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Organic basics: naming, formulae and isomerism

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 · 181 parts · mark schemes follow the questions · www.chemistryaleveltutor.com · Questions and mark schemes © OCR

1. June 2025 · AS Paper 1 · Q14 · 1 marks ·
14 The skeletal formulae of four alcohols, W, X, Y, Z, are shown below. OH W OH X OH Y Z OH Which pair of alcohols are structural isomers of each other? A W and X B W and Y C W and Z D X and Y Your answer [1]
2. June 2025 · AS Paper 1 · Q15 · 1 marks ·
15 A compound is shown below. What is the systematic name of this compound? F CH3 C C CH3CH2 H A E-3-fluoropent-2-ene B E-3-fluoropent-3-ene C Z-3-fluoropent-2-ene D Z-2-fluoropent-3-ene Your answer [1]
3. 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]
4. June 2025 · AS Paper 1 · Q24(a)(i) · 1 marks ·
24 This question is about alkenes. (a) 2-Chloropropene can form an addition polymer. (i) Draw two repeat units of the polymer formed by 2-chloropropene. [1]
5. June 2025 · AS Paper 1 · Q24(c)(i) · 5 marks ·
(c) Methylpropene, (CH3)2C=CH2, reacts with HCl to form a mixture of two products. Compound A is the major product. (i) Outline the mechanism for the formation of the major product, compound A. The structure of (CH3)2C=CH2 has been provided. Include curly arrows and relevant dipoles, the structure of compound A and the name of the mechanism. H3C H C C H3C H Compound A Name of mechanism ........................................................................................................................ [5]
6. 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]
7. June 2025 · Paper 2 · Q1 · 1 marks ·
1 Which compound is alicyclic and unsaturated? A B C D Your answer [1]
8. June 2025 · Paper 2 · Q3 · 1 marks ·
3 The skeletal structure of a medicinal drug is shown below. How many hydrogen atoms are in its molecular formula? H N Cl Cl A 14 B 15 C 17 D 19 Your answer [1]
9. June 2025 · AS Paper 2 · Q4(b)(iv) · 1 marks ·
(iv) Use the data in Table 4.1 to estimate a value for the enthalpy change of combustion of butane. Give your answer to 2 significant figures. Estimated enthalpy change of combustion of butane .............................................kJ mol–1 [1]
10. June 2025 · AS Paper 2 · Q4(c) · 2 marks ·
(c) Besides pentane, there are two other structural isomers of C5H12. Draw the skeletal formulae of these two other structural isomers and state the systematic name of each. Isomer 1 Isomer 2 Skeletal formula Systematic name [2]
11. June 2025 · AS Paper 2 · Q4(d)(ii) · 1 marks ·
(ii) The first step in the mechanism of the reaction is the homolytic fission of a Br–Br bond. Explain what is meant by homolytic fission. .......................................................................................................................................................... ..................................................................................................................................................... [1]
12. June 2025 · AS Paper 2 · Q4(d)(iii) · 2 marks ·
(iii) Complete the equations for the propagation steps in the mechanism. Use molecular formulae for organic species and dots (•) for unpaired electrons on radicals. C3H8 + Br• ............................ + ............................ ............................ + ............................ C3H7Br + ............................ [2]
13. June 2025 · Paper 2 · Q16(a) · 1 marks ·
16 This question is about hydrocarbons with six carbon atoms. (a) Compound A is a hydrocarbon: Compound A What is the systematic name of compound A? ..................................................................................................................................................... [1]
14. June 2025 · Paper 2 · Q16(b) · 3 marks ·
(b) The table below shows incomplete information about two hydrocarbons. Complete the table. Skeletal formula Molecular formula Number of σ bonds Number of π bonds [3]
15. June 2025 · Paper 2 · Q19(a)(i) · 3 marks ·
19 This question is about reactions of haloalkanes. (a) Haloalkanes can react with potassium cyanide to form new carbon–carbon bonds. (i) Outline the mechanism for the reaction of 2-bromopropane with cyanide ions. Show curly arrows, relevant dipoles and products. Br [3]
16. June 2025 · Paper 2 · Q21(a) · 1 marks ·
21 This question is about carbonyl compounds. The three compounds below each contain a ketone and one other functional group. O O O O O OH OH Pyruvic acid Methylglyoxal Acetol (a) What is a functional group? .......................................................................................................................................................... ..................................................................................................................................................... [1]
17. 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]
18. June 2025 · Paper 3 · Q2(a)(i) · 1 marks ·
2 This question is about different compounds that each contain O and H atoms covalently bonded together. (a) The alcohol 2,3‑dimethylhexan‑1‑ol has the molecular formula C8H18O. (i) Draw the skeletal formula of 2,3‑dimethylhexan‑1‑ol. [1]
19. June 2025 · Paper 3 · Q5(a)(i) · 1 marks ·
