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Topical›Chemistry 9701›Halogen compounds›Halogenoalkanes›Paper 1

Halogenoalkanes — Paper 1 · A Level Chemistry 9701

15.1· 259 questions · 259 marks · 311 min · 2005–2025· Multiple choice

Every Cambridge A Level Chemistry Paper 1 question on halogenoalkanes, laid out as 66 A4 pages with the mark scheme below. Nothing is left out. Free to read, no account.

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Question 1: An amine is produced in the following reaction. C2H5I + 2NH3 → C2H5NH2 + NH4I What is the mechanism? A electrophilic addition B electrophil…Question 2: Use of the Data Booklet is relevant to this question. In which reaction is the relative molecular mass of the organic product the largest? …Question 3: High-energy irradiation in the stratosphere produces radicals from chlorofluoroalkanes, commonly known as CFCs. Which radical could result …Question 4: What is the total number of different chloroethanes, formula C2H6-nCln, where n can be any integer from 1 to 4? A 4 B 6 C 7 D 8Question 5: Which reaction is an example of nucleophilic substitution? A CH3CH2Br → CH2=CH2 + HBr B CH2=CH2 + HBr → CH3CH2Br C C3H7Br + H2O → C3H7OH + …1 / 66
Question 6: Compound X on refluxing with aqueous sodium hydroxide gave mixture Y which on distillation with acidified potassium dichromate(VI) produced…Question 7: The anaesthetic halothane, CF3CHBrCl, is made industrially as shown below. HF Br2 CCl2=CHCl CF3CH2Cl CF3CHBrCl stage 1 stage 2 Which type o…Question 8: Chlorofluoroalkanes, CFCs, can be used as refrigerants, aerosol propellants and fire extinguishers. CFCs such as CCl3F and CCl2F2 are more …Question 9: Which pair of reaction types is illustrated by the reaction sequence below? HI in CH3CO2H NaOH(aq) CH3CH=CHCH3 CH3CH2CHICH3 CH3CH2CH(OH)CH3…2 / 66
Question 10: Halogenoalkanes are important molecules in organic synthetic reactions. In particular they undergo a range of nucleophilic reactions. Which…Question 11: The structure of monosodium glutamate, a flavour enhancer, is shown. Na+ O– C CH2 CH2 CH CO2H O NH2 It may be prepared starting from the fo…Question 12: Aluminium chloride catalyses certain reactions by forming carbocations (carbonium ions) with chloroalkanes as shown. RCl + Al Cl3 → R+ + A …3 / 66
Question 13: Four drops of 1-chlorobutane, 1-bromobutane and 1-iodobutane were put separately into three test-tubes containing 1.0 cm3 of aqueous silver…Question 14: A possible mechanism of the exothermic hydrolysis of 2-chloro-2-methylpropane is shown. CH3 CH3 slow + _ CH3 C Cl CH3 C + Cl CH3 CH3 CH3 CH…Question 15: In the hydrolysis of bromoethane by aqueous sodium hydroxide, what is the nature of the attacking group and of the leaving group? attacking…4 / 66
Question 16: Which reaction would not give propene as one product? A adding an excess of concentrated sulfuric acid to propan-1-ol B adding warm aqueous…Question 17: Which statements are true for an SN2 reaction? 1 One bond is broken as another bond is formed. 2 The formation of a transition state involv…Question 18: In many countries plastic waste is collected separately and sorted. Some of this is incinerated to provide heat for power stations. Why is …Question 19: When an isomer Y of molecular formula C4H9Br undergoes hydrolysis in aqueous alkali to form an alcohol C4H9OH, the rate of reaction is foun…Question 20: Which reactions are examples of nucleophilic substitution? 1 CH3CH2Br + OH– → CH3CH2OH + Br– H + 2 CH3I + H2O → CH3OH + HI 3 CH3CH2CH2Cl…Question 21: When an isomer Y of molecular formula C4H9Br undergoes hydrolysis in aqueous alkali to form an alcohol C4H9OH, the rate of reaction is foun…5 / 66
Question 22: In many countries plastic waste is collected separately and sorted. Some of this is incinerated to provide heat for power stations. Why is …Question 23: Which reactions are examples of nucleophilic substitution? 1 CH3CH2Br + OH– → CH3CH2OH + Br– H + 2 CH3I + H2O → CH3OH + HI 3 CH3CH2CH2Cl…Question 24: In many countries plastic waste is collected separately and sorted. Some of this is incinerated to provide heat for power stations. Why is …Question 25: When an isomer Y of molecular formula C4H9Br undergoes hydrolysis in aqueous alkali to form an alcohol C4H9OH, the rate of reaction is foun…Question 26: Which reactions are examples of nucleophilic substitution? 1 CH3CH2Br + OH– → CH3CH2OH + Br– H + 2 CH3I + H2O → CH3OH + HI 3 CH3CH2CH2Cl…6 / 66
Question 27: The diagram shows some laboratory apparatus. water heat Which preparations could this apparatus be used for? 1 bromoethane, from ethanol, s…Question 28: 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 29: Which compound undergoes an SN1 substitution reaction? A CH3CH2CH2Br B (CH3)3CCH2I CH3 Cl C D CH2=CHCl7 / 66
Question 30: Textiles for use in aircraft are treated with a finish containing a halogenoalkane. What is the reason for this? 1 The textile burns less e…Question 31: How many structural isomers are there of trichloropropane, C3H5Cl 3? A 3 B 4 C 5 D 6Question 32: Nine compounds have molecular formula C4H8Br2. Which compound may be synthesised from an alkene by an addition reaction? A 1,1-dibromobutan…Question 33: Which sequence of reagents may be used in the laboratory to convert propan-1-ol into 2-bromopropane? A concentrated sulfuric acid, followed…Question 34: Many, but not all, organic reactions need to be heated before reaction occurs. Which reaction occurs at a good rate at room temperature (20…8 / 66
Question 35: A reaction pathway diagram is shown. energy reaction pathway Which reactions would have such a profile? 1 (CH3)3CBr + NaOH → (CH3)3COH + Na…Question 36: 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 37: Which compound undergoes an SN1 substitution reaction? A CH3CH2CH2Br B (CH3)3CCH2I CH3 Cl C D CH2=CHCl9 / 66
Question 38: Textiles for use in aircraft are treated with a finish containing a halogenoalkane. What is the reason for this? 1 The textile burns less e…Question 39: Butanedioic acid occurs in amber, algae, lichens, sugar cane and beets. It may be synthesised in two steps from 1,2-dibromoethane. step 1 s…Question 40: Bromoethane undergoes all of the conversions shown. Which conversions are examples of nucleophilic substitution? 1 C2H5Br → C2H5CN 2 C2H5Br…Question 41: Which halogenoalkane will undergo an SN1 reaction and produce a yellow precipitate when AgNO3(aq) is added to it? A 1-chlorobutane B 1-iodo…Question 42: Which reaction will give 2-chloropropane in the best yield? A propane gas with chlorine gas in the presence of ultraviolet light B propan-2…10 / 66
Question 43: 1,1-dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give propanal. NaOH(aq) CH3CH2CHCl 2 CH3CH2CHO Which term …Question 44: Bromoethane undergoes all of the conversions shown. Which conversions are examples of nucleophilic substitution? 1 C2H5Br → C2H5CN 2 C2H5Br…Question 45: What is involved in the mechanism of the reaction between aqueous sodium hydroxide and 1-bromobutane? A attack by a nucleophile on a carbon…Question 46: 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 47: What is involved in the mechanism of the reaction between aqueous sodium hydroxide and 2-bromo-2-methylbutane? A heterolytic bond fission, …11 / 66
Question 48: Y is an organic compound. Y gives a precipitate with aqueous silver nitrate. All of this precipitate dissolves when concentrated aqueous am…Question 49: Y and Z are two widely-used selective weed killers. OCH2CO2H OCH2CH2OH CH3 Cl Cl Cl Y Z Which reagent will distinguish Y from Z? A acidifie…Question 50: What is involved in the mechanism of the reaction between aqueous sodium hydroxide and 1-bromobutane? A attack by a nucleophile on a carbon…Question 51: Many different compounds have been used in aerosol sprays, refrigerators and in making foamed plastics. Which compound will cause the most …12 / 66
Question 52: Aluminium chloride catalyses certain reactions by forming carbocations with chloroalkanes as shown. RCl + Al Cl 3 → R+ + Al Cl 4 – Which pr…Question 53: The presence of halogen in an organic compound may be detected by warming the organic compound with aqueous silver nitrate. Which compound …Question 54: A reaction pathway diagram is shown. energy reaction pathway Which reaction does not have such a profile? NaCN A CH3CHO + HCN CH3CH(OH)CN B…Question 55: The depletion of the ozone layer in the upper atmosphere reduces the Earth’s natural protection from harmful ultraviolet radiation. Which c…13 / 66
Question 56: How can a good yield of ethylamine be made using bromoethane as starting material? 1 by heating bromoethane with an excess of ammonia gas i…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: When phenacyl chloride, C6H5COCH2Cl, is reacted with aqueous NaOH, the substitution reaction follows an SN2 mechanism. Which structure repr…Question 59: The depletion of the ozone layer in the upper atmosphere reduces the Earth’s natural protection from harmful ultraviolet radiation. Which c…14 / 66
Question 60: The presence of halogen in an organic compound may be detected by warming the organic compound with aqueous silver nitrate. Which compound …Question 61: A reaction pathway diagram is shown. energy reaction pathway Which reaction does not have such a profile? NaCN A CH3CHO + HCN CH3CH(OH)CN B…Question 62: How can a good yield of ethylamine be made using bromoethane as starting material? 1 by heating bromoethane with an excess of ammonia gas i…Question 63: High-energy radiation in the stratosphere produces free-radicals from chlorofluoroalkanes, commonly known as CFCs. Which free-radical is mo…15 / 66
Question 64: Many, but not all, organic reactions need to be heated before reaction occurs. Which reaction occurs at a good rate at room temperature (20…Question 65: Chloroethane can be formed from bromoethane in two steps. step X step Y C2H5Br C2H5OH C2H5Cl Which statements about these steps are correct…Question 66: High-energy radiation in the stratosphere produces free-radicals from chlorofluoroalkanes, commonly known as CFCs. Which free-radical is mo…Question 67: Many, but not all, organic reactions need to be heated before reaction occurs. Which reaction occurs at a good rate at room temperature (20…Question 68: Which reagents and conditions will convert propane into 1-chloropropane? 1 Cl 2 and sunlight 2 conc. HCl, reflux 3 PCl 516 / 66
Question 69: Chloroethane can be formed from bromoethane in two steps. step X step Y C2H5Br C2H5OH C2H5Cl Which statements about these steps are correct…Question 70: A possible mechanism for the exothermic hydrolysis of 2-chloro-2-methylpropane is shown. CH3 CH3 slow + CH3 C Cl CH3 C + Cl – CH3 CH3 CH3 C…17 / 66
Question 71: Chloroethane can be used to make sodium propanoate. chloroethane → Q → sodium propanoate The intermediate, Q, is hydrolysed with boilin…Question 72: Aqueous sodium hydroxide reacts with 1-bromopropane to give propan-1-ol. How should the first step in the mechanism be described? A by a cu…Question 73: Aqueous sodium hydroxide reacts with 2-bromo-2-methylpropane to give 2-methylpropan-2-ol. The reaction proceeds by an SN1 mechanism. How sh…Question 74: Compound Y can be hydrolysed by warm aqueous silver nitrate to form a precipitate that is soluble in dilute aqueous ammonia. Compound Y can…Question 75: Which are properties of fluoroalkanes? 1 They are less reactive than the corresponding chloroalkanes. 2 They are non-flammable. 3 The C–F b…18 / 66
Question 76: Which sequence of reagents may be used in the laboratory to convert propan-1-ol into 2-bromopropane? A concentrated sulfuric acid, followed…Question 77: A carbanion is an organic ion in which a carbon atom has a negative charge. A carbocation is an organic ion in which a carbon atom has a po…Question 78: Fabrics for use in aircraft seating are treated with a coating containing a halogenoalkane. Why is this coating used? 1 The treated fabric …Question 79: Which reaction will give the best yield of 1-chloropropane? A chlorine gas with propene gas in the dark B propan-1-ol with dilute NaCl (aq)…Question 80: A carbanion is an organic ion in which a carbon atom has a negative charge. A carbocation is an organic ion in which a carbon atom has a po…19 / 66
Question 81: The organic compound X gives a precipitate when warmed with aqueous silver nitrate. This precipitate dissolves when concentrated aqueous am…Question 82: Which reactions can be used to make an alcohol in the laboratory? 1 hydrolysis of a bromoalkane with NaOH(aq) 2 reduction of a ketone with …Question 83: Which reaction will give the best yield of 1-chloropropane? A chlorine gas with propene gas in the dark B propan-1-ol with dilute NaCl (aq)…Question 84: A carbanion is an organic ion in which a carbon atom has a negative charge. A carbocation is an organic ion in which a carbon atom has a po…Question 85: The organic compound X gives a precipitate when warmed with aqueous silver nitrate. This precipitate dissolves when concentrated aqueous am…Question 86: Which reactions can be used to make an alcohol in the laboratory? 1 hydrolysis of a bromoalkane with NaOH(aq) 2 reduction of a ketone with …20 / 66
Question 87: Including structural and stereoisomers, how many isomers are there of C2H2Br2? A 2 B 3 C 4 D 5Question 88: Which reaction will give the best yield of 2-chloropropane? A chlorine gas with propane gas in the presence of uv light B chlorine gas with…Question 89: Including structural and stereoisomers, how many isomeric products are produced when alcoholic KOH reacts with 2-chlorobutane? A 1 B 2 C 3 …Question 90: Chlorofluorocarbons, CFCs, can be used as refrigerants, aerosol propellants and fire extinguishers. CFCs such as CCl 3F and CCl 2F2 are mor…Question 91: Halogenoalkanes react with aqueous NaOH to give alcohols. The mechanism involved is either SN1 or SN2. Which halogenoalkane produces the hi…Question 92: Which fragment could appear in the chain produced by polymerising 1,1-dichloroethene? A – CH2 – CH2 – CCl 2 – CCl 2 – CH2 – CH2 – B – CHCl …21 / 66
Question 93: The hydrolysis of 1-chloropropane to produce propan-1-ol is much slower than the corresponding hydrolysis of 1-iodopropane. Which statement…Question 94: Butanoic acid can be produced from 1-bromopropane using reagents X and Y as shown below. reagent X reagent Y 1-bromopropane compound Q buta…Question 95: Halogenoalkanes undergo a range of nucleophilic substitution reactions. Which reaction proceeds only by an SN1 mechanism? A CH3CH2Br + NH…Question 96: Which statement does not correctly describe a problem related to the disposal of PVC? A PVC is slowly degraded in the environment by bacter…Question 97: When heated with KOH dissolved in ethanol, halogenoalkanes can undergo an elimination reaction to form alkenes. What are the possible elimi…22 / 66
Question 98: 1,1-dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give propanal. NaOH(aq) CH3CH2CHCl 2 CH3CH2CHO Which term …Question 99: In the hydrolysis of bromoethane by aqueous sodium hydroxide, what is the nature of the attacking group and of the leaving group? attacking…Question 100: X is an organic compound that gives a precipitate with aqueous silver nitrate. This precipitate remains undissolved when concentrated aqueo…Question 101: A reaction pathway diagram is shown. energy extent of reaction Which reactions would have this profile? 1 (CH3)3CBr + NaOH → (CH3)3COH …23 / 66
Question 102: 1,1-dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give propanal. NaOH(aq) CH3CH2CHCl 2 CH3CH2CHO Which term …Question 103: In the hydrolysis of bromoethane by aqueous sodium hydroxide, what is the nature of the attacking group and of the leaving group? attacking…Question 104: A reaction pathway diagram is shown. energy extent of reaction Which reactions would have this profile? 1 (CH3)3CBr + NaOH → (CH3)3COH …Question 105: A compound Y, C4H9Br, undergoes hydrolysis in aqueous alkali to form an alcohol, C4H9OH. The rate of this reaction is found to be unaffecte…24 / 66
Question 106: Which compounds produce pent-2-ene as either one of the products, or as the only product, on heating with potassium hydroxide in ethanol? 1…Question 107: 2-bromopropane reacts with a hot concentrated solution of sodium hydroxide in ethanol. Which substance is the major product of this reactio…Question 108: What is the major product formed when compound Q is warmed with excess HBr? OH OH Q A B Br Br OH OH Br Br C D Br Br Br Br Br BrQuestion 109: Butanedioic acid may be synthesised in two steps from 1,2-dibromoethane. step 1 step 2 BrCH2CH2Br X HO2CCH2CH2CO2H Which reagents could be …25 / 66
Question 110: Which reaction would not give propene? A adding excess hot concentrated sulfuric acid to propan-1-ol B adding warm aqueous sodium hydroxide…Question 111: Halogenated hydrocarbons have many uses. What have halogenated hydrocarbons been used for? 1 solvents 2 refrigerants 3 monomers in polymer …Question 112: The depletion of the ozone layer in the upper atmosphere reduces the Earth’s natural protection from harmful ultraviolet radiation. Which c…Question 113: X is an organic compound. X gives a precipitate with aqueous silver nitrate. Some or all of this precipitate remains undissolved when exces…Question 114: 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,…26 / 66
Question 115: Structural isomerism and stereoisomerism should be considered in answering this question. Compound J is reacted with KOH dissolved in ethan…Question 116: A student prepares pentan-1-ol by the alkaline hydrolysis of 1-iodopentane. She gently warms the reaction mixture for 20 minutes. CH3CH2CH2…Question 117: Which types of reaction can occur with 1-bromobutane? 1 elimination 2 hydrolysis 3 free radical substitution27 / 66
Question 118: 1-chloro-1-methylcyclohexane is hydrolysed by heating with NaOH(aq). CH3 CH3 + OH– → + Cl – Cl OH The reaction pathway is shown. energy …Question 119: A reaction pathway diagram is shown. energy extent of reaction The four reactions that follow are all exothermic. Which reaction would not …Question 120: Which reaction will give 2-chloropropane in the best yield? A propane gas with chlorine gas in the presence of ultraviolet light B propan-2…28 / 66
Question 121: Halogenoalkanes show trends in their physical and chemical properties. Which properties steadily increase from C2H5Cl to C2H5Br to C2H5I ? …Question 122: Chloroethane can be used to make sodium propanoate. chloroethane → Q → sodium propanoate The intermediate, Q, is hydrolysed with boilin…Question 123: Bromoethane reacts with NaOH in different ways depending on the solvent used. Which statements about these reactions are correct? solvent u…Question 124: PVC is difficult to dispose of. Two possible methods are burying it in landfill sites and disposal by combustion. Which row of the table is…29 / 66
Question 125: Chloroethane can be used to make sodium propanoate. chloroethane → Q → sodium propanoate The intermediate, Q, is hydrolysed with boilin…Question 126: Bromoethane reacts with NaOH in different ways depending on the solvent used. Which statements about these reactions are correct? solvent u…Question 127: Aqueous sodium hydroxide reacts with 1-bromopropane to give propan-1-ol. What should be included in a diagram of the first step in the mech…Question 128: 2-bromo-2-methylpropane undergoes nucleophilic substitution when heated under reflux with an aqueous solution of sodium hydroxide. Which ro…30 / 66
Question 129: An organic compound, X, has the following skeletal formula. OH X Which statements about X are correct? 1 X is a primary alcohol. 2 X will d…Question 130: Butanoic acid can be produced from 1-bromopropane using reagents X and Y as shown. reagent X reagent Y 1-bromopropane compound Q butanoic a…Question 131: Which organic reaction is an example of nucleophilic substitution? A CH3CH2Br + NaOH → CH2CH2 + H2O + NaBr B CH3CH2Br + NaOH → …Question 132: A reaction pathway diagram is shown. energy progress of reaction Which reactions would have this reaction pathway diagram? 1 (CH3)3CBr + …31 / 66
Question 133: Equal volumes of aqueous silver nitrate were added to separate small volumes of bromoethane and iodoethane in two test-tubes. The test-tube…Question 134: Many, but not all, organic reactions need to be heated before a reaction occurs. Which reaction occurs quickly at room temperature (20 °C)?…Question 135: Which statements are correct for an SN2 mechanism? 1 One bond is being broken at the same time as another bond is being formed. 2 The forma…Question 136: Bromoethane is heated under reflux with concentrated aqueous NaOH. Which statements are correct? 1 The major product is a primary alcohol. …Question 137: Which organic reaction is an example of nucleophilic substitution? A CH3CH2Br + NaOH → CH2CH2 + H2O + NaBr B CH3CH2Br + NaOH → …32 / 66
Question 138: A reaction pathway diagram is shown. energy progress of reaction Which reactions would have this reaction pathway diagram? 1 (CH3)3CBr + …Question 139: An organic ion containing a carbon atom with a negative charge is called a carbanion. An organic ion containing a carbon atom with a positi…Question 140: A reaction occurs when a sample of 1-chloropropane is heated under reflux with sodium hydroxide dissolved in ethanol. Which row is correct?…33 / 66
Question 141: Sodium methoxide, Na+CH3O–, reacts with 2-chloro-2-methylpropane in a nucleophilic substitution reaction. The nucleophile is the CH3O– ion.…Question 142: Primary halogenoalkanes undergo hydrolysis reactions. Which reaction would occur most rapidly if they are all warmed to the same temperatur…Question 143: Structural isomerism and stereoisomerism should be considered when answering this question. A colourless liquid, C5H11Cl , exists as a mixt…Question 144: When warm water is added to halogenoalkane X, an SN1 reaction occurs. AgNO3(aq) is then added; a yellow precipitate is formed. What could b…34 / 66
Question 145: 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 146: The presence of a halogen in an organic compound may be detected by warming the organic compound with aqueous silver nitrate. Which compoun…Question 147: Halogenoalkanes react with NaOH(aq) either by an SN1 mechanism or by an SN2 mechanism. The mechanism followed by the reaction depends on th…35 / 66
Question 148: Compound Y is a straight chain molecule with formula CnH2n+1X. X is a halogen. The Mr of Y is 137. The halogen atom is on the second carbon…Question 149: 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 150: The halogenoalkanes listed below all react with NaOH(aq). Which reactions proceed mainly by an SN1 mechanism? 1 1-iodopropane 2 2-iodo-2-me…Question 151: Compound P reacts separately with KOH(aq) and HBr. CH2CHCH2CH2Cl compound P What are the mechanisms of these two reactions? KOH (aq) HBr A …36 / 66
Question 152: A halogenoalkane has the molecular formula C5H11Br. The halogenoalkane does not form an alkene when treated with ethanolic sodium hydroxide…Question 153: 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…Question 154: 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 155: The halogenoalkanes listed below all react with NaOH(aq). Which reactions proceed mainly by an SN1 mechanism? 1 1-iodopropane 2 2-iodo-2-me…37 / 66
Question 156: Structural isomerism and stereoisomerism should be considered when answering this question. 2-bromopentane is heated with an excess of etha…Question 157: Bromopropane reacts with water as shown. CH3CH2CH2Br + H2O → CH3CH2CH2OH + HBr Which statement is correct? A This is an elimination r…Question 158: Which reaction is most likely to involve the formation of a positively charged intermediate? A 1-bromopentane and warm dilute NaOH(aq) B 1-…Question 159: The structure of coniine is shown. coniine N CH2CH2CH3 H Coniine can be synthesised by reacting ammonia with a dibromo compound, X. NH3 + C…38 / 66
Question 160: Which compound is chiral? A 1-chloro-3-methylbutane B 2-chloro-2-methylbutane C 2-chloro-3-methylbutane D 3-chloropentane Section BQuestion 161: Which product can be made from bromoethane by an elimination reaction? A ethanol B ethene C ethylamine D propanenitrileQuestion 162: Propene, bromine and hydrogen bromide are mixed in the dark. A number of products are formed, some in very small quantities. Which substanc…Question 163: Halogenoalkanes can be hydrolysed using aqueous sodium hydroxide. Which compounds tend to be hydrolysed by an SN1 mechanism? 1 CH3CH2CCl (C…39 / 66
Question 164: The Finkelstein reaction occurs when NaI in propanone reacts with a chloroalkane or bromoalkane. The halogen is directly replaced by I. The…Question 165: Water is added to a sample of 2,3-dibromohexane. Some of the 2,3-dibromohexane undergoes complete hydrolysis and some of it undergoes parti…Question 166: Which statement about the mechanism of an SN1 reaction of a halogenoalkane is correct? A A nucleophile is substituted by an electrophile. B…40 / 66
Question 167: A tertiary bromoalkane, indicated here by C–Br, reacts with aqueous NaOH. The mechanism has the reaction pathway shown. X C–Br + OH– Y ener…Question 168: Bromoethane and chloroethane are added separately to water. Hydrolysis reactions occur. Which compound hydrolyses more rapidly and what is …41 / 66
Question 169: 1-chloro-2-methylbutane reacts with sodium cyanide in ethanol in a nucleophilic substitution reaction. What is the most likely intermediate…Question 170: Bromoethane undergoes nucleophilic substitution reactions. Which statements are correct? 1 Bromoethane reacts with aqueous NaOH to make eth…42 / 66
Question 171: A tertiary bromoalkane, indicated here by C–Br, reacts with aqueous NaOH. The mechanism has the reaction pathway shown. X C–Br + OH– Y ener…Question 172: Bromoethane and chloroethane are added separately to water. Hydrolysis reactions occur. Which compound hydrolyses more rapidly and what is …Question 173: Which row identifies a suitable starting material and reagent that can be used to produce butanenitrile? starting material reagent A CH3CH2…43 / 66
Question 174: An excess of dry HBr is warmed with compound Y. Y OH What is the major product of the reaction? A B C D Br HO HO Br Br Br Br Br Br Br BrQuestion 175: 2-bromo-2-methylpentane is a tertiary halogenoalkane. Which organic products are formed when 2-bromo-2-methylpentane reacts with a hot conc…Question 176: Which row correctly shows the type of mechanism of each of the two reactions? C2H5Br + KCN CH3COCH3 + HCN A electrophilic substitution …44 / 66
Question 177: A reaction mechanism is shown. H2C CH2 H2C CH2 H2C CH2 H2C CH2 + Br – H2C C Br H2C C H HO– H OH Which statements about this reaction are co…Question 178: 1,2-dibromopropane can be made from 1-bromopropane in two steps. Which row is correct? step 1 step 2 A addition substitution B elimination …Question 179: 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 180: A reaction mechanism is shown. CH2 CH2 H2C CH2 H2C CH2 + Cl – H2C C Cl H2C C H H OH HO– Which statements about this reaction are correct? 1…45 / 66
Question 181: Which statement is correct when referring to the complete combustion of PVC? A A gas is made which contributes to global warming. B Carbon …Question 182: Iodoethane, CH3CH2I, reacts with aqueous silver nitrate at 50 C. A precipitate forms during this reaction. Which row of the table is corre…Question 183: A student converts 1-iodopropane, C3H7I, into butanoic acid, C3H7CO2H, by a two-stage chemical synthesis. In the first of the two stages, w…Question 184: 1-chloro-1-methylcyclohexane is hydrolysed by heating with NaOH(aq). CH3 CH3 + OH– → + Cl – Cl OH The reaction pathway is shown. energy …46 / 66
Question 185: Diols in which both hydroxy groups are bonded to the same carbon atom can spontaneously eliminate a molecule of water to produce a carbonyl…Question 186: Which statement is correct when referring to the complete combustion of PVC? A A gas is made which contributes to global warming. B Carbon …Question 187: Iodoethane, CH3CH2I, reacts with aqueous silver nitrate at 50 C. A precipitate forms during this reaction. Which row of the table is corre…Question 188: 1-chloro-1-methylcyclohexane is hydrolysed by heating with NaOH(aq). CH3 CH3 + OH– → + Cl – Cl OH The reaction pathway is shown. energy …47 / 66
Question 189: Dibromopentanes can undergo ‘double elimination’ reactions to produce hydrocarbons. 2NaOH + C5H10Br2  C5H8 + 2NaBr + 2H2O Which is…Question 190: In which reactions is the major product formed by a nucleophilic substitution reaction? 1 bromoethane + potassium cyanide in ethanol 2 brom…Question 191: Bromoethane reacts with cyanide ions, producing propanenitrile. Which statement about the SN2 mechanism of this reaction is correct? A The …Question 192: A few drops of 2-bromopropane were placed in a test-tube. An equal volume of aqueous silver nitrate was added. A precipitate was formed. Th…48 / 66
Question 193: Sodium methoxide, Na+CH3O–, reacts with 2-chloro-2-methylpropane in a nucleophilic substitution reaction. The nucleophile is the CH3O– ion.…Question 194: Halogenoalkanes react with nucleophiles such as OH–. Which pair of halogenoalkanes both react via an SN1 mechanism? A B Br Cl and and Cl Br…Question 195: Bromoethane reacts with NaOH in different ways depending on the solvent used. Which rows about these reactions are correct? solvent used or…49 / 66
Question 196: 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 197: Structural isomerism and stereoisomerism should be considered when answering this question. A colourless liquid, C5H11Cl , exists as a mixt…Question 198: When 2-bromo-2-methylpropane reacts with aqueous sodium hydroxide, an alcohol is formed. Which diagram describes the first step in the rea…Question 199: Which statements about chlorofluoroalkanes are correct? 1 Both the C–Cl and C–F bonds are readily dissociated by ultra-violet light. 2 They…50 / 66
Question 200: Butanoic acid can be made from 1-bromopropane in two stages. stage 1 CH3CH2CH2Br  CH3CH2CH2CN stage 2 CH3CH2CH2CN  CH3CH2CH2CO2H Whic…Question 201: A halogenoalkane has the molecular formula C5H11Br. The halogenoalkane does not form an alkene when treated with ethanolic sodium hydroxide…Question 202: Structural isomerism and stereoisomerism should be considered when answering this question. A colourless liquid, C5H11Cl , exists as a mixt…Question 203: When 2-bromo-2-methylpropane reacts with aqueous sodium hydroxide, an alcohol is formed. Which diagram describes the first step in the rea…51 / 66
Question 204: Ethanol can be used to make propanenitrile in two steps. X Y CH3CH2OH CH3CH2Br CH3CH2CN What types of reaction are X and Y? X Y A free-radi…Question 205: Structural isomerism and stereoisomerism should be taken into account when answering this question. How many isomeric alkenes with formula …Question 206: Compound Z, C7H13Br, has two chiral centres. A sample of Z contains all four possible optical isomers. This sample of Z reacts with hot eth…Question 207: 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…52 / 66
Question 208: The diagram shows the structures of two halogenoalkanes, P and Q. P Q C2H5 C2H5 CH3 C C3H7 CH3 C C3H7 Br F Both compounds can be hydrolysed…Question 209: The structure of coniine is shown. coniine N CH2CH2CH3 H Coniine can be synthesised by reacting ammonia with a dibromo compound, X. X NH3 …Question 210: Which statement concerning the hydrolysis of 1-bromopropane with water is correct? A The hydrolysis reaction between water and 1-iodopropan…53 / 66
Question 211: Compound R can be formed from 1-bromopropane using a nucleophilic substitution reaction followed by an oxidation reaction. What is the iden…Question 212: 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 213: 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 214: For which reaction will the major organic product have the lowest relative molecular mass? A Bromoethane is heated under reflux with an aqu…Question 215: C4H9Cl reacts with warm dilute aqueous sodium hydroxide solution. Which isomer of C4H9Cl will form the most stable cation intermediate? A 1…54 / 66
Question 216: Compound R can be formed from 1-bromopropane using a nucleophilic substitution reaction followed by an oxidation reaction. What is the iden…Question 217: 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 218: Compound X, C7H13Br, reacts with hot alcoholic NaOH to produce two compounds, Y and Z. On reaction with Br2, Y gives a product, C7H12Br2, w…Question 219: Which type of reaction happens during the hydrolysis of 2-bromopropane? A electrophilic addition B free radical substitution C nucleophilic…Question 220: 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 O55 / 66
Question 221: 1,1-dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give propanal. NaOH(aq) CH3CH2CHCl 2 CH3CH2CHO Which term …Question 222: Which row shows the correct name and classification of the halogenoalkane shown? CH3(CH2)2CBr(CH3)CH2CH3 classification of name halogenoalk…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…56 / 66
Question 224: 1,1-dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give propanal. NaOH(aq) CH3CH2CHCl 2 CH3CH2CHO Which term …Question 225: Which statement is correct? A Bromoethane reacts with NaOH(aq) to form ethene as a major product. B 1-chlorobutane reacts more rapidly than…Question 226: In the hydrolysis of bromoethane by aqueous NaOH, what is the nature of the attacking group and of the leaving group? attacking group leavi…Question 227: Structural isomerism only should be considered when answering this question. How many compounds with molecular formula C5H11Br are primary …Question 228: Q is either a primary or a tertiary halogenoalkane. Q undergoes hydrolysis with aqueous sodium hydroxide. The first step in the mechanism o…57 / 66
Question 229: 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 230: Which reagents could be used to form 2-bromobutane from butan-1-ol? A bromine and ultraviolet light B concentrated sulfuric acid with potas…Question 231: Aqueous NaOH reacts with 1-bromopropane to give propan-1-ol. What should be included in a diagram of the first step in the mechanism? A a c…Question 232: 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 233: What is involved in the mechanism of the reaction between aqueous NaOH and 1-bromobutane? A attack by a nucleophile on a carbon atom with a…58 / 66
Question 234: When heated with KOH dissolved in ethanol, halogenoalkanes can undergo an elimination reaction to form alkenes. What are the possible elimi…Question 235: Chloroethane can be used to make sodium propanoate. chloroethane  intermediate Q  sodium propanoate Intermediate Q is hydrolysed with boi…Question 236: When X is added to NaOH(aq) and heated under reflux, pentan-2-ol is made. Which organic product is made when X is heated with a solution of…Question 237: 1-chlorobutane and 1-iodobutane both react with aqueous sodium hydroxide by a nucleophilic substitution mechanism. Which reaction has the g…59 / 66
Question 238: The table shows three sets of reagents and reaction conditions. reagents reaction conditions 1 CH2C(CH3)CH3 and HCl (g) room temperature 2 …Question 239: When X is added to NaOH(aq) and heated under reflux, pentan-2-ol is made. Which organic product is made when X is heated with a solution of…Question 240: 1-chlorobutane and 1-iodobutane both react with aqueous sodium hydroxide by a nucleophilic substitution mechanism. Which reaction has the g…Question 241: 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 242: Compound Y is hydrolysed by warm aqueous silver nitrate to form a precipitate that is soluble in dilute aqueous ammonia. Compound Y undergo…60 / 66
Question 243: Propan-2-ol can be converted into 2-chloropropane using reagent M followed by reagent N. Which row is correct? reagent M reagent N A concen…Question 244: A possible mechanism for the exothermic hydrolysis of 2-chloro-2-methylpropane is shown. CH3 C Cl CH3 CH3 CH3 C Cl– CH3 CH3 + CH3 C CH3 CH3…61 / 66
Question 245: Two reactions are described. 1 2-bromo-2-methylbutane heated with NaOH(aq) 2 2-chloro-2-methylbutane heated with NaOH(aq) In both reactions…Question 246: Which statement about the mechanism of an SN1 reaction of a halogenoalkane is correct? A A nucleophile is substituted by an electrophile. B…Question 247: Which row gives pentanenitrile as one product? reagents and halogenoalkane conditions A heat with HCN Br B heat with KCN using Br ethanol a…Question 248: An amine is produced in the following reaction. C2H5I + 2NH3 → C2H5NH2 + NH4I What is the mechanism? A electrophilic addition B free-…62 / 66
Question 249: 1-chloro-2-methylbutane reacts with sodium cyanide in a nucleophilic substitution reaction. What is the most likely intermediate or transit…Question 250: Which reagent would react with 1-bromopropane to give the highest yield of propene? A ammonia B aqueous potassium hydroxide C potassium cya…Question 251: Separate samples of 1-bromopropane are used in two different reactions. reaction 1 1-bromopropane is converted into compound X by heating i…63 / 66
Question 252: Compound X, C7H11ICl2, is dissolved in ethanol and the solution mixed with warm aqueous silver nitrate. A precipitate is seen immediately. …Question 253: 1,4-dibromobutane reacts with an excess of ethanolic sodium hydroxide until no further reaction takes place. What is the relative formula m…64 / 66
Question 254: 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…Question 255: 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…Question 256: Which reaction mixture produces a nitrile? A halogenoalkane with KCN in ethanol B halogenoalkane with NH3 in ethanol C ketone with 2,4-DNPH…Question 257: Which reaction is classified as SN1? A the reaction of 1-chloropropane with ammonia in ethanol B the reaction of 1-chloropropane with potas…65 / 66
Question 258: Compound X, C7H11ICl2, is dissolved in ethanol and the solution mixed with warm aqueous silver nitrate. A precipitate is seen immediately. …Question 259: 1,4-dibromobutane reacts with an excess of ethanolic sodium hydroxide until no further reaction takes place. What is the relative formula m…66 / 66

Mark scheme259 answers

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

Pastlit

Chemistry 9701 · Halogenoalkanes — Paper 1

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

Question

Answer

Marks

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

Chemistry 9701 · Halogenoalkanes — Paper 1

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

Question

Answer

Marks

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

Pastlit

Chemistry 9701 · Halogenoalkanes — Paper 1

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

Question

Answer

Marks

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

Chemistry 9701 · Halogenoalkanes — Paper 1

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

Question

Answer

Marks

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

Pastlit

Chemistry 9701 · Halogenoalkanes — Paper 1

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

Question

Answer

Marks

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

Pastlit

Chemistry 9701 · Halogenoalkanes — Paper 1

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

Question

Answer

Marks

246C1
247B1
248D1
249A1
250D1
251B1
252D1
253A1
254B1
255D1
256A1
257C1
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Questions as text

Q1 · An amine is produced in the following reaction 9701/11 Oct/Nov 2005

23 An amine is produced in the following reaction. C2H5I + 2NH3 → C2H5NH2 + NH4I What is the mechanism? A electrophilic addition B electrophilic substitution C nucleophilic addition D nucleophilic substitution

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2005

Q2 · Use of the Data Booklet is relevant to this question 9701/11 May/June 2006

23 Use of the Data Booklet is relevant to this question. In which reaction is the relative molecular mass of the organic product the largest? A bromoethane + aqueous sodium hydroxide B bromoethane + alcoholic sodium hydroxide C ethane + bromine D ethanol + phosphorus pentachloride

1 marks

Answer: C

This question in 9701/11 May/June 2006

Q3 · High-energy irradiation in the stratosphere produces radicals from chlorofluoroalkanes… 9701/11 May/June 2006

25 High-energy irradiation in the stratosphere produces radicals from chlorofluoroalkanes, commonly known as CFCs. Which radical could result from this irradiation of CHFClCF2Cl? A CHFClCFCl B CHClCF2Cl C CHFCF2Cl D CFClCF2Cl

1 marks

Answer: C

This question in 9701/11 May/June 2006

Q4 · What is the total number of different chloroethanes, formula C2H6-nCln, where n can be… 9701/11 Oct/Nov 2006

21 What is the total number of different chloroethanes, formula C2H6-nCln, where n can be any integer from 1 to 4? A 4 B 6 C 7 D 8

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2006

Q5 · Which reaction is an example of nucleophilic substitution? 9701/11 Oct/Nov 2006

22 Which reaction is an example of nucleophilic substitution? A CH3CH2Br → CH2=CH2 + HBr B CH2=CH2 + HBr → CH3CH2Br C C3H7Br + H2O → C3H7OH + HBr D C2H6 + Br2 → C2H5Br + HBr

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2006

Q6 · Compound X on refluxing with aqueous sodium hydroxide gave mixture Y which on… 9701/11 Oct/Nov 2007

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

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2007

Q7 · The anaesthetic halothane, CF3CHBrCl, is made industrially as shown below 9701/11 Oct/Nov 2007

24 The anaesthetic halothane, CF3CHBrCl, is made industrially as shown below. HF Br2 CCl2=CHCl CF3CH2Cl CF3CHBrCl stage 1 stage 2 Which type of reaction is occurring in stage 2? A electrophilic addition B electrophilic substitution C free radical substitution D nucleophilic addition

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2007

Q8 · Chlorofluoroalkanes, CFCs, can be used as refrigerants, aerosol propellants and fire… 9701/11 Oct/Nov 2007

25 Chlorofluoroalkanes, CFCs, can be used as refrigerants, aerosol propellants and fire extinguishers. CFCs such as CCl3F and CCl2F2 are more stable than chloroalkanes such as CCl4. What is the reason for their greater stability? A Fluorine has a higher first ionisation energy than chlorine. B Fluorine radicals are more stable than chlorine radicals. C The C–F bond energy is larger than the C–Cl bond energy. D The C–F bond is more polar than the C–Cl bond.

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2007

Q9 · 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

Q10 · Halogenoalkanes are important molecules in organic synthetic reactions 9701/11 May/June 2008

25 Halogenoalkanes are important molecules in organic synthetic reactions. In particular they undergo a range of nucleophilic reactions. Which reaction proceeds only by an SN1 mechanism? A CH3CH2Br + NH3 B CH3CH2CH2I + OH– C CH3CHBrCH3 + NH3 D (CH3)3CI + OH–

1 marks

Answer: D

This question in 9701/11 May/June 2008

Q11 · The structure of monosodium glutamate, a flavour enhancer, is shown 9701/11 May/June 2008

38 The structure of monosodium glutamate, a flavour enhancer, is shown. Na+ O– C CH2 CH2 CH CO2H O NH2 It may be prepared starting from the following compound. Cl CH2 CH2 CH CO2H NH2 Which set of reagents and reaction conditions could be used to prepare monosodium glutamate? 1 Heat under reflux with ethanolic KCN followed by hydrolysis with NaOH(aq). 2 Heat with sodium methanoate, HCO Na − + . 2 3 Heat under reflux with NaOH(aq).

1 marks

Answer: D

This question in 9701/11 May/June 2008

Q12 · Aluminium chloride catalyses certain reactions by forming carbocations (carbonium ions)… 9701/11 Oct/Nov 2008

15 Aluminium chloride catalyses certain reactions by forming carbocations (carbonium ions) with chloroalkanes as shown. RCl + Al Cl3 → R+ + A l C l − 4 Which property makes this reaction possible? A AlCl3 exists as the dimer Al2Cl6 in the vapour. B AlCl3 is a covalent molecule. C The aluminium atom in Al Cl3 has an incomplete octet of electrons. D The chlorine atom in RCl has a vacant p orbital.

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2008

Q13 · Four drops of 1-chlorobutane, 1-bromobutane and 1-iodobutane were put separately into… 9701/11 Oct/Nov 2008

23 Four drops of 1-chlorobutane, 1-bromobutane and 1-iodobutane were put separately into three test-tubes containing 1.0 cm3 of aqueous silver nitrate at 60 °C. A hydrolysis reaction occurred. (R represents the butane chain C4H9– and X the halogen atom.) H2O(l) + R–X(l) + Ag+(aq) → R–OH(aq) + AgX(s) + H+(aq) The rate of formation of cloudiness in the tubes was in the order RCl < RBr < RI. Why is this? A The R–X bond polarity decreases from RCl to RI. B The solubility of AgX(s) decreases from AgCl to AgI. C The ionisation energy of the halogen decreases from Cl to I. D The bond energy of R–X decreases from RCl to RI.

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2008

Q14 · A possible mechanism of the exothermic hydrolysis of 2-chloro-2-methylpropane is shown 9701/11 Oct/Nov 2008

24 A possible mechanism of the exothermic hydrolysis of 2-chloro-2-methylpropane is shown. CH3 CH3 slow + _ CH3 C Cl CH3 C + Cl CH3 CH3 CH3 CH3 + _ fast CH3 C + OH CH3 C OH CH3 CH3 Which diagram represents the reaction profile for this mechanism? A B C D energy energy energy energy reaction pathway reaction pathway reaction pathway reaction pathway

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2008

Q15 · In the hydrolysis of bromoethane by aqueous sodium hydroxide, what is the nature of the… 9701/11 May/June 2009

24 In the hydrolysis of bromoethane by aqueous sodium hydroxide, what is the nature of the attacking group and of the leaving group? attacking group leaving group A electrophile electrophile B electrophile nucleophile C nucleophile electrophile D nucleophile nucleophile

1 marks

Answer: D

This question in 9701/11 May/June 2009

Q16 · Which reaction would not give propene as one product? 9701/11 May/June 2009

25 Which reaction would not give propene as one product? A adding an excess of concentrated sulfuric acid to propan-1-ol B adding warm aqueous sodium hydroxide to 2-bromopropane C adding warm ethanolic sodium hydroxide to 1-bromopropane D passing propan-2-ol vapour over heated aluminium oxide

1 marks

Answer: B

This question in 9701/11 May/June 2009

Q17 · Which statements are true for an SN2 reaction? 9701/11 Oct/Nov 2009

37 Which statements are true for an SN2 reaction? 1 One bond is broken as another bond is formed. 2 The formation of a transition state involves the collision of two molecules or ions. 3 A carbon atom in the transition state is bonded, either fully or partially, to five other atoms.

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2009

Q18 · In many countries plastic waste is collected separately and sorted 9701/11 May/June 2010

26 In many countries plastic waste is collected separately and sorted. Some of this is incinerated to provide heat for power stations. Why is pvc, polyvinylchloride, removed from any waste that is to be incinerated? A It destroys the ozone layer. B It does not burn easily. C It is easily biodegradable. D Its combustion products are harmful.

1 marks

Answer: D

This question in 9701/11 May/June 2010

Q19 · When an isomer Y of molecular formula C4H9Br undergoes hydrolysis in aqueous alkali to… 9701/11 May/June 2010

28 When an isomer Y of molecular formula C4H9Br undergoes hydrolysis in aqueous alkali to form an alcohol C4H9OH, the rate of reaction is found to be unaffected by changes in the concentration of OH– ions present. Which is the most likely molecular structure of Y? A CH3CH2CH2CH2Br B CH3CH2CHBrCH3 C (CH3)2CHCH2Br D (CH3)3CBr

1 marks

Answer: D

This question in 9701/11 May/June 2010

Q20 · Which reactions are examples of nucleophilic substitution? 9701/11 May/June 2010

39 Which reactions are examples of nucleophilic substitution? 1 CH3CH2Br + OH– → CH3CH2OH + Br– H + 2 CH3I + H2O → CH3OH + HI 3 CH3CH2CH2Cl + NH3 → CH3CH2CH2NH2 + HCl

1 marks

Answer: A

This question in 9701/11 May/June 2010

Q21 · When an isomer Y of molecular formula C4H9Br undergoes hydrolysis in aqueous alkali to… 9701/12 May/June 2010

26 When an isomer Y of molecular formula C4H9Br undergoes hydrolysis in aqueous alkali to form an alcohol C4H9OH, the rate of reaction is found to be unaffected by changes in the concentration of OH– ions present. Which is the most likely molecular structure of Y? A CH3CH2CH2CH2Br B CH3CH2CHBrCH3 C (CH3)2CHCH2Br D (CH3)3CBr

1 marks

Answer: D

This question in 9701/12 May/June 2010

Q22 · In many countries plastic waste is collected separately and sorted 9701/12 May/June 2010

29 In many countries plastic waste is collected separately and sorted. Some of this is incinerated to provide heat for power stations. Why is pvc, polyvinylchloride, removed from any waste that is to be incinerated? A It destroys the ozone layer. B It does not burn easily. C It is easily biodegradable. D Its combustion products are harmful.

1 marks

Answer: D

This question in 9701/12 May/June 2010

Q23 · Which reactions are examples of nucleophilic substitution? 9701/12 May/June 2010

37 Which reactions are examples of nucleophilic substitution? 1 CH3CH2Br + OH– → CH3CH2OH + Br– H + 2 CH3I + H2O → CH3OH + HI 3 CH3CH2CH2Cl + NH3 → CH3CH2CH2NH2 + HCl

1 marks

Answer: A

This question in 9701/12 May/June 2010

Q24 · In many countries plastic waste is collected separately and sorted 9701/13 May/June 2010

27 In many countries plastic waste is collected separately and sorted. Some of this is incinerated to provide heat for power stations. Why is pvc, polyvinylchloride, removed from any waste that is to be incinerated? A It destroys the ozone layer. B It does not burn easily. C It is easily biodegradable. D Its combustion products are harmful.

1 marks

Answer: D

This question in 9701/13 May/June 2010

Q25 · When an isomer Y of molecular formula C4H9Br undergoes hydrolysis in aqueous alkali to… 9701/13 May/June 2010

29 When an isomer Y of molecular formula C4H9Br undergoes hydrolysis in aqueous alkali to form an alcohol C4H9OH, the rate of reaction is found to be unaffected by changes in the concentration of OH– ions present. Which is the most likely molecular structure of Y? A CH3CH2CH2CH2Br B CH3CH2CHBrCH3 C (CH3)2CHCH2Br D (CH3)3CBr

1 marks

Answer: D

This question in 9701/13 May/June 2010

Q26 · Which reactions are examples of nucleophilic substitution? 9701/13 May/June 2010

38 Which reactions are examples of nucleophilic substitution? 1 CH3CH2Br + OH– → CH3CH2OH + Br– H + 2 CH3I + H2O → CH3OH + HI 3 CH3CH2CH2Cl + NH3 → CH3CH2CH2NH2 + HCl

1 marks

Answer: A

This question in 9701/13 May/June 2010

Q27 · The diagram shows some laboratory apparatus 9701/13 May/June 2010

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

1 marks

Answer: B

This question in 9701/13 May/June 2010

Q28 · 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

Q29 · Which compound undergoes an SN1 substitution reaction? 9701/11 Oct/Nov 2010

28 Which compound undergoes an SN1 substitution reaction? A CH3CH2CH2Br B (CH3)3CCH2I CH3 Cl C D CH2=CHCl

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2010

Q30 · Textiles for use in aircraft are treated with a finish containing a halogenoalkane 9701/11 Oct/Nov 2010

40 Textiles for use in aircraft are treated with a finish containing a halogenoalkane. What is the reason for this? 1 The textile burns less easily, improving safety. 2 The fabric forms hydrogen bonds to water more readily, making the fabric easier to wash. 3 The halogenoalkane undergoes addition polymerisation, stiffening the fabric.

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2010

Q31 · How many structural isomers are there of trichloropropane, C3H5Cl 3? 9701/12 Oct/Nov 2010

20 How many structural isomers are there of trichloropropane, C3H5Cl 3? A 3 B 4 C 5 D 6

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2010

Q32 · 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

Q33 · Which sequence of reagents may be used in the laboratory to convert propan-1-ol into… 9701/12 Oct/Nov 2010

23 Which sequence of reagents may be used in the laboratory to convert propan-1-ol into 2-bromopropane? A concentrated sulfuric acid, followed by bromine B concentrated sulfuric acid, followed by hydrogen bromide C ethanolic sodium hydroxide, followed by bromine D ethanolic sodium hydroxide, followed by hydrogen bromide

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2010

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

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

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2010

Q35 · A reaction pathway diagram is shown 9701/12 Oct/Nov 2010

40 A reaction pathway diagram is shown. energy reaction pathway Which reactions would have such a profile? 1 (CH3)3CBr + NaOH → (CH3)3COH + NaBr 2 CH3CH2Br + NaOH → CH3CH2OH + NaBr 3 (CH3)3CCH2CH2Cl + 2NH3 → (CH3)3CCH2CH2NH2 + NH4Cl

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2010

Q36 · 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

Q37 · Which compound undergoes an SN1 substitution reaction? 9701/13 Oct/Nov 2010

28 Which compound undergoes an SN1 substitution reaction? A CH3CH2CH2Br B (CH3)3CCH2I CH3 Cl C D CH2=CHCl

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2010

Q38 · Textiles for use in aircraft are treated with a finish containing a halogenoalkane 9701/13 Oct/Nov 2010

39 Textiles for use in aircraft are treated with a finish containing a halogenoalkane. What is the reason for this? 1 The textile burns less easily, improving safety. 2 The fabric forms hydrogen bonds to water more readily, making the fabric easier to wash. 3 The halogenoalkane undergoes addition polymerisation, stiffening the fabric.

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2010

Q39 · Butanedioic acid occurs in amber, algae, lichens, sugar cane and beets 9701/11 May/June 2011

21 Butanedioic acid occurs in amber, algae, lichens, sugar cane and beets. It may be synthesised in two steps from 1,2-dibromoethane. step 1 step 2 BrCH2CH2Br X HO2CCH2CH2CO2H Which reagents could be used for this synthesis? step 1 step 2 A HCN(g) HCl (aq) B HCO2Na(aq) HCl (aq) C KCN(aq / alcoholic) H2SO4(aq) D NaOH(aq) K2Cr2O7 / H2SO4(aq)

1 marks

Answer: C

This question in 9701/11 May/June 2011

Q40 · Bromoethane undergoes all of the conversions shown 9701/11 May/June 2011

39 Bromoethane undergoes all of the conversions shown. Which conversions are examples of nucleophilic substitution? 1 C2H5Br → C2H5CN 2 C2H5Br → C2H5OH 3 C2H5Br → C2H5NH2

1 marks

Answer: A

This question in 9701/11 May/June 2011

Q41 · Which halogenoalkane will undergo an SN1 reaction and produce a yellow precipitate when… 9701/12 May/June 2011

21 Which halogenoalkane will undergo an SN1 reaction and produce a yellow precipitate when AgNO3(aq) is added to it? A 1-chlorobutane B 1-iodobutane C 2-chloro-2-methylpropane D 2-iodo-2-methylpropane

1 marks

Answer: D

This question in 9701/12 May/June 2011

Q42 · Which reaction will give 2-chloropropane in the best yield? 9701/12 May/June 2011

22 Which reaction will give 2-chloropropane in the best yield? A propane gas with chlorine gas in the presence of ultraviolet light B propan-2-ol with dilute NaCl (aq) C propan-2-ol with SOCl 2 D propene with dilute HCl (aq)

1 marks

Answer: C

This question in 9701/12 May/June 2011

Q43 · 1,1-dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give… 9701/12 May/June 2011

27 1,1-dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give propanal. NaOH(aq) CH3CH2CHCl 2 CH3CH2CHO Which term describes the first step of this reaction? A electrophilic addition B elimination C nucleophilic substitution D oxidation

1 marks

Answer: C

This question in 9701/12 May/June 2011

Q44 · Bromoethane undergoes all of the conversions shown 9701/13 May/June 2011

40 Bromoethane undergoes all of the conversions shown. Which conversions are examples of nucleophilic substitution? 1 C2H5Br → C2H5CN 2 C2H5Br → C2H5OH 3 C2H5Br → C2H5NH2

1 marks

Answer: A

This question in 9701/13 May/June 2011

Q45 · What is involved in the mechanism of the reaction between aqueous sodium hydroxide and… 9701/11 Oct/Nov 2011

24 What is involved in the mechanism of the reaction between aqueous sodium hydroxide and 1-bromobutane? A attack by a nucleophile on a carbon atom with a partial positive charge B heterolytic bond fission and attack by a nucleophile on a carbocation C homolytic bond fission and attack by an electrophile on a carbanion D homolytic bond fission and attack by a nucleophile on a carbocation

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2011

Q46 · 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

Q47 · What is involved in the mechanism of the reaction between aqueous sodium hydroxide and… 9701/12 Oct/Nov 2011

25 What is involved in the mechanism of the reaction between aqueous sodium hydroxide and 2-bromo-2-methylbutane? A heterolytic bond fission, attack by an electrophile on a carbanion B heterolytic bond fission, attack by a nucleophile on a carbocation C homolytic bond fission, attack by an electrophile on a carbanion D homolytic bond fission, attack by a nucleophile on a carbocation

1 marks

This question in 9701/12 Oct/Nov 2011

Q48 · Y is an organic compound 9701/12 Oct/Nov 2011

38 Y is an organic compound. Y gives a precipitate with aqueous silver nitrate. All of this precipitate dissolves when concentrated aqueous ammonia is added. What is a possible identity for Y? 1 1-bromopropane 2 chloroethane 3 2-iodo-2-methylpropane

1 marks

This question in 9701/12 Oct/Nov 2011

Q49 · Y and Z are two widely-used selective weed killers 9701/13 Oct/Nov 2011

21 Y and Z are two widely-used selective weed killers. OCH2CO2H OCH2CH2OH CH3 Cl Cl Cl Y Z Which reagent will distinguish Y from Z? A acidified AgNO3(aq) B Fehling’s solution C Na D Na2CO3(aq)

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2011

Q50 · What is involved in the mechanism of the reaction between aqueous sodium hydroxide and… 9701/13 Oct/Nov 2011

22 What is involved in the mechanism of the reaction between aqueous sodium hydroxide and 1-bromobutane? A attack by a nucleophile on a carbon atom with a partial positive charge B heterolytic bond fission and attack by a nucleophile on a carbocation C homolytic bond fission and attack by an electrophile on a carbanion D homolytic bond fission and attack by a nucleophile on a carbocation

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2011

Q51 · Many different compounds have been used in aerosol sprays, refrigerators and in making… 9701/13 Oct/Nov 2011

24 Many different compounds have been used in aerosol sprays, refrigerators and in making foamed plastics. Which compound will cause the most ozone depletion? A CCl 3F B CH2FCHCl F C CH3CH2CH2CH3 D N2O

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2011

Q52 · Aluminium chloride catalyses certain reactions by forming carbocations with chloroalkanes… 9701/11 May/June 2012

12 Aluminium chloride catalyses certain reactions by forming carbocations with chloroalkanes as shown. RCl + Al Cl 3 → R+ + Al Cl 4 – Which property makes this reaction possible? A Al Cl 3 exists as the dimer Al 2Cl 6 in the vapour. B Al Cl 3 is a covalent molecule. C The aluminium atom in Al Cl 3 has an incomplete octet of electrons. D The chlorine atom in RCl has a vacant p orbital.

1 marks

Answer: C

This question in 9701/11 May/June 2012

Q53 · The presence of halogen in an organic compound may be detected by warming the organic… 9701/11 May/June 2012

27 The presence of halogen in an organic compound may be detected by warming the organic compound with aqueous silver nitrate. Which compound would produce a precipitate quickest? A B C D Cl F Cl F Cl Cl Br F Cl F F I

1 marks

Answer: D

This question in 9701/11 May/June 2012

Q54 · A reaction pathway diagram is shown 9701/11 May/June 2012

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

1 marks

Answer: B

This question in 9701/11 May/June 2012

Q55 · The depletion of the ozone layer in the upper atmosphere reduces the Earth’s natural… 9701/11 May/June 2012

29 The depletion of the ozone layer in the upper atmosphere reduces the Earth’s natural protection from harmful ultraviolet radiation. Which compound would cause the most depletion of the ozone layer? A CCl 3F B CF4 C CHCl F2 D CH2F2

1 marks

Answer: A

This question in 9701/11 May/June 2012

Q56 · How can a good yield of ethylamine be made using bromoethane as starting material? 9701/11 May/June 2012

40 How can a good yield of ethylamine be made using bromoethane as starting material? 1 by heating bromoethane with an excess of ammonia gas in a sealed tube 2 by adding dilute aqueous ammonia to bromoethane at room temperature 3 by heating bromoethane under reflux with aqueous ammonium chloride

1 marks

Answer: D

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 · When phenacyl chloride, C6H5COCH2Cl, is reacted with aqueous NaOH, the substitution… 9701/12 May/June 2012

25 When phenacyl chloride, C6H5COCH2Cl, is reacted with aqueous NaOH, the substitution reaction follows an SN2 mechanism. Which structure represents a species formed during the reaction? A B H OH H δ+ δ– C6H5 C C + C6H5 C C Cl O H O– H C D – – H H H H δ– δ– δ– HO C Cl HO C Cl δ– C O C O C6H5 C6H5

1 marks

Answer: C

This question in 9701/12 May/June 2012

Q59 · The depletion of the ozone layer in the upper atmosphere reduces the Earth’s natural… 9701/13 May/June 2012

27 The depletion of the ozone layer in the upper atmosphere reduces the Earth’s natural protection from harmful ultraviolet radiation. Which compound would cause the most depletion of the ozone layer? A CCl 3F B CF4 C CHCl F2 D CH2F2

1 marks

Answer: A

This question in 9701/13 May/June 2012

Q60 · The presence of halogen in an organic compound may be detected by warming the organic… 9701/13 May/June 2012

28 The presence of halogen in an organic compound may be detected by warming the organic compound with aqueous silver nitrate. Which compound would produce a precipitate quickest? A B C D Cl F Cl F Cl Cl Br F Cl F F I

1 marks

Answer: D

This question in 9701/13 May/June 2012

Q61 · A reaction pathway diagram is shown 9701/13 May/June 2012

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

1 marks

Answer: B

This question in 9701/13 May/June 2012

Q62 · How can a good yield of ethylamine be made using bromoethane as starting material? 9701/13 May/June 2012

39 How can a good yield of ethylamine be made using bromoethane as starting material? 1 by heating bromoethane with an excess of ammonia gas in a sealed tube 2 by adding dilute aqueous ammonia to bromoethane at room temperature 3 by heating bromoethane under reflux with aqueous ammonium chloride

1 marks

Answer: D

This question in 9701/13 May/June 2012

Q63 · High-energy radiation in the stratosphere produces free-radicals from… 9701/11 Oct/Nov 2012

26 High-energy radiation in the stratosphere produces free-radicals from chlorofluoroalkanes, commonly known as CFCs. Which free-radical is most likely to result from the irradiation of CHFCl CF2Cl ? A CHFCl CFCl B CHCl CF2Cl C CHFCF2Cl D CFCl CF2Cl

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2012

Q64 · Many, but not all, organic reactions need to be heated before reaction occurs 9701/11 Oct/Nov 2012

29 Many, but not all, organic reactions need to be heated before reaction occurs. Which reaction occurs at a good rate at room temperature (20 °C)? A CH3OH + PCl 5 → CH3Cl + POCl 3 + HCl B CH3CH2Br + KCN → CH3CH2CN + KBr C CH3CH2OH → C2H4 + H2O D CH3CH2CN + 2H2O → CH3CH2CO2H + NH3

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2012

Q65 · Chloroethane can be formed from bromoethane in two steps 9701/11 Oct/Nov 2012

38 Chloroethane can be formed from bromoethane in two steps. step X step Y C2H5Br C2H5OH C2H5Cl Which statements about these steps are correct? 1 Step X involves nucleophilic substitution. 2 Hot aqueous sodium hydroxide is the reagent in step X. 3 Hot aqueous sodium chloride is the reagent in step Y.

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2012

Q66 · High-energy radiation in the stratosphere produces free-radicals from… 9701/12 Oct/Nov 2012

26 High-energy radiation in the stratosphere produces free-radicals from chlorofluoroalkanes, commonly known as CFCs. Which free-radical is most likely to result from the irradiation of CHFCl CF2Cl ? A CHFCl CFCl B CHCl CF2Cl C CHFCF2Cl D CFCl CF2Cl

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2012

Q67 · Many, but not all, organic reactions need to be heated before reaction occurs 9701/12 Oct/Nov 2012

29 Many, but not all, organic reactions need to be heated before reaction occurs. Which reaction occurs at a good rate at room temperature (20 °C)? A CH3OH + PCl 5 → CH3Cl + POCl 3 + HCl B CH3CH2Br + KCN → CH3CH2CN + KBr C CH3CH2OH → C2H4 + H2O D CH3CH2CN + 2H2O → CH3CH2CO2H + NH3

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2012

Q68 · Which reagents and conditions will convert propane into 1-chloropropane? 9701/12 Oct/Nov 2012

37 Which reagents and conditions will convert propane into 1-chloropropane? 1 Cl 2 and sunlight 2 conc. HCl, reflux 3 PCl 5

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2012

Q69 · Chloroethane can be formed from bromoethane in two steps 9701/12 Oct/Nov 2012

38 Chloroethane can be formed from bromoethane in two steps. step X step Y C2H5Br C2H5OH C2H5Cl Which statements about these steps are correct? 1 Step X involves nucleophilic substitution. 2 Hot aqueous sodium hydroxide is the reagent in step X. 3 Hot aqueous sodium chloride is the reagent in step Y.

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2012

Q70 · A possible mechanism for the exothermic hydrolysis of 2-chloro-2-methylpropane is shown 9701/13 Oct/Nov 2012

30 A possible mechanism for the exothermic hydrolysis of 2-chloro-2-methylpropane is shown. CH3 CH3 slow + CH3 C Cl CH3 C + Cl – CH3 CH3 CH3 CH3 + OH– fast CH3 C + CH3 C OH CH3 CH3 Which diagram represents the reaction pathway diagram for this mechanism? A B energy energy reaction pathway reaction pathway C D energy energy reaction pathway reaction pathway

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2012

Q71 · Chloroethane can be used to make sodium propanoate 9701/11 May/June 2013

23 Chloroethane can be used to make sodium propanoate. chloroethane → Q → sodium propanoate The intermediate, Q, is hydrolysed with boiling aqueous sodium hydroxide, to give sodium propanoate. Which reagent would produce the intermediate, Q, from chloroethane? A concentrated ammonia solution B dilute sulfuric acid C hydrogen cyanide D potassium cyanide

1 marks

Answer: D

This question in 9701/11 May/June 2013

Q72 · Aqueous sodium hydroxide reacts with 1-bromopropane to give propan-1-ol 9701/11 May/June 2013

24 Aqueous sodium hydroxide reacts with 1-bromopropane to give propan-1-ol. How should the first step in the mechanism be described? A by a curly arrow from a lone pair on the OH– ion to the Cδ+ atom of 1-bromopropane B by a curly arrow from the Cδ+ atom of 1-bromopropane to the OH– ion C by a curly arrow from the C–Br bond to the C atom D by the homolytic fission of the C–Br bond

1 marks

Answer: A

This question in 9701/11 May/June 2013

Q73 · Aqueous sodium hydroxide reacts with 2-bromo-2-methylpropane to give 2-methylpropan-2-ol 9701/12 May/June 2013

23 Aqueous sodium hydroxide reacts with 2-bromo-2-methylpropane to give 2-methylpropan-2-ol. The reaction proceeds by an SN1 mechanism. How should the first step in the mechanism be described? A by a curly arrow from a lone pair on the OH– ion to the Cδ+ atom of 2-bromopropane B by a curly arrow from the C–Br bond to the Br atom C by a curly arrow from the C–Br bond to the C atom D by the homolytic fission of the C–Br bond

1 marks

Answer: B

This question in 9701/12 May/June 2013

Q74 · Compound Y can be hydrolysed by warm aqueous silver nitrate to form a precipitate that is… 9701/12 May/June 2013

24 Compound Y can be hydrolysed by warm aqueous silver nitrate to form a precipitate that is soluble in dilute aqueous ammonia. Compound Y can undergo an elimination reaction to form an alkene. What could be the skeletal formula of compound Y? A B C D Br I Cl Cl

1 marks

Answer: C

This question in 9701/12 May/June 2013

Q75 · Which are properties of fluoroalkanes? 9701/12 May/June 2013

37 Which are properties of fluoroalkanes? 1 They are less reactive than the corresponding chloroalkanes. 2 They are non-flammable. 3 The C–F bond is stronger than the C–Cl bond.

1 marks

Answer: A

This question in 9701/12 May/June 2013

Q76 · Which sequence of reagents may be used in the laboratory to convert propan-1-ol into… 9701/13 May/June 2013

24 Which sequence of reagents may be used in the laboratory to convert propan-1-ol into 2-bromopropane? A concentrated sulfuric acid, followed by bromine B concentrated sulfuric acid, followed by hydrogen bromide C ethanolic sodium hydroxide, followed by bromine D ethanolic sodium hydroxide, followed by hydrogen bromide

1 marks

Answer: B

This question in 9701/13 May/June 2013

Q77 · A carbanion is an organic ion in which a carbon atom has a negative charge 9701/13 May/June 2013

25 A carbanion is an organic ion in which a carbon atom has a negative charge. A carbocation is an organic ion in which a carbon atom has a positive charge. What is involved in the mechanism of the reaction between aqueous sodium hydroxide and 2-bromo-2-methylbutane? A heterolytic bond fission followed by an attack by an electrophile on a carbanion B heterolytic bond fission followed by an attack by a nucleophile on a carbocation C homolytic bond fission followed by an attack by an electrophile on a carbanion D homolytic bond fission followed by an attack by a nucleophile on a carbocation

1 marks

Answer: B

This question in 9701/13 May/June 2013

Q78 · Fabrics for use in aircraft seating are treated with a coating containing a halogenoalkane 9701/13 May/June 2013

38 Fabrics for use in aircraft seating are treated with a coating containing a halogenoalkane. Why is this coating used? 1 The treated fabric burns less easily, improving safety. 2 The treated fabric forms hydrogen bonds to water more readily, so it is easier to wash. 3 The halogenoalkane undergoes addition polymerisation, stiffening the fabric.

1 marks

Answer: D

This question in 9701/13 May/June 2013

Q79 · Which reaction will give the best yield of 1-chloropropane? 9701/11 Oct/Nov 2013

21 Which reaction will give the best yield of 1-chloropropane? A chlorine gas with propene gas in the dark B propan-1-ol with dilute NaCl (aq) C propan-1-ol with PCl 5 D propene with dilute HCl (aq)

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2013

Q80 · A carbanion is an organic ion in which a carbon atom has a negative charge 9701/11 Oct/Nov 2013

24 A carbanion is an organic ion in which a carbon atom has a negative charge. A carbocation is an organic ion in which a carbon atom has a positive charge. The reaction between aqueous sodium hydroxide and 1-bromobutane proceeds by an SN2 mechanism. How should the first step in the mechanism be described? A attack by a nucleophile on a carbon atom with a partial positive charge B heterolytic bond fission followed by an attack by an electrophile on a carbanion C heterolytic bond fission followed by an attack by a nucleophile on a carbocation D homolytic bond fission followed by an attack by a nucleophile on a carbocation

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2013

Q81 · The organic compound X gives a precipitate when warmed with aqueous silver nitrate 9701/11 Oct/Nov 2013

37 The organic compound X gives a precipitate when warmed with aqueous silver nitrate. This precipitate dissolves when concentrated aqueous ammonia is added. What is a possible identity for X? 1 1-bromopropane 2 2-chlorobutane 3 2-iodo,2-methylpropane

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2013

Q82 · Which reactions can be used to make an alcohol in the laboratory? 9701/11 Oct/Nov 2013

39 Which reactions can be used to make an alcohol in the laboratory? 1 hydrolysis of a bromoalkane with NaOH(aq) 2 reduction of a ketone with NaBH4 3 reduction of an aldehyde with NaBH4

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2013

Q83 · Which reaction will give the best yield of 1-chloropropane? 9701/12 Oct/Nov 2013

21 Which reaction will give the best yield of 1-chloropropane? A chlorine gas with propene gas in the dark B propan-1-ol with dilute NaCl (aq) C propan-1-ol with PCl 5 D propene with dilute HCl (aq)

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2013

Q84 · A carbanion is an organic ion in which a carbon atom has a negative charge 9701/12 Oct/Nov 2013

24 A carbanion is an organic ion in which a carbon atom has a negative charge. A carbocation is an organic ion in which a carbon atom has a positive charge. The reaction between aqueous sodium hydroxide and 1-bromobutane proceeds by an SN2 mechanism. How should the first step in the mechanism be described? A attack by a nucleophile on a carbon atom with a partial positive charge B heterolytic bond fission followed by an attack by an electrophile on a carbanion C heterolytic bond fission followed by an attack by a nucleophile on a carbocation D homolytic bond fission followed by an attack by a nucleophile on a carbocation

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2013

Q85 · The organic compound X gives a precipitate when warmed with aqueous silver nitrate 9701/12 Oct/Nov 2013

37 The organic compound X gives a precipitate when warmed with aqueous silver nitrate. This precipitate dissolves when concentrated aqueous ammonia is added. What is a possible identity for X? 1 1-bromopropane 2 2-chlorobutane 3 2-iodo,2-methylpropane

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2013

Q86 · Which reactions can be used to make an alcohol in the laboratory? 9701/12 Oct/Nov 2013

39 Which reactions can be used to make an alcohol in the laboratory? 1 hydrolysis of a bromoalkane with NaOH(aq) 2 reduction of a ketone with NaBH4 3 reduction of an aldehyde with NaBH4

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2013

Q87 · Including structural and stereoisomers, how many isomers are there of C2H2Br2? 9701/13 Oct/Nov 2013

21 Including structural and stereoisomers, how many isomers are there of C2H2Br2? A 2 B 3 C 4 D 5

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2013

Q88 · Which reaction will give the best yield of 2-chloropropane? 9701/13 Oct/Nov 2013

22 Which reaction will give the best yield of 2-chloropropane? A chlorine gas with propane gas in the presence of uv light B chlorine gas with propene gas in the dark C propan-2-ol with dilute NaCl (aq) D propan-2-ol with PCl 5

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2013

Q89 · Including structural and stereoisomers, how many isomeric products are produced when… 9701/13 Oct/Nov 2013

24 Including structural and stereoisomers, how many isomeric products are produced when alcoholic KOH reacts with 2-chlorobutane? A 1 B 2 C 3 D 4

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2013

Q90 · Chlorofluorocarbons, CFCs, can be used as refrigerants, aerosol propellants and fire… 9701/13 Oct/Nov 2013

25 Chlorofluorocarbons, CFCs, can be used as refrigerants, aerosol propellants and fire extinguishers. CFCs such as CCl 3F and CCl 2F2 are more stable than chloroalkanes such as CCl 4. What is the reason for their greater stability? A Fluorine has a higher first ionisation energy than chlorine. B Fluorine radicals are more stable than chlorine radicals. C The C–F bond energy is larger than the C–Cl bond energy. D The C–F bond is more polar than the C–Cl bond.

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2013

Q91 · Halogenoalkanes react with aqueous NaOH to give alcohols 9701/13 Oct/Nov 2013

26 Halogenoalkanes react with aqueous NaOH to give alcohols. The mechanism involved is either SN1 or SN2. Which halogenoalkane produces the highest percentage of product by an SN1 mechanism, when treated with aqueous NaOH? A 2-bromopropane B 2-chloropropane C 1-iodo-2-methylpropane D 2-iodo-2-methylpropane

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2013

Q92 · Which fragment could appear in the chain produced by polymerising 1,1-dichloroethene? 9701/13 Oct/Nov 2013

30 Which fragment could appear in the chain produced by polymerising 1,1-dichloroethene? A – CH2 – CH2 – CCl 2 – CCl 2 – CH2 – CH2 – B – CHCl – CHCl – CHCl – CHCl – CHCl – CHCl – C – CH2 – CCl 2 – CH2 – CH2 – CH2 – CCl 2 – D – CCl 2 – CCl 2 – CH2 – CH2 – CH2 – CCl 2 –

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2013

Q93 · The hydrolysis of 1-chloropropane to produce propan-1-ol is much slower than the… 9701/11 May/June 2014

23 The hydrolysis of 1-chloropropane to produce propan-1-ol is much slower than the corresponding hydrolysis of 1-iodopropane. Which statement explains this observation? A Chlorine is more electronegative than iodine. B The bond strength of the C – I bond is less than that of the C – Cl bond. C The carbon atom in the C – Cl bond is more δ+ than that in the C – I bond. D The hydrolysis involves a nucleophilic addition reaction.

1 marks

Answer: B

This question in 9701/11 May/June 2014

Q94 · Butanoic acid can be produced from 1-bromopropane using reagents X and Y as shown below 9701/11 May/June 2014

30 Butanoic acid can be produced from 1-bromopropane using reagents X and Y as shown below. reagent X reagent Y 1-bromopropane compound Q butanoic acid What could be reagents X and Y? X Y A KCN in ethanol HCl (aq) B KCN in ethanol NaOH(aq) C NH3 in ethanol HCl (aq) D NaOH(aq) H+ / Cr2O7 2–(aq)

1 marks

Answer: A

This question in 9701/11 May/June 2014

Q95 · Halogenoalkanes undergo a range of nucleophilic substitution reactions 9701/12 May/June 2014

21 Halogenoalkanes undergo a range of nucleophilic substitution reactions. Which reaction proceeds only by an SN1 mechanism? A CH3CH2Br + NH3 B CH3CH2CH2I + OH– C CH3CHBrCH3 + NH3 D (CH3)3CI + OH–

1 marks

Answer: D

This question in 9701/12 May/June 2014

Q96 · Which statement does not correctly describe a problem related to the disposal of PVC? 9701/12 May/June 2014

25 Which statement does not correctly describe a problem related to the disposal of PVC? A PVC is slowly degraded in the environment by bacteria and fungi. B PVC is slowly degraded in the environment by sunlight. C When PVC is burnt, a significant amount of ethene gas is present in the products. D When PVC is burnt, a significant amount of HCl gas is present in the products.

1 marks

Answer: C

This question in 9701/12 May/June 2014

Q97 · When heated with KOH dissolved in ethanol, halogenoalkanes can undergo an elimination… 9701/12 May/June 2014

29 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 9701/12 May/June 2014

Q98 · 1,1-dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give… 9701/11 Oct/Nov 2014

22 1,1-dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give propanal. NaOH(aq) CH3CH2CHCl 2 CH3CH2CHO Which term describes the first step of this reaction? A addition B elimination C oxidation D substitution

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2014

Q99 · In the hydrolysis of bromoethane by aqueous sodium hydroxide, what is the nature of the… 9701/11 Oct/Nov 2014

25 In the hydrolysis of bromoethane by aqueous sodium hydroxide, what is the nature of the attacking group and of the leaving group? attacking group leaving group A electrophile electrophile B electrophile nucleophile C nucleophile electrophile D nucleophile nucleophile

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2014

Q100 · X is an organic compound that gives a precipitate with aqueous silver nitrate 9701/11 Oct/Nov 2014

38 X is an organic compound that gives a precipitate with aqueous silver nitrate. This precipitate remains undissolved when concentrated aqueous ammonia is added. What is a possible identity for X? 1 iodomethane 2 2-bromobutane 3 2-chlorobutane

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2014

Q101 · A reaction pathway diagram is shown 9701/11 Oct/Nov 2014

40 A reaction pathway diagram is shown. energy extent of reaction Which reactions would have this profile? 1 (CH3)3CBr + NaOH → (CH3)3COH + NaBr 2 CH3CH2Br + NaOH → CH3CH2OH + NaBr 3 (CH3)3CCH2CH2Cl + 2NH3 → (CH3)3CCH2CH2NH2 + NH4Cl

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2014

Q102 · 1,1-dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give… 9701/12 Oct/Nov 2014

22 1,1-dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give propanal. NaOH(aq) CH3CH2CHCl 2 CH3CH2CHO Which term describes the first step of this reaction? A addition B elimination C oxidation D substitution

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2014

Q103 · In the hydrolysis of bromoethane by aqueous sodium hydroxide, what is the nature of the… 9701/12 Oct/Nov 2014

25 In the hydrolysis of bromoethane by aqueous sodium hydroxide, what is the nature of the attacking group and of the leaving group? attacking group leaving group A electrophile electrophile B electrophile nucleophile C nucleophile electrophile D nucleophile nucleophile

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2014

Q104 · A reaction pathway diagram is shown 9701/12 Oct/Nov 2014

40 A reaction pathway diagram is shown. energy extent of reaction Which reactions would have this profile? 1 (CH3)3CBr + NaOH → (CH3)3COH + NaBr 2 CH3CH2Br + NaOH → CH3CH2OH + NaBr 3 (CH3)3CCH2CH2Cl + 2NH3 → (CH3)3CCH2CH2NH2 + NH4Cl

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2014

Q105 · A compound Y, C4H9Br, undergoes hydrolysis in aqueous alkali to form an alcohol, C4H9OH 9701/13 Oct/Nov 2014

23 A compound Y, C4H9Br, undergoes hydrolysis in aqueous alkali to form an alcohol, C4H9OH. The rate of this reaction is found to be unaffected by changes in the concentration of OH– ions present. Which is the most likely molecular structure of Y? A CH3CH2CH2CH2Br B CH3CH2CHBrCH3 C (CH3)2CHCH2Br D (CH3)3CBr

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2014

Q106 · Which compounds produce pent-2-ene as either one of the products, or as the only product… 9701/13 Oct/Nov 2014

38 Which compounds produce pent-2-ene as either one of the products, or as the only product, on heating with potassium hydroxide in ethanol? 1 CH3CH2CH2CH2CH2Br 2 CH3CHBrCH2CH2CH3 3 CH3CH2CHBrCH2CH3

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2014

Q107 · 2-bromopropane reacts with a hot concentrated solution of sodium hydroxide in ethanol 9701/11 May/June 2015

25 2-bromopropane reacts with a hot concentrated solution of sodium hydroxide in ethanol. 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 May/June 2015

Q108 · What is the major product formed when compound Q is warmed with excess HBr? 9701/12 May/June 2015

21 What is the major product formed when compound Q is warmed with excess HBr? OH OH Q A B Br Br OH OH Br Br C D Br Br Br Br Br Br

1 marks

Answer: C

This question in 9701/12 May/June 2015

Q109 · Butanedioic acid may be synthesised in two steps from 1,2-dibromoethane 9701/12 May/June 2015

23 Butanedioic acid may be synthesised in two steps from 1,2-dibromoethane. step 1 step 2 BrCH2CH2Br X HO2CCH2CH2CO2H Which reagents could be used for this synthesis? step 1 step 2 A HCN(g) HCl (aq) B HCO2Na(aq) HCl (aq) C KCN(alcoholic) H2SO4(aq) D NaOH(aq) K2Cr2O7 / H2SO4(aq)

1 marks

Answer: C

This question in 9701/12 May/June 2015

Q110 · Which reaction would not give propene? 9701/12 May/June 2015

24 Which reaction would not give propene? A adding excess hot concentrated sulfuric acid to propan-1-ol B adding warm aqueous sodium hydroxide to 2-bromopropane C adding warm ethanolic sodium hydroxide to 1-bromopropane D passing propan-2-ol vapour over heated aluminium oxide

1 marks

Answer: B

This question in 9701/12 May/June 2015

Q111 · Halogenated hydrocarbons have many uses 9701/12 May/June 2015

36 Halogenated hydrocarbons have many uses. What have halogenated hydrocarbons been used for? 1 solvents 2 refrigerants 3 monomers in polymer manufacture

1 marks

Answer: A

This question in 9701/12 May/June 2015

Q112 · The depletion of the ozone layer in the upper atmosphere reduces the Earth’s natural… 9701/12 Oct/Nov 2015

24 The depletion of the ozone layer in the upper atmosphere reduces the Earth’s natural protection from harmful ultraviolet radiation. Which compound would cause the most depletion of the ozone layer? A CCl 3F B CF4 C CO2 D SO2

1 marks

This question in 9701/12 Oct/Nov 2015

Q113 · X is an organic compound 9701/12 Oct/Nov 2015

38 X is an organic compound. X gives a precipitate with aqueous silver nitrate. Some or all of this precipitate remains undissolved when excess dilute aqueous ammonia is added. What could be the identity of X? 1 2-chlorobutane 2 2-bromobutane 3 iodomethane

1 marks

This question in 9701/12 Oct/Nov 2015

Q114 · 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

Q115 · 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

Q116 · A student prepares pentan-1-ol by the alkaline hydrolysis of 1-iodopentane 9701/11 May/June 2016

25 A student prepares pentan-1-ol by the alkaline hydrolysis of 1-iodopentane. She gently warms the reaction mixture for 20 minutes. CH3CH2CH2CH2CH2I + OH– → CH3CH2CH2CH2CH2OH + I– When the student uses 1-chloropentane to prepare the same alcohol she has to change the condition of the reaction. Which change in condition should she use and what is the correct reason for its use? change in condition reason A heat under reflux C–Cl bond is more polar than the C–I bond B heat under reflux C–Cl bond is stronger than the C–I bond C room temperature C–Cl bond is more polar than the C–I bond D room temperature C–Cl bond is shorter than the C–I bond

1 marks

Answer: B

This question in 9701/11 May/June 2016

Q117 · Which types of reaction can occur with 1-bromobutane? 9701/11 May/June 2016

36 Which types of reaction can occur with 1-bromobutane? 1 elimination 2 hydrolysis 3 free radical substitution

1 marks

Answer: A

This question in 9701/11 May/June 2016

Q118 · 1-chloro-1-methylcyclohexane is hydrolysed by heating with NaOH(aq) 9701/12 May/June 2016

24 1-chloro-1-methylcyclohexane is hydrolysed by heating with NaOH(aq). CH3 CH3 + OH– → + Cl – Cl OH The reaction pathway is shown. energy Z reaction pathway One carbon atom in 1-chloro-1-methylcyclohexane is bonded to three other carbon atoms. What is the charge on this carbon atom at point Z? A δ+ B + C δ – D –

1 marks

Answer: B

This question in 9701/12 May/June 2016

Q119 · A reaction pathway diagram is shown 9701/13 May/June 2016

25 A reaction pathway diagram is shown. energy extent of reaction The four reactions that follow are all exothermic. Which reaction would not have such a pathway? A CH3I + NaCN → CH3CN + NaI CH3 CH3 B + 2NH3 → + NH4Br Br NH2 C + HBr → Br conc. H2SO4 OH D CH3 + H2O heat CH3

1 marks

Answer: A

This question in 9701/13 May/June 2016

Q120 · Which reaction will give 2-chloropropane in the best yield? 9701/13 May/June 2016

28 Which reaction will give 2-chloropropane in the best yield? A propane gas with chlorine gas in the presence of ultraviolet light B propan-2-ol with dilute NaCl (aq) C propan-2-ol with SOCl 2(l) D propene with dilute HCl (aq)

1 marks

Answer: C

This question in 9701/13 May/June 2016

Q121 · Halogenoalkanes show trends in their physical and chemical properties 9701/13 May/June 2016

37 Halogenoalkanes show trends in their physical and chemical properties. Which properties steadily increase from C2H5Cl to C2H5Br to C2H5I ? 1 the polarity of the carbon-halogen bond 2 the boiling point of the halogenoalkane 3 the rate of reaction of the halogenoalkane with nucleophiles

1 marks

Answer: C

This question in 9701/13 May/June 2016

Q122 · Chloroethane can be used to make sodium propanoate 9701/11 Oct/Nov 2016

24 Chloroethane can be used to make sodium propanoate. chloroethane → Q → sodium propanoate The intermediate, Q, is hydrolysed with boiling aqueous sodium hydroxide to give sodium propanoate. Which reagent would produce the intermediate, Q, from chloroethane? A concentrated ammonia solution B dilute sulfuric acid C hydrogen cyanide in water D potassium cyanide in ethanol

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2016

Q123 · Bromoethane reacts with NaOH in different ways depending on the solvent used 9701/11 Oct/Nov 2016

38 Bromoethane reacts with NaOH in different ways depending on the solvent used. Which statements about these reactions are correct? solvent used main organic product 1 water ethane-1,2-diol 2 ethanol ethene 3 water ethanol

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2016

Q124 · PVC is difficult to dispose of 9701/13 Oct/Nov 2016

22 PVC is difficult to dispose of. Two possible methods are burying it in landfill sites and disposal by combustion. Which row of the table is correct? rate of biodegradation gases produced when of PVC in landfill sites PVC combusts A fast CO2, H2O, HCl B fast CO2, H2O, Cl 2 C slow CO2, H2O, Cl 2 D slow CO2, H2O, HCl

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2016

Q125 · Chloroethane can be used to make sodium propanoate 9701/13 Oct/Nov 2016

24 Chloroethane can be used to make sodium propanoate. chloroethane → Q → sodium propanoate The intermediate, Q, is hydrolysed with boiling aqueous sodium hydroxide to give sodium propanoate. Which reagent would produce the intermediate, Q, from chloroethane? A concentrated ammonia solution B dilute sulfuric acid C hydrogen cyanide in water D potassium cyanide in ethanol

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2016

Q126 · Bromoethane reacts with NaOH in different ways depending on the solvent used 9701/13 Oct/Nov 2016

38 Bromoethane reacts with NaOH in different ways depending on the solvent used. Which statements about these reactions are correct? solvent used main organic product 1 water ethane-1,2-diol 2 ethanol ethene 3 water ethanol

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2016

Q127 · Aqueous sodium hydroxide reacts with 1-bromopropane to give propan-1-ol 9701/12 May/June 2017

23 Aqueous sodium hydroxide reacts with 1-bromopropane to give propan-1-ol. What should be included in a diagram of the first step in the mechanism? A a curly arrow from a lone pair on the OH– ion to the Cδ+ atom of 1-bromopropane B a curly arrow from the Cδ+ atom of 1-bromopropane to the OH– ion C a curly arrow from the C–Br bond to the C atom D the homolytic fission of the C–Br bond

1 marks

Answer: A

This question in 9701/12 May/June 2017

Q128 · 2-bromo-2-methylpropane undergoes nucleophilic substitution when heated under reflux with… 9701/12 May/June 2017

26 2-bromo-2-methylpropane undergoes nucleophilic substitution when heated under reflux with an aqueous solution of sodium hydroxide. Which row is correct? mechanism for reason this reaction A SN1 the hydroxide ion is helped in its approach to the central carbon atom by the methyl groups B SN1 the intermediate carbocation is stabilised by the inductive effect of the methyl groups C SN2 the hydroxide ion is hindered in its approach to the central carbon atom by the methyl groups D SN2 the intermediate carbocation is destabilised by the inductive effect of the methyl groups

1 marks

Answer: B

This question in 9701/12 May/June 2017

Q129 · An organic compound, X, has the following skeletal formula 9701/12 May/June 2017

39 An organic compound, X, has the following skeletal formula. OH X Which statements about X are correct? 1 X is a primary alcohol. 2 X will dehydrate to give a single alkene. 3 X will undergo a substitution reaction with chloride ions.

1 marks

Answer: A

This question in 9701/12 May/June 2017

Q130 · Butanoic acid can be produced from 1-bromopropane using reagents X and Y as shown 9701/13 May/June 2017

29 Butanoic acid can be produced from 1-bromopropane using reagents X and Y as shown. reagent X reagent Y 1-bromopropane compound Q butanoic acid What could be reagents X and Y? X Y A KCN in ethanol HCl (aq) B KCN in ethanol NaOH(aq) C NH3 in ethanol HCl (aq) D NaOH(aq) H+ / Cr2O7 2–(aq)

1 marks

Answer: A

This question in 9701/13 May/June 2017

Q131 · Which organic reaction is an example of nucleophilic substitution? 9701/11 Oct/Nov 2017

24 Which organic reaction is an example of nucleophilic substitution? A CH3CH2Br + NaOH → CH2CH2 + H2O + NaBr B CH3CH2Br + NaOH → CH3CH2OH + NaBr C CH2CH2 + HCl → C2H5Cl D C2H6 + Cl 2 → C2H5Cl + HCl

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2017

Q132 · A reaction pathway diagram is shown 9701/11 Oct/Nov 2017

38 A reaction pathway diagram is shown. energy progress of reaction Which reactions would have this reaction pathway diagram? 1 (CH3)3CBr + NaOH → (CH3)3COH + NaBr 2 CH3CH2CH2Br + NaOH → CH3CH2CH2OH + NaBr 3 (CH3)3CCH2CH2Cl + 2NH3 → (CH3)3CCH2CH2NH2 + NH4Cl

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2017

Q133 · Equal volumes of aqueous silver nitrate were added to separate small volumes of… 9701/12 Oct/Nov 2017

25 Equal volumes of aqueous silver nitrate were added to separate small volumes of bromoethane and iodoethane in two test-tubes. The test-tubes were shaken. Which row about the observations made for bromoethane is correct? colour of precipitate rate of reaction A cream faster than for iodoethane B cream slower than for iodoethane C yellow faster than for iodoethane D yellow slower than for iodoethane

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2017

Q134 · Many, but not all, organic reactions need to be heated before a reaction occurs 9701/12 Oct/Nov 2017

26 Many, but not all, organic reactions need to be heated before a reaction occurs. Which reaction occurs quickly at room temperature (20 °C)? A CH3OH + PCl 5 → CH3Cl + POCl 3 + HCl B CH3CH2Br + KCN → CH3CH2CN + KBr C CH3CH2OH → C2H4 + H2O D CH3CH2CN + 2H2O → CH3CH2CO2H + NH3

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2017

Q135 · Which statements are correct for an SN2 mechanism? 9701/12 Oct/Nov 2017

37 Which statements are correct for an SN2 mechanism? 1 One bond is being broken at the same time as another bond is being formed. 2 The formation of the intermediate involves the collision of two molecules or ions. 3 A carbon atom in the transition state is bonded, either fully or partially, to five atoms.

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2017

Q136 · Bromoethane is heated under reflux with concentrated aqueous NaOH 9701/12 Oct/Nov 2017

38 Bromoethane is heated under reflux with concentrated aqueous NaOH. Which statements are correct? 1 The major product is a primary alcohol. 2 The major reaction is hydrolysis by an SN2 mechanism. 3 The major product would be the same if the NaOH is dissolved in ethanol.

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2017

Q137 · Which organic reaction is an example of nucleophilic substitution? 9701/13 Oct/Nov 2017

24 Which organic reaction is an example of nucleophilic substitution? A CH3CH2Br + NaOH → CH2CH2 + H2O + NaBr B CH3CH2Br + NaOH → CH3CH2OH + NaBr C CH2CH2 + HCl → C2H5Cl D C2H6 + Cl 2 → C2H5Cl + HCl

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2017

Q138 · A reaction pathway diagram is shown 9701/13 Oct/Nov 2017

38 A reaction pathway diagram is shown. energy progress of reaction Which reactions would have this reaction pathway diagram? 1 (CH3)3CBr + NaOH → (CH3)3COH + NaBr 2 CH3CH2CH2Br + NaOH → CH3CH2CH2OH + NaBr 3 (CH3)3CCH2CH2Cl + 2NH3 → (CH3)3CCH2CH2NH2 + NH4Cl

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2017

Q139 · An organic ion containing a carbon atom with a negative charge is called a carbanion 9701/12 Feb/March 2018

21 An organic ion containing a carbon atom with a negative charge is called a carbanion. An organic ion containing a carbon atom with a positive charge is called a carbocation. The reaction between aqueous sodium hydroxide and 1-bromobutane proceeds by an SN2 mechanism. What is the first step in the mechanism? A attack by a nucleophile on a carbon atom with a partial positive charge B heterolytic bond fission followed by attack by an electrophile on a carbanion C heterolytic bond fission followed by attack by a nucleophile on a carbocation D homolytic bond fission followed by attack by a nucleophile on a carbocation

1 marks

Answer: A

This question in 9701/12 Feb/March 2018

Q140 · 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

Q141 · Sodium methoxide, Na+CH3O–, reacts with 2-chloro-2-methylpropane in a nucleophilic… 9701/11 May/June 2018

22 Sodium methoxide, Na+CH3O–, reacts with 2-chloro-2-methylpropane in a nucleophilic substitution reaction. The nucleophile is the CH3O– ion. Which row is correct? intermediate or product transition state A (CH3)3C+ (CH3)3COCH3 B (CH3)3C+ (CH3)3CCH2OH C [HOCH2- - -C(CH3)3- - -Cl ]– HOCH2C(CH3)3 D [H3CO- - -C(CH3)3- - -Cl ]– H3COC(CH3)3

1 marks

Answer: A

This question in 9701/11 May/June 2018

Q142 · Primary halogenoalkanes undergo hydrolysis reactions 9701/12 May/June 2018

23 Primary halogenoalkanes undergo hydrolysis reactions. Which reaction would occur most rapidly if they are all warmed to the same temperature? A C2H5Br with H2O B C2H5Br with NaOH(aq) C C2H5Cl with H2O D C2H5Cl with NaOH(aq)

1 marks

Answer: B

This question in 9701/12 May/June 2018

Q143 · Structural isomerism and stereoisomerism should be considered when answering this question 9701/12 May/June 2018

24 Structural isomerism and stereoisomerism should be considered when answering this question. A colourless liquid, C5H11Cl , exists as a mixture of two optical isomers. When heated with sodium hydroxide in ethanol, a mixture of only two alkenes is formed. What could the colourless liquid be? A (CH3CH2)2CHCl B CH3CH2CH2CHCl CH3 C (CH3)2CHCHCl CH3 D CH3CH2CCl (CH3)2

1 marks

Answer: C

This question in 9701/12 May/June 2018

Q144 · When warm water is added to halogenoalkane X, an SN1 reaction occurs 9701/12 May/June 2018

25 When warm water is added to halogenoalkane X, an SN1 reaction occurs. AgNO3(aq) is then added; a yellow precipitate is formed. What could be X? A 1-chlorobutane B 1-iodobutane C 2-chloro-2-methylpropane D 2-iodo-2-methylpropane

1 marks

Answer: D

This question in 9701/12 May/June 2018

Q145 · 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

Q146 · The presence of a halogen in an organic compound may be detected by warming the organic… 9701/13 May/June 2018

23 The presence of a halogen in an organic compound may be detected by warming the organic compound with aqueous silver nitrate. Which compound would be the quickest to produce a precipitate? A B C D Cl F F Cl Cl Cl F Br Cl F I F

1 marks

Answer: C

This question in 9701/13 May/June 2018

Q147 · Halogenoalkanes react with NaOH(aq) either by an SN1 mechanism or by an SN2 mechanism 9701/13 May/June 2018

24 Halogenoalkanes react with NaOH(aq) either by an SN1 mechanism or by an SN2 mechanism. The mechanism followed by the reaction depends on the structure of the halogenoalkane. This question is about the reaction of 3-bromo-3-ethylpentane, (C2H5)3CBr. Which statement is correct? A The mechanism is SN1, due to the stabilisation of an intermediate anion by three alkyl groups. B The mechanism is SN1, due to the stabilisation of an intermediate cation by three alkyl groups. C The mechanism is SN2, due to the stabilisation of an intermediate anion by three alkyl groups. D The mechanism is SN2, due to the stabilisation of an intermediate cation by three alkyl groups.

1 marks

Answer: B

This question in 9701/13 May/June 2018

Q148 · Compound Y is a straight chain molecule with formula CnH2n+1X 9701/13 May/June 2018

38 Compound Y is a straight chain molecule with formula CnH2n+1X. X is a halogen. The Mr of Y is 137. The halogen atom is on the second carbon atom in the chain. Which statements are correct? 1 Y contains a chiral centre. 2 Y can eliminate HX to form two structurally isomeric alkenes. 3 Y can eliminate HX to form two geometrically isomeric alkenes.

1 marks

Answer: A

This question in 9701/13 May/June 2018

Q149 · 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

Q150 · The halogenoalkanes listed below all react with NaOH(aq) 9701/11 Oct/Nov 2018

38 The halogenoalkanes listed below all react with NaOH(aq). Which reactions proceed mainly by an SN1 mechanism? 1 1-iodopropane 2 2-iodo-2-methylpropane 3 2-bromo-2-methylbutane

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2018

Q151 · Compound P reacts separately with KOH(aq) and HBr 9701/12 Oct/Nov 2018

23 Compound P reacts separately with KOH(aq) and HBr. CH2CHCH2CH2Cl compound P What are the mechanisms of these two reactions? KOH (aq) HBr A nucleophilic addition electrophilic addition B nucleophilic addition free radical substitution C nucleophilic substitution electrophilic addition D nucleophilic substitution free radical substitution

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2018

Q152 · A halogenoalkane has the molecular formula C5H11Br 9701/12 Oct/Nov 2018

25 A halogenoalkane has the molecular formula C5H11Br. The halogenoalkane does not form an alkene when treated with ethanolic sodium hydroxide. What could be the halogenoalkane? A 1-bromo-2-methylbutane B 2-bromo-2-methylbutane C 3-bromopentane D bromodimethylpropane

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2018

Q153 · The conversion of propene to propan-2-ol can be carried out in two stages represented by… 9701/13 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 9701/13 Oct/Nov 2018

Q154 · 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

Q155 · The halogenoalkanes listed below all react with NaOH(aq) 9701/13 Oct/Nov 2018

38 The halogenoalkanes listed below all react with NaOH(aq). Which reactions proceed mainly by an SN1 mechanism? 1 1-iodopropane 2 2-iodo-2-methylpropane 3 2-bromo-2-methylbutane

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2018

Q156 · Structural isomerism and stereoisomerism should be considered when answering this question 9701/12 Feb/March 2019

23 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 9701/12 Feb/March 2019

Q157 · Bromopropane reacts with water as shown 9701/12 Feb/March 2019

24 Bromopropane reacts with water as shown. CH3CH2CH2Br + H2O → CH3CH2CH2OH + HBr Which statement is correct? A This is an elimination reaction. B This is a hydrolysis reaction. C This is a redox reaction. D This reaction tends to proceed via the SN1 mechanism.

1 marks

Answer: B

This question in 9701/12 Feb/March 2019

Q158 · Which reaction is most likely to involve the formation of a positively charged… 9701/11 May/June 2019

23 Which reaction is most likely to involve the formation of a positively charged intermediate? A 1-bromopentane and warm dilute NaOH(aq) B 1-bromo-2,2-dimethylpropane and warm dilute NaOH(aq) C 1-bromo-3-methylbutane and warm dilute NaOH(aq) D 2-bromo-2-methylbutane and warm dilute NaOH(aq)

1 marks

Answer: D

This question in 9701/11 May/June 2019

Q159 · The structure of coniine is shown 9701/11 May/June 2019

25 The structure of coniine is shown. coniine N CH2CH2CH3 H Coniine can be synthesised by reacting ammonia with a dibromo compound, X. NH3 + C8H16Br2 → coniine + 2HBr X What is the name of compound X? A 1,1-dibromo-2-propylcyclopentane B 1,2-dibromo-2-propylcyclopentane C 1,4-dibromooctane D 1,5-dibromooctane

1 marks

Answer: D

This question in 9701/11 May/June 2019

Q160 · Which compound is chiral? 9701/11 May/June 2019

30 Which compound is chiral? A 1-chloro-3-methylbutane B 2-chloro-2-methylbutane C 2-chloro-3-methylbutane D 3-chloropentane Section B

1 marks

Answer: C

This question in 9701/11 May/June 2019

Q161 · 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

Q162 · 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

Q163 · Halogenoalkanes can be hydrolysed using aqueous sodium hydroxide 9701/12 May/June 2019

38 Halogenoalkanes can be hydrolysed using aqueous sodium hydroxide. Which compounds tend to be hydrolysed by an SN1 mechanism? 1 CH3CH2CCl (CH3)CH2CH3 2 CH3CH2CBr(CH3)CH2CH3 3 CH3CH2CH(CH3)CH2CH2Br

1 marks

Answer: B

This question in 9701/12 May/June 2019

Q164 · The Finkelstein reaction occurs when NaI in propanone reacts with a chloroalkane or… 9701/13 May/June 2019

20 The Finkelstein reaction occurs when NaI in propanone reacts with a chloroalkane or bromoalkane. The halogen is directly replaced by I. The reaction only works for primary halogenoalkanes. Which halogenoalkane produces compound X? X I A (CH3)2CHCH(CH3)CH2CH2Br B (CH3)2CHCH(CH3)CH2Br C (CH3)2CHCH2CH2CH(CH3)Cl D (CH3)2CHCH2CH(CH3)CH2Cl

1 marks

Answer: D

This question in 9701/13 May/June 2019

Q165 · Water is added to a sample of 2,3-dibromohexane 9701/13 May/June 2019

24 Water is added to a sample of 2,3-dibromohexane. Some of the 2,3-dibromohexane undergoes complete hydrolysis and some of it undergoes partial hydrolysis. What is not present in the mixture of products? A CH3CH(OH)CHBrCH2CH2CH3 B CH3CH(OH)CH(OH)CH2CH2CH3 C CH3CH2CH(OH)CH(OH)CH2CH3 D CH3CH2CH2CH(OH)CHBrCH3

1 marks

Answer: C

This question in 9701/13 May/June 2019

Q166 · Which statement about the mechanism of an SN1 reaction of a halogenoalkane is correct? 9701/13 May/June 2019

25 Which statement about the mechanism of an SN1 reaction of a halogenoalkane is correct? A A nucleophile is substituted by an electrophile. B One intermediate is formed from two reacting molecules. C The intermediate is stabilised by adjacent alkyl groups. D The intermediate is uncharged.

1 marks

Answer: C

This question in 9701/13 May/June 2019

Q167 · A tertiary bromoalkane, indicated here by C–Br, reacts with aqueous NaOH 9701/11 Oct/Nov 2019

23 A tertiary bromoalkane, indicated here by C–Br, reacts with aqueous NaOH. The mechanism has the reaction pathway shown. X C–Br + OH– Y energy C–OH + Br – progress of reaction Which point in the diagram is correctly identified? A X is C+ – B X is HO C Br C Y is C+ – D Y is HO C Br

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2019

Q168 · Bromoethane and chloroethane are added separately to water 9701/11 Oct/Nov 2019

24 Bromoethane and chloroethane are added separately to water. Hydrolysis reactions occur. Which compound hydrolyses more rapidly and what is the mechanism? compound that mechanism hydrolyses more rapidly A bromoethane electrophilic substitution B bromoethane nucleophilic substitution C chloroethane electrophilic substitution D chloroethane nucleophilic substitution

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2019

Q169 · 1-chloro-2-methylbutane reacts with sodium cyanide in ethanol in a nucleophilic… 9701/12 Oct/Nov 2019

23 1-chloro-2-methylbutane reacts with sodium cyanide in ethanol in a nucleophilic substitution reaction. What is the most likely intermediate or transition state in this reaction? A B – – H H H3C CH2CH3 NC C Cl NC C Cl CH(CH3)CH2CH3 CH3 C D H3C CH2CH3 H H +C +C CH3 CH(CH3)CH2CH3

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2019

Q170 · Bromoethane undergoes nucleophilic substitution reactions 9701/12 Oct/Nov 2019

38 Bromoethane undergoes nucleophilic substitution reactions. Which statements are correct? 1 Bromoethane reacts with aqueous NaOH to make ethanol. 2 Bromoethane reacts with ethanolic NH3 to make ethylamine. 3 Bromoethane reacts with ethanolic KCN to make ethanenitrile.

1 marks

Answer: B

This question in 9701/12 Oct/Nov 2019

Q171 · A tertiary bromoalkane, indicated here by C–Br, reacts with aqueous NaOH 9701/13 Oct/Nov 2019

23 A tertiary bromoalkane, indicated here by C–Br, reacts with aqueous NaOH. The mechanism has the reaction pathway shown. X C–Br + OH– Y energy C–OH + Br – progress of reaction Which point in the diagram is correctly identified? A X is C+ – B X is HO C Br C Y is C+ – D Y is HO C Br

1 marks

Answer: C

This question in 9701/13 Oct/Nov 2019

Q172 · Bromoethane and chloroethane are added separately to water 9701/13 Oct/Nov 2019

24 Bromoethane and chloroethane are added separately to water. Hydrolysis reactions occur. Which compound hydrolyses more rapidly and what is the mechanism? compound that mechanism hydrolyses more rapidly A bromoethane electrophilic substitution B bromoethane nucleophilic substitution C chloroethane electrophilic substitution D chloroethane nucleophilic substitution

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2019

Q173 · Which row identifies a suitable starting material and reagent that can be used to produce… 9701/12 Feb/March 2020

21 Which row identifies a suitable starting material and reagent that can be used to produce butanenitrile? starting material reagent A CH3CH2CH2Br HCN B CH3CH2CH2Br NaCN C CH3CH2CH2CH2Br HCN D CH3CH2CH2CH2Br NaCN

1 marks

Answer: B

This question in 9701/12 Feb/March 2020

Q174 · An excess of dry HBr is warmed with compound Y 9701/12 Feb/March 2020

26 An excess of dry HBr is warmed with compound Y. Y OH What is the major product of the reaction? A B C D Br HO HO Br Br Br Br Br Br Br Br

1 marks

Answer: C

This question in 9701/12 Feb/March 2020

Q175 · 2-bromo-2-methylpentane is a tertiary halogenoalkane 9701/11 May/June 2020

23 2-bromo-2-methylpentane is a tertiary halogenoalkane. Which organic products are formed when 2-bromo-2-methylpentane reacts with a hot concentrated ethanolic solution of sodium hydroxide? A 2-methylpent-1-ene only B 2-methylpent-1-ene and 2-methylpent-2-ene C 2-methylpent-2-ene only D 2-methylpent-2-ene and 4-methylpent-2-ene

1 marks

Answer: B

This question in 9701/11 May/June 2020

Q176 · Which row correctly shows the type of mechanism of each of the two reactions? 9701/12 May/June 2020

22 Which row correctly shows the type of mechanism of each of the two reactions? C2H5Br + KCN CH3COCH3 + HCN A electrophilic substitution electrophilic addition B electrophilic substitution nucleophilic addition C nucleophilic substitution electrophilic addition D nucleophilic substitution nucleophilic addition

1 marks

Answer: D

This question in 9701/12 May/June 2020

Q177 · A reaction mechanism is shown 9701/12 May/June 2020

40 A reaction mechanism is shown. H2C CH2 H2C CH2 H2C CH2 H2C CH2 + Br – H2C C Br H2C C H HO– H OH Which statements about this reaction are correct? 1 Heterolytic bond fission occurs. 2 It is a substitution reaction. 3 OH– behaves as an electrophile.

1 marks

Answer: B

This question in 9701/12 May/June 2020

Q178 · 1,2-dibromopropane can be made from 1-bromopropane in two steps 9701/13 May/June 2020

27 1,2-dibromopropane can be made from 1-bromopropane in two steps. Which row is correct? step 1 step 2 A addition substitution B elimination addition C hydrolysis elimination D substitution hydrolysis

1 marks

Answer: B

This question in 9701/13 May/June 2020

Q179 · 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

Q180 · A reaction mechanism is shown 9701/13 May/June 2020

38 A reaction mechanism is shown. CH2 CH2 H2C CH2 H2C CH2 + Cl – H2C C Cl H2C C H H OH HO– Which statements about this reaction are correct? 1 It is a substitution reaction. 2 OH– behaves as a nucleophile. 3 Heterolytic bond fission is involved.

1 marks

Answer: A

This question in 9701/13 May/June 2020

Q181 · Which statement is correct when referring to the complete combustion of PVC? 9701/11 Oct/Nov 2020

22 Which statement is correct when referring to the complete combustion of PVC? A A gas is made which contributes to global warming. B Carbon dioxide and water are the only products. C If water is used to clean the exhaust gases, the water becomes alkaline. D There is no need to treat the exhaust gases as the products are non-hazardous.

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2020

Q182 · Iodoethane, CH3CH2I, reacts with aqueous silver nitrate at 50 C 9701/11 Oct/Nov 2020

23 Iodoethane, CH3CH2I, reacts with aqueous silver nitrate at 50 C. A precipitate forms during this reaction. Which row of the table is correct about this reaction? type of organic reaction colour of precipitate A electrophilic substitution cream B electrophilic substitution yellow C nucleophilic substitution cream D nucleophilic substitution yellow

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2020

Q183 · A student converts 1-iodopropane, C3H7I, into butanoic acid, C3H7CO2H, by a two-stage… 9701/11 Oct/Nov 2020

24 A student converts 1-iodopropane, C3H7I, into butanoic acid, C3H7CO2H, by a two-stage chemical synthesis. In the first of the two stages, which reagent is reacted with 1-iodopropane? A aqueous sodium hydroxide B ethanolic ammonia C ethanolic potassium cyanide D ethanolic sodium hydroxide

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2020

Q184 · 1-chloro-1-methylcyclohexane is hydrolysed by heating with NaOH(aq) 9701/11 Oct/Nov 2020

25 1-chloro-1-methylcyclohexane is hydrolysed by heating with NaOH(aq). CH3 CH3 + OH– → + Cl – Cl OH The reaction pathway is shown. energy Z reaction pathway One carbon atom in 1-chloro-1-methylcyclohexane is bonded to three other carbon atoms. What is the charge on this carbon atom at point Z? A 1– B  – C + D 1+

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2020

Q185 · Diols in which both hydroxy groups are bonded to the same carbon atom can spontaneously… 9701/12 Oct/Nov 2020

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

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2020

Q186 · Which statement is correct when referring to the complete combustion of PVC? 9701/13 Oct/Nov 2020

22 Which statement is correct when referring to the complete combustion of PVC? A A gas is made which contributes to global warming. B Carbon dioxide and water are the only products. C If water is used to clean the exhaust gases, the water becomes alkaline. D There is no need to treat the exhaust gases as the products are non-hazardous.

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2020

Q187 · Iodoethane, CH3CH2I, reacts with aqueous silver nitrate at 50 C 9701/13 Oct/Nov 2020

23 Iodoethane, CH3CH2I, reacts with aqueous silver nitrate at 50 C. A precipitate forms during this reaction. Which row of the table is correct about this reaction? type of organic reaction colour of precipitate A electrophilic substitution cream B electrophilic substitution yellow C nucleophilic substitution cream D nucleophilic substitution yellow

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2020

Q188 · 1-chloro-1-methylcyclohexane is hydrolysed by heating with NaOH(aq) 9701/13 Oct/Nov 2020

25 1-chloro-1-methylcyclohexane is hydrolysed by heating with NaOH(aq). CH3 CH3 + OH– → + Cl – Cl OH The reaction pathway is shown. energy Z reaction pathway One carbon atom in 1-chloro-1-methylcyclohexane is bonded to three other carbon atoms. What is the charge on this carbon atom at point Z? A 1– B  – C + D 1+

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2020

Q189 · 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

Q190 · In which reactions is the major product formed by a nucleophilic substitution reaction? 9701/12 Feb/March 2021

37 In which reactions is the major product formed by a nucleophilic substitution reaction? 1 bromoethane + potassium cyanide in ethanol 2 bromoethane + ammonia in ethanol under pressure 3 bromoethane + hot concentrated sodium hydroxide in ethanol

1 marks

Answer: B

This question in 9701/12 Feb/March 2021

Q191 · Bromoethane reacts with cyanide ions, producing propanenitrile 9701/11 May/June 2021

20 Bromoethane reacts with cyanide ions, producing propanenitrile. Which statement about the SN2 mechanism of this reaction is correct? A The lone pair of electrons on C of CN– attacks the carbon atom of the C–Br bond. B The lone pair of electrons on C of CN– attacks the carbocation formed when the C–Br bond breaks. C The lone pair of electrons on N of CN– attacks the carbon atom of the C–Br bond. D The lone pair of electrons on N of CN– attacks the carbocation formed when the C–Br bond breaks.

1 marks

Answer: A

This question in 9701/11 May/June 2021

Q192 · A few drops of 2-bromopropane were placed in a test-tube 9701/12 May/June 2021

24 A few drops of 2-bromopropane were placed in a test-tube. An equal volume of aqueous silver nitrate was added. A precipitate was formed. The experiment was repeated with 2-iodopropane. Which row is correct? colour of precipitate from faster rate of reaction 2-bromopropane + AgNO3(aq) A cream 2-bromopropane + AgNO3(aq) B yellow 2-bromopropane + AgNO3(aq) C cream 2-iodopropane + AgNO3(aq) D yellow 2-iodopropane + AgNO3(aq)

1 marks

Answer: C

This question in 9701/12 May/June 2021

Q193 · Sodium methoxide, Na+CH3O–, reacts with 2-chloro-2-methylpropane in a nucleophilic… 9701/12 May/June 2021

25 Sodium methoxide, Na+CH3O–, reacts with 2-chloro-2-methylpropane in a nucleophilic substitution reaction. The nucleophile is the CH3O– ion. Which row is correct? intermediate or product transition state A (CH3)3C+ (CH3)3COCH3 B (CH3)3C+ (CH3)3CCH2OH – H3C CH3 C H3CO C Cl HOCH2C(CH3)3 CH3 – H3C CH3 D H3CO C Cl H3COC(CH3)3 CH3

1 marks

Answer: A

This question in 9701/12 May/June 2021

Q194 · Halogenoalkanes react with nucleophiles such as OH– 9701/13 May/June 2021

23 Halogenoalkanes react with nucleophiles such as OH–. Which pair of halogenoalkanes both react via an SN1 mechanism? A B Br Cl and and Cl Br C D Br and and Br Cl Br

1 marks

Answer: A

This question in 9701/13 May/June 2021

Q195 · Bromoethane reacts with NaOH in different ways depending on the solvent used 9701/13 May/June 2021

38 Bromoethane reacts with NaOH in different ways depending on the solvent used. Which rows about these reactions are correct? solvent used organic product 1 water ethan-1,2-diol 2 ethanol ethene 3 water ethanol

1 marks

Answer: C

This question in 9701/13 May/June 2021

Q196 · Hex-2-ene can be made by the reaction shown 9701/11 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 9701/11 Oct/Nov 2021

Q197 · Structural isomerism and stereoisomerism should be considered when answering this question 9701/11 Oct/Nov 2021

22 Structural isomerism and stereoisomerism should be considered when answering this question. A colourless liquid, C5H11Cl , exists as a mixture of two optical isomers. When heated with sodium hydroxide in ethanol, a mixture of only two alkenes is formed. What could the colourless liquid be? A (CH3CH2)2CHCl B CH3CH2CH2CHCl CH3 C CH3CH2CCl (CH3)2 D (CH3)2CHCHCl CH3

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2021

Q198 · When 2-bromo-2-methylpropane reacts with aqueous sodium hydroxide, an alcohol is formed 9701/11 Oct/Nov 2021

23 When 2-bromo-2-methylpropane reacts with aqueous sodium hydroxide, an alcohol is formed. Which diagram describes the first step in the reaction mechanism? H;c— A CH, \~ CH, Br Ss B HO: CH,

1 marks

Answer: B

This question in 9701/11 Oct/Nov 2021

Q199 · Which statements about chlorofluoroalkanes are correct? 9701/11 Oct/Nov 2021

39 Which statements about chlorofluoroalkanes are correct? 1 Both the C–Cl and C–F bonds are readily dissociated by ultra-violet light. 2 They have caused ozone depletion. 3 They are relatively chemically inert.

1 marks

Answer: C

This question in 9701/11 Oct/Nov 2021

Q200 · Butanoic acid can be made from 1-bromopropane in two stages 9701/12 Oct/Nov 2021

24 Butanoic acid can be made from 1-bromopropane in two stages. stage 1 CH3CH2CH2Br  CH3CH2CH2CN stage 2 CH3CH2CH2CN  CH3CH2CH2CO2H Which types of reaction are stage 1 and stage 2? stage 1 stage 2 A electrophilic addition hydrolysis B electrophilic addition oxidation C nucleophilic substitution hydrolysis D nucleophilic substitution oxidation

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2021

Q201 · A halogenoalkane has the molecular formula C5H11Br 9701/12 Oct/Nov 2021

25 A halogenoalkane has the molecular formula C5H11Br. The halogenoalkane does not form an alkene when treated with ethanolic sodium hydroxide. What could be the halogenoalkane? A 1-bromo-2-methylbutane B 2-bromo-2-methylbutane C 3-bromopentane D 1-bromo-2,2-dimethylpropane

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2021

Q202 · Structural isomerism and stereoisomerism should be considered when answering this question 9701/13 Oct/Nov 2021

22 Structural isomerism and stereoisomerism should be considered when answering this question. A colourless liquid, C5H11Cl , exists as a mixture of two optical isomers. When heated with sodium hydroxide in ethanol, a mixture of only two alkenes is formed. What could the colourless liquid be? A (CH3CH2)2CHCl B CH3CH2CH2CHCl CH3 C CH3CH2CCl (CH3)2 D (CH3)2CHCHCl CH3

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2021

Q203 · When 2-bromo-2-methylpropane reacts with aqueous sodium hydroxide, an alcohol is formed 9701/13 Oct/Nov 2021

23 When 2-bromo-2-methylpropane reacts with aqueous sodium hydroxide, an alcohol is formed. Which diagram describes the first step in the reaction mechanism? H;c— A CH, \~ CH, Br Ss B HO: CH,

1 marks

Answer: B

This question in 9701/13 Oct/Nov 2021

Q204 · Ethanol can be used to make propanenitrile in two steps 9701/11 May/June 2022

26 Ethanol can be used to make propanenitrile in two steps. X Y CH3CH2OH CH3CH2Br CH3CH2CN What types of reaction are X and Y? X Y A free-radical substitution electrophilic substitution B free-radical substitution nucleophilic substitution C nucleophilic substitution nucleophilic substitution D nucleophilic substitution electrophilic substitution

1 marks

Answer: C

This question in 9701/11 May/June 2022

Q205 · Structural isomerism and stereoisomerism should be taken into account when answering this… 9701/11 May/June 2022

31 Structural isomerism and stereoisomerism should be taken into account when answering this question. How many isomeric alkenes with formula C5H8 are present in the mixture produced when 1,4-dibromopentane is reacted with NaOH in ethanol? A 1 B 2 C 3 D 4

1 marks

Answer: C

This question in 9701/11 May/June 2022

Q206 · Compound Z, C7H13Br, has two chiral centres 9701/12 May/June 2022

28 Compound Z, C7H13Br, has two chiral centres. A sample of Z contains all four possible optical isomers. This sample of Z reacts with hot ethanolic NaOH to produce a mixture of only three isomers. Two of these isomers are optical isomers of each other. What could be the formula of Z? A B C D Br Br Br Br

1 marks

Answer: A

This question in 9701/12 May/June 2022

Q207 · 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

Q208 · The diagram shows the structures of two halogenoalkanes, P and Q 9701/12 May/June 2022

31 The diagram shows the structures of two halogenoalkanes, P and Q. P Q C2H5 C2H5 CH3 C C3H7 CH3 C C3H7 Br F Both compounds can be hydrolysed. Which row is correct? compound more reaction mechanism readily hydrolysed A P SN1 B P SN2 C Q SN1 D Q SN2

1 marks

Answer: A

This question in 9701/12 May/June 2022

Q209 · The structure of coniine is shown 9701/12 May/June 2022

32 The structure of coniine is shown. coniine N CH2CH2CH3 H Coniine can be synthesised by reacting ammonia with a dibromo compound, X. X NH3 + C8H16Br2  coniine + 2HBr What is compound X? A 1,1-dibromo-2-propylcyclopentane B 1,2-dibromo-2-propylcyclopentane C Br(CH2)3CHBr(CH2)3CH3 D Br(CH2)4CHBr(CH2)2CH3

1 marks

Answer: D

This question in 9701/12 May/June 2022

Q210 · Which statement concerning the hydrolysis of 1-bromopropane with water is correct? 9701/13 May/June 2022

31 Which statement concerning the hydrolysis of 1-bromopropane with water is correct? A The hydrolysis reaction between water and 1-iodopropane is faster because the C–Br bond is less polar than the C–I bond. B The hydrolysis reaction with water is very slow because water is a weak electrophile. C The mechanism of the reaction involves the formation of a stable carbocation. D The reaction is slower with 1-chloropropane because the C–Cl bond is stronger than the C–Br bond.

