CH3 CH CH CH2OH CH3 CH2 CH2 CH CH2 CH…Question 44: Which alkenes, on reaction with steam at 600 K and 6 x 106 Pa pressure in the presence of a phosphoric acid catalyst, could produce an alco…12 / 77
Question 45: This question should be answered by considering the reactions of KMnO4 with different functional groups under the stated conditions. The di…Question 46: Energy is released in the human body by the oxidation of glucose in a complex sequence of reactions. Part of this sequence is the Krebs cyc…13 / 77
Question 47: Geraniol is a constituent of some perfumes. OH geraniol Which statement about geraniol is not correct? A Geraniol causes hot acidified pota…Question 48: Bromine and propene undergo an addition reaction. Which is a property of the product? A It exists in cis-trans isomers. B It is more volati…Question 49: Which reagent could best be used to distinguish between cyclohexene and cyclohexanol? A Ag(NH3)2 + in H2O B Br2 in CCl 4 C 2,4-dinitropheny…Question 50: Compound X, molecular formula C4H8, undergoes the following reactions. Br2 aq.NaOH / heat C4H8 C4H8Br2 C4H10O2 X Y Z H2 / Ni C4H8 methylpro…Question 51: How many of the isomeric alcohols with the formula C4H9OH will produce an alkene that has cis and trans isomers, on treatment with conc. H2…14 / 77
Question 52: This question should be answered by considering the reactions of KMnO4 with different functional groups under the stated conditions. The di…Question 53: An unpleasant smelling chemical produced in the human armpit is 3-methylhex-2-enoic acid. CH3 CH3 CH2 CH2 C CH C OH O If this compound is r…15 / 77
Question 54: Energy is released in the human body by the oxidation of glucose in a complex sequence of reactions. Part of this sequence is the Krebs cyc…Question 55: Geraniol is a constituent of some perfumes. OH geraniol Which statement about geraniol is not correct? A Geraniol causes hot acidified pota…Question 56: Two conversions are outlined below. NH4 + → NH3 C2H4 → C2H6 What similar feature do these two conversions have? A a lone pair of electrons …16 / 77
Question 57: Isomers X and Y both react with HBr. H3C Br Br Br C C C C H3C Br H3C CH3 X Y A mixture of X and Y is reacted with HBr. Which three structur…Question 58: Oct-1-ene, CH3(CH2)5CH=CH2, is subjected to thermal cracking. Which combination of compounds W, X, Y and Z can be obtained? CH2=CH2 CH3CH=C…Question 59: An organic compound will decolorise dilute acidified aqueous potassium manganate(VII) on warming, but will not decolorise bromine water. Wh…Question 60: Which compounds can be obtained from propene in a single reaction? 1 CH2OHCHOHCH3 2 ( CH2CH(CH3) ) n 3 CH2BrCH2CH2BrQuestion 61: An alkene has the formula CH3CH=CR CH2CH3 and does not possess cis-trans isomers. What is R ? A H B Cl C CH3 D C2H517 / 77
Question 62: 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 63: Oleic acid is found in olive oil. It has the following formula. H H C C O CH3(CH2)7 (CH2)7 C OH Which reagents will give a positive result …Question 64: An alkene has the formula CH3CH=CR CH2CH3 and does not possess cis-trans isomers. What is R ? A H B Cl C CH3 D C2H5Question 65: 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…18 / 77
Question 66: Oleic acid is found in olive oil. It has the following formula. H H C C O CH3(CH2)7 (CH2)7 C OH Which reagents will give a positive result …Question 67: A molecule of a polymer contained the sequence shown. H H H H H Cl H H H Cl H H C C C C C C C C C C C C H Cl Cl H H H Cl H H H H Cl Which m…Question 68: Bromine reacts with ethene to form 1,2-dibromoethane. What is the correct description of the organic intermediate in this reaction? A It ha…19 / 77
Question 69: Synthetic resins, plasticisers and many other chemicals can be made by polymerisation of a variety of monomers including prop-2-en-1-ol, CH…Question 70: The compound hex-3-en-1-ol, P, has a strong ‘leafy’ smell of newly cut grass and is used in perfumery. CH3CH2CH=CHCH2CH2OH P What is produc…Question 71: Sorbic acid is used as a food preservative because it kills fungi and moulds. H H O C C C H3C C C OH H H sorbic acid Sorbic acid will react…20 / 77
Question 72: The compound shown is menthol, a naturally-occurring alcohol found in peppermint oil. OH menthol When menthol is heated with concentrated s…Question 73: Ethene reacts with steam in the presence of sulfuric acid. C2H4 + H2O → CH3CH2OH What type of reaction is this? A acid / base B additio…Question 74: How many isomers, including structural and stereoisomers, with the formula C4H8 have structures that involve π bonding? A 1 B 2 C 3 D 4Question 75: 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…21 / 77
Question 76: 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…Question 77: Many organic reactions need to be heated before reaction occurs, but some do not require heating. Which reaction occurs quickly at room tem…Question 78: How many moles of oxygen molecules are needed for the complete combustion of one mole of 3-methylpent-2-ene? A 9 B 9 2 1 C 18 D 19Question 79: How many geometrical (cis-trans) isomers are there of hex-2,4-diene, CH3CH=CHCH=CHCH3? A none; hex-2,4-diene does not show geometric isomer…Question 80: Which pairs of reagents will take part in a redox reaction? 1 CH3COCH3 + Tollens’ reagent 2 CH3CH2CHO + Fehling’s reagent 3 CH3CH=CH2 …Question 81: Ethene reacts with aqueous bromine to give two products, CH2BrCH2Br and CH2BrCH2OH. Which statement about these products is correct? A Both…22 / 77
Question 82: Most alcohols can be dehydrated to give alkenes. Which alcohol can be dehydrated to give three different isomeric alkenes? A CH3(CH2)3CH2OH…Question 83: 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 84: The naturally-occurring molecule shown below can be made by the addition of four identical monomer molecules. H H3C C C CH2 CH2 CH2 CH3 H2C…23 / 77
Question 85: Which row correctly describes the reaction between propene and bromine, Br2(l)? reaction mechanism organic product A electrophilic addition…Question 86: Use of the Data Booklet is relevant to this question. Which compound has an Mr of 84 and will react with HBr to give a product with an Mr o…Question 87: For which mixtures of reagents are the colour changes described correctly? reagents colour change 1 pentanal + hot, acidified potassium dic…Question 88: Which row correctly describes the reaction between propene and bromine, Br2(l)? reaction mechanism organic product A electrophilic addition…Question 89: Use of the Data Booklet is relevant to this question. Which compound has an Mr of 84 and will react with HBr to give a product with an Mr o…24 / 77
Question 90: Methyl methylpropenoate is the monomer used to make Perspex. Which diagram correctly shows methyl methylpropenoate? A B CH3 CH2 C CH3 CH CH…Question 91: 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 92: The compound known as ‘gamma-linolenic acid’ is found in the seeds of the evening primrose plant. CH3(CH2)4CH=CHCH2CH=CHCH2CH=CH(CH2)4CO2H …25 / 77
Question 93: The diagram shows the structure of the naturally-occurring molecule cholesterol. H3C CH3 H CH3 H H H HO cholesterol Student X stated that t…Question 94: Cottonseed oil contains large amounts of polyunsaturated carboxylic acids. When this oil is used to make margarine, the C=C double bonds in…Question 95: Which intermediate ion forms in the greatest amount during the addition of HBr to propene? A CH3CH+CH3 B CH3CH2CH2 + C CH3CH–CH2Br D CH3CHB…26 / 77
Question 96: The citrus flavour of lemons is due to the compound limonene, present in both the peel and the juice. limonene What is the mole ratio of ca…Question 97: The diagram shows the structure of an alkene molecule. CH3 CH3 CH3 C C H C C H H H CH3 Which statements about this molecule are correct? 1 …Question 98: Which compounds will react with HBr to give the compound R? Br R 1 2 3 OH27 / 77
Question 99: Four students, W, X, Y and Z, made the following statements about alkanes and alkenes. W ‘Bromine reacts with alkanes by electrophilic subs…Question 100: In which structures do the four carbon atoms labelled C lie in the same plane? 1 2 3 C C C C C C C C C C C CQuestion 101: Calcium forms an ionic compound with carbon, called calcium carbide. The oxidation number of carbon in calcium carbide is –1. Calcium carbi…Question 102: Which compounds, on heating with excess concentrated sulfuric acid, produce only one product with molecular formula C7H10? 1 2 3 OH OH OH O…Question 103: Compound Z is heated with concentrated acidified potassium manganate(VII). This produces an equimolar mixture of CO2 and CH3COCH2CH2CH(COCH…28 / 77
Question 104: Geraniol and nerol are compounds found in some flower fragrances. They are isomers of each other. CH3 CH3 C CH2OH C H H2C C H2C C H CH2OH H…Question 105: A section showing two repeat units of an addition polymer is shown. CH3 CH3 CH3 CH3 C C C C Cl CH3 Cl CH3 What is the identity of the monom…29 / 77
Question 106: Hydrogen bromide can be added to T to give compound U. Compound U can be hydrolysed to compound V. step 1 step 2 Br OH T U V Four students,…Question 107: Structural isomerism and stereoisomerism should be considered in answering this question. Compound J is reacted with KOH dissolved in ethan…Question 108: Which pair of reagents will take part in a redox reaction? A CH3CHCH2 + Br2 B CH3CH2CH2OH + concentrated H3PO4 C CH3COCH3 + HCN D HCO…30 / 77
Question 109: The diagram shows the structure of cyclohexene. cyclohexene Which structures could be formed by addition reactions with cyclohexene as the …Question 110: Oct-1-ene, CH3(CH2)5CH=CH2, can be thermally cracked. Which combination of compounds W, X, Y and Z can be obtained by thermally cracking oc…Question 111: A cycloalkene with the molecular formula C7H12 was oxidised by hot concentrated acidified MnO4 –. The only organic product was 2-methylhexa…31 / 77
Question 112: The diagram shows the structure of 1,3-butadiene. H H C C H H C C H H 1,3-butadiene The addition reaction between 1,3-butadiene and two mol…Question 113: Vitamin A contains retinol. OH retinol Under appropriate conditions, acidified KMnO4(aq) can be used to break apart C=C bonds. After these …32 / 77
Question 114: Part of the structure of a fungicide, strobilurin, is shown. R and R' are inert groups. O OCH3 R' R strobilurin In this reaction, strobilur…Question 115: X, Y and Z are three isomeric alcohols. X CH3CH2CH2CH2CH2OH Y CH3CH2CH(OH)CH2CH3 Z (CH3)2C(OH)CH2CH3 Two or more of these alcohols react wi…33 / 77
Question 116: Which compounds would produce a carboxylic acid and a ketone when treated with hot, concentrated, acidified KMnO4? 1 2 3Question 117: X, Y and Z are three isomeric alcohols. X CH3CH2CH2CH2CH2OH Y CH3CH2CH(OH)CH2CH3 Z (CH3)2C(OH)CH2CH3 Two or more of these alcohols react wi…Question 118: Which compounds would produce a carboxylic acid and a ketone when treated with hot, concentrated, acidified KMnO4? 1 2 3Question 119: Which equation correctly describes the complete combustion of an alkene, CnH2n? A CnH2n + 2 3 nO2 → nCO2 + 2nH2O B CnH2n + 2 3 nO2 …34 / 77
Question 120: The formulae of three compounds are shown. C3H7CHO C2H5COCH3 CH2CHCH2CH2OH Only one of these compounds will decolourise…Question 121: Bromine reacts with ethene in the dark. Which description of the organic intermediate in this reaction is correct? A It has a negative char…Question 122: Many, but not all, organic reactions need to be heated before a reaction occurs. Which reaction occurs quickly at room temperature, 20 °C? …Question 123: Which compound would produce two different carboxylic acids when treated with hot, concentrated, acidified manganate(VII) ions? A B C D35 / 77
Question 124: 2,3-dimethylpent-2-ene, (CH3)2C=C(CH3)CH2CH3, is treated with cold, dilute KMnO4. The product of this reaction is treated with an excess of…Question 125: Many, but not all, organic reactions need to be heated before a reaction occurs. Which reaction occurs quickly at room temperature, 20 °C? …Question 126: Which types of stereoisomerism are shown by 2,4-dimethylhex-2-ene? A both cis-trans isomerism and optical isomerism B cis-trans isomerism o…Question 127: A reaction occurs when a sample of 1-chloropropane is heated under reflux with sodium hydroxide dissolved in ethanol. Which row is correct?…Question 128: Which reagent could detect the presence of alcohol in a mixture consisting mainly of alkanes and alkenes? A Na B Br2 (in CCl 4) C KMnO4(aq)…36 / 77
Question 129: Limonene is found in lemons. limonene Limonene is heated with concentrated acidified potassium manganate(VII). Which compounds are produced…Question 130: Compound Y is treated with an excess of hydrogen gas in the presence of a nickel catalyst. The product is fully saturated. compound Y What …Question 131: Maleic acid is used in the food industry and for stabilising drugs. It is the cis-isomer of butenedioic acid and has the structural formula…Question 132: Which compounds show geometrical (cis-trans) isomerism? 1 CH3CH=C(CH3)C2H5 2 CH3CH=CHCH2CH2CH3 3 C2H5CH=CHC2H537 / 77
Question 133: Sibirene, C15H24, is reacted with an excess of HBr(g). The major product is X. excess HBr(g) X sibirene What is the skeletal formula of X? …Question 134: Which compound is a secondary alcohol that can be dehydrated to form an alkene with Mr = 70? A B C D OH OH OH OHQuestion 135: Complete combustion of a sample of a hydrocarbon gave 0.132 g of carbon dioxide and 0.054 g of water. Which formulae could correctly repres…Question 136: Acrolein is an organic compound with the molecular formula C3H4O. It is used in water treatment and as a herbicide. When acrolein reacts wi…38 / 77
Question 137: A new jet fuel has been produced that is a mixture of different structural isomers of compound Q. Q Which skeletal formula represents a str…Question 138: The conversion of propene to propan-2-ol can be carried out in two stages represented by the equations shown. reaction 1 CH3CH=CH2(g) + H…39 / 77
Question 139: Compound J, C15H23Br2Cl, is reacted with an excess of a hot concentrated solution of sodium hydroxide in ethanol. One of the products is X.…Question 140: 2-methylpropene can react in more than one way with chlorine. One of the reactions follows the pathway shown. CH3 CH3 CH3 + CH2 C + Cl 2 → …Question 141: Polyethene is made by the polymerisation of ethene. Which statement is correct? A The monomer and the polymer have different empirical form…40 / 77
Question 142: Which statement about compound Q is correct? CH3C CHCH2CH3 CO2CH3 Q H CH3 A It could be polymerised to give a polymer with the repeat unit …Question 143: Which bromopropenes would react with cold bromine in the dark to form a product containing a chiral carbon atom? 1 CHBr=CHCH3 2 CH2=CHCH2Br…41 / 77
Question 144: A new jet fuel has been produced that is a mixture of different structural isomers of compound Q. Q Which skeletal formula represents a str…Question 145: Compound J, C15H23Br2Cl, is reacted with an excess of a hot concentrated solution of sodium hydroxide in ethanol. One of the products is X.…42 / 77
Question 146: 2-methylpropene can react in more than one way with chlorine. One of the reactions follows the pathway shown. CH3 CH3 CH3 + CH2 C + Cl 2 → …Question 147: Compound L has the molecular formula C10H16. A sample of L reacted with an excess of hot, concentrated, acidified potassium manganate(VII).…Question 148: What is the structural formula of the major product when hydrogen bromide reacts with 2-methylbut-2-ene? A CH2BrCH(CH3)CH2CH3 B (CH3)2CBrCH…43 / 77
Question 149: 3-methylbut-1-ene can undergo different types of reaction. Cl 1 2 Cl Which row correctly identifies the reaction types? reaction 1 reaction…Question 150: Compound X does not show cis-trans isomerism. What could be the identity of compound X? A 1,1,2-trichloropropene B 1,2,3-trichloropropene C…Question 151: A molecule of geraniol is shown. geraniol OH What is formed when geraniol is reacted with an excess of cold, dilute, acidified manganate(VI…44 / 77
Question 152: Which product can be made from bromoethane by an elimination reaction? A ethanol B ethene C ethylamine D propanenitrileQuestion 153: Propene, bromine and hydrogen bromide are mixed in the dark. A number of products are formed, some in very small quantities. Which substanc…Question 154: In polymer Z every carbon atom in the polymer chain is bonded to one hydrogen atom and one methyl group. Which alkene could be polymerised …Question 155: Which compound would produce a carboxylic acid and a ketone when treated with hot, concentrated acidified manganate(VII) ions? A B C DQuestion 156: Bromine reacts with ethene in an addition reaction. Which statements about this reaction are correct? 1 It is the basis of a test for unsat…Question 157: Which substance reacts with trichloroethene to give a chiral product? A Br2 B HCl C NaCN D NaOH45 / 77
Question 158: An alkene reacts with hot, concentrated, acidified potassium manganate(VII) to produce a single organic product as shown. hot, concentrated…Question 159: Structural isomerism and stereoisomerism should be considered when answering this question. How many isomers with the formula C5H10 have st…Question 160: An organic compound X reacts with hot, concentrated acidified potassium manganate(VII) solution to give a single carbon-containing product.…Question 161: Following fractional distillation of crude oil, which processes can be used to produce propene from larger hydrocarbon molecules? 1 crackin…Question 162: Which substance reacts with trichloroethene to give a chiral product? A Br2 B HCl C NaCN D NaOH46 / 77
Question 163: An alkene reacts with hot, concentrated, acidified potassium manganate(VII) to produce a single organic product as shown. hot, concentrated…Question 164: A section of a polymer chain is shown. What is the correct monomer? A B C DQuestion 165: Which statements comparing ethene and ethane are correct? 1 The bond angles in ethene are larger than the bond angles in ethane. 2 Ethene r…47 / 77
Question 166: But-1-ene and but-2-ene are treated separately with cold, dilute acidified manganate(VII) ions. Four students, W, X, Y and Z, make statemen…Question 167: What is the major product Z of the following reaction? an excess of dry HBr Z warm A B C D Br Br Br Br Br Br Br BrQuestion 168: Which substance forms propanoic acid as one of the products when it reacts with hot concentrated acidified potassium manganate(VII)? A but-…Question 169: Ethene reacts with aqueous bromine to give two products, CH2BrCH2Br and CH2BrCH2OH. Which statement about these products is correct? A Both…48 / 77
Question 170: The diagram shows the structure of buta-1,3-diene. buta-1,3-diene H H C C H H C C H H The addition reaction between buta-1,3-diene and two …Question 171: Structural and stereoisomerism should be considered when answering this question. When trans-pent-2-ene reacts with HBr, how many different…Question 172: 2-methylbut-2-ene reacts with HBr(g) to form two isomeric products. During the reaction two positively charged intermediates can be made. W…Question 173: Two students each make a statement about 2-methylbut-1-ene. Student 1 states that 2-methylbut-1-ene has geometrical isomers. Student 2 stat…Question 174: The unsaturated hydrocarbon octa-1,3,5,7-tetraene, C8H10, can display geometric isomerism. octa-1,3,5,7-tetraene CH2=CHCH=CHCH=CHCH=CH2 How…49 / 77
Question 175: A polymer has the following repeat unit. It is made from two different monomers. CH2 CHCl CH2 CH CH CH2 Which pair of monomers could be use…Question 176: Two students each make a statement about 2-methylbut-1-ene. Student 1 states that 2-methylbut-1-ene has geometrical isomers. Student 2 stat…Question 177: The diagram shows the structure of a bromo compound that may be formed by the reaction of bromine with a hydrocarbon. CH2Br H3C C CH3 CH2Br…50 / 77
Question 178: Part of the structure of strobilurin is shown. R and R' are inert groups. strobilurin O OCH3 R' R Strobilurin is warmed with aqueous sulfur…Question 179: Dibromopentanes can undergo ‘double elimination’ reactions to produce hydrocarbons. 2NaOH + C5H10Br2  C5H8 + 2NaBr + 2H2O Which is…Question 180: Which compound would produce two different carboxylic acids when treated with hot, concentrated, acidified manganate(VII) ions? A B C D51 / 77
Question 181: Limonene is a hydrocarbon found in the rind of citrus fruits. limonene What is the molecular formula of limonene? A C10H12 B C10H14 C C10H1…Question 182: The table describes four reactions of propene. Which row is correct? name of main reagent used organic product A aqueous bromine 2-bromopro…Question 183: Which reactions have a coloured organic product? 1 ethanal + 2,4-dinitrophenylhydrazine reagent 2 ethanol + acidified potassium dichrom…Question 184: Compound P is treated with an excess of hydrogen gas in the presence of a nickel catalyst. The product Q is fully saturated. compound P Wha…Question 185: Compound X is a straight chain hydrocarbon with an Mr of 84. What can be determined about X? 1 empirical formula 2 molecular formula 3 whet…52 / 77
Question 186: Two carbon-containing products result from the reaction of alkene Z with a hot, concentrated, acidified solution of potassium manganate(VII…Question 187: What is the correct mechanism for the addition of hydrogen bromide to ethene? H H H 4H H 4H \_ / |_| |_| C=C H—C—C* —»> H—C—C—Br /¢ \ | [N…53 / 77
Question 188: Structural isomerism only should be considered when answering this question. Molecule X contains three C=C double bonds. One mole of X is r…Question 189: A diketo acid is a compound with two ketone groups and one carboxylic acid group. limonene terpinolene Which statements about the reactions…Question 190: One molecule of dodecane, C12H26, is cracked, producing three product molecules, X, Y and Z. X is a straight chain alkane. Y and Z are stra…Question 191: Structural and stereoisomerism should be taken into account when answering this question. Y is a gaseous hydrocarbon which decolourises aqu…54 / 77
Question 192: Structural and stereoisomerism should be taken into account when answering this question. An organic compound, X, is dehydrated by heating …Question 193: Which of the molecular formulae represent at least one compound that can undergo addition polymerisation? 1 C4H8 2 C2H3Cl 3 C3H6OQuestion 194: Hex-2-ene can be made by the reaction shown. O– HO H + I– I Which statement about this reaction is correct? A (CH3)3CO– is behaving as a Br…Question 195: Structural isomerism only should be considered when answering this question. Molecule X contains three C=C double bonds. One mole of X is r…55 / 77
Question 196: A diketo acid is a compound with two ketone groups and one carboxylic acid group. limonene terpinolene Which statements about the reactions…Question 197: One molecule of dodecane, C12H26, is cracked, producing three product molecules, X, Y and Z. X is a straight chain alkane. Y and Z are stra…Question 198: Oct-1-ene, CH3(CH2)5CH=CH2, can be thermally cracked. Which of the compounds W, X, Y and Z can be obtained by thermally cracking oct-1-ene?…56 / 77
Question 199: Crotyl alcohol, CH3CH=CHCH2OH, is a colourless liquid which is used as a solvent. Crotyl alcohol will react separately with Br2, K2Cr2O7 / …Question 200: The alkene shown reacts with an excess of HBr via an electrophilic addition reaction. What is the major product formed? A 3,5-dibromo-2-met…Question 201: Cyclohexene, as shown in the diagram, can form an addition polymer. cyclohexene Which structure represents a section of the polymer? A B C D57 / 77
Question 202: Structural isomerism and stereoisomerism should be considered when answering this question. Y is a gaseous hydrocarbon which decolourises a…Question 203: Mixture R consists of one mole of C3H6 and one mole of C4H6. What is the minimum number of moles of oxygen molecules needed for complete co…Question 204: Which pair of reagents react together in a redox reaction? A CH3CHCH2 + Br2 B CH3CH2CH2OH + concentrated H3PO4 C CH3COCH3 + HCN D HCO…Question 205: 2-bromopropane reacts with hot ethanolic sodium hydroxide. Which substance is the major product of this reaction? A propan-1-ol B propan-2-…Question 206: Photochemical smog is a type of air pollution produced in urban areas by the effect of sunlight on substances released from vehicle exhaust…58 / 77
Question 207: What is the major product formed when compound R is warmed with an excess of HBr? R OH OH A B C D Br Br OH Br OH Br Br Br OH Br Br BrQuestion 208: cis-but-2-ene reacts with cold dilute acidified potassium manganate(VII) solution to give product X. cis-but-2-ene reacts with hot concentr…Question 209: For which reaction will the major organic product have the lowest relative molecular mass? A Bromoethane is heated under reflux with an aqu…Question 210: Which pair of reagents react together in a redox reaction? A CH3CHCH2 + Br2 B CH3CH2CH2OH + concentrated H3PO4 C CH3COCH3 + HCN D HCO…59 / 77
Question 211: 2-bromopropane reacts with hot ethanolic sodium hydroxide. Which substance is the major product of this reaction? A propan-1-ol B propan-2-…Question 212: Cyclohexene, C6H10, is a hydrocarbon with a six-membered ring of carbon atoms. It has several structural isomers that are straight-chain al…Question 213: Cyclohexa-1,4-diene is treated with a solution of bromine in tetrachloromethane in the dark. cyclohexa-1,4-diene Which product is formed? A…Question 214: 2-methylbut-2-ene is reacted with hot, concentrated, acidified potassium manganate(VII) solution. What are the products of this reaction? A…60 / 77
Question 215: Structural isomerism and stereoisomerism should be considered when answering this question. 2-bromopentane is heated with an excess of etha…Question 216: When 1-methylcyclohexene reacts with Br, the product is X. When 1-methylcyclohexene reacts with HBr the major product is Y. Br, HBr xX ——…Question 217: How many and bonds are in the molecule HCCCH2CH2CHC(CH3)2? A 17 3 B 17 5 C 18 4 D 19 3Question 218: Which compound has an Mr of 84 and will react with HBr to give a product with an Mr of 164.9? A B C D O61 / 77
Question 219: 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 220: Menthol is a naturally occurring alcohol. menthol OH When menthol is heated with concentrated sulfuric acid it reacts. The products formed …Question 221: Which feature is present in both ethene and poly(ethene)? A bond angles of 109.5° B covalent bonds C covalent bonds D sp3 orbitals62 / 77
Question 222: How many geometrical (cis/trans) isomers are there of hex-2,4-diene, CH3CH=CHCH=CHCH3? A none; hex-2,4-diene does not show geometric isomer…Question 223: The structure of compound X is shown. compound X One mole of compound X reacts completely with two moles of hydrogen bromide. What is the s…Question 224: The formulae of three compounds are shown. C3H7CHO C2H5COCH3 CH2CHCH2CH2OH Only one of these compounds will decolourise bromine water. Only…63 / 77
Question 225: Which compound has an Mr of 84 and will react with HBr to give a product with an Mr of 164.9? A B C D OQuestion 226: 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 227: Menthol is a naturally occurring alcohol. menthol OH When menthol is heated with concentrated sulfuric acid it reacts. The products formed …64 / 77
Question 228: Which row shows the correct number of covalent bonds in a molecule of methylpropene? total number of sigma () total number of pi () bonds…Question 229: The diagram shows the structure of the naturally occurring molecule cholesterol. cholesterol H3C CH3 CH3 HO Student X stated that the 17 ca…Question 230: 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…65 / 77
Question 231: A sequence of reactions takes place. The major product is compound Z. concentrated LiAl H4 H2SO4 propanoic acid compound X compound Y pass …Question 232: The formula shows the repeat unit of an addition polymer. –CH(CH3)CH(CH2CH3)– What is the correct name of the monomer from which this polym…Question 233: Structural isomerism and stereoisomerism should be taken into account when answering this question. The structure of 3-methylcyclobutene is…66 / 77
Question 234: A molecule of geraniol is shown. geraniol OH What is formed when geraniol is reacted with an excess of cold dilute acidified MnO4 –? A B O …Question 235: 2-bromopropane is converted to 1,2-dibromopropane in a pathway involving two reactions. reaction 1 reaction 2 2-bromopropane compound X 1,2…Question 236: 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 237: The molecule of limonene, C10H16, contains a 6-membered ring. This is the only cyclic component in its structure. Which volume of hydrogen,…67 / 77
Question 238: 1-bromopropane reacts with hot ethanolic NaOH. What is the molecular formula of the product in this reaction? A C3H6 B C3H8 C C3H7O D C3H8OQuestion 239: Which pair of reagents reacts to form a product with a chiral carbon atom? A CH3CH=CH2 + HBr B (CH3)2C=O + NaBH4 C CH3CH2CHO + HCN D …Question 240: Which alkene shows geometric isomerism? A CH3CH2CH2CH CH2 B CH3CH2CH CHCH3 C CH3CH2C CH2 CH3 D CH3CH CCH3 CH3Question 241: What is the correct name of the major product of the reaction of HBr with 3-ethylhex-3-ene? A 3-bromo-3-ethylhexane B 3-bromo-4-ethylhexane…Question 242: 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…68 / 77
Question 243: When heated with KOH dissolved in ethanol, halogenoalkanes can undergo an elimination reaction to form alkenes. What are the possible elimi…Question 244: Ethene reacts with steam in the presence of sulfuric acid. C2H4 + H2O  CH3CH2OH Which type of reaction is this? A acid–base B addition…Question 245: Which compound has the greatest number of stereoisomers? A 2-methylhex-2-ene B 3-methylhex-2-ene C 4-methylhex-2-ene D 5-methylhex-2-eneQuestion 246: The structure of limonene is shown. limonene What are the number of moles of carbon dioxide and water produced when a sample of limonene is…69 / 77
Question 247: The diagram shows a section of an addition polymer. The polymer is made using two different monomers. H Cl H CH3 H Cl H CH3 C C C C C C C C…Question 248: What are the only structures formed when butan-2-ol is heated with concentrated H2SO4? CH3CH2 H CH3 H A C C C C H H H CH3 CH3 CH3 CH3 H H H…Question 249: Ethene reacts with steam in the presence of sulfuric acid. C2H4 + H2O  CH3CH2OH Which type of reaction is this? A acid–base B addition…70 / 77
Question 250: Which compound has the greatest number of stereoisomers? A 2-methylhex-2-ene B 3-methylhex-2-ene C 4-methylhex-2-ene D 5-methylhex-2-eneQuestion 251: Vitamin A contains retinol. retinol OH Under appropriate conditions, acidified KMnO4(aq) can be used to break C=C bonds. After these bonds …Question 252: The structure of limonene is shown. limonene What are the number of moles of carbon dioxide and water produced when a sample of limonene is…71 / 77
Question 253: Which compound may be synthesised from an alkene, with formula C4H8, by an addition reaction? A 1,1-dibromobutane B 1,2-dibromobutane C 1,3…Question 254: A molecule of hexane can be cracked in a number of different ways. Three compounds are listed. 1 C3H8 2 C4H8 3 C5H12 Which compounds are fo…Question 255: What is the total number of sp3 hybridised atomic orbitals used in the bonding of but-2-ene? A 2 B 4 C 6 D 8Question 256: Structural isomerism and stereoisomerism should be considered when answering this question. 2,5-dibromohexane is heated under reflux with e…Question 257: An alkene P reacts with an excess of hot concentrated acidified KMnO4(aq). Methylpropanoic acid is the only organic product. What is alkene…Question 258: The structural formula of hept-1,4,5-triene is shown. CH2CHCH2CHCCHCH3 How many of the carbon atoms in one molecule of hept-1,4,5-triene ar…72 / 77
Question 259: Propan-1-ol, C3H7OH, is dehydrated by passing its vapour over hot aluminium oxide to give a hydrocarbon. Which structural formula represent…Question 260: Alkane S has molecular formula C4H10. S reacts with Cl 2(g) in the presence of sunlight to produce only two different monochloroalkanes, C4…73 / 77
Question 261: Which row shows the products formed when cyclohexene reacts with acidified KMnO4 under different conditions? product formed on reaction wit…Question 262: When 0.010 mol of a hydrocarbon X reacts with 720 cm3 of hydrogen at room conditions, an alkane is formed. What is hydrocarbon X? A B C D74 / 77
Question 263: An alkene reacts with hot concentrated acidified KMnO4 to produce a single organic product as shown. hot concentrated O O acidified KMnO4(a…Question 264: Which intermediate ion forms in the greatest amount during the addition of HBr to propene? A CH3CH+CH3 B CH3CH2CH2 + C CH3CH–CH2Br D CH3CHB…Question 265: 1,4-dibromobutane reacts with an excess of ethanolic sodium hydroxide until no further reaction takes place. What is the relative formula m…Question 266: A small section of a polymer produced from two monomers is shown. –CH2–C(CH3)2–CH(CH3)–CH2– What are the two monomers? A but-1-ene and prop…Question 267: What is the major product when 2-methylpent-2-ene reacts with hydrogen bromide? A 1-bromo-2-methylpentane B 2-bromo-2-methylpentane C 3-bro…75 / 77
Question 268: Pent-2-ene is reacted with cold, dilute, acidified manganate(VII) ions. What is the major product? A CH3CH2CH(OH)CH(OH)CH3 B CH3CH2COCOCH3 …Question 269: Limonene is an oil formed in the peel of citrus fruits. limonene CH3 CH2 C CH3 Which product is formed when an excess of bromine, Br2(l), r…76 / 77
Question 270: The purity of a compound can be determined using infrared spectroscopy. The table gives the characteristic infrared absorption frequencies …Question 271: Which intermediate ion forms in the greatest amount during the addition of HBr to propene? A CH3CH+CH3 B CH3CH2CH2 + C CH3CH–CH2Br D CH3CHB…Question 272: A small section of a polymer produced from two monomers is shown. –CH2–C(CH3)2–CH(CH3)–CH2– What are the two monomers? A but-1-ene and prop…77 / 77

Mark scheme272 answers

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

Pastlit

Chemistry 9701 · Alkenes — Paper 1

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

Question

Answer

Marks

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

Pastlit

Chemistry 9701 · Alkenes — Paper 1

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

Question

Answer

Marks

50—1
51—1
52C1
53C1
54D1
55D1
56C1
57B1
58A1
59B1
60B1
61D1
62C1
63D1
64D1
65C1
66D1
67B1
68D1
69B1
70D1
71A1
72D1
73B1
74D1
75A1
76B1
77A1
78A1
79C1
80C1
81C1
82B1
83A1
84D1
85A1
86D1
87B1
88A1
89D1
90A1
91B1
92C1
93B1
94A1
95A1
96B1
97C1
98A1
2 / 6

Pastlit

Chemistry 9701 · Alkenes — Paper 1

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

Question

Answer

Marks

99D1
100B1
101—1
102—1
103—1
104B1
105B1
106D1
107B1
108A1
109B1
110A1
111A1
112C1
113D1
114A1
115C1
116A1
117C1
118A1
119B1
120D1
121D1
122A1
123B1
124B1
125A1
126D1
127B1
128A1
129C1
130A1
131A1
132A1
133D1
134B1
135A1
136C1
137C1
138B1
139B1
140B1
141B1
142C1
143D1
144C1
145B1
146B1
147A1
3 / 6

Pastlit

Chemistry 9701 · Alkenes — Paper 1

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

Question

Answer

Marks

148B1
149C1
150A1
151A1
152B1
153C1
154B1
155D1
156D1
157A1
158D1
159D1
160B1
161D1
162A1
163D1
164A1
165A1
166C1
167B1
168A1
169C1
170C1
171C1
172A1
173D1
174B1
175B1
176D1
177D1
178A1
179A1
180B1
181C1
182C1
183D1
184B1
185A1
186B1
187B1
188B1
189B1
190D1
191C1
192A1
193A1
194A1
195B1
196B1
4 / 6

Pastlit

Chemistry 9701 · Alkenes — Paper 1

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

Question

Answer

Marks

197D1
198A1
199D1
200B1
201C1
202C1
203C1
204A1
205D1
206C1
207A1
208B1
209D1
210A1
211D1
212D1
213B1
214B1
215C1
216C1
217D1
218D1
219B1
220D1
221C1
222C1
223A1
224D1
225D1
226B1
227D1
228C1
229B1
230B1
231D1
232C1
233B1
234A1
235D1
236D1
237C1
238A1
239C1
240B1
241A1
242C1
243C1
244B1
245C1
5 / 6

Pastlit

Chemistry 9701 · Alkenes — Paper 1

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

Question

Answer

Marks

246B1
247A1
248B1
249B1
250C1
251D1
252B1
253B1
254B1
255D1
256C1
257A1
258A1
259D1
260B1
261A1
262C1
263D1
264A1
265A1
266D1
267B1
268A1
269D1
270D1
271A1
272D1
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Questions as text

Q1 · Which hydrocarbon, on treatment with hot acidified potassium manganate(VII), would give… 9701/11 Oct/Nov 2005

21 Which hydrocarbon, on treatment with hot acidified potassium manganate(VII), would give ethanoic acid only? A CH3CH CH2 B CH3CH CHCH3 CH3 C C CHCH3 CH3 CH3 CH3 D C C CH3 CH3

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2005

Q2 · The sex-attractant of the house-fly is muscalure, with the following formula 9701/11 Oct/Nov 2005

40 The sex-attractant of the house-fly is muscalure, with the following formula. CH3(CH2)7CH = CH(CH2)12CH3 Which statements about muscalure are correct? 1 It will decolourise aqueous bromine. 2 It will be oxidised by cold aqueous alkaline KMnO4 to give a diol. 3 It will be optically active.

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2005

Q3 · The structures below show isomers of C6H12 9701/11 May/June 2006

22 The structures below show isomers of C6H12. 1 2 3 4 CH3 CH3 CH3 C2H5 C2H5 H C2H5 CH3 C C C C C C C C H C2H5 H CH3 CH3 CH3 H CH3 In which pair are the members cis-trans isomers of each other? A 1 and 2 B 1 and 3 C 1 and 4 D 2 and 4

1 marks

Answer: A

This question in 9701/11 May/June 2006

Q4 · Which reagent could detect the presence of alcohol in a petrol consisting mainly of a… 9701/11 May/June 2006

26 Which reagent could detect the presence of alcohol in a petrol consisting mainly of a mixture of alkanes and alkenes? A Na B Br2 (in CCl4) C KMnO4(aq) D 2,4-dinitrophenylhydrazine

1 marks

Answer: A

This question in 9701/11 May/June 2006

Q5 · Deuterium, D, is the H 2 isotope of hydrogen 9701/11 May/June 2006

38 Deuterium, D, is the H 2 isotope of hydrogen. DBr has the same chemical properties as HBr. 1 Which compounds could be made by the reaction of DBr with another compound in a single reaction? Br D 1 2 CHBr2CHDBr OD 3 CH3CH Br

1 marks

Answer: B

This question in 9701/11 May/June 2006

Q6 · Which alkene could exist in cis and trans forms? 9701/11 Oct/Nov 2006

23 Which alkene could exist in cis and trans forms? A CH3CH2CH2CH CH2 B CH3CH2CH CHCH3 C CH3CH2C CH2 CH3 D CH3CH CCH3 CH3

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2006

Q7 · 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

Q8 · Which compounds are able to react with concentrated sulphuric acid to give a product that… 9701/11 Oct/Nov 2006

39 Which compounds are able to react with concentrated sulphuric acid to give a product that will decolourise acidic potassium manganate(VII)? 1 (CH3)3COH 2 CH3CH2CH(OH)CH3 3 CH3CO2H

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2006

Q9 · Limonene is an oil formed in the peel of citrus fruits 9701/11 Oct/Nov 2007

23 Limonene is an oil formed in the peel of citrus fruits. CH3 CH2 C CH3 limonene Which product is formed when molecular bromine reacts with limonene at room temperature in the dark? A B C D Br Br CH3 CH2 CH3 CH2 C C CH3 C CH2Br CH3 C CH2Br Br Br Br CH3 CH3 Br CH3 CH3 Br

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2007

Q10 · Which pair of reaction types is illustrated by the reaction sequence below? 9701/11 May/June 2008

20 Which pair of reaction types is illustrated by the reaction sequence below? HI in CH3CO2H NaOH(aq) CH3CH=CHCH3 CH3CH2CHICH3 CH3CH2CH(OH)CH3 A electrophilic addition and electrophilic substitution B electrophilic addition and nucleophilic substitution C nucleophilic addition and electrophilic substitution D nucleophilic addition and nucleophilic substitution

1 marks

Answer: B

This question in 9701/11 May/June 2008

Q11 · Trichloroethene is widely used as a dry-cleaning agent 9701/11 May/June 2008

21 Trichloroethene is widely used as a dry-cleaning agent. H Cl \ 4 C=C Ve C Cl With which of the following does trichloroethene react to give a chiral product? A Br B HCl C NaCN(aq) D NaOH(aq)

1 marks

Answer: A

This question in 9701/11 May/June 2008

Q12 · Compound X • has the molecular formula C10H14O; • is unreactive towards mild oxidising… 9701/11 May/June 2008

27 Compound X • has the molecular formula C10H14O; • is unreactive towards mild oxidising agents. What is the structure of the compound formed by dehydration of X? A B CH2 CH2 CH CH2 CH2 CH CH CH3 C D CH3 CH3 CH CH CH2 C CH CH3

1 marks

Answer: D

This question in 9701/11 May/June 2008

Q13 · Ferulic acid is an antioxidant that occurs widely in plants 9701/11 May/June 2008

40 Ferulic acid is an antioxidant that occurs widely in plants. HO CH=CHCO2H CH3O ferulic acid Which reagents can react with the –CH=CHCO2H part of the molecule? 1 NaOH(aq) 2 acidified KMnO4 3 HBr

1 marks

Answer: A

This question in 9701/11 May/June 2008

Q14 · The compound ‘leaf alcohol’ is partly responsible for the smell of new-mown grass 9701/11 Oct/Nov 2008

21 The compound ‘leaf alcohol’ is partly responsible for the smell of new-mown grass. CH3CH2CH=CHCH2CH2OH leaf alcohol Which two compounds will be formed when ‘leaf alcohol’ is oxidised using hot, concentrated manganate(VII) ions? A CH3CO2H and HOCH2CH2CH2CO2H B CH3CO2H and HO2CCH2CH2CO2H C CH3CH2CO2H and HO2CCH2CO2H D CH3CH2CO2H and HOCH2CH2CO2H

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2008

Q15 · Which hydrocarbon can form a monochloro-substitution derivative which shows both… 9701/11 Oct/Nov 2008

22 Which hydrocarbon can form a monochloro-substitution derivative which shows both chirality and cis-trans isomerism? A CH3CH=CH2 B (CH3)2C=CH2 C CH3CH=C(CH3)2 D CH3CH=CHCH2CH3

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2008

Q16 · Which statements about alkenes are correct? 9701/11 Oct/Nov 2008

37 Which statements about alkenes are correct? 1 They are formed when higher alkanes are cracked. 2 They are used as monomers for polymerisation. 3 They are less reactive than alkanes towards electrophiles.

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2008

Q17 · In which reaction does the carbon-containing product have a smaller bond angle than the… 9701/11 May/June 2009

6 In which reaction does the carbon-containing product have a smaller bond angle than the organic reactant? A bromoethane refluxed with ethanolic sodium hydroxide B complete combustion of methane in air C methane and an excess of chlorine under ultraviolet light D polymerisation of ethene

1 marks

Answer: D

This question in 9701/11 May/June 2009

Q18 · 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

Q19 · A fraction of distilled crude oil contains molecules with between 15 and 19 carbon atoms 9701/11 May/June 2009

37 A fraction of distilled crude oil contains molecules with between 15 and 19 carbon atoms. This fraction is cracked by strong heating. Why is this done? 1 To produce alkenes. 2 To produce smaller molecules which are in higher demand. 3 To insert oxygen atoms into the hydrocarbons.

1 marks

Answer: B

This question in 9701/11 May/June 2009

Q20 · Geraniol is one of several compounds produced by the scent glands of honey bees to help… 9701/11 May/June 2009

38 Geraniol is one of several compounds produced by the scent glands of honey bees to help them mark nectar-bearing flowers and locate the entrances to their hives. OH geraniol Which reactions will geraniol undergo? 1 reaction with hot concentrated acidic KMnO4 to give propanone 2 addition of halogens 3 reaction with aqueous NaHCO3 to give CO2

1 marks

Answer: B

This question in 9701/11 May/June 2009

Q21 · The presence of 11-cis retinal, C20H28O, in cells in the eye is important for vision 9701/11 Oct/Nov 2009

21 The presence of 11-cis retinal, C20H28O, in cells in the eye is important for vision. The structure of retinal includes an aldehyde group, a cyclohexene ring and a long aliphatic side chain, in which a carbon-carbon double bond exists between carbons numbered 11 and 12. Which pair of statements about 11-cis retinal could be correct? arrangement around total number of the adjacent carbons >C=C< double bonds 11 and 12 R1 R2 A 5 C C H H R1 H B 5 C C H R2 R1 R2 C 6 C C H H R1 H D 6 C C H R2

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2009

Q22 · Sorbic acid is used as a food preservative because it kills fungi and moulds 9701/11 Oct/Nov 2009

24 Sorbic acid is used as a food preservative because it kills fungi and moulds. H H O C C C H3C C C OH H H sorbic acid Sorbic acid will react with • hydrogen in the presence of a nickel catalyst, • bromine in an organic solvent. How many moles of hydrogen and of bromine will be incorporated into one mole of sorbic acid by these reactions? moles of hydrogen moles of bromine A 2 2 1 B 2 2 2 C 3 2 1 D 3 2 2

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2009

Q23 · Bromine reacts with ethene to form 1,2-dibromoethane 9701/11 Oct/Nov 2009

25 Bromine reacts with ethene to form 1,2-dibromoethane. What is the correct description of the organic intermediate in this reaction? A It has a negative charge. B It is a free radical. C It is a nucleophile. D It is an electrophile.

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2009

Q24 · Which compound exhibits both cis-trans and optical isomerism? 9701/13 May/June 2010

26 Which compound exhibits both cis-trans and optical isomerism? A CH3CH=CHCH2CH3 B CH3CHBrCH=CH2 C CH3CBr=CBrCH3 D CH3CH2CHBrCH=CHBr

1 marks

Answer: D

This question in 9701/13 May/June 2010

Q25 · Which isomer of C4H10O forms three alkenes on dehydration? 9701/13 May/June 2010

30 Which isomer of C4H10O forms three alkenes on dehydration? 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 May/June 2010

Q26 · Limonene is an oil formed in the peel of citrus fruits 9701/11 Oct/Nov 2010

25 Limonene is an oil formed in the peel of citrus fruits. CH3 CH2 C CH3 limonene Which product is formed when an excess of bromine, Br2(l), reacts with limonene at room temperature in the dark? A B C D Br Br CH3 CH2 CH3 CH2 C C CH3 C CH2Br CH3 C CH2Br Br Br Br CH3 CH3 Br CH3 CH3 Br

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2010

Q27 · The compound 2-methylpropene, C4H8, is a monomer used in the production of synthetic… 9701/11 Oct/Nov 2010

29 The compound 2-methylpropene, C4H8, is a monomer used in the production of synthetic rubber. H CH3 C C H CH3 In addition to 2-methylpropene there are x other isomers of C4H8, structural or otherwise, which contain a double bond. What is the value of x? A 1 B 2 C 3 D 4

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2010

Q28 · An organic compound decolourises aqueous bromine and reacts with sodium to produce… 9701/11 Oct/Nov 2010

39 An organic compound decolourises aqueous bromine and reacts with sodium to produce hydrogen. Which molecular formula could represent this compound? 1 C3H6O 2 C3H4O2 3 C3H8O

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2010

Q29 · Nine compounds have molecular formula C4H8Br2 9701/12 Oct/Nov 2010

21 Nine compounds have molecular formula C4H8Br2. Which compound may be synthesised from an alkene by an addition reaction? A 1,1-dibromobutane B 1,2-dibromobutane C 1,3-dibromobutane D 1,3-dibromomethylpropane

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2010

Q30 · Part of the structure of strobilurin, a fungicide, is shown 9701/12 Oct/Nov 2010

27 Part of the structure of strobilurin, a fungicide, is shown. R and R' are inert groups. O OCH3 R' R If strobilurin is first warmed with aqueous sulfuric acid, and its product then treated with hydrogen in the presence of a palladium catalyst, what could be the structure of the final product? A B O OH HO OCH3 R' R' R R C D OH O OH OH OH R' R' R R OH

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2010

Q31 · Fluoroalkenes are used to make polymers such as poly(vinyl)fluoride (PVF) 9701/12 Oct/Nov 2010

28 Fluoroalkenes are used to make polymers such as poly(vinyl)fluoride (PVF). PVF is used to make non-flammable interiors for aircraft. The diagram shows the repeat unit of the polymer PVF. H H C C H F What is the skeletal formula of the monomer of PVF? H F F F F A B C D H H

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2010

Q32 · One of the characteristics of addition polymerisation is that the empirical formulae of… 9701/13 Oct/Nov 2010

21 One of the characteristics of addition polymerisation is that the empirical formulae of the polymer and of its monomer are the same. The absorbent material in babies’ disposable nappies is made from the addition polymer shown. CH2 CH2 CH2 CH CH CH CO2H CO2H CO2H From which monomer could this addition polymer be obtained? A CH3CH(OH)CO2H B HOCH2CH2CO2H C H2C=CHCO2H D HO2CCH=CHCO2H

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2010

Q33 · Limonene is an oil formed in the peel of citrus fruits 9701/13 Oct/Nov 2010

23 Limonene is an oil formed in the peel of citrus fruits. CH3 CH2 C CH3 limonene Which product is formed when an excess of bromine, Br2(l), reacts with limonene at room temperature in the dark? A B C D Br Br CH3 CH2 CH3 CH2 C C CH3 C CH2Br CH3 C CH2Br Br Br Br CH3 CH3 Br CH3 CH3 Br

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2010

Q34 · The compound 2-methylpropene, C4H8, is a monomer used in the production of synthetic… 9701/13 Oct/Nov 2010

29 The compound 2-methylpropene, C4H8, is a monomer used in the production of synthetic rubber. H CH3 C C H CH3 In addition to 2-methylpropene there are x other isomers of C4H8, structural or otherwise, which contain a double bond. What is the value of x? A 1 B 2 C 3 D 4

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2010

Q35 · An organic compound decolourises aqueous bromine and reacts with sodium to produce… 9701/13 Oct/Nov 2010

38 An organic compound decolourises aqueous bromine and reacts with sodium to produce hydrogen. Which molecular formula could represent this compound? 1 C3H6O 2 C3H4O2 3 C3H8O

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2010

Q36 · In the reaction pathway below, an alkane is converted into a carboxylic acid through… 9701/11 May/June 2011

19 In the reaction pathway below, an alkane is converted into a carboxylic acid through several stages. stage 1 stage 2 stage 3 C10H22 C2H4 C2H5OH CH3CO2H catalytic hydration Which processes occur at stage 1 and at stage 3? stage 1 stage 3 A condensation combustion B cracking dehydration C cracking oxidation D dehydration combustion

1 marks

Answer: C

This question in 9701/11 May/June 2011

Q37 · 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

Q38 · Which alkenes, on reaction with steam at 600 K and 6 x 106 Pa pressure in the presence of… 9701/11 May/June 2011

38 Which alkenes, on reaction with steam at 600 K and 6 x 106 Pa pressure in the presence of a phosphoric acid catalyst, could produce an alcohol containing a chiral carbon atom? 1 (CH3)2C=CH2 2 CH3CH=CHCH3 3 CH3CH2CH=CH2

1 marks

Answer: C

This question in 9701/11 May/June 2011

Q39 · The products obtained by cracking an alkane, X, are methane, ethene and propene 9701/12 May/June 2011

23 The products obtained by cracking an alkane, X, are methane, ethene and propene. The mole fraction of ethene in the products is 0.5. What is the identity of X? A C6H14 B C8H18 C C9H20 D C11H24

1 marks

Answer: B

This question in 9701/12 May/June 2011

Q40 · Which compound does not show cis-trans isomerism? 9701/12 May/June 2011

24 Which compound does not show cis-trans isomerism? A 2-methylpent-2-ene B 3-methylpent-2-ene C 3,4-dimethylhex-3-ene D pent-2-ene

1 marks

Answer: A

This question in 9701/12 May/June 2011

Q41 · Which compounds can be obtained from ethene in a single reaction? 9701/12 May/June 2011

37 Which compounds can be obtained from ethene in a single reaction? 1 CH3CH3 2 ( CH2CH2 )n 3 HOCH2CH2OH

1 marks

Answer: A

This question in 9701/12 May/June 2011

Q42 · Acrylic acid is produced from propene, a gaseous product of oil refineries 9701/13 May/June 2011

21 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 9701/13 May/June 2011

Q43 · Which isomer of C6H13OH gives the greatest number of different alkenes when it is… 9701/13 May/June 2011

26 Which isomer of C6H13OH gives the greatest number of different alkenes when it is dehydrated? A B CH3 CH3 CH CH CH2OH CH3 CH2 CH2 CH CH2 CH3 CH3 OH C D CH3 CH3 CH3 CH2 C CH2 CH3 CH3 C CH2 CH2OH OH CH3

1 marks

Answer: B

This question in 9701/13 May/June 2011

Q44 · Which alkenes, on reaction with steam at 600 K and 6 x 106 Pa pressure in the presence of… 9701/13 May/June 2011

37 Which alkenes, on reaction with steam at 600 K and 6 x 106 Pa pressure in the presence of a phosphoric acid catalyst, could produce an alcohol containing a chiral carbon atom? 1 (CH3)2C=CH2 2 CH3CH=CHCH3 3 CH3CH2CH=CH2

1 marks

Answer: C

This question in 9701/13 May/June 2011

Q45 · This question should be answered by considering the reactions of KMnO4 with different… 9701/11 Oct/Nov 2011

20 This question should be answered by considering the reactions of KMnO4 with different functional groups under the stated conditions. The diagram shows the structure of the naturally-occurring molecule cholesterol. H3C CH3 H CH3 H H H HO cholesterol Separate oxidation reactions are carried out using different conditions. ● cold, dilute acidified KMnO4 ● hot, concentrated acidified KMnO4 Which statements about the products formed are correct? cold, dilute acidified KMnO4: hot, concentrated acidified KMnO4: number of hydroxy groups number of 6-membered rings present remaining A 1 2 B 1 3 C 3 2 D 3 3

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2011

Q46 · Energy is released in the human body by the oxidation of glucose in a complex sequence of… 9701/11 Oct/Nov 2011

26 Energy is released in the human body by the oxidation of glucose in a complex sequence of reactions. Part of this sequence is the Krebs cycle. One reaction in the Krebs cycle is the conversion of fumaric acid into malic acid. HO2CCH=CHCO2H → HO2CCH(OH)CH2CO2H fumaric acid malic acid Which reagents could achieve this transformation in the laboratory? A acidified KMnO4 B Br2(aq) followed by hot NaOH(aq) C H2O with Pt catalyst D steam with H2SO4

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2011

Q47 · Geraniol is a constituent of some perfumes 9701/11 Oct/Nov 2011

29 Geraniol is a constituent of some perfumes. OH geraniol Which statement about geraniol is not correct? A Geraniol causes hot acidified potassium dichromate(VI) to change colour from orange to green. B Geraniol decolourises bromine water. C There are three methyl groups and three methylene (CH2) groups in geraniol. D There are two pairs of cis-trans isomers of geraniol.

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2011

Q48 · Bromine and propene undergo an addition reaction 9701/12 Oct/Nov 2011

20 Bromine and propene undergo an addition reaction. Which is a property of the product? A It exists in cis-trans isomers. B It is more volatile than propene. C It possesses a chiral centre. D It possesses hydrogen bonding.

1 marks

This question in 9701/12 Oct/Nov 2011

Q49 · Which reagent could best be used to distinguish between cyclohexene and cyclohexanol? 9701/12 Oct/Nov 2011

28 Which reagent could best be used to distinguish between cyclohexene and cyclohexanol? A Ag(NH3)2 + in H2O B Br2 in CCl 4 C 2,4-dinitrophenylhydrazine in CH3OH D NaBH4 in CH3OH

1 marks

This question in 9701/12 Oct/Nov 2011

Q50 · Compound X, molecular formula C4H8, undergoes the following reactions 9701/12 Oct/Nov 2011

29 Compound X, molecular formula C4H8, undergoes the following reactions. Br2 aq.NaOH / heat C4H8 C4H8Br2 C4H10O2 X Y Z H2 / Ni C4H8 methylpropane X What is the formula of compound Z? A CH3CH2CH(OH)CH2OH B CH3CH(OH)CH(OH)CH3 C CH3CH(CH2OH)CH2OH D (CH3)2C(OH)CH2OH

1 marks

This question in 9701/12 Oct/Nov 2011

Q51 · How many of the isomeric alcohols with the formula C4H9OH will produce an alkene that has… 9701/12 Oct/Nov 2011

30 How many of the isomeric alcohols with the formula C4H9OH will produce an alkene that has cis and trans isomers, on treatment with conc. H2SO4? A 1 B 2 C 3 D 4

1 marks

This question in 9701/12 Oct/Nov 2011

Q52 · This question should be answered by considering the reactions of KMnO4 with different… 9701/13 Oct/Nov 2011

18 This question should be answered by considering the reactions of KMnO4 with different functional groups under the stated conditions. The diagram shows the structure of the naturally-occurring molecule cholesterol. H3C CH3 H CH3 H H H HO cholesterol Separate oxidation reactions are carried out using different conditions. ● cold, dilute acidified KMnO4 ● hot, concentrated acidified KMnO4 Which statements about the products formed are correct? cold, dilute acidified KMnO4: hot, concentrated acidified KMnO4: number of hydroxy groups number of 6-membered rings present remaining A 1 2 B 1 3 C 3 2 D 3 3

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2011

Q53 · An unpleasant smelling chemical produced in the human armpit is 3-methylhex-2-enoic acid 9701/13 Oct/Nov 2011

26 An unpleasant smelling chemical produced in the human armpit is 3-methylhex-2-enoic acid. CH3 CH3 CH2 CH2 C CH C OH O If this compound is reacted with a cold, dilute, acidified solution of potassium manganate(VII), how many chiral centres will be produced? A 0 B 1 C 2 D 3

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2011

Q54 · Energy is released in the human body by the oxidation of glucose in a complex sequence of… 9701/13 Oct/Nov 2011

27 Energy is released in the human body by the oxidation of glucose in a complex sequence of reactions. Part of this sequence is the Krebs cycle. One reaction in the Krebs cycle is the conversion of fumaric acid into malic acid. HO2CCH=CHCO2H → HO2CCH(OH)CH2CO2H fumaric acid malic acid Which reagents could achieve this transformation in the laboratory? A acidified KMnO4 B Br2(aq) followed by hot NaOH(aq) C H2O with Pt catalyst D steam with H2SO4

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2011

Q55 · Geraniol is a constituent of some perfumes 9701/13 Oct/Nov 2011

30 Geraniol is a constituent of some perfumes. OH geraniol Which statement about geraniol is not correct? A Geraniol causes hot acidified potassium dichromate(VI) to change colour from orange to green. B Geraniol decolourises bromine water. C There are three methyl groups and three methylene (CH2) groups in geraniol. D There are two pairs of cis-trans isomers of geraniol.

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2011

Q56 · Two conversions are outlined below 9701/11 May/June 2012

5 Two conversions are outlined below. NH4 + → NH3 C2H4 → C2H6 What similar feature do these two conversions have? A a lone pair of electrons in the product B change in oxidation state of an element C decrease in bond angle of the species involved D disappearance of a π bond

1 marks

Answer: C

This question in 9701/11 May/June 2012

Q57 · Isomers X and Y both react with HBr 9701/12 May/June 2012

23 Isomers X and Y both react with HBr. H3C Br Br Br C C C C H3C Br H3C CH3 X Y A mixture of X and Y is reacted with HBr. Which three structures represent three different possible products of this reaction? A (CH3)2CHCBr3 (CH3)2CBrCHBr2 CH3CHBrCHBrCH3 B (CH3)2CHCBr3 (CH3)2CBrCHBr2 CH3CBr2CHBrCH3 C (CH3)2CBrCBr3 (CH3)2CHCBr3 CH3CBr2CHBrCH3 D (CH3)2CBrCHBr2 CHBr2CBr(CH3)CH3 CH3CHBrCBr2CH3

1 marks

Answer: B

This question in 9701/12 May/June 2012

Q58 · Oct-1-ene, CH3(CH2)5CH=CH2, is subjected to thermal cracking 9701/12 May/June 2012

24 Oct-1-ene, CH3(CH2)5CH=CH2, is subjected to thermal cracking. Which combination of compounds W, X, Y and Z can be obtained? CH2=CH2 CH3CH=CH2 CH3CH2CH3 CH2=CHCH=CH2 W X Y Z A W, X, Y and Z B W, X and Y only C W, X and Z only D W and X only

1 marks

Answer: A

This question in 9701/12 May/June 2012

Q59 · An organic compound will decolorise dilute acidified aqueous potassium manganate(VII) on… 9701/12 May/June 2012

30 An organic compound will decolorise dilute acidified aqueous potassium manganate(VII) on warming, but will not decolorise bromine water. What could the organic compound be? A butane B ethanol C ethene D ethanoic acid

1 marks

Answer: B

This question in 9701/12 May/June 2012

Q60 · Which compounds can be obtained from propene in a single reaction? 9701/12 May/June 2012

37 Which compounds can be obtained from propene in a single reaction? 1 CH2OHCHOHCH3 2 ( CH2CH(CH3) ) n 3 CH2BrCH2CH2Br

1 marks

Answer: B

This question in 9701/12 May/June 2012

Q61 · An alkene has the formula CH3CH=CR CH2CH3 and does not possess cis-trans isomers 9701/11 Oct/Nov 2012

21 An alkene has the formula CH3CH=CR CH2CH3 and does not possess cis-trans isomers. What is R ? A H B Cl C CH3 D C2H5

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2012

Q62 · But-2-ene-1,4-diol is converted in two steps through an intermediate X into… 9701/11 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 9701/11 Oct/Nov 2012

Q63 · Oleic acid is found in olive oil 9701/11 Oct/Nov 2012

40 Oleic acid is found in olive oil. It has the following formula. H H C C O CH3(CH2)7 (CH2)7 C OH Which reagents will give a positive result with oleic acid? 1 aqueous bromine 2 acidified potassium dichromate(VI) 3 Fehling’s reagent

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2012

Q64 · An alkene has the formula CH3CH=CR CH2CH3 and does not possess cis-trans isomers 9701/12 Oct/Nov 2012

21 An alkene has the formula CH3CH=CR CH2CH3 and does not possess cis-trans isomers. What is R ? A H B Cl C CH3 D C2H5

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2012

Q65 · 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

Q66 · Oleic acid is found in olive oil 9701/12 Oct/Nov 2012

40 Oleic acid is found in olive oil. It has the following formula. H H C C O CH3(CH2)7 (CH2)7 C OH Which reagents will give a positive result with oleic acid? 1 aqueous bromine 2 acidified potassium dichromate(VI) 3 Fehling’s reagent

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2012

Q67 · A molecule of a polymer contained the sequence shown 9701/13 Oct/Nov 2012

22 A molecule of a polymer contained the sequence shown. H H H H H Cl H H H Cl H H C C C C C C C C C C C C H Cl Cl H H H Cl H H H H Cl Which monomer could produce this polymer by addition polymerisation? A CHCl =CHCl B CH2=CHCl C CH3CCl =CHCl D CH3CCl =CH2

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2012

Q68 · Bromine reacts with ethene to form 1,2-dibromoethane 9701/11 May/June 2013

22 Bromine reacts with ethene to form 1,2-dibromoethane. What is the correct description of the organic intermediate in this reaction? A It has a negative charge. B It is a free radical. C It is a nucleophile. D It is an electrophile.

1 marks

Answer: D

This question in 9701/11 May/June 2013

Q69 · Synthetic resins, plasticisers and many other chemicals can be made by polymerisation of… 9701/11 May/June 2013

29 Synthetic resins, plasticisers and many other chemicals can be made by polymerisation of a variety of monomers including prop-2-en-1-ol, CH2=CHCH2OH. Which structure represents the repeat unit in poly(prop-2-en-1-ol)? A CH2 CH CH2 OH B CH2 CH CH2OH C CH C CH2OH D CH2 CH CH2 OH

1 marks

Answer: B

This question in 9701/11 May/June 2013

Q70 · The compound hex-3-en-1-ol, P, has a strong ‘leafy’ smell of newly cut grass and is used… 9701/12 May/June 2013

20 The compound hex-3-en-1-ol, P, has a strong ‘leafy’ smell of newly cut grass and is used in perfumery. CH3CH2CH=CHCH2CH2OH P What is produced when P is treated with an excess of hot concentrated acidified KMnO4? A CH3CH2CH(OH)CH(OH)CH2CH2OH B CH3CH2CH=CHCH2CO2H C CH3CH2CHO and OCHCH2CH2OH D CH3CH2CO2H and HO2CCH2CO2H

1 marks

Answer: D

This question in 9701/12 May/June 2013

Q71 · Sorbic acid is used as a food preservative because it kills fungi and moulds 9701/12 May/June 2013

21 Sorbic acid is used as a food preservative because it kills fungi and moulds. H H O C C C H3C C C OH H H sorbic acid Sorbic acid will react with • hydrogen in the presence of a nickel catalyst, • bromine in an organic solvent. How many moles of hydrogen and of bromine will be incorporated into one mole of sorbic acid by these reactions? moles of hydrogen moles of bromine A 2 2 1 B 2 2 2 C 3 2 1 D 3 2 2

1 marks

Answer: A

This question in 9701/12 May/June 2013

Q72 · The compound shown is menthol, a naturally-occurring alcohol found in peppermint oil 9701/12 May/June 2013

25 The compound shown is menthol, a naturally-occurring alcohol found in peppermint oil. OH menthol When menthol is heated with concentrated sulfuric acid it reacts. The products that form include compound T. What could be the structure of compound T? A B C D O

1 marks

Answer: D

This question in 9701/12 May/June 2013

Q73 · Ethene reacts with steam in the presence of sulfuric acid 9701/13 May/June 2013

20 Ethene reacts with steam in the presence of sulfuric acid. C2H4 + H2O → CH3CH2OH What type of reaction is this? A acid / base B addition C hydrolysis D substitution

1 marks

Answer: B

This question in 9701/13 May/June 2013

Q74 · How many isomers, including structural and stereoisomers, with the formula C4H8 have… 9701/13 May/June 2013

22 How many isomers, including structural and stereoisomers, with the formula C4H8 have structures that involve π bonding? A 1 B 2 C 3 D 4

1 marks

Answer: D

This question in 9701/13 May/June 2013

Q75 · 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

Q76 · 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

Q77 · Many organic reactions need to be heated before reaction occurs, but some do not require… 9701/11 May/June 2014

20 Many organic reactions need to be heated before reaction occurs, but some do not require heating. Which reaction occurs quickly at room temperature? A C2H4 + Br2 → C2H4Br2 B C2H4 + H2O → CH3CH2OH C CH3CH2OH → C2H4 + H2O D CH3CH2OH + HBr → CH3CH2Br + H2O

1 marks

Answer: A

This question in 9701/11 May/June 2014

Q78 · How many moles of oxygen molecules are needed for the complete combustion of one mole of… 9701/11 May/June 2014

26 How many moles of oxygen molecules are needed for the complete combustion of one mole of 3-methylpent-2-ene? A 9 B 9 2 1 C 18 D 19

1 marks

Answer: A

This question in 9701/11 May/June 2014

Q79 · How many geometrical (cis-trans) isomers are there of hex-2,4-diene, CH3CH=CHCH=CHCH3? 9701/11 May/June 2014

29 How many geometrical (cis-trans) isomers are there of hex-2,4-diene, CH3CH=CHCH=CHCH3? A none; hex-2,4-diene does not show geometric isomerism B 2 C 3 D 4

1 marks

Answer: C

This question in 9701/11 May/June 2014

Q80 · 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

Q81 · Ethene reacts with aqueous bromine to give two products, CH2BrCH2Br and CH2BrCH2OH 9701/12 May/June 2014

24 Ethene reacts with aqueous bromine to give two products, CH2BrCH2Br and CH2BrCH2OH. Which statement about these products is correct? A Both products are obtained in this reaction by electrophilic substitution. B Both products are obtained in this reaction by nucleophilic addition. C Both products can be hydrolysed to form the same organic compound. D Both products can form hydrogen bonds with water.

1 marks

Answer: C

This question in 9701/12 May/June 2014

Q82 · Most alcohols can be dehydrated to give alkenes 9701/13 May/June 2014

25 Most alcohols can be dehydrated to give alkenes. Which alcohol can be dehydrated to give three different isomeric alkenes? A CH3(CH2)3CH2OH B CH3(CH2)2CH(OH)CH3 C CH3CH2CH(OH)CH2CH3 D CH3C(CH3)2CH2OH

1 marks

Answer: B

This question in 9701/13 May/June 2014

Q83 · 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

Q84 · The naturally-occurring molecule shown below can be made by the addition of four… 9701/13 May/June 2014

27 The naturally-occurring molecule shown below can be made by the addition of four identical monomer molecules. H H3C C C CH2 CH2 CH2 CH3 H2C C H2C CH CH C CH2 CH2 CH3 HC CH2 C CH3 What could be the structural formula of the monomer? A CH3CH2CH2CH=CH2 B CH3CH=CHCH=CH2 C CH2=C(CH3)CH2CH3 D CH2=C(CH3)CH=CH2

1 marks

Answer: D

This question in 9701/13 May/June 2014

Q85 · Which row correctly describes the reaction between propene and bromine, Br2(l)? 9701/11 Oct/Nov 2014

20 Which row correctly describes the reaction between propene and bromine, Br2(l)? reaction mechanism organic product A electrophilic addition CH3CHBrCH2Br B electrophilic addition CH3CH2CH2Br C nucleophilic substitution CH3CH2CH2Br D nucleophilic substitution CH3CHBrCH2Br

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2014

Q86 · Use of the Data Booklet is relevant to this question 9701/11 Oct/Nov 2014

21 Use of the Data Booklet is relevant to this question. Which compound has an Mr of 84 and will react with HBr to give a product with an Mr of 164.9? A B C D O

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2014

Q87 · 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

Q88 · Which row correctly describes the reaction between propene and bromine, Br2(l)? 9701/12 Oct/Nov 2014

20 Which row correctly describes the reaction between propene and bromine, Br2(l)? reaction mechanism organic product A electrophilic addition CH3CHBrCH2Br B electrophilic addition CH3CH2CH2Br C nucleophilic substitution CH3CH2CH2Br D nucleophilic substitution CH3CHBrCH2Br

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2014

Q89 · Use of the Data Booklet is relevant to this question 9701/12 Oct/Nov 2014

21 Use of the Data Booklet is relevant to this question. Which compound has an Mr of 84 and will react with HBr to give a product with an Mr of 164.9? A B C D O

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2014

Q90 · Methyl methylpropenoate is the monomer used to make Perspex 9701/12 Oct/Nov 2014

27 Methyl methylpropenoate is the monomer used to make Perspex. Which diagram correctly shows methyl methylpropenoate? A B CH3 CH2 C CH3 CH CH CO2CH3 CO2CH3 C D CH3 CH2 CH CO2CH2CH3 C CH CO2CH3 CH3

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2014

Q91 · 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

Q92 · The compound known as ‘gamma-linolenic acid’ is found in the seeds of the evening… 9701/13 Oct/Nov 2014

25 The compound known as ‘gamma-linolenic acid’ is found in the seeds of the evening primrose plant. CH3(CH2)4CH=CHCH2CH=CHCH2CH=CH(CH2)4CO2H gamma-linolenic acid How many cis-trans isomers are there with this structural formula? A 3 B 6 C 8 D 12

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2014

Q93 · The diagram shows the structure of the naturally-occurring molecule cholesterol 9701/13 Oct/Nov 2014

29 The diagram shows the structure of the naturally-occurring molecule cholesterol. H3C CH3 H CH3 H H H HO cholesterol Student X stated that the seventeen carbon atoms in the four rings all lie in the same plane. Student Y stated that this molecule displays cis-trans isomerism at the C = C double bond. Which of the students are correct? A both X and Y B neither X nor Y C X only D Y only

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2014

Q94 · Cottonseed oil contains large amounts of polyunsaturated carboxylic acids 9701/11 May/June 2015

22 Cottonseed oil contains large amounts of polyunsaturated carboxylic acids. When this oil is used to make margarine, the C=C double bonds in the unsaturated carboxylic acids are hydrogenated. What reagents and conditions would be suitable to bring about this hydrogenation reaction? A H2 gas, nickel catalyst, 400 °C B LiAl H4 in dry ether C NaBH4, aqueous solution D steam, concentrated H2SO4, 300 °C and 60 atm pressure

1 marks

Answer: A

This question in 9701/11 May/June 2015

Q95 · Which intermediate ion forms in the greatest amount during the addition of HBr to propene? 9701/11 May/June 2015

23 Which intermediate ion forms in the greatest amount during the addition of HBr to propene? A CH3CH+CH3 B CH3CH2CH2 + C CH3CH–CH2Br D CH3CHBrCH2 –

1 marks

Answer: A

This question in 9701/11 May/June 2015

Q96 · The citrus flavour of lemons is due to the compound limonene, present in both the peel… 9701/11 May/June 2015

29 The citrus flavour of lemons is due to the compound limonene, present in both the peel and the juice. limonene What is the mole ratio of carbon dioxide to water produced when limonene is completely burnt in oxygen? number of moles number of moles carbon dioxide water A 4 3 B 5 4 C 5 8 D 9 7

1 marks

Answer: B

This question in 9701/11 May/June 2015

Q97 · The diagram shows the structure of an alkene molecule 9701/11 May/June 2015

37 The diagram shows the structure of an alkene molecule. CH3 CH3 CH3 C C H C C H H H CH3 Which statements about this molecule are correct? 1 All the carbon atoms are in the same plane. 2 It has geometrical isomers. 3 It is optically active.

1 marks

Answer: C

This question in 9701/11 May/June 2015

Q98 · Which compounds will react with HBr to give the compound R? 9701/11 May/June 2015

39 Which compounds will react with HBr to give the compound R? Br R 1 2 3 OH

1 marks

Answer: A

This question in 9701/11 May/June 2015

Q99 · Four students, W, X, Y and Z, made the following statements about alkanes and alkenes 9701/12 May/June 2015

22 Four students, W, X, Y and Z, made the following statements about alkanes and alkenes. W ‘Bromine reacts with alkanes by electrophilic substitution.’ X ‘Bromine reacts with alkenes by a free-radical addition mechanism.’ Y ‘Alkenes can be oxidised by acidified manganate(VII) ions.’ Z ‘Alkenes are formed from alkanes by cracking.’ Which two students are correct? A W and X B W and Z C X and Y D Y and Z

1 marks

Answer: D

This question in 9701/12 May/June 2015

Q100 · In which structures do the four carbon atoms labelled C lie in the same plane? 9701/12 May/June 2015

37 In which structures do the four carbon atoms labelled C lie in the same plane? 1 2 3 C C C C C C C C C C C C

1 marks

Answer: B

This question in 9701/12 May/June 2015

Q101 · Calcium forms an ionic compound with carbon, called calcium carbide 9701/12 Oct/Nov 2015

5 Calcium forms an ionic compound with carbon, called calcium carbide. The oxidation number of carbon in calcium carbide is –1. Calcium carbide is readily hydrolysed by water giving two products only. What could be the formulae of calcium carbide and the two products of hydrolysis? calcium carbide products A Ca2C CaO and C2H4 B Ca2C Ca(OH)2 and C2H2 C CaC2 CaO and C2H4 D CaC2 Ca(OH)2 and C2H2

1 marks

This question in 9701/12 Oct/Nov 2015

Q102 · Which compounds, on heating with excess concentrated sulfuric acid, produce only one… 9701/12 Oct/Nov 2015

39 Which compounds, on heating with excess concentrated sulfuric acid, produce only one product with molecular formula C7H10? 1 2 3 OH OH OH OH OH OH

1 marks

This question in 9701/12 Oct/Nov 2015

Q103 · 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

Q104 · Geraniol and nerol are compounds found in some flower fragrances 9701/12 Feb/March 2016

21 Geraniol and nerol are compounds found in some flower fragrances. They are isomers of each other. CH3 CH3 C CH2OH C H H2C C H2C C H CH2OH H3C H2C H3C H2C C C C C H3C H H3C H geraniol nerol Which type of isomerism is shown here? A chain B geometrical (cis-trans) C optical D positional

1 marks

Answer: B

This question in 9701/12 Feb/March 2016

Q105 · A section showing two repeat units of an addition polymer is shown 9701/12 Feb/March 2016

22 A section showing two repeat units of an addition polymer is shown. CH3 CH3 CH3 CH3 C C C C Cl CH3 Cl CH3 What is the identity of the monomer that produced this polymer? A 2-chloro-3-methylbutane B 2-chloro-3-methylbut-2-ene C 2-chloropent-2-ene D 2,4-dichloro-3,3,4,5-tetramethylhexane

1 marks

Answer: B

This question in 9701/12 Feb/March 2016

Q106 · Hydrogen bromide can be added to T to give compound U 9701/12 Feb/March 2016

24 Hydrogen bromide can be added to T to give compound U. Compound U can be hydrolysed to compound V. step 1 step 2 Br OH T U V Four students, W, X, Y and Z, made the following statements. W All the atoms in a molecule of compound T lie in the same plane. X Compound V contains only one chiral centre. Y Step 1 is an electrophilic addition reaction. Z Step 2 is a nucleophilic substitution reaction. Which two students are correct? A W and Y B W and Z C X and Y D Y and Z

1 marks

Answer: D

This question in 9701/12 Feb/March 2016

Q107 · Structural isomerism and stereoisomerism should be considered in answering this question 9701/12 Feb/March 2016

25 Structural isomerism and stereoisomerism should be considered in answering this question. Compound J is reacted with KOH dissolved in ethanol. Three isomeric alkenes with molecular formula C4H8 are formed. What is J? A CH3 CH2 CH2 CH2 Br B CH3 CH CH2 CH3 Br C CH3 CH CH2 Br CH3 CH3 D CH3 C Br CH3

1 marks

Answer: B

This question in 9701/12 Feb/March 2016

Q108 · Which pair of reagents will take part in a redox reaction? 9701/11 May/June 2016

22 Which pair of reagents will take part in a redox reaction? A CH3CHCH2 + Br2 B CH3CH2CH2OH + concentrated H3PO4 C CH3COCH3 + HCN D HCO2C2H5 + dilute H2SO4

1 marks

Answer: A

This question in 9701/11 May/June 2016

Q109 · The diagram shows the structure of cyclohexene 9701/11 May/June 2016

38 The diagram shows the structure of cyclohexene. cyclohexene Which structures could be formed by addition reactions with cyclohexene as the only reactant? 1 2 3 n n

1 marks

Answer: B

This question in 9701/11 May/June 2016

Q110 · Oct-1-ene, CH3(CH2)5CH=CH2, can be thermally cracked 9701/12 May/June 2016

22 Oct-1-ene, CH3(CH2)5CH=CH2, can be thermally cracked. Which combination of compounds W, X, Y and Z can be obtained by thermally cracking oct-1-ene? CH2=CH2 CH3CH=CH2 CH3CH2CH3 CH2=CHCH=CH2 W X Y Z A W, X, Y and Z B W, X and Y only C W, X and Z only D W and X only

1 marks

Answer: A

This question in 9701/12 May/June 2016

Q111 · 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

Q112 · The diagram shows the structure of 1,3-butadiene 9701/13 May/June 2016

21 The diagram shows the structure of 1,3-butadiene. H H C C H H C C H H 1,3-butadiene The addition reaction between 1,3-butadiene and two molecules of hydrogen bromide can produce three structurally isomeric products. How many of these products have at least one chiral centre? A 0 B 1 C 2 D 3

1 marks

Answer: C

This question in 9701/13 May/June 2016

Q113 · 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

Q114 · Part of the structure of a fungicide, strobilurin, is shown 9701/11 Oct/Nov 2016

23 Part of the structure of a fungicide, strobilurin, is shown. R and R' are inert groups. O OCH3 R' R strobilurin In this reaction, strobilurin is warmed with aqueous sulfuric acid producing compound X. Compound X is then treated with hydrogen in the presence of a nickel catalyst producing compound Y. What could be the structure of compound Y? A B O OH HO OCH3 R' R' R R C D OH O OH OH OH R' R' R R OH

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2016

Q115 · X, Y and Z are three isomeric alcohols 9701/11 Oct/Nov 2016

25 X, Y and Z are three isomeric alcohols. X CH3CH2CH2CH2CH2OH Y CH3CH2CH(OH)CH2CH3 Z (CH3)2C(OH)CH2CH3 Two or more of these alcohols react with mild oxidising agents. One of these alcohols, when dehydrated, will give a pair of cis-trans isomers with molecular formula C5H10. Which row is correct? reacts with mild gives cis-trans oxidising reagents isomers A X, Y and Z Y only B X, Y and Z Z only C X and Y only Y only D X and Y only Z only

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2016

Q116 · 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

Q117 · X, Y and Z are three isomeric alcohols 9701/13 Oct/Nov 2016

25 X, Y and Z are three isomeric alcohols. X CH3CH2CH2CH2CH2OH Y CH3CH2CH(OH)CH2CH3 Z (CH3)2C(OH)CH2CH3 Two or more of these alcohols react with mild oxidising agents. One of these alcohols, when dehydrated, will give a pair of cis-trans isomers with molecular formula C5H10. Which row is correct? reacts with mild gives cis-trans oxidising reagents isomers A X, Y and Z Y only B X, Y and Z Z only C X and Y only Y only D X and Y only Z only

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2016

Q118 · 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

Q119 · Which equation correctly describes the complete combustion of an alkene, CnH2n? 9701/13 May/June 2017

3 Which equation correctly describes the complete combustion of an alkene, CnH2n? A CnH2n + 2 3 nO2 → nCO2 + 2nH2O B CnH2n + 2 3 nO2 → nCO2 + nH2O C CnH2n + 2nO2 → nCO2 + nH2O D CnH2n + 2nO2 → nCO2 + 2nH2O

1 marks

Answer: B

This question in 9701/13 May/June 2017

Q120 · 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

Q121 · Bromine reacts with ethene in the dark 9701/13 May/June 2017

25 Bromine reacts with ethene in the dark. Which description of the organic intermediate in this reaction is correct? A It has a negative charge. B It is a free radical. C It is a nucleophile. D It is an electrophile.

1 marks

Answer: D

This question in 9701/13 May/June 2017

Q122 · Many, but not all, organic reactions need to be heated before a reaction occurs 9701/11 Oct/Nov 2017

22 Many, but not all, organic reactions need to be heated before a reaction occurs. Which reaction occurs quickly at room temperature, 20 °C? A C2H4 + Br2 → C2H4Br2 B C2H4 + H2O → CH3CH2OH C CH3CH2OH → C2H4 + H2O D CH3CH2OH + HBr → CH3CH2Br + H2O

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2017

Q123 · 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

Q124 · 2,3-dimethylpent-2-ene, (CH3)2C=C(CH3)CH2CH3, is treated with cold, dilute KMnO4 9701/12 Oct/Nov 2017

24 2,3-dimethylpent-2-ene, (CH3)2C=C(CH3)CH2CH3, is treated with cold, dilute KMnO4. The product of this reaction is treated with an excess of concentrated H2SO4 at 180 °C, giving a mixture of isomeric hydrocarbons with molecular formula C7H12. What is the name of one of the isomeric hydrocarbons? A 2,3-dimethylpenta-1,2-diene B cis-2,3-dimethylpenta-1,3-diene C 2,3-dimethylpenta-1,4-diene D 3,4-dimethylpenta-1,3-diene

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2017

Q125 · Many, but not all, organic reactions need to be heated before a reaction occurs 9701/13 Oct/Nov 2017

22 Many, but not all, organic reactions need to be heated before a reaction occurs. Which reaction occurs quickly at room temperature, 20 °C? A C2H4 + Br2 → C2H4Br2 B C2H4 + H2O → CH3CH2OH C CH3CH2OH → C2H4 + H2O D CH3CH2OH + HBr → CH3CH2Br + H2O

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2017

Q126 · Which types of stereoisomerism are shown by 2,4-dimethylhex-2-ene? 9701/12 Feb/March 2018

20 Which types of stereoisomerism are shown by 2,4-dimethylhex-2-ene? A both cis-trans isomerism and optical isomerism B cis-trans isomerism only C neither cis-trans isomerism nor optical isomerism D optical isomerism only

1 marks

Answer: D

This question in 9701/12 Feb/March 2018

Q127 · A reaction occurs when a sample of 1-chloropropane is heated under reflux with sodium… 9701/12 Feb/March 2018

27 A reaction occurs when a sample of 1-chloropropane is heated under reflux with sodium hydroxide dissolved in ethanol. Which row is correct? type of reaction name of product A elimination propan-1-ol B elimination propene C substitution propan-1-ol D substitution propene

1 marks

Answer: B

This question in 9701/12 Feb/March 2018

Q128 · Which reagent could detect the presence of alcohol in a mixture consisting mainly of… 9701/11 May/June 2018

24 Which reagent could detect the presence of alcohol in a mixture consisting mainly of alkanes and alkenes? A Na B Br2 (in CCl 4) C KMnO4(aq) D 2,4-dinitrophenylhydrazine

1 marks

Answer: A

This question in 9701/11 May/June 2018

Q129 · 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

Q130 · Compound Y is treated with an excess of hydrogen gas in the presence of a nickel catalyst 9701/12 May/June 2018

20 Compound Y is treated with an excess of hydrogen gas in the presence of a nickel catalyst. The product is fully saturated. compound Y What is the number of chiral carbon atoms in the product? A 5 B 6 C 7 D 8

1 marks

Answer: A

This question in 9701/12 May/June 2018

Q131 · Maleic acid is used in the food industry and for stabilising drugs 9701/12 May/June 2018

22 Maleic acid is used in the food industry and for stabilising drugs. It is the cis-isomer of butenedioic acid and has the structural formula HO2CCH=CHCO2H. What is the product formed from the reaction of maleic acid with cold, dilute, acidified manganate(VII) ions? A HO2CCH(OH)CH(OH)CO2H B HO2CCO2H C HO2CCH2CH(OH)CO2H D HO2CCOCOCO2H

1 marks

Answer: A

This question in 9701/12 May/June 2018

Q132 · Which compounds show geometrical (cis-trans) isomerism? 9701/12 May/June 2018

37 Which compounds show geometrical (cis-trans) isomerism? 1 CH3CH=C(CH3)C2H5 2 CH3CH=CHCH2CH2CH3 3 C2H5CH=CHC2H5

1 marks

Answer: A

This question in 9701/12 May/June 2018

Q133 · Sibirene, C15H24, is reacted with an excess of HBr(g) 9701/13 May/June 2018

21 Sibirene, C15H24, is reacted with an excess of HBr(g). The major product is X. excess HBr(g) X sibirene What is the skeletal formula of X? A B Br Br Br Br C D Br Br Br Br

1 marks

Answer: D

This question in 9701/13 May/June 2018

Q134 · Which compound is a secondary alcohol that can be dehydrated to form an alkene with Mr =… 9701/13 May/June 2018

25 Which compound is a secondary alcohol that can be dehydrated to form an alkene with Mr = 70? A B C D OH OH OH OH

1 marks

Answer: B

This question in 9701/13 May/June 2018

Q135 · Complete combustion of a sample of a hydrocarbon gave 0.132 g of carbon dioxide and 0.054… 9701/13 May/June 2018

31 Complete combustion of a sample of a hydrocarbon gave 0.132 g of carbon dioxide and 0.054 g of water. Which formulae could correctly represent this hydrocarbon? 1 CH2=CH2 2 CH3CH=CH2 3 CH3CH=CHCH3

1 marks

Answer: A

This question in 9701/13 May/June 2018

Q136 · 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

Q137 · A new jet fuel has been produced that is a mixture of different structural isomers of… 9701/11 Oct/Nov 2018

22 A new jet fuel has been produced that is a mixture of different structural isomers of compound Q. Q Which skeletal formula represents a structural isomer of Q? A B C D

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2018

Q138 · The conversion of propene to propan-2-ol can be carried out in two stages represented by… 9701/11 Oct/Nov 2018

23 The conversion of propene to propan-2-ol can be carried out in two stages represented by the equations shown. reaction 1 CH3CH=CH2(g) + HI(g) → CH3CHICH3(l) reaction 2 CH3CHICH3(l) + KOH(aq) → CH3CH(OH)CH3(aq) + K+(aq) + I–(aq) How can these two reactions be described? reaction 1 reaction 2 A addition elimination B addition substitution C elimination substitution D substitution elimination

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2018

Q139 · Compound J, C15H23Br2Cl, is reacted with an excess of a hot concentrated solution of… 9701/11 Oct/Nov 2018

25 Compound J, C15H23Br2Cl, is reacted with an excess of a hot concentrated solution of sodium hydroxide in ethanol. One of the products is X. excess NaOH Cl Br in ethanol X Br compound J What could be the skeletal formula of X? A B C D

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2018

Q140 · 2-methylpropene can react in more than one way with chlorine 9701/11 Oct/Nov 2018

37 2-methylpropene can react in more than one way with chlorine. One of the reactions follows the pathway shown. CH3 CH3 CH3 + CH2 C + Cl 2 → Cl CH2 C + Cl – → Cl CH2 C + HCl CH3 CH3 CH2 2-methylpropene intermediate product Which statements about this mechanism are correct? 1 The intermediate has all carbon atoms in the same plane. 2 There is an electrophilic attack on the double bond. 3 It is a free radical mechanism.

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2018

Q141 · Polyethene is made by the polymerisation of ethene 9701/12 Oct/Nov 2018

22 Polyethene is made by the polymerisation of ethene. Which statement is correct? A The monomer and the polymer have different empirical formulae. B The monomer can be oxidised without heat whereas the polymer cannot. C The monomer can be used as a fuel whereas the polymer cannot. D The monomer has greater van der Waals’ forces than the polymer.

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2018

Q142 · Which statement about compound Q is correct? 9701/12 Oct/Nov 2018

24 Which statement about compound Q is correct? CH3C CHCH2CH3 CO2CH3 Q H CH3 A It could be polymerised to give a polymer with the repeat unit C C . CO2CH3 CH2CH3 Cl Cl B It reacts with chlorine by a free radical mechanism to give CH3CH C CH CH3 . CO2CH3 H OH OH C It reacts with cold, dilute acidified manganate(VII) to give CH3C C CH2CH3 . CO2CH3 H Br Br D It reacts with bromine via a free radical mechanism to give CH3 C C CH2CH3 . CO2CH3 H

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2018

Q143 · Which bromopropenes would react with cold bromine in the dark to form a product… 9701/12 Oct/Nov 2018

37 Which bromopropenes would react with cold bromine in the dark to form a product containing a chiral carbon atom? 1 CHBr=CHCH3 2 CH2=CHCH2Br 3 CH2=CBrCH3

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2018

Q144 · A new jet fuel has been produced that is a mixture of different structural isomers of… 9701/13 Oct/Nov 2018

22 A new jet fuel has been produced that is a mixture of different structural isomers of compound Q. Q Which skeletal formula represents a structural isomer of Q? A B C D

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2018

Q145 · Compound J, C15H23Br2Cl, is reacted with an excess of a hot concentrated solution of… 9701/13 Oct/Nov 2018

25 Compound J, C15H23Br2Cl, is reacted with an excess of a hot concentrated solution of sodium hydroxide in ethanol. One of the products is X. excess NaOH Cl Br in ethanol X Br compound J What could be the skeletal formula of X? A B C D

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2018

Q146 · 2-methylpropene can react in more than one way with chlorine 9701/13 Oct/Nov 2018

37 2-methylpropene can react in more than one way with chlorine. One of the reactions follows the pathway shown. CH3 CH3 CH3 + CH2 C + Cl 2 → Cl CH2 C + Cl – → Cl CH2 C + HCl CH3 CH3 CH2 2-methylpropene intermediate product Which statements about this mechanism are correct? 1 The intermediate has all carbon atoms in the same plane. 2 There is an electrophilic attack on the double bond. 3 It is a free radical mechanism.

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2018

Q147 · 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

Q148 · What is the structural formula of the major product when hydrogen bromide reacts with… 9701/11 May/June 2019

22 What is the structural formula of the major product when hydrogen bromide reacts with 2-methylbut-2-ene? A CH2BrCH(CH3)CH2CH3 B (CH3)2CBrCH2CH3 C (CH3)2CHCHBrCH3 D (CH3)2CHCH2CH2Br

1 marks

Answer: B

This question in 9701/11 May/June 2019

Q149 · 3-methylbut-1-ene can undergo different types of reaction 9701/12 May/June 2019

20 3-methylbut-1-ene can undergo different types of reaction. Cl 1 2 Cl Which row correctly identifies the reaction types? reaction 1 reaction 2 A oxidation electrophilic addition B oxidation nucleophilic addition C reduction electrophilic addition D reduction nucleophilic addition

1 marks

Answer: C

This question in 9701/12 May/June 2019

Q150 · Compound X does not show cis-trans isomerism 9701/12 May/June 2019

21 Compound X does not show cis-trans isomerism. What could be the identity of compound X? A 1,1,2-trichloropropene B 1,2,3-trichloropropene C 1-chlorobut-1-ene D 1-chlorobut-2-ene

1 marks

Answer: A

This question in 9701/12 May/June 2019

Q151 · 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

Q152 · Which product can be made from bromoethane by an elimination reaction? 9701/12 May/June 2019

25 Which product can be made from bromoethane by an elimination reaction? A ethanol B ethene C ethylamine D propanenitrile

1 marks

Answer: B

This question in 9701/12 May/June 2019

Q153 · Propene, bromine and hydrogen bromide are mixed in the dark 9701/12 May/June 2019

26 Propene, bromine and hydrogen bromide are mixed in the dark. A number of products are formed, some in very small quantities. Which substance will not be present in the mixture of products? A 1-bromopropane B 2-bromopropane C 1,1-dibromopropane D 1,2-dibromopropane

1 marks

Answer: C

This question in 9701/12 May/June 2019

Q154 · In polymer Z every carbon atom in the polymer chain is bonded to one hydrogen atom and… 9701/13 May/June 2019

22 In polymer Z every carbon atom in the polymer chain is bonded to one hydrogen atom and one methyl group. Which alkene could be polymerised to make polymer Z? A but-1-ene B but-2-ene C methylpropene D propene

1 marks

Answer: B

This question in 9701/13 May/June 2019

Q155 · 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

Q156 · Bromine reacts with ethene in an addition reaction 9701/13 May/June 2019

38 Bromine reacts with ethene in an addition reaction. Which statements about this reaction are correct? 1 It is the basis of a test for unsaturation in alkenes. 2 It leads to an increase in each of the H–C–H bond angles. 3 A nucleophile attacks the C=C bond in ethene.

1 marks

Answer: D

This question in 9701/13 May/June 2019

Q157 · Which substance reacts with trichloroethene to give a chiral product? 9701/11 Oct/Nov 2019

20 Which substance reacts with trichloroethene to give a chiral product? A Br2 B HCl C NaCN D NaOH

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2019

Q158 · 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

Q159 · Structural isomerism and stereoisomerism should be considered when answering this question 9701/12 Oct/Nov 2019

20 Structural isomerism and stereoisomerism should be considered when answering this question. How many isomers with the formula C5H10 have structures that involve π bonding? A 3 B 4 C 5 D 6

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2019

Q160 · 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

Q161 · Following fractional distillation of crude oil, which processes can be used to produce… 9701/12 Oct/Nov 2019

37 Following fractional distillation of crude oil, which processes can be used to produce propene from larger hydrocarbon molecules? 1 cracking 2 reduction 3 polymerisation

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2019

Q162 · Which substance reacts with trichloroethene to give a chiral product? 9701/13 Oct/Nov 2019

20 Which substance reacts with trichloroethene to give a chiral product? A Br2 B HCl C NaCN D NaOH

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2019

Q163 · 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

Q164 · A section of a polymer chain is shown 9701/12 Feb/March 2020

24 A section of a polymer chain is shown. What is the correct monomer? A B C D

1 marks

Answer: A

This question in 9701/12 Feb/March 2020

Q165 · Which statements comparing ethene and ethane are correct? 9701/12 Feb/March 2020

40 Which statements comparing ethene and ethane are correct? 1 The bond angles in ethene are larger than the bond angles in ethane. 2 Ethene reacts much more quickly with bromine in the dark than ethane does. 3 Complete combustion of 0.01 mol of ethene or ethane produces the same volume of gas measured at room temperature and pressure.

1 marks

Answer: A

This question in 9701/12 Feb/March 2020

Q166 · But-1-ene and but-2-ene are treated separately with cold, dilute acidified manganate(VII)… 9701/11 May/June 2020

22 But-1-ene and but-2-ene are treated separately with cold, dilute acidified manganate(VII) ions. Four students, W, X, Y and Z, make statements about these alkenes and the diols formed from them. W One diol contains two primary alcohol groups. X One diol contains a primary and a secondary alcohol group. Y One diol contains two secondary alcohol groups. Z Both alkenes exhibit cis-trans isomerism. Which two students are correct? A W and Y B W and Z C X and Y D X and Z

1 marks

Answer: C

This question in 9701/11 May/June 2020

Q167 · What is the major product Z of the following reaction? 9701/11 May/June 2020

27 What is the major product Z of the following reaction? an excess of dry HBr Z warm A B C D Br Br Br Br Br Br Br Br

1 marks

Answer: B

This question in 9701/11 May/June 2020

Q168 · Which substance forms propanoic acid as one of the products when it reacts with hot… 9701/12 May/June 2020

25 Which substance forms propanoic acid as one of the products when it reacts with hot concentrated acidified potassium manganate(VII)? A but-1-ene B but-2-ene C 2-methylpropene D 2-methylbut-1-ene

1 marks

Answer: A

This question in 9701/12 May/June 2020

Q169 · Ethene reacts with aqueous bromine to give two products, CH2BrCH2Br and CH2BrCH2OH 9701/12 May/June 2020

28 Ethene reacts with aqueous bromine to give two products, CH2BrCH2Br and CH2BrCH2OH. Which statement about these products is correct? A Both products are obtained in this reaction by nucleophilic substitution. B Both products are obtained in this reaction by nucleophilic addition. C Both products can be hydrolysed to form the same organic compound. D Both products can form hydrogen bonds with water.

1 marks

Answer: C

This question in 9701/12 May/June 2020

Q170 · The diagram shows the structure of buta-1,3-diene 9701/12 May/June 2020

30 The diagram shows the structure of buta-1,3-diene. buta-1,3-diene H H C C H H C C H H The addition reaction between buta-1,3-diene and two molecules of hydrogen bromide can produce three structurally isomeric products. How many of these products have at least one chiral centre? A 0 B 1 C 2 D 3

1 marks

Answer: C

This question in 9701/12 May/June 2020

Q171 · Structural and stereoisomerism should be considered when answering this question 9701/13 May/June 2020

20 Structural and stereoisomerism should be considered when answering this question. When trans-pent-2-ene reacts with HBr, how many different products can form? A 1 B 2 C 3 D 4

1 marks

Answer: C

This question in 9701/13 May/June 2020

Q172 · 2-methylbut-2-ene reacts with HBr(g) to form two isomeric products 9701/13 May/June 2020

28 2-methylbut-2-ene reacts with HBr(g) to form two isomeric products. During the reaction two positively charged intermediates can be made. Which diagram shows the more stable of the two positively charged intermediates? A B C D Br + Br + + +

1 marks

Answer: A

This question in 9701/13 May/June 2020

Q173 · Two students each make a statement about 2-methylbut-1-ene 9701/11 Oct/Nov 2020

21 Two students each make a statement about 2-methylbut-1-ene. Student 1 states that 2-methylbut-1-ene has geometrical isomers. Student 2 states that 2-methylbut-1-ene reacts with HBr in an addition reaction to give 1-bromo-2-methylbutane as the main product. Which students 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 9701/11 Oct/Nov 2020

Q174 · The unsaturated hydrocarbon octa-1,3,5,7-tetraene, C8H10, can display geometric isomerism 9701/12 Oct/Nov 2020

20 The unsaturated hydrocarbon octa-1,3,5,7-tetraene, C8H10, can display geometric isomerism. octa-1,3,5,7-tetraene CH2=CHCH=CHCH=CHCH=CH2 How many isomers exist? A 2 B 3 C 4 D 8

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2020

Q175 · A polymer has the following repeat unit 9701/12 Oct/Nov 2020

22 A polymer has the following repeat unit. It is made from two different monomers. CH2 CHCl CH2 CH CH CH2 Which pair of monomers could be used to make this polymer? A CH2=CHCl and CH2=CH2 B CH2=CHCl and CH2=CH–CH=CH2 C CH3–CH2Cl and CH3–CH=CH–CH3 D CH3–CH=CH–CH3 and CH2=CHCl

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2020

Q176 · Two students each make a statement about 2-methylbut-1-ene 9701/13 Oct/Nov 2020

21 Two students each make a statement about 2-methylbut-1-ene. Student 1 states that 2-methylbut-1-ene has geometrical isomers. Student 2 states that 2-methylbut-1-ene reacts with HBr in an addition reaction to give 1-bromo-2-methylbutane as the main product. Which students 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 9701/13 Oct/Nov 2020

Q177 · The diagram shows the structure of a bromo compound that may be formed by the reaction of… 9701/12 Feb/March 2021

22 The diagram shows the structure of a bromo compound that may be formed by the reaction of bromine with a hydrocarbon. CH2Br H3C C CH3 CH2Br Which row is correct? type of reaction mechanism A addition electrophilic B addition nucleophilic C substitution nucleophilic D substitution free-radical

1 marks

Answer: D

This question in 9701/12 Feb/March 2021

Q178 · Part of the structure of strobilurin is shown 9701/12 Feb/March 2021

23 Part of the structure of strobilurin is shown. R and R' are inert groups. strobilurin O OCH3 R' R Strobilurin is warmed with aqueous sulfuric acid producing compound X. Compound X is then treated with hydrogen in the presence of a nickel catalyst producing compound Y. What could be the structure of compound Y? A B O OH HO OCH3 R' R' R R C D OH O OH OH OH R' R' R R OH

1 marks

Answer: A

This question in 9701/12 Feb/March 2021

Q179 · Dibromopentanes can undergo ‘double elimination’ reactions to produce hydrocarbons 9701/12 Feb/March 2021

25 Dibromopentanes can undergo ‘double elimination’ reactions to produce hydrocarbons. 2NaOH + C5H10Br2  C5H8 + 2NaBr + 2H2O Which isomer produces only one hydrocarbon product? A 1,5-dibromopentane B 1,4-dibromopentane C 2,3-dibromopentane D 2,4-dibromopentane

1 marks

Answer: A

This question in 9701/12 Feb/March 2021

Q180 · 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

Q181 · Limonene is a hydrocarbon found in the rind of citrus fruits 9701/11 May/June 2021

23 Limonene is a hydrocarbon found in the rind of citrus fruits. limonene What is the molecular formula of limonene? A C10H12 B C10H14 C C10H16 D C10H18

1 marks

Answer: C

This question in 9701/11 May/June 2021

Q182 · The table describes four reactions of propene 9701/11 May/June 2021

29 The table describes four reactions of propene. Which row is correct? name of main reagent used organic product A aqueous bromine 2-bromopropane B cold acidified aqueous potassium manganate(VII) propane-1,3-diol C hydrogen chloride 2-chloropropane D steam propan-1-ol

1 marks

Answer: C

This question in 9701/11 May/June 2021

Q183 · 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

Q184 · Compound P is treated with an excess of hydrogen gas in the presence of a nickel catalyst 9701/12 May/June 2021

20 Compound P is treated with an excess of hydrogen gas in the presence of a nickel catalyst. The product Q is fully saturated. compound P What is the number of chiral carbon atoms in the product Q? A 4 B 5 C 6 D 7

1 marks

Answer: B

This question in 9701/12 May/June 2021

Q185 · Compound X is a straight chain hydrocarbon with an Mr of 84 9701/12 May/June 2021

32 Compound X is a straight chain hydrocarbon with an Mr of 84. What can be determined about X? 1 empirical formula 2 molecular formula 3 whether X contains a C=C bond or not

1 marks

Answer: A

This question in 9701/12 May/June 2021

Q186 · 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

Q187 · What is the correct mechanism for the addition of hydrogen bromide to ethene? 9701/13 May/June 2021

22 What is the correct mechanism for the addition of hydrogen bromide to ethene? H H H 4H H 4H \_ / |_| |_| C=C H—C—C* —»> H—C—C—Br /¢ \ | [Near || H H Br H H H ro Chis. H H H 4H H H \_ / |_| |_| C=C —, H—C—C; —»> H—C—C—Br H _H H H H H ato Chee H H H H H H \ |_| |_| C==C —, H—C—C — > H—C—C—Br H wa Br H H oH Bro Che. H H H H H H \ |_| |_| D —=C H—C—C* H—C—C—Br “( \ \ Br H H H H H Ho

1 marks

Answer: B

This question in 9701/13 May/June 2021

Q188 · Structural isomerism only should be considered when answering this question 9701/11 Oct/Nov 2021

21 Structural isomerism only should be considered when answering this question. Molecule X contains three C=C double bonds. One mole of X is reacted with three moles of HBr. The carbon skeleton is unchanged. molecule X How many different products are formed? A 3 B 4 C 6 D 8

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2021

Q189 · A diketo acid is a compound with two ketone groups and one carboxylic acid group 9701/11 Oct/Nov 2021

37 A diketo acid is a compound with two ketone groups and one carboxylic acid group. limonene terpinolene Which statements about the reactions of limonene and terpinolene are correct? 1 When reacted with an excess of hydrogen and a nickel catalyst, limonene and terpinolene produce the same compound. 2 An excess of hot concentrated acidified KMnO4 reacts with limonene and with terpinolene to form different diketo acids. 3 The reactions of limonene and terpinolene with an excess of Br2 produce positional isomers with the same number of chiral carbon atoms.

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2021

Q190 · One molecule of dodecane, C12H26, is cracked, producing three product molecules, X, Y and… 9701/11 Oct/Nov 2021

38 One molecule of dodecane, C12H26, is cracked, producing three product molecules, X, Y and Z. X is a straight chain alkane. Y and Z are straight chain alkenes with different Mr values. Which statements about X, Y and Z are correct? 1 If Y and Z are but-1-ene and ethene respectively, X will be hexane. 2 If X is butane, then Y and Z could both show cis-trans isomerism. 3 X could be octane.

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2021

Q191 · Structural and stereoisomerism should be taken into account when answering this question 9701/12 Oct/Nov 2021

22 Structural and stereoisomerism should be taken into account when answering this question. Y is a gaseous hydrocarbon which decolourises aqueous bromine. It contains no rings. 10.0 g of Y occupies a volume of 3.43 dm3 under room conditions. How many isomeric structures are possible for Y? A 4 B 5 C 6 D 7

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2021

Q192 · Structural and stereoisomerism should be taken into account when answering this question 9701/12 Oct/Nov 2021

27 Structural and stereoisomerism should be taken into account when answering this question. An organic compound, X, is dehydrated by heating with concentrated phosphoric(V) acid. Only two organic products are formed. What could be X? A B C D OH OH OH OH OH

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2021

Q193 · Which of the molecular formulae represent at least one compound that can undergo addition… 9701/12 Oct/Nov 2021

38 Which of the molecular formulae represent at least one compound that can undergo addition polymerisation? 1 C4H8 2 C2H3Cl 3 C3H6O

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2021

Q194 · Hex-2-ene can be made by the reaction shown 9701/13 Oct/Nov 2021

20 Hex-2-ene can be made by the reaction shown. O– HO H + I– I Which statement about this reaction is correct? A (CH3)3CO– is behaving as a Brønsted-Lowry base. B (CH3)3CO– is behaving as an oxidising agent. C The C–I bond breaks via homolytic fission. D This is a hydrolysis reaction.

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2021

Q195 · Structural isomerism only should be considered when answering this question 9701/13 Oct/Nov 2021

21 Structural isomerism only should be considered when answering this question. Molecule X contains three C=C double bonds. One mole of X is reacted with three moles of HBr. The carbon skeleton is unchanged. molecule X How many different products are formed? A 3 B 4 C 6 D 8

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2021

Q196 · A diketo acid is a compound with two ketone groups and one carboxylic acid group 9701/13 Oct/Nov 2021

37 A diketo acid is a compound with two ketone groups and one carboxylic acid group. limonene terpinolene Which statements about the reactions of limonene and terpinolene are correct? 1 When reacted with an excess of hydrogen and a nickel catalyst, limonene and terpinolene produce the same compound. 2 An excess of hot concentrated acidified KMnO4 reacts with limonene and with terpinolene to form different diketo acids. 3 The reactions of limonene and terpinolene with an excess of Br2 produce positional isomers with the same number of chiral carbon atoms.

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2021

Q197 · One molecule of dodecane, C12H26, is cracked, producing three product molecules, X, Y and… 9701/13 Oct/Nov 2021

38 One molecule of dodecane, C12H26, is cracked, producing three product molecules, X, Y and Z. X is a straight chain alkane. Y and Z are straight chain alkenes with different Mr values. Which statements about X, Y and Z are correct? 1 If Y and Z are but-1-ene and ethene respectively, X will be hexane. 2 If X is butane, then Y and Z could both show cis-trans isomerism. 3 X could be octane.

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2021

Q198 · Oct-1-ene, CH3(CH2)5CH=CH2, can be thermally cracked 9701/11 May/June 2022

30 Oct-1-ene, CH3(CH2)5CH=CH2, can be thermally cracked. Which of the compounds W, X, Y and Z can be obtained by thermally cracking oct-1-ene? W X Y Z CH2=CH2 CH3CH=CH2 CH3CH2CH3 CH2=CHCH=CH2 A W, X, Y and Z B W, X and Y only C W, X and Z only D W and X only

1 marks

Answer: A

This question in 9701/11 May/June 2022

Q199 · Crotyl alcohol, CH3CH=CHCH2OH, is a colourless liquid which is used as a solvent 9701/11 May/June 2022

34 Crotyl alcohol, CH3CH=CHCH2OH, is a colourless liquid which is used as a solvent. Crotyl alcohol will react separately with Br2, K2Cr2O7 / H+, conc. KMnO4 / H+ and PCl 5 under suitable conditions. Which row is correct? reactant conditions main product A Br2 room temperature CH3CH=CHCH2Br B K2Cr2O7 / H+ heat under reflux CH3CH=CHCHO C conc. KMnO4 / H+ heat under reflux CH3CH=CHCO2H D PCl 5 room temperature CH3CH=CHCH2Cl

1 marks

Answer: D

This question in 9701/11 May/June 2022

Q200 · The alkene shown reacts with an excess of HBr via an electrophilic addition reaction 9701/12 May/June 2022

30 The alkene shown reacts with an excess of HBr via an electrophilic addition reaction. What is the major product formed? A 3,5-dibromo-2-methylhexane B 2,5-dibromo-2-methylhexane C 2,6-dibromo-2-methylhexane D 3,6-dibromo-2-methylhexane

1 marks

Answer: B

This question in 9701/12 May/June 2022

Q201 · Cyclohexene, as shown in the diagram, can form an addition polymer 9701/12 May/June 2022

39 Cyclohexene, as shown in the diagram, can form an addition polymer. cyclohexene Which structure represents a section of the polymer? A B C D

1 marks

Answer: C

This question in 9701/12 May/June 2022

Q202 · Structural isomerism and stereoisomerism should be considered when answering this question 9701/13 May/June 2022

29 Structural isomerism and stereoisomerism should be considered when answering this question. Y is a gaseous hydrocarbon which decolourises aqueous bromine. 10.0 g of Y occupies a volume of 3.43 dm3 under room conditions. How many isomeric structures are possible for Y? A 4 B 5 C 6 D 7

1 marks

Answer: C

This question in 9701/13 May/June 2022

Q203 · Mixture R consists of one mole of C3H6 and one mole of C4H6 9701/11 Oct/Nov 2022

2 Mixture R consists of one mole of C3H6 and one mole of C4H6. What is the minimum number of moles of oxygen molecules needed for complete combustion of mixture R? A 6.5 B 7 C 10 D 20

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2022

Q204 · Which pair of reagents react together in a redox reaction? 9701/11 Oct/Nov 2022

28 Which pair of reagents react together in a redox reaction? A CH3CHCH2 + Br2 B CH3CH2CH2OH + concentrated H3PO4 C CH3COCH3 + HCN D HCO2C2H5 + dilute H2SO4

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2022

Q205 · 2-bromopropane reacts with hot ethanolic sodium hydroxide 9701/11 Oct/Nov 2022

37 2-bromopropane reacts with hot ethanolic sodium hydroxide. Which substance is the major product of this reaction? A propan-1-ol B propan-2-ol C 2-hydroxypropene D propene

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2022

Q206 · Photochemical smog is a type of air pollution produced in urban areas by the effect of… 9701/12 Oct/Nov 2022

24 Photochemical smog is a type of air pollution produced in urban areas by the effect of sunlight on substances released from vehicle exhausts. Which mixture of primary pollutants leads to the formation of photochemical smog? A carbon dioxide and water vapour B carbon monoxide and unburnt hydrocarbons C nitrogen oxide and unburnt hydrocarbons D sulfur dioxide and water vapour

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2022

Q207 · What is the major product formed when compound R is warmed with an excess of HBr? 9701/12 Oct/Nov 2022

29 What is the major product formed when compound R is warmed with an excess of HBr? R OH OH A B C D Br Br OH Br OH Br Br Br OH Br Br Br

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2022

Q208 · Cis-but-2-ene reacts with cold dilute acidified potassium manganate(VII) solution to give… 9701/12 Oct/Nov 2022

30 cis-but-2-ene reacts with cold dilute acidified potassium manganate(VII) solution to give product X. cis-but-2-ene reacts with hot concentrated acidified potassium manganate(VII) solution to give product Y. Which row describing the reactions of X and Y is correct? when sodium metal is added to when sodium hydroxide solution is separate samples of X and Y added to separate samples of X and Y A both X and Y will react neither X nor Y will react B both X and Y will react only one of X and Y will react C only one of X and Y will react neither X nor Y will react D only one of X and Y will react only one of X and Y will react

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2022

Q209 · For which reaction will the major organic product have the lowest relative molecular mass? 9701/12 Oct/Nov 2022

31 For which reaction will the major organic product have the lowest relative molecular mass? A Bromoethane is heated under reflux with an aqueous solution of sodium hydroxide. B Bromoethane is heated under reflux with a solution of sodium cyanide in ethanol. C 2-bromopropane is heated under reflux with an aqueous solution of sodium hydroxide. D 2-bromopropane is heated under reflux with concentrated ethanolic sodium hydroxide.

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2022

Q210 · Which pair of reagents react together in a redox reaction? 9701/13 Oct/Nov 2022

28 Which pair of reagents react together in a redox reaction? A CH3CHCH2 + Br2 B CH3CH2CH2OH + concentrated H3PO4 C CH3COCH3 + HCN D HCO2C2H5 + dilute H2SO4

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2022

Q211 · 2-bromopropane reacts with hot ethanolic sodium hydroxide 9701/13 Oct/Nov 2022

37 2-bromopropane reacts with hot ethanolic sodium hydroxide. Which substance is the major product of this reaction? A propan-1-ol B propan-2-ol C 2-hydroxypropene D propene

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2022

Q212 · Cyclohexene, C6H10, is a hydrocarbon with a six-membered ring of carbon atoms 9701/12 Feb/March 2023

29 Cyclohexene, C6H10, is a hydrocarbon with a six-membered ring of carbon atoms. It has several structural isomers that are straight-chain alkenes. The number of double bonds in each of these molecules is P. What is the shape of the cyclohexene molecule and what is the value of P? shape P A planar 1 B planar 2 C non-planar 1 D non-planar 2

1 marks

Answer: D

This question in 9701/12 Feb/March 2023

Q213 · Cyclohexa-1,4-diene is treated with a solution of bromine in tetrachloromethane in the… 9701/12 Feb/March 2023

39 Cyclohexa-1,4-diene is treated with a solution of bromine in tetrachloromethane in the dark. cyclohexa-1,4-diene Which product is formed? A B C D Br Br Br Br Br Br Br Br Br Br Br Br Br Br

1 marks

Answer: B

This question in 9701/12 Feb/March 2023

Q214 · 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

Q215 · Structural isomerism and stereoisomerism should be considered when answering this question 9701/13 May/June 2023

27 Structural isomerism and stereoisomerism should be considered when answering this question. 2-bromopentane is heated with an excess of ethanolic sodium hydroxide. How many different hydrocarbons are produced? A 1 B 2 C 3 D 4

1 marks

Answer: C

This question in 9701/13 May/June 2023

Q216 · When 1-methylcyclohexene reacts with Br, the product is X 9701/13 May/June 2023

32 When 1-methylcyclohexene reacts with Br, the product is X. When 1-methylcyclohexene reacts with HBr the major product is Y. Br, HBr xX —— —. Y A Xisamixture of two stereoisomers; Y does not have stereoisomers. Which statement is correct? X is a mixture of two stereoisomers; Y is a mixture of four stereoisomers. X is a mixture of four stereoisomers; Y does not have stereoisomers. Oo OO DW X is a mixture of four stereoisomers; Y is a mixture of four stereoisomers.

1 marks

Answer: C

This question in 9701/13 May/June 2023

Q217 · How many and bonds are in the molecule HCCCH2CH2CHC(CH3)2? 9701/11 Oct/Nov 2023

27 How many and bonds are in the molecule HCCCH2CH2CHC(CH3)2? A 17 3 B 17 5 C 18 4 D 19 3

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2023

Q218 · Which compound has an Mr of 84 and will react with HBr to give a product with an Mr of… 9701/11 Oct/Nov 2023

29 Which compound has an Mr of 84 and will react with HBr to give a product with an Mr of 164.9? A B C D O

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2023

Q219 · 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

Q220 · Menthol is a naturally occurring alcohol 9701/11 Oct/Nov 2023

35 Menthol is a naturally occurring alcohol. menthol OH When menthol is heated with concentrated sulfuric acid it reacts. The products formed include compound T. What is the structure of compound T? A B C D O

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2023

Q221 · Which feature is present in both ethene and poly(ethene)? 9701/12 Oct/Nov 2023

6 Which feature is present in both ethene and poly(ethene)? A bond angles of 109.5° B covalent bonds C covalent bonds D sp3 orbitals

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2023

Q222 · How many geometrical (cis/trans) isomers are there of hex-2,4-diene, CH3CH=CHCH=CHCH3? 9701/12 Oct/Nov 2023

29 How many geometrical (cis/trans) isomers are there of hex-2,4-diene, CH3CH=CHCH=CHCH3? A none; hex-2,4-diene does not show geometric isomerism B 2 C 3 D 4

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2023

Q223 · The structure of compound X is shown 9701/12 Oct/Nov 2023

30 The structure of compound X is shown. compound X One mole of compound X reacts completely with two moles of hydrogen bromide. What is the structure of the major product of this reaction? A B Br Br Br Br C D Br Br Br Br

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2023

Q224 · 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

Q225 · Which compound has an Mr of 84 and will react with HBr to give a product with an Mr of… 9701/13 Oct/Nov 2023

29 Which compound has an Mr of 84 and will react with HBr to give a product with an Mr of 164.9? A B C D O

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2023

Q226 · 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

Q227 · Menthol is a naturally occurring alcohol 9701/13 Oct/Nov 2023

35 Menthol is a naturally occurring alcohol. menthol OH When menthol is heated with concentrated sulfuric acid it reacts. The products formed include compound T. What is the structure of compound T? A B C D O

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2023

Q228 · Which row shows the correct number of covalent bonds in a molecule of methylpropene? 9701/12 Feb/March 2024

5 Which row shows the correct number of covalent bonds in a molecule of methylpropene? total number of sigma () total number of pi () bonds in the molecule bonds in the molecule A 10 1 B 10 2 C 11 1 D 11 2

1 marks

Answer: C

This question in 9701/12 Feb/March 2024

Q229 · The diagram shows the structure of the naturally occurring molecule cholesterol 9701/12 Feb/March 2024

25 The diagram shows the structure of the naturally occurring molecule cholesterol. cholesterol H3C CH3 CH3 HO Student X stated that the 17 carbon atoms in the 4 rings all lie in the same plane. Student Y stated that this molecule displays cis/trans isomerism at the C=C double bond. Which students are correct? A both student X and student Y B neither student X nor student Y C student X only D student Y only

1 marks

Answer: B

This question in 9701/12 Feb/March 2024

Q230 · 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

Q231 · A sequence of reactions takes place 9701/12 Feb/March 2024

28 A sequence of reactions takes place. The major product is compound Z. concentrated LiAl H4 H2SO4 propanoic acid compound X compound Y pass vapour with steam over H3PO4 compound Z What is compound Z? A propanone B propene C propan-1-ol D propan-2-ol

1 marks

Answer: D

This question in 9701/12 Feb/March 2024

Q232 · The formula shows the repeat unit of an addition polymer 9701/12 Feb/March 2024

39 The formula shows the repeat unit of an addition polymer. –CH(CH3)CH(CH2CH3)– What is the correct name of the monomer from which this polymer is made? A 1-methyl-2-ethylethene B 1-ethylprop-1-ene C pent-2-ene D pent-1-ene

1 marks

Answer: C

This question in 9701/12 Feb/March 2024

Q233 · Structural isomerism and stereoisomerism should be taken into account when answering this… 9701/11 May/June 2024

25 Structural isomerism and stereoisomerism should be taken into account when answering this question. The structure of 3-methylcyclobutene is shown. 3-methylcyclobutene A mixture containing all stereoisomers of 3-methylcyclobutene is treated with HBr. This produces a mixture of isomeric bromomethylcyclobutanes. How many stereoisomers does 3-methylcyclobutene have, and how many isomeric bromomethylcyclobutanes are present in the product mixture? 3-methylcyclobutene bromomethylcyclobutanes A 2 4 B 2 6 C 4 4 D 4 8

1 marks

Answer: B

This question in 9701/11 May/June 2024

Q234 · A molecule of geraniol is shown 9701/11 May/June 2024

29 A molecule of geraniol is shown. geraniol OH What is formed when geraniol is reacted with an excess of cold dilute acidified MnO4 –? 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 9701/11 May/June 2024

Q235 · 2-bromopropane is converted to 1,2-dibromopropane in a pathway involving two reactions 9701/11 May/June 2024

31 2-bromopropane is converted to 1,2-dibromopropane in a pathway involving two reactions. reaction 1 reaction 2 2-bromopropane compound X 1,2-dibromopropane What are the reagents and conditions for the two reactions? reaction 1 reaction 2 A heat under reflux with aqueous NaOH HBr(g) at room temperature B heat under reflux with aqueous NaOH Br2(l) at room temperature C heat under reflux with ethanolic NaOH HBr(g) at room temperature D heat under reflux with ethanolic NaOH Br2(l) at room temperature

1 marks

Answer: D

This question in 9701/11 May/June 2024

Q236 · 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

Q237 · The molecule of limonene, C10H16, contains a 6-membered ring 9701/12 May/June 2024

34 The molecule of limonene, C10H16, contains a 6-membered ring. This is the only cyclic component in its structure. Which volume of hydrogen, at room conditions, is required to react completely with the C=C double bonds in one mole of limonene? A 12 dm3 B 24 dm3 C 48 dm3 D 72 dm3

1 marks

Answer: C

This question in 9701/12 May/June 2024

Q238 · 1-bromopropane reacts with hot ethanolic NaOH 9701/12 May/June 2024

35 1-bromopropane reacts with hot ethanolic NaOH. What is the molecular formula of the product in this reaction? A C3H6 B C3H8 C C3H7O D C3H8O

1 marks

Answer: A

This question in 9701/12 May/June 2024

Q239 · Which pair of reagents reacts to form a product with a chiral carbon atom? 9701/12 May/June 2024

37 Which pair of reagents reacts to form a product with a chiral carbon atom? A CH3CH=CH2 + HBr B (CH3)2C=O + NaBH4 C CH3CH2CHO + HCN D CH3COOH + CH3CH2OH

1 marks

Answer: C

This question in 9701/12 May/June 2024

Q240 · Which alkene shows geometric isomerism? 9701/13 May/June 2024

25 Which alkene shows geometric isomerism? A CH3CH2CH2CH CH2 B CH3CH2CH CHCH3 C CH3CH2C CH2 CH3 D CH3CH CCH3 CH3

1 marks

Answer: B

This question in 9701/13 May/June 2024

Q241 · What is the correct name of the major product of the reaction of HBr with… 9701/13 May/June 2024

26 What is the correct name of the major product of the reaction of HBr with 3-ethylhex-3-ene? A 3-bromo-3-ethylhexane B 3-bromo-4-ethylhexane C 4-bromo-3-ethylhexane D 4-bromo-4-ethylhexane

1 marks

Answer: A

This question in 9701/13 May/June 2024

Q242 · 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

Q243 · When heated with KOH dissolved in ethanol, halogenoalkanes can undergo an elimination… 9701/13 May/June 2024

30 When heated with KOH dissolved in ethanol, halogenoalkanes can undergo an elimination reaction to form alkenes. What are the possible elimination products when 2-bromobutane is heated with KOH dissolved in ethanol? A CH3CH=CHCH3 only B CH3CH2CH=CH2 only C CH3CH=CHCH3 and CH3CH2CH=CH2 D CH3CH=CHCH3 and CH2=CHCH=CH2

1 marks

Answer: C

This question in 9701/13 May/June 2024

Q244 · Ethene reacts with steam in the presence of sulfuric acid 9701/11 Oct/Nov 2024

25 Ethene reacts with steam in the presence of sulfuric acid. C2H4 + H2O  CH3CH2OH Which type of reaction is this? A acid–base B addition C hydrolysis D substitution

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2024

Q245 · Which compound has the greatest number of stereoisomers? 9701/11 Oct/Nov 2024

28 Which compound has the greatest number of stereoisomers? A 2-methylhex-2-ene B 3-methylhex-2-ene C 4-methylhex-2-ene D 5-methylhex-2-ene

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2024

Q246 · The structure of limonene is shown 9701/11 Oct/Nov 2024

30 The structure of limonene is shown. limonene What are the number of moles of carbon dioxide and water produced when a sample of limonene is completely combusted in oxygen? number of moles number of moles of carbon dioxide of water A 4 3 B 5 4 C 5 8 D 9 7

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2024

Q247 · The diagram shows a section of an addition polymer 9701/11 Oct/Nov 2024

39 The diagram shows a section of an addition polymer. The polymer is made using two different monomers. H Cl H CH3 H Cl H CH3 C C C C C C C C C Cl CH3 CH3 Cl Cl CH3 CH3 Cl Cl CH3 What are the names of the two monomers needed to make this polymer? A 1,2-dichloropropene and 2-chlorobut-2-ene B 2,3-dichlorobut-2-ene and chloropropene C 1,2-dichloropropene and chloroethene D chloropropene and 2-chlorobut-2-ene

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2024

Q248 · What are the only structures formed when butan-2-ol is heated with concentrated H2SO4? 9701/12 Oct/Nov 2024

32 What are the only structures formed when butan-2-ol is heated with concentrated H2SO4? CH3CH2 H CH3 H A C C C C H H H CH3 CH3 CH3 CH3 H H H B C C C C C C H H H CH3 CH3CH2 H H H H H C C C C C CH3CH2 H CH3 CH3 CH3 H CH3CH2 H H H D C C C C C C CH3 H H H CH3 CH3

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2024

Q249 · Ethene reacts with steam in the presence of sulfuric acid 9701/13 Oct/Nov 2024

25 Ethene reacts with steam in the presence of sulfuric acid. C2H4 + H2O  CH3CH2OH Which type of reaction is this? A acid–base B addition C hydrolysis D substitution

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2024

Q250 · Which compound has the greatest number of stereoisomers? 9701/13 Oct/Nov 2024

28 Which compound has the greatest number of stereoisomers? A 2-methylhex-2-ene B 3-methylhex-2-ene C 4-methylhex-2-ene D 5-methylhex-2-ene

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2024

Q251 · 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

Q252 · The structure of limonene is shown 9701/13 Oct/Nov 2024

30 The structure of limonene is shown. limonene What are the number of moles of carbon dioxide and water produced when a sample of limonene is completely combusted in oxygen? number of moles number of moles of carbon dioxide of water A 4 3 B 5 4 C 5 8 D 9 7

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2024

Q253 · Which compound may be synthesised from an alkene, with formula C4H8, by an addition… 9701/12 Feb/March 2025

28 Which compound may be synthesised from an alkene, with formula C4H8, by an addition reaction? A 1,1-dibromobutane B 1,2-dibromobutane C 1,3-dibromobutane D 1,3-dibromomethylpropane

1 marks

Answer: B

This question in 9701/12 Feb/March 2025

Q254 · A molecule of hexane can be cracked in a number of different ways 9701/12 Feb/March 2025

37 A molecule of hexane can be cracked in a number of different ways. Three compounds are listed. 1 C3H8 2 C4H8 3 C5H12 Which compounds are found in the mixture of products from the cracking of hexane molecules? A 1, 2 and 3 B 1 and 2 only C 1 and 3 only D 2 and 3 only

1 marks

Answer: B

This question in 9701/12 Feb/March 2025

Q255 · What is the total number of sp3 hybridised atomic orbitals used in the bonding of… 9701/12 Feb/March 2025

39 What is the total number of sp3 hybridised atomic orbitals used in the bonding of but-2-ene? A 2 B 4 C 6 D 8

1 marks

Answer: D

This question in 9701/12 Feb/March 2025

Q256 · Structural isomerism and stereoisomerism should be considered when answering this question 9701/11 May/June 2025

30 Structural isomerism and stereoisomerism should be considered when answering this question. 2,5-dibromohexane is heated under reflux with ethanolic KOH. How many isomeric compounds are formed with molecular formula C6H10? A 3 B 5 C 6 D 7

1 marks

Answer: C

This question in 9701/11 May/June 2025

Q257 · 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

Q258 · The structural formula of hept-1,4,5-triene is shown 9701/11 May/June 2025

39 The structural formula of hept-1,4,5-triene is shown. CH2CHCH2CHCCHCH3 How many of the carbon atoms in one molecule of hept-1,4,5-triene are sp2 hybridised? A 4 B 5 C 6 D 7

1 marks

Answer: A

This question in 9701/11 May/June 2025

Q259 · Propan-1-ol, C3H7OH, is dehydrated by passing its vapour over hot aluminium oxide to give… 9701/12 May/June 2025

36 Propan-1-ol, C3H7OH, is dehydrated by passing its vapour over hot aluminium oxide to give a hydrocarbon. Which structural formula represents the product obtained when the hydrocarbon reacts with bromine? A B H H H H Br H H C C C Br H C C C H H H H H H H C D H H Br H Br Br H C C C Br H C C C H H H H H H H

1 marks

Answer: D

This question in 9701/12 May/June 2025

Q260 · Alkane S has molecular formula C4H10 9701/12 May/June 2025

37 Alkane S has molecular formula C4H10. S reacts with Cl 2(g) in the presence of sunlight to produce only two different monochloroalkanes, C4H9Cl. Both of these monochloroalkanes are treated with hot ethanolic KOH. They both produce the same alkene T, and no other organic products. What is produced when T is treated with hot concentrated acidified KMnO4? A CO2 and CH3CH2CO2H B CO2 and CH3COCH3 C HCO2H and CH3COCH3 D CH3CO2H only

1 marks

Answer: B

This question in 9701/12 May/June 2025

Q261 · Which row shows the products formed when cyclohexene reacts with acidified KMnO4 under… 9701/13 May/June 2025

35 Which row shows the products formed when cyclohexene reacts with acidified KMnO4 under different conditions? product formed on reaction with cold, dilute acidified KMnO4 product formed on reaction with hot, concentrated acidified KMnO4 A OH OH O OH HO O B O OH HO O OH OH C O O O H H O D O H H O O O

1 marks

Answer: A

This question in 9701/13 May/June 2025

Q262 · When 0.010 mol of a hydrocarbon X reacts with 720 cm3 of hydrogen at room conditions, an… 9701/14 May/June 2025

29 When 0.010 mol of a hydrocarbon X reacts with 720 cm3 of hydrogen at room conditions, an alkane is formed. What is hydrocarbon X? A B C D

1 marks

Answer: C

This question in 9701/14 May/June 2025

Q263 · 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

Q264 · Which intermediate ion forms in the greatest amount during the addition of HBr to propene? 9701/11 Oct/Nov 2025

27 Which intermediate ion forms in the greatest amount during the addition of HBr to propene? A CH3CH+CH3 B CH3CH2CH2 + C CH3CH–CH2Br D CH3CHBrCH2 –

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2025

Q265 · 1,4-dibromobutane reacts with an excess of ethanolic sodium hydroxide until no further… 9701/11 Oct/Nov 2025

31 1,4-dibromobutane reacts with an excess of ethanolic sodium hydroxide until no further reaction takes place. What is the relative formula mass of the major organic product? A 54 B 56 C 74 D 90

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2025

Q266 · A small section of a polymer produced from two monomers is shown 9701/11 Oct/Nov 2025

32 A small section of a polymer produced from two monomers is shown. –CH2–C(CH3)2–CH(CH3)–CH2– What are the two monomers? A but-1-ene and propene B but-2-ene and propene C ethene and pent-2-ene D methylpropene and propene

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2025

Q267 · What is the major product when 2-methylpent-2-ene reacts with hydrogen bromide? 9701/12 Oct/Nov 2025

27 What is the major product when 2-methylpent-2-ene reacts with hydrogen bromide? A 1-bromo-2-methylpentane B 2-bromo-2-methylpentane C 3-bromo-2-methylpentane D 4-bromo-2-methylpentane

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2025

Q268 · Pent-2-ene is reacted with cold, dilute, acidified manganate(VII) ions 9701/12 Oct/Nov 2025

28 Pent-2-ene is reacted with cold, dilute, acidified manganate(VII) ions. What is the major product? 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 9701/12 Oct/Nov 2025

Q269 · Limonene is an oil formed in the peel of citrus fruits 9701/12 Oct/Nov 2025

29 Limonene is an oil formed in the peel of citrus fruits. limonene CH3 CH2 C CH3 Which product is formed when an excess of bromine, Br2(l), reacts with limonene at room temperature in the dark? A B C D Br Br CH3 CH2 CH3 CH2 C C CH3 C CH2Br CH3 C CH2Br Br Br Br CH3 CH3 Br CH3 CH3 Br

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2025

Q270 · The purity of a compound can be determined using infrared spectroscopy 9701/12 Oct/Nov 2025

40 The purity of a compound can be determined using infrared spectroscopy. The table gives the characteristic infrared absorption frequencies for some selected bonds. characteristic infrared absorption range bond functional groups containing the bond (in wavenumbers) / cm–1 C–O hydroxy, ester 1040–1300 C=C aromatic compound, alkene 1500–1680 C=O amide 1640–1690 carbonyl, carboxyl 1670–1740 ester 1710–1750 C≡N nitrile 2200–2250 C–H alkane 2850–2950 N–H amine, amide 3300–3500 O–H carboxyl 2500–3000 hydroxy 3200–3650 Propan-2-ol is made by hydration of propene. A sample of the product is obtained. Which feature of the infrared spectrum of the product would show that no propene remains in the product? A absorption in the 2900 cm–1 region B strong absorption below 1000 cm–1 C the lack of absorption at or near 1250 cm–1 D the lack of absorption at or near 1550 cm–1

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2025

Q271 · Which intermediate ion forms in the greatest amount during the addition of HBr to propene? 9701/13 Oct/Nov 2025

27 Which intermediate ion forms in the greatest amount during the addition of HBr to propene? A CH3CH+CH3 B CH3CH2CH2 + C CH3CH–CH2Br D CH3CHBrCH2 –

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2025

Q272 · A small section of a polymer produced from two monomers is shown 9701/13 Oct/Nov 2025

32 A small section of a polymer produced from two monomers is shown. –CH2–C(CH3)2–CH(CH3)–CH2– What are the two monomers? A but-1-ene and propene B but-2-ene and propene C ethene and pent-2-ene D methylpropene and propene

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2025