5 This question is about two metal hydrides, lithium aluminium hydride, LiAl H4, and sodium borohydride, NaBH4. Both hydrides are used as reducing agents in organic chemistry. (a) LiAl H4, is a stronger reducing agent than NaBH4, and can reduce esters to alcohols. A student plans to use LiAl H4 to reduce the liquid ester, ethyl phenylmethanoate, C6H5COOC2H5 (density = 1.05 g cm–3) to the alcohol, C6H5CH2OH (Mr = 108). The student uses C6H5COOC2H5 and LiAl H4 (an excess) in a 1.0 : 2.5 molar ratio. The student’s method is outlined below. Step 1 7.50 cm3 of C6H5COOC2H5 is dissolved in an organic solvent. Step 2 LiAl H4 is added to the solution from Step 1. The reduction takes place. Step 3 The mixture from Step 2 is heated with dilute aqueous acid. Step 4 The impure C6H5CH2OH is purified. The student carries out this preparation and obtains 4.40 g of pure C6H5CH2OH. (i) What is the systematic name of the alcohol C6H5CH2OH? ..................................................................................................................................................... [1]
20. June 2025 · Paper 3 · Q5(a)(iv) · 4 marks ·
(iv) The mechanism for Step 2 in the reduction of C6H5COOC2H5 is shown below. In the mechanism, LiAl H4 can be represented as H–. Complete the mechanism by adding curly arrows to the three boxes. _ O O C6H5 C C6H5 C OC2H5 OC2H5 H– H O _ C6H5 C + OC2H5 H H– _ O _ C6H5 C H + OC2H5 H [4]
21. June 2024 · AS Paper 1 · Q14 · 1 marks ·
14 What is the name of the compound below? Cl OH A 1‑chloro‑1,2‑dimethylpropan‑3‑ol B 2‑chloro‑3‑methylbutan‑4‑ol C 3‑chloro‑2‑methylbutan‑1‑ol D 3‑chloro‑2,3‑dimethylpropan‑1‑ol Your answer [1]
22. June 2024 · AS Paper 1 · Q15 · 1 marks ·
15 The structure of a hydrocarbon is shown below. Which terms describe this hydrocarbon? A Alicyclic and saturated B Aliphatic and alicyclic C Aliphatic and aromatic D Aromatic and unsaturated Your answer [1]
23. June 2024 · AS Paper 1 · Q24(b) · 5 marks ·
(b) The hydrocarbon C2H6 reacts with bromine, Br2, to form C2H5Br under suitable conditions. Complete the table below to show the mechanism for the three stages of the reaction of C2H6 with Br2 to form C2H5Br. The equation for one of the possible reactions for termination has been completed. In your equations, use molecular formulae and ‘dots’ (•) with any radicals. Initiation Conditions ......................................................................................................... Equation ................................................... ................................................... Propagation 1 ......................................................... ......................................................... 2 ......................................................... ......................................................... Termination 1 Br• + Br• Br2 2 ......................................................... ......................................................... 3 ......................................................... ......................................................... [5]
24. 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]
25. June 2024 · AS Paper 1 · Q25(d)(i) · 2 marks ·
(d) Alcohols can be prepared by the hydrolysis of haloalkanes with aqueous alkali. (i) Write an equation for the hydrolysis of 2‑bromo‑2‑methylpropane. Show organic compounds as structures. [2]
26. June 2024 · AS Paper 2 · Q5(b)(i) · 4 marks ·
(b) HBr reacts readily with alkenes. (i) Outline the mechanism for the reaction of but-1-ene with HBr to form 2-bromobutane. Include curly arrows, relevant dipoles and the structure of the product. H CH2CH3 C C H H [4]
27. June 2024 · Paper 2 · Q16(a) · 1 marks ·
16 This question is about hydrocarbons. The structures of hydrocarbons A–E are shown below. A B C D E (a) Which hydrocarbons are unsaturated? ..................................................................................................................................................... [1]
28. June 2024 · Paper 2 · Q16(b) · 1 marks ·
(b) Which hydrocarbons are alicyclic? ..................................................................................................................................................... [1]
29. June 2024 · Paper 2 · Q16(c) · 1 marks ·
(c) Which hydrocarbons have the general formula CnH2n? ..................................................................................................................................................... [1]
30. June 2024 · Paper 2 · Q18(a)(i) · 3 marks ·
18 This question is about haloalkanes. (a) Haloalkanes can be synthesised by reacting alkanes with halogens in the presence of ultraviolet radiation. An alkane reacts with bromine to form 2-bromo-2-methylpropane. (i) Write the equation for this reaction, showing the structures of the organic compounds. Name the reaction mechanism and the type of bond fission that occurs. Equation Name of reaction mechanism .......................................................................................................... Type of bond fission ......................................................................................................................... [3]
31. June 2024 · Paper 2 · Q19 · 6 marks ·
19* Alkenes and carbonyl compounds take part in addition reactions. Describe one addition reaction of an alkene and one addition reaction of a carbonyl compound. Include reagents and reaction mechanisms. [6] .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... Extra answer space if required. .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... ..........................................................................................................................................................
32. June 2024 · Paper 2 · Q20(b)(i) · 1 marks ·
(b) Ester F has the structure shown below. O O Ester F (i) What is the systematic name for this ester? ..................................................................................................................................................... [1]
33. June 2024 · Paper 2 · Q21(a)(ii) · 5 marks ·
(ii) Outline the mechanism for this reaction, including the role of Al Cl 3 as a halogen carrier. