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Alcohols

Past-paper questions pack

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Questions are numbered; the mark schemes (the answer key) follow on separate pages so the question pages can be handed out alone. www.chemistryaleveltutor.com

OCR AS and A-level Chemistry past-paper questions since 2016 · 75 parts · mark schemes follow the questions · www.chemistryaleveltutor.com · Questions and mark schemes © OCR

1. June 2025 · AS Paper 1 · Q17 · 1 marks ·
17 How many structural isomers of C5H12O are secondary alcohols? A 1 B 2 C 3 D 4 Your answer [1]
2. June 2025 · AS Paper 1 · Q25(a) · 3 marks ·
25 This question is about alcohols. Alcohols D, E, F and G, shown below, are structural isomers of C4H10O. H H OH H H H CH3 H H H H H C C C C H H3C C C OH H3C C OH HO C C C C H H H H H CH3 H CH3 H H H H Alcohol D Alcohol E Alcohol F Alcohol G (a) Alcohols D, E, F and G are each heated under reflux with H+ / Cr2O7 2–. Draw the structure of the organic product that is formed from each alcohol. If there is no reaction, state ‘No reaction’. Alcohol Organic product D E F G [3]
3. June 2025 · AS Paper 1 · Q25(b) · 1 marks ·
(b) Alcohols D, E, F and G are each heated with concentrated H2SO4, which acts as an acid catalyst. Which alcohol forms a mixture of two alkenes that are structural isomers of one another? Alcohol ..................... [1]
4. June 2025 · AS Paper 2 · Q3(c) · 2 marks ·
(c) The structure of malic acid is shown below. OH H HOOC C C COOH H H When malic acid is heated with an acid catalyst, a mixture of cis and trans stereoisomers is produced. Draw the structures of the cis and trans isomers. cis trans [2]
5. June 2025 · Paper 2 · Q4 · 1 marks ·
4 Which diagram shows the correct way to set up apparatus for converting ethanol to ethanoic acid? water out water in A B water in water out water out water in water in water out C D Your answer [1]
6. June 2025 · Paper 2 · Q13 · 1 marks ·
13 Which molecule(s) would form a ketone group when oxidised? OH 1 HO OH O 2 HO OH 3 OH A 1, 2 and 3 B Only 1 and 2 C Only 2 and 3 D Only 1 Your answer [1]
7. June 2025 · Paper 2 · Q14 · 1 marks ·
14 The structure of vitamin C is shown. HO OH OH O O OH Which reagent(s) will react with vitamin C? 1 Aqueous bromine water 2 Acidified potassium dichromate(VI) 3 Aqueous silver nitrate in ethanol A 1, 2 and 3 B Only 1 and 2 C Only 2 and 3 D Only 1 Your answer [1]
8. June 2025 · Paper 2 · Q17 · 6 marks ·
17* This question is about an organic synthesis. A student plans a two-stage synthesis of compound F from compound D, as shown below. Cl OH OH O Stage 1 Stage 2 Compound E Compound D Compound F Plan a two-stage synthesis for the preparation of 2.50 g of compound F from compound D. The overall percentage yield of compound F from compound D is 31.5%. In your answer include the mass of compound D required, reagents and equations for each step. 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9. June 2025 · Paper 2 · Q19(b)(i) · 1 marks ·
(b) The table below shows the boiling points of propan-1-ol and 1-bromopropane. Propan-1-ol 1-Bromopropane Boiling point / °C 97 71 Propan-1-ol can be reacted to form 1-bromopropane. (i) Suggest suitable reagents for this reaction. ..................................................................................................................................................... [1]
10. June 2025 · Paper 2 · Q23(a) · 4 marks ·
23 This question is about spectral analysis. (a) Compound K, C4H10O, is refluxed with H2SO4 to form a mixture of compound L and compound M. The infrared spectrum of compound K is shown. 100 50 Transmittance (%) 0 4000 3000 2000 1500 1000 500 Wavenumber / cm−1 Compound L and compound M are analysed using 13C NMR spectroscopy. • The 13C NMR spectrum of compound L has 4 peaks. • The 13C NMR spectrum of compound M has 2 peaks. Suggest the functional group in compound K, showing your reasoning, and suggest possible structures for compound K, compound L and compound M. Functional group .............................................................. Reasoning ........................................................................................................................................ Possible structure K L M [4]
11. June 2024 · AS Paper 1 · Q25(a) · 2 marks ·
25 Three alcohols, A, B and C, are structural isomers with the molecular formula C5H12O. (a) A, B and C take part in combustion reactions. Complete the equation for the complete combustion of C5H12O. C5H12O + ...................................................................................................................................... [2]
12. June 2024 · AS Paper 1 · Q25(b) · 3 marks ·
(b) Alcohols A, B and C are each refluxed with acidified dichromate(VI), H+/Cr2O7 2–. The organic products are shown in the table below. Complete the table to show the structures of alcohols A, B and C. Organic product after Alcohol Structure of alcohol refluxing with H+/Cr2O7 2– O A OH O B C No reaction [3]
13. June 2024 · Paper 2 · Q17(a) · 2 marks ·
17 This question is about reactions of alcohols. There are 4 structural isomers of C4H10O that are alcohols: CH3CH2CH2CH2OH CH3CH2CHOHCH3 (CH3)2CHCH2OH (CH3)3COH Alcohols take part in many different types of reaction, including • elimination • oxidation • substitution • esterification. For each type of reaction, choose appropriate reagent(s) and/or catalyst, and show the organic product formed. (a) Elimination reaction of CH3CH2CH2CH2OH Reagent(s) and/or catalyst .......................................................................................................................................................... .......................................................................................................................................................... organic product [2]
14. June 2024 · Paper 2 · Q17(b) · 2 marks ·
(b) Oxidation reaction of CH3CH2CHOHCH3 Reagent(s) and/or catalyst .......................................................................................................................................................... .......................................................................................................................................................... organic product [2]
15. June 2024 · Paper 2 · Q17(c) · 2 marks ·
(c) Substitution reaction of (CH3)2CHCH2OH Reagent(s) and/or catalyst .......................................................................................................................................................... .......................................................................................................................................................... organic product [2]
16. June 2023 · AS Paper 1 · Q17 · 1 marks · AO2
17 3-Methylcyclohexanol is reacted with NaBr and H2SO4. What is the organic product? Br A Br B C D Your answer [1]
17. June 2023 · AS Paper 1 · Q26 · 5 marks ·
26 This question is about the oxidation of two alcohols that are structural isomers of C3H8O. Compare the oxidation of these two structural isomers using different reaction conditions. For each reaction include: • the reaction conditions • the functional group of any organic product • a balanced equation. In your equations, use [O] to represent the oxidising agent and show any organic compounds as structures. .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... ..................................................................................................................................................... [5]
18. June 2023 · AS Paper 2 · Q5(a)(ii) · 2 marks · AO2
(ii) Alcohol A is refluxed with an acid catalyst. • A mixture of alkene isomers B, C and D is formed. • Alkenes B and C show E/Z isomerism but alkene D does not. Construct the equation for the formation of alkene D from alcohol A. Show the structure of the organic product. [2]
19. June 2023 · AS Paper 2 · Q5(b)(i) · 2 marks · AO2, 3
(b) A chemistry company is developing water-soluble polymers. The chemists decide to use compound E, shown below, as the monomer. H CH2 OH C C H H Compound E (i) Draw a section of the polymer formed, showing two repeat units, and suggest why this polymer is likely to be soluble in water. Section of polymer (two repeat units) Reason for solubility in water ............................................................................................. ........................................................................................................................................... ........................................................................................................................................... ........................................................................................................................................... [2]
20. June 2023 · Paper 2 · Q17(a) · 2 marks · AO2
17 This question is about alcohols. (a) An unsaturated alcohol has 6 carbon atoms and contains one C=C bond. Construct an equation for the complete combustion of this alcohol. .............................................................................................................................................. [2]
21. June 2023 · Paper 2 · Q17(b) · 3 marks · AO2
(b) Compound C, shown below, is refluxed with excess acidified potassium dichromate(VI) to form a single organic product and one other product. Complete the equation for this reaction. OH OH + ............ [O] OH Compound C [3]
22. June 2023 · Paper 2 · Q17(c)(i) · 3 marks · AO2
(c) Compound D, shown below, is refluxed with H2SO4, as an acid catalyst, to form a mixture of three isomers with the molecular formula C7H10. HO OH Compound D (i) Draw the structures of the three isomers of C7H10 formed from compound D. [3]
23. June 2023 · Paper 2 · Q17(c)(ii) · 1 marks · AO1
(ii) A student converts compound D into a diiodoalkane. Suggest suitable reagents for this reaction. ...................................................................................................................................... [1]
24. June 2023 · Paper 3 · Q3 · 6 marks · AO3
3* A chemist is investigating compound A, shown below, as a potential organic intermediate. O OH CN Compound A Describe the type of stereoisomerism shown by compound A and suggest three reactions of compound A, one for each of the three functional groups using reagents of your choice. In your answer, show stereoisomers of compound A, your chosen reactants and conditions, and the structures for the organic products produced. Mechanisms and equations are not required. 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25. June 2022 · AS Paper 2 · Q1(d) · 2 marks · AO2
(d) Other fruits contain different organic acids. Apple juice contains malic acid which has the following structure. H OH HOOC C C COOH H H Malic acid can be oxidised by heating with acidified potassium dichromate(VI). Write a balanced equation for the reaction, showing the structure of the organic product. Use [O] to represent the oxidising agent. [2]
26. June 2022 · Paper 2 · Q20(c) · 2 marks · AO2
(c) Compound J, C6H5CH2CH2OH, is reacted with acidified potassium dichromate(VI) under reflux to form organic product M. Write an equation for this reaction. Use [O] to represent the oxidising agent and show the structure of M. [2]
27. June 2022 · Paper 2 · Q20(e) · 4 marks · AO2, 3
(e) 1-phenylethanol is a naturally occurring compound found in many vegetables and flowers. 1-phenylethanol can be synthesised from 2-phenylethanol in two stages. H H OH H Stage 1 Stage 2 C C OH Intermediate C C H H H H H 2-phenylethanol 1-phenylethanol Suggest reagents, conditions and equations for each stage in the synthesis. Show structures for organic compounds. Stage 1 reagents and conditions ........................................................................................................... equation: Stage 2 reagents and conditions ........................................................................................................... equation: [4]
28. June 2022 · Paper 3 · Q3(b) · 4 marks · AO3
(b) Butan-1-ol reacts with sodium bromide and sulfuric acid to form 1-bromobutane by nucleophilic substitution. The mechanism for this reaction takes place by two steps. Step 1 The oxygen atom of the alcohol group accepts a proton to form a positively- charged intermediate. Step 2 Bromide ions react with the intermediate from Step 1 by nucleophilic substitution to form 1-bromobutane. Show both steps in this mechanism. [4]
29. June 2022 · Paper 3 · Q5(b)(i) · 1 marks · AO2
(b) Internal combustion engines have historically used fuels obtained from crude oil as a source of power. The environmental effects of fossil fuel use can be reduced by blending petrol with biofuels such as ethanol. A fuel is being developed using a 1:1 molar ratio of octane and ethanol. (i) Write the equation for the complete combustion of this fuel. ...................................................................................................................................... [1]
30. June 2022 · Paper 3 · Q6(b)(i) · 1 marks · AO2
(b) Vitamin C is extremely soluble in water. This means that vitamin C is removed rapidly from the body. ‘Vitamin C ester’ is available in tablet form as a less soluble source of vitamin C which stays in the body for longer. (i) Suggest why vitamin C is extremely soluble in water. ........................................................................................................................................... ........................................................................................................................................... ...................................................................................................................................... [1]
31. November 2021 · Paper 2 · Q4 · 1 marks ·
4 What is the correct equation for the incomplete combustion of butan-1-ol? A CH3CH2CH2CH2OH + 1½O2 4CO + 5H2 B CH3CH2CH2CH2OH + 2O2 4CO + 5H2 C CH3CH2CH2CH2OH + 4O2 4CO + 5H2O D CH3CH2CH2CH2OH + 4½O2 4CO + 5H2O Your answer [1]
32. November 2021 · Paper 2 · Q7 · 1 marks ·
7 Menthol, shown below, is heated with an acid catalyst. OH menthol Which structure could be formed? A B C D Your answer [1]
33. November 2021 · AS Paper 2 · Q7(a) · 2 marks · AO2
7 2-Chloro-2-methylpropane, (CH3)3CCl , is an organic liquid with a boiling point of 50 °C. A student prepares (CH3)3CCl by reacting 2-methylpropan-2-ol, (CH3)3COH, with concentrated hydrochloric acid. (a) Write a balanced equation for this reaction. Use skeletal formulae for organic compounds. [2]
34. November 2021 · AS Paper 2 · Q7(c)(i) · 1 marks · AO1
(c) Compounds A and B are structural isomers of (CH3)3COH. (i) Compound A is a secondary alcohol. What is the systematic name of compound A? ...................................................................................................................................... [1]
35. November 2021 · AS Paper 2 · Q7(c)(ii) · 3 marks · AO2
(ii) Compound B is a branched primary alcohol. Compound B is refluxed with acidified potassium dichromate(VI) as an oxidising agent. Write the equation for the reaction that takes place. Use structures for organic compounds and [O] for the oxidising agent. [3]
36. November 2021 · Paper 2 · Q18(b) · 7 marks · AO1, 2
(b) Complete the flowchart for two synthetic routes to the amino acid valine. ester C7H14O3 .................................................. O HO OH .................................. C5H10O3 acyl chloride C5H9O2Cl .................................................. O H2N OH ........................................... valine haloalkane C5H11NO2 C5H9BrO2 [7]
37. November 2020 · AS Paper 1 · Q16 · 1 marks · AO1
16 What are the correct reagents for the conversion below? CH3CH2CHOHCH3 → CH3CH2CHBrCH3 A Br2 and H2SO4 B Br2 and NaOH C NaBr and H2SO4 D NaBr and NaOH Your answer [1]
38. November 2020 · AS Paper 1 · Q17 · 1 marks · AO1
17 Which compound could react with both • K2Cr2O7/H2SO4 in an oxidation reaction and • an acid catalyst (e.g. H2SO4) in an elimination reaction? A OH B OH C HO D HO OH Your answer [1]
39. November 2020 · Paper 2 · Q3 · 1 marks · AO1
3 Which of these reagent(s) will not react with HOCH2CH2CH2COOH? A NaCN in ethanol B C2H5OH in the presence of an acid catalyst C (CH3CO)2O D concentrated H2SO4 Your answer [1]
40. November 2020 · Paper 2 · Q4 · 1 marks · AO2
4 Which compound can be refluxed with acidified potassium dichromate(VI) to form an organic product with molecular formula C5H8O2? A HO O B HO O O HO C O D HO Your answer [1]
41. November 2020 · AS Paper 2 · Q5(a) · 2 marks · AO1, 2
5 This question is about the alcohols A–F shown below. OH OH OH A B C OH OH OH D E F (a) Which of the alcohols A–F are secondary alcohols? .............................................................................................................................................. [2]
42. November 2020 · AS Paper 2 · Q5(b) · 1 marks · AO2
(b) Complete a balanced equation for the complete combustion of alcohol C. CH3CH2CH(OH)CH3 + ........................... ........................... + ........................... [1]
43. November 2020 · AS Paper 2 · Q5(f) · 6 marks · AO2, 3
(f)* The structures of A–F are repeated below. OH OH OH A B C OH OH OH D E F Compound X is one of the alcohols A–F. A student refluxes compound X with acidified potassium dichromate(VI) as an oxidising agent. A pure sample of the organic product Y is obtained from the resulting mixture. The mass spectrum and IR spectrum of Y are shown below. Mass spectrum of Y 100 80 relative 60 intensity 40 20 0 10 20 30 40 50 60 70 80 90 m / z IR spectrum of Y 100 transmittance 50 (100%) 0 4000 3000 2000 1500 1000 500 wavenumber / cm–1 Using this information, identify compound X and product Y, and write an equation for the formation of product Y from compound X. You may use [O] to represent the oxidising agent. In your answer you should make clear how your conclusions are linked to the evidence. [6] ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... Additional answer space if required ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ...................................................................................................................................................
44. November 2020 · Paper 2 · Q6 · 1 marks · AO2
6 Which alcohol reacts with an acid catalyst to form a mixture of stereoisomers? A 3-methylbutan-2-ol B pentan-1-ol C 2-methylhexan-2-ol D heptan-4-ol Your answer [1]
45. November 2020 · Paper 2 · Q18(a)(i) · 3 marks · AO1, 2
18 Alcohols can be used to prepare organic compounds with different functional groups. (a) HO(CH2)4OH can be oxidised to form HOOC(CH2)2COOH. (i) State the reagents and conditions and write an equation for this oxidation. In the equation, use [O] for the oxidising agent. Reagents and conditions: .................................................................................................. ........................................................................................................................................... Equation: [3]
46. November 2020 · Paper 2 · Q21(a) · 5 marks · AO2
21 This question is about organic compounds containing nitrogen. (a) Salt H, (CH3)2CHNH3Cl , is used in the manufacture of garden weedkillers. The flowchart shows the synthesis of the salt H from propanone. Complete the flowchart. Show structures for organic compounds. propanone NaBH4 reagent: ...................................... Br CH H3C CH3 reagent: ...................................... NH3Cl reagent: ...................................... CH H3C CH3 salt H [5]
47. June 2019 · AS Paper 1 · Q25(a)(i) · 3 marks · AO1, 2
25 This question is about alcohols and alkanes. (a) Three alcohols A, B and C are structural isomers of C4H10O. Each alcohol is refluxed with acidified dichromate(VI), H+/Cr2O7 2−. (i) Draw the structures for the organic products. If there is no reaction, write ‘NONE’. OH A OH B OH C [3]
48. June 2019 · AS Paper 1 · Q25(a)(iii) · 1 marks · AO2
(iii) Complete the equation below for the complete combustion of alcohol A. C4H10O ............................................. → ....................................................................... [1]
49. June 2019 · AS Paper 2 · Q5(b)(ii) · 2 marks · AO3
(ii) Another student suggested that hex-1-ene could be prepared from hexan-2-ol by the same method. Would you expect the percentage yield of hex-1-ene to be greater than, less than or about the same as when using hexan-1-ol? Explain your answer. ........................................................................................................................................... ........................................................................................................................................... ........................................................................................................................................... ...................................................................................................................................... [2]
50. June 2019 · Paper 2 · Q13 · 1 marks · AO1
13 A carbonyl compound is reacted with NaBH4. Which compound(s) could be formed? 1 2-Methylpentan-2-ol 2 2-Methylpentan-1-ol 3 3-Methylpentan-2-ol A 1, 2 and 3 B Only 1 and 2 C Only 2 and 3 D Only 1 Your answer [1]
51. June 2019 · Paper 2 · Q19(b)(iv) · 7 marks · AO2
(iv) Complete the flowchart for the synthesis of compounds D and E from phenylethanone. H3C O C NaBH4 phenylethanone NaCN(aq) / H+(aq) .................................................. H H C H C .................................................. CH3 compound D Br C CN .................................................. CH3 H2N C COOH .................................... compound E [7]
52. June 2019 · Paper 3 · Q2(c) · 1 marks · AO2
(c) Write the overall equation for the preparation of benzoic acid from phenylmethanol. Use [O] for the oxidising agent. .............................................................................................................................................. [1]
53. June 2019 · Paper 3 · Q4(b)(iii) · 4 marks · AO3
(iii) α-Terpineol contains two functional groups. For each functional group, choose a reagent that reacts with that group only. Draw the structures for the organic products of the reactions. Show structures for organic compounds. Reagent(s) ................................................................................................................................ Name of functional group that reacts ........................................................................................ Structure of organic product Reagent(s) ................................................................................................................................ Name of functional group that reacts ........................................................................................ Structure of organic product [4]
54. June 2018 · AS Paper 1 · Q15 · 1 marks ·
15 1 mol of a compound reacts with 8 mol O2 for complete combustion. What is the formula of the compound? A C4H8 B C4H9OH C C5H11OH D C5H12 Your answer [1]
55. June 2018 · AS Paper 1 · Q16 · 1 marks ·
16 How many structural isomers of C6H14O are tertiary alcohols? A 1 B 2 C 3 D 4 Your answer [1]
56. June 2018 · AS Paper 1 · Q25(a)(i) · 3 marks ·
25 This question is about reactions involving alcohols. (a) Three reactions of an alcohol E are shown in Fig. 25.1. (i) Complete Fig. 25.1 to show the structures of the organic products formed in the reactions. F H2SO4 + heat CH3 H H3C C C OH H H E H2SO4 / K2Cr2O7 H2SO4 / K2Cr2O7 distil reflux G H Fig. 25.1 [3]
57. June 2018 · Paper 2 · Q16(a)(iii) · 2 marks ·
(iii) The chemist heats alcohol A with an acid catalyst to form a mixture containing two alkenes. Draw the structures of the two alkenes formed in this reaction. [2]
58. June 2018 · Paper 2 · Q16(a)(iv) · 2 marks ·
(iv) The chemist heats alcohol A with sodium chloride and sulfuric acid. Construct a balanced equation for this reaction. Show structures for the organic compounds in your equation. [2]
59. June 2018 · Paper 2 · Q16(b) · 2 marks ·
(b) Compound B, shown below, is refluxed with excess acidified potassium dichromate(VI) to form a single organic product. Complete the equation for this reaction. CH3 H H H3C C C C OH + .......... [O] OH OH H compound B [2]
60. June 2018 · Paper 2 · Q22(b) · 4 marks ·
(b) Explain the difference in the boiling points of the fuels in Table 22.1. ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... .............................................................................................................................................. [4]
61. June 2017 · AS Paper 1 · Q18 · 1 marks ·
18 Which alcohol reacts with an acid catalyst to form E and Z stereoisomers? A pentan-3-ol B pentan-1-ol C 2-methylbutan-2-ol D 2,2-dimethylpropan-1-ol Your answer [1]
62. June 2017 · AS Paper 1 · Q19 · 1 marks ·
19 An alcohol A is heated under reflux with sulfuric acid and potassium dichromate(VI). The organic compound formed produces the infrared spectrum below. 100 transmittance (%) 50 0 4000 3000 2000 1500 1000 500 wavenumber / cm–1 Which compound could be alcohol A? A OH OH B C OH D HO Your answer [1]
63. June 2017 · AS Paper 2 · Q4(a) · 2 marks ·
4 The hydroxyl group, –OH, is responsible for many properties of alcohols. (a) Methanol, CH3OH, is soluble in water because it has polar bonds. Pauling electronegativity values for carbon, oxygen and hydrogen are shown below. Element Electronegativity Carbon 2.5 Oxygen 3.5 Hydrogen 2.1 Use a labelled diagram to explain why methanol is soluble in water. • Use displayed formulae showing one molecule of methanol and one molecule of water. • Add partial charges d+ and d– to show the two most polar bonds in a methanol molecule and the polar bonds in a water molecule. • Show all lone pairs. • Label the most important intermolecular bond between the molecules. [2]
64. June 2017 · AS Paper 2 · Q4(c) · 6 marks ·
(c)* Describe the oxidation reactions of butan-1-ol forming an aldehyde and a carboxylic acid. Explain, using a diagram, how the aldehyde can be produced in the laboratory by controlling the reaction conditions. ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... .............................................................................................................................................. [6]
65. June 2017 · AS Paper 2 · Q6(a)(i) · 2 marks ·
6 Organic compounds can be prepared in the laboratory using synthetic routes with two or more stages. (a) A student devises a two-stage synthesis of cyclohexene from bromocyclohexane. Br Step 1 Step 2 Intermediate E NaOH(aq) bromocyclohexane cyclohexene (i) Suggest the structure of intermediate E and the reagent(s) and conditions for step 2. reagent(s) and conditions .............................................................................................. [2]
66. June 2017 · Paper 2 · Q19(a) · 1 marks ·
19 This question is about alcohols. (a) Construct an equation for the complete combustion of an unsaturated alcohol with 5 carbon atoms. ............................................................................................................................................. [1]
67. June 2017 · Paper 2 · Q19(b)(i) · 2 marks ·
(b) Many alcohols, including ethanol, are soluble in water. (i) Explain, with the aid of a diagram, why ethanol is soluble in water. Include relevant dipoles and lone pairs. ........................................................................................................................................... ........................................................................................................................................... ..................................................................................................................................... [2]
68. June 2017 · Paper 2 · Q19(b)(ii) · 1 marks ·
(ii) The solubility of hexan-1-ol and hexane-1,6-diol in water is shown below in Table 19.1. Alcohol Solubility in water / g dm−3 hexan-1-ol 5.9 hexane-1,6-diol 500 Table 19.1 Explain the difference in solubility of hexan-1-ol and hexane-1,6-diol. ........................................................................................................................................... ........................................................................................................................................... ........................................................................................................................................... ........................................................................................................................................... ..................................................................................................................................... [1]
69. June 2017 · Paper 2 · Q19(c)(i) · 5 marks ·
(c) Alcohols are important in organic synthesis and can be formed by the reduction of carbonyl compounds. (i) Complete the flowchart by filling in each box. carbonyl compound reduction reagent(s): .......................................... OH NaBr / H2SO4 compound K acid catalyst heat + structural isomers [5]
70. June 2017 · Paper 2 · Q19(d) · 5 marks ·
(d) Butan-1-ol can be oxidised to form two different organic products, depending on the reaction conditions used. Describe both oxidation reactions of butan-1-ol. For each reaction include • the structure of the organic product • a balanced equation • the essential reaction conditions. In your equations you may use [O] to represent the oxidising agent. ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ............................................................................................................................................. [5]
71. June 2016 · AS Paper 1 · Q18 · 1 marks ·
9 18 Which alcohol can be oxidised by K2Cr2O7 and H2SO4 to form a ketone? A OH B OH C OH OH D Your answer [1]
72. June 2016 · AS Paper 1 · Q26(b) · 2 marks · AO2
(b) Some reactions involving compound B are shown in the flowchart below. Complete the flowchart, showing the structures of organic compounds C and D. H CH3 concentrated C C H2SO4, heat H CH3 Compound C Compound B K2Cr2O7 / H2SO4 polymerisation reflux no reaction Compound D (repeat unit) [2]
73. June 2016 · AS Paper 2 · Q3(b) · 2 marks ·
7 (b) Compound A can be made from alcohol B by heating with an acid catalyst. Suggest two possible structures for alcohol B. [2]
74. June 2016 · AS Paper 2 · Q6(a) · 1 marks · AO1
14 6 This question is about the properties and reactions of butan-2-ol. H H H H H C C C C H H OH H H Some properties of butan-2-ol are listed in the table. Melting point –115 °C Boiling point 99.5 °C (a) Why is butan-2-ol classified as a secondary alcohol? ................................................................................................................................................... .............................................................................................................................................. [1]
75. June 2016 · AS Paper 2 · Q6(c)(i) · 2 marks · AO2
(c) Butan-2-ol can be oxidised by heating with an oxidising agent. (i) Write an equation for the reaction. Use [O] to represent the oxidising agent and show the structure of the organic product. [2]

Mark schemes

1. June 2025 · AS Paper 1 · Q17
Mark scheme June 2025 Paper 1 Q17
2. June 2025 · AS Paper 1 · Q25(a)
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3. June 2025 · AS Paper 1 · Q25(b)
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4. June 2025 · AS Paper 2 · Q3(c)
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5. June 2025 · Paper 2 · Q4
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6. June 2025 · Paper 2 · Q13
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7. June 2025 · Paper 2 · Q14
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8. June 2025 · Paper 2 · Q17
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9. June 2025 · Paper 2 · Q19(b)(i)
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10. June 2025 · Paper 2 · Q23(a)
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11. June 2024 · AS Paper 1 · Q25(a)
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12. June 2024 · AS Paper 1 · Q25(b)
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13. June 2024 · Paper 2 · Q17(a)
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14. June 2024 · Paper 2 · Q17(b)
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15. June 2024 · Paper 2 · Q17(c)
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16. June 2023 · AS Paper 1 · Q17
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17. June 2023 · AS Paper 1 · Q26
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18. June 2023 · AS Paper 2 · Q5(a)(ii)
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19. June 2023 · AS Paper 2 · Q5(b)(i)
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20. June 2023 · Paper 2 · Q17(a)
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21. June 2023 · Paper 2 · Q17(b)
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22. June 2023 · Paper 2 · Q17(c)(i)
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23. June 2023 · Paper 2 · Q17(c)(ii)
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24. June 2023 · Paper 3 · Q3
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25. June 2022 · AS Paper 2 · Q1(d)
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26. June 2022 · Paper 2 · Q20(c)
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27. June 2022 · Paper 2 · Q20(e)
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28. June 2022 · Paper 3 · Q3(b)
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29. June 2022 · Paper 3 · Q5(b)(i)
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30. June 2022 · Paper 3 · Q6(b)(i)
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31. November 2021 · Paper 2 · Q4
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32. November 2021 · Paper 2 · Q7
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33. November 2021 · AS Paper 2 · Q7(a)
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34. November 2021 · AS Paper 2 · Q7(c)(i)
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35. November 2021 · AS Paper 2 · Q7(c)(ii)
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36. November 2021 · Paper 2 · Q18(b)
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37. November 2020 · AS Paper 1 · Q16
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38. November 2020 · AS Paper 1 · Q17
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39. November 2020 · Paper 2 · Q3
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40. November 2020 · Paper 2 · Q4
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41. November 2020 · AS Paper 2 · Q5(a)
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42. November 2020 · AS Paper 2 · Q5(b)
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43. November 2020 · AS Paper 2 · Q5(f)
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44. November 2020 · Paper 2 · Q6
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45. November 2020 · Paper 2 · Q18(a)(i)
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46. November 2020 · Paper 2 · Q21(a)
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47. June 2019 · AS Paper 1 · Q25(a)(i)
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48. June 2019 · AS Paper 1 · Q25(a)(iii)
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49. June 2019 · AS Paper 2 · Q5(b)(ii)
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50. June 2019 · Paper 2 · Q13
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51. June 2019 · Paper 2 · Q19(b)(iv)
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52. June 2019 · Paper 3 · Q2(c)
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53. June 2019 · Paper 3 · Q4(b)(iii)
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54. June 2018 · AS Paper 1 · Q15
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55. June 2018 · AS Paper 1 · Q16
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56. June 2018 · AS Paper 1 · Q25(a)(i)
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57. June 2018 · Paper 2 · Q16(a)(iii)
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58. June 2018 · Paper 2 · Q16(a)(iv)
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59. June 2018 · Paper 2 · Q16(b)
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60. June 2018 · Paper 2 · Q22(b)
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61. June 2017 · AS Paper 1 · Q18
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62. June 2017 · AS Paper 1 · Q19
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63. June 2017 · AS Paper 2 · Q4(a)
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64. June 2017 · AS Paper 2 · Q4(c)
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65. June 2017 · AS Paper 2 · Q6(a)(i)
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66. June 2017 · Paper 2 · Q19(a)
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67. June 2017 · Paper 2 · Q19(b)(i)
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68. June 2017 · Paper 2 · Q19(b)(ii)
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69. June 2017 · Paper 2 · Q19(c)(i)
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70. June 2017 · Paper 2 · Q19(d)
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71. June 2016 · AS Paper 1 · Q18
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72. June 2016 · AS Paper 1 · Q26(b)
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73. June 2016 · AS Paper 2 · Q3(b)
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74. June 2016 · AS Paper 2 · Q6(a)
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75. June 2016 · AS Paper 2 · Q6(c)(i)
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