1 marks

Answer: D

This question in 9701/13 May/June 2022

Q211 · Compound R can be formed from 1-bromopropane using a nucleophilic substitution reaction… 9701/11 Oct/Nov 2022

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

1 marks

Answer: A

This question in 9701/11 Oct/Nov 2022

Q212 · 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

Q213 · 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

Q214 · 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

Q215 · C4H9Cl reacts with warm dilute aqueous sodium hydroxide solution 9701/12 Oct/Nov 2022

32 C4H9Cl reacts with warm dilute aqueous sodium hydroxide solution. Which isomer of C4H9Cl will form the most stable cation intermediate? A 1-chlorobutane B 2-chlorobutane C 1-chloro-2-methylpropane D 2-chloro-2-methylpropane

1 marks

Answer: D

This question in 9701/12 Oct/Nov 2022

Q216 · Compound R can be formed from 1-bromopropane using a nucleophilic substitution reaction… 9701/13 Oct/Nov 2022

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

1 marks

Answer: A

This question in 9701/13 Oct/Nov 2022

Q217 · 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

Q218 · Compound X, C7H13Br, reacts with hot alcoholic NaOH to produce two compounds, Y and Z 9701/12 Feb/March 2023

27 Compound X, C7H13Br, reacts with hot alcoholic NaOH to produce two compounds, Y and Z. On reaction with Br2, Y gives a product, C7H12Br2, which exists as a mixture of four optical isomers. On reaction with Br2, Z gives a product, C7H12Br2, which is non-chiral. What could X be? A B C D CH3 Br CH2Br CH3 CH3 Br Br

1 marks

Answer: A

This question in 9701/12 Feb/March 2023

Q219 · Which type of reaction happens during the hydrolysis of 2-bromopropane? 9701/13 May/June 2023

30 Which type of reaction happens during the hydrolysis of 2-bromopropane? A electrophilic addition B free radical substitution C nucleophilic addition D nucleophilic substitution

1 marks

Answer: D

This question in 9701/13 May/June 2023

Q220 · 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

Q221 · 1,1-dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give… 9701/11 Oct/Nov 2023

31 1,1-dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give propanal. NaOH(aq) CH3CH2CHCl 2 CH3CH2CHO Which term describes the first step of this reaction? A addition B elimination C oxidation D substitution

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2023

Q222 · Which row shows the correct name and classification of the halogenoalkane shown? 9701/12 Oct/Nov 2023

28 Which row shows the correct name and classification of the halogenoalkane shown? CH3(CH2)2CBr(CH3)CH2CH3 classification of name halogenoalkane A 3-bromo-3-methylhexane secondary B 3-bromo-3-methylhexane tertiary C 3-bromo-4-methylhexane tertiary D 4-bromo-5-methylhexane secondary

1 marks

Answer: B

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 · 1,1-dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give… 9701/13 Oct/Nov 2023

31 1,1-dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give propanal. NaOH(aq) CH3CH2CHCl 2 CH3CH2CHO Which term describes the first step of this reaction? A addition B elimination C oxidation D substitution

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2023

Q225 · Which statement is correct? 9701/12 Feb/March 2024

29 Which statement is correct? A Bromoethane reacts with NaOH(aq) to form ethene as a major product. B 1-chlorobutane reacts more rapidly than 1-bromobutane with NaOH(aq) at the same temperature. C Hydrolysis of (C2H5)3CBr occurs mostly by the SN2 mechanism. D The CH3CH2CH2CH2 + ion is less stable than the (CH3)3C+ ion.

1 marks

Answer: D

This question in 9701/12 Feb/March 2024

Q226 · In the hydrolysis of bromoethane by aqueous NaOH, what is the nature of the attacking… 9701/12 Feb/March 2024

30 In the hydrolysis of bromoethane by aqueous NaOH, what is the nature of the attacking group and of the leaving group? attacking group leaving group A electrophile electrophile B electrophile nucleophile C nucleophile electrophile D nucleophile nucleophile

1 marks

Answer: D

This question in 9701/12 Feb/March 2024

Q227 · Structural isomerism only should be considered when answering this question 9701/12 Feb/March 2024

36 Structural isomerism only should be considered when answering this question. How many compounds with molecular formula C5H11Br are primary halogenoalkanes? A 4 B 5 C 7 D 8

1 marks

Answer: A

This question in 9701/12 Feb/March 2024

Q228 · Q is either a primary or a tertiary halogenoalkane 9701/11 May/June 2024

30 Q is either a primary or a tertiary halogenoalkane. Q undergoes hydrolysis with aqueous sodium hydroxide. The first step in the mechanism of this reaction involves two species reacting together. Which row is correct? Q behaviour of hydroxide ion A primary halogenoalkane electrophile B primary halogenoalkane nucleophile C tertiary halogenoalkane electrophile D tertiary halogenoalkane nucleophile

1 marks

Answer: B

This question in 9701/11 May/June 2024

Q229 · 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

Q230 · Which reagents could be used to form 2-bromobutane from butan-1-ol? 9701/11 May/June 2024

33 Which reagents could be used to form 2-bromobutane from butan-1-ol? A bromine and ultraviolet light B concentrated sulfuric acid with potassium bromide, under reflux C concentrated sulfuric acid followed by bromine D concentrated sulfuric acid followed by hydrogen bromide

1 marks

Answer: D

This question in 9701/11 May/June 2024

Q231 · Aqueous NaOH reacts with 1-bromopropane to give propan-1-ol 9701/12 May/June 2024

28 Aqueous NaOH reacts with 1-bromopropane to give propan-1-ol. What should be included in a diagram of the first step in the mechanism? A a curly arrow from a lone pair on the OH– ion to the C+ atom of 1-bromopropane B a curly arrow from the C+ atom of 1-bromopropane to the OH– ion C a curly arrow from the C–Br bond to the C atom D the homolytic fission of the C–Br bond

1 marks

Answer: A

This question in 9701/12 May/June 2024

Q232 · 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

Q233 · What is involved in the mechanism of the reaction between aqueous NaOH and 1-bromobutane? 9701/13 May/June 2024

28 What is involved in the mechanism of the reaction between aqueous NaOH and 1-bromobutane? A attack by a nucleophile on a carbon atom with a partial positive charge B heterolytic bond fission and attack by a nucleophile on a carbocation C homolytic bond fission and attack by an electrophile on a carbanion D homolytic bond fission and attack by a nucleophile on a carbocation

1 marks

Answer: A

This question in 9701/13 May/June 2024

Q234 · 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

Q235 · Chloroethane can be used to make sodium propanoate 9701/13 May/June 2024

31 Chloroethane can be used to make sodium propanoate. chloroethane  intermediate Q  sodium propanoate Intermediate Q is hydrolysed with boiling aqueous NaOH to give sodium propanoate. Which reagent would produce intermediate Q from chloroethane? A concentrated ammonia solution B dilute sulfuric acid C hydrogen cyanide in water D potassium cyanide in ethanol

1 marks

Answer: D

This question in 9701/13 May/June 2024

Q236 · When X is added to NaOH(aq) and heated under reflux, pentan-2-ol is made 9701/11 Oct/Nov 2024

32 When X is added to NaOH(aq) and heated under reflux, pentan-2-ol is made. Which organic product is made when X is heated with a solution of KCN dissolved in ethanol? A B C D CN CN CN CN

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2024

Q237 · 1-chlorobutane and 1-iodobutane both react with aqueous sodium hydroxide by a… 9701/11 Oct/Nov 2024

33 1-chlorobutane and 1-iodobutane both react with aqueous sodium hydroxide by a nucleophilic substitution mechanism. Which reaction has the greatest rate under the same conditions and which mechanism is followed by this reaction? greatest rate mechanism A 1-chlorobutane SN1 B 1-chlorobutane SN2 C 1-iodobutane SN1 D 1-iodobutane SN2

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2024

Q238 · The table shows three sets of reagents and reaction conditions 9701/12 Oct/Nov 2024

31 The table shows three sets of reagents and reaction conditions. reagents reaction conditions 1 CH2C(CH3)CH3 and HCl (g) room temperature 2 CH3C(CH3)(OH)CH3 and SOCl 2 room temperature 3 CH3CH(CH3)CH3 and Cl 2 the presence of ultraviolet light Which sets of reagents and conditions can be used to produce 2-chloro-2-methylpropane as one of the organic products? A 1, 2 and 3 B 1 and 2 only C 1 and 3 only D 2 and 3 only

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2024

Q239 · When X is added to NaOH(aq) and heated under reflux, pentan-2-ol is made 9701/13 Oct/Nov 2024

32 When X is added to NaOH(aq) and heated under reflux, pentan-2-ol is made. Which organic product is made when X is heated with a solution of KCN dissolved in ethanol? A B C D CN CN CN CN

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2024

Q240 · 1-chlorobutane and 1-iodobutane both react with aqueous sodium hydroxide by a… 9701/13 Oct/Nov 2024

33 1-chlorobutane and 1-iodobutane both react with aqueous sodium hydroxide by a nucleophilic substitution mechanism. Which reaction has the greatest rate under the same conditions and which mechanism is followed by this reaction? greatest rate mechanism A 1-chlorobutane SN1 B 1-chlorobutane SN2 C 1-iodobutane SN1 D 1-iodobutane SN2

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2024

Q241 · 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

Q242 · Compound Y is hydrolysed by warm aqueous silver nitrate to form a precipitate that is… 9701/12 Feb/March 2025

32 Compound Y is hydrolysed by warm aqueous silver nitrate to form a precipitate that is soluble in dilute aqueous ammonia. Compound Y undergoes an elimination reaction to form an alkene. What is the skeletal formula of compound Y? A B C D Br I Cl Cl

1 marks

Answer: C

This question in 9701/12 Feb/March 2025

Q243 · Propan-2-ol can be converted into 2-chloropropane using reagent M followed by reagent N 9701/12 Feb/March 2025

33 Propan-2-ol can be converted into 2-chloropropane using reagent M followed by reagent N. Which row is correct? reagent M reagent N A concentrated NaOH Cl 2 B concentrated H2SO4 Cl 2 C concentrated H3PO4 HCl D concentrated NaOH HCl

1 marks

Answer: C

This question in 9701/12 Feb/March 2025

Q244 · A possible mechanism for the exothermic hydrolysis of 2-chloro-2-methylpropane is shown 9701/11 May/June 2025

33 A possible mechanism for the exothermic hydrolysis of 2-chloro-2-methylpropane is shown. CH3 C Cl CH3 CH3 CH3 C Cl– CH3 CH3 + CH3 C CH3 CH3 CH3 C CH3 CH3 slow fast OH– + OH + + Which diagram represents the reaction pathway diagram for this mechanism? reaction pathway energy reaction pathway energy reaction pathway energy reaction pathway energy A B C D

1 marks

Answer: B

This question in 9701/11 May/June 2025

Q245 · Two reactions are described 9701/11 May/June 2025

35 Two reactions are described. 1 2-bromo-2-methylbutane heated with NaOH(aq) 2 2-chloro-2-methylbutane heated with NaOH(aq) In both reactions, the conditions are the same and NaOH(aq) is in excess. 30.18g of 2-bromo-2-methylbutane forms 12.32g of product X. [Mr: 2-bromo-2-methylbutane, 150.9; 2-chloro-2-methylbutane, 106.5] Which row is correct? percentage yield of product X/% relative rate of reaction A 41 1 is faster than 2 B 41 2 is faster than 1 C 70 1 is faster than 2 D 70 2 is faster than 1

1 marks

Answer: C

This question in 9701/11 May/June 2025

Q246 · Which statement about the mechanism of an SN1 reaction of a halogenoalkane is correct? 9701/12 May/June 2025

25 Which statement about the mechanism of an SN1 reaction of a halogenoalkane is correct? A A nucleophile is substituted by an electrophile. B One intermediate is formed from two reacting molecules. C The intermediate is stabilised by adjacent alkyl groups. D The intermediate is uncharged.

1 marks

Answer: C

This question in 9701/12 May/June 2025

Q247 · Which row gives pentanenitrile as one product? 9701/12 May/June 2025

28 Which row gives pentanenitrile as one product? reagents and halogenoalkane conditions A heat with HCN Br B heat with KCN using Br ethanol as solvent C heat with HCN Br D heat with KCN using Br ethanol as solvent

1 marks

Answer: B

This question in 9701/12 May/June 2025

Q248 · An amine is produced in the following reaction 9701/13 May/June 2025

33 An amine is produced in the following reaction. C2H5I + 2NH3 → C2H5NH2 + NH4I What is the mechanism? A electrophilic addition B free-radical substitution C nucleophilic addition D nucleophilic substitution

1 marks

Answer: D

This question in 9701/13 May/June 2025

Q249 · 1-chloro-2-methylbutane reacts with sodium cyanide in a nucleophilic substitution reaction 9701/14 May/June 2025

28 1-chloro-2-methylbutane reacts with sodium cyanide in a nucleophilic substitution reaction. What is the most likely intermediate or transition state in this reaction? A B – – H H H3C CH2CH3 NC C Cl NC C Cl CH(CH3)CH2CH3 CH3 C D H3C CH2CH3 H H +C +C CH3 CH(CH3)CH2CH3

1 marks

Answer: A

This question in 9701/14 May/June 2025

Q250 · Which reagent would react with 1-bromopropane to give the highest yield of propene? 9701/14 May/June 2025

33 Which reagent would react with 1-bromopropane to give the highest yield of propene? A ammonia B aqueous potassium hydroxide C potassium cyanide D ethanolic sodium hydroxide

1 marks

Answer: D

This question in 9701/14 May/June 2025

Q251 · Separate samples of 1-bromopropane are used in two different reactions 9701/14 May/June 2025

38 Separate samples of 1-bromopropane are used in two different reactions. reaction 1 1-bromopropane is converted into compound X by heating it under pressure with ammonia in ethanol. reaction 2 1-bromopropane is converted into compound Y. Compound Y undergoes hydrolysis to form butanoic acid. Which row identifies compound X and describes the reagents used in reaction 2 to make compound Y? identity of compound X reagents for reaction 2 A CH3CH2CH2NH2 HCN(aq) B CH3CH2CH2NH2 KCN dissolved in ethanol C CH3CH2CH2OH HCN(aq) D CH3CH2CH2OH KCN dissolved in ethanol

1 marks

Answer: B

This question in 9701/14 May/June 2025

Q252 · Compound X, C7H11ICl2, is dissolved in ethanol and the solution mixed with warm aqueous… 9701/11 Oct/Nov 2025

30 Compound X, C7H11ICl2, is dissolved in ethanol and the solution mixed with warm aqueous silver nitrate. A precipitate is seen immediately. CH2Cl Cl I compound X What is the colour of this precipitate and what is the structural formula of the first organic product? colour of the precipitate structural formula of the first organic product A cream CH2Cl HO OH B cream CH2OH HO OH C white CH2OH HO I D yellow CH2Cl Cl OH

1 marks

Answer: D

This question in 9701/11 Oct/Nov 2025

Q253 · 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

Q254 · 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

Q255 · 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

Q256 · Which reaction mixture produces a nitrile? 9701/12 Oct/Nov 2025

30 Which reaction mixture produces a nitrile? A halogenoalkane with KCN in ethanol B halogenoalkane with NH3 in ethanol C ketone with 2,4-DNPH D carboxylic acid with NH3 in water

1 marks

Answer: A

This question in 9701/12 Oct/Nov 2025

Q257 · Which reaction is classified as SN1? 9701/12 Oct/Nov 2025

31 Which reaction is classified as SN1? A the reaction of 1-chloropropane with ammonia in ethanol B the reaction of 1-chloropropane with potassium hydroxide in ethanol C the reaction of 2-chloro-2-methylpropane with potassium cyanide in ethanol D the reaction of 2-chloro-2-methylpropane with potassium hydroxide in ethanol

1 marks

Answer: C

This question in 9701/12 Oct/Nov 2025

Q258 · Compound X, C7H11ICl2, is dissolved in ethanol and the solution mixed with warm aqueous… 9701/13 Oct/Nov 2025

30 Compound X, C7H11ICl2, is dissolved in ethanol and the solution mixed with warm aqueous silver nitrate. A precipitate is seen immediately. CH2Cl Cl I compound X What is the colour of this precipitate and what is the structural formula of the first organic product? colour of the precipitate structural formula of the first organic product A cream CH2Cl HO OH B cream CH2OH HO OH C white CH2OH HO I D yellow CH2Cl Cl OH

1 marks

Answer: D

This question in 9701/13 Oct/Nov 2025

Q259 · 1,4-dibromobutane reacts with an excess of ethanolic sodium hydroxide until no further… 9701/13 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 9701/13 Oct/Nov 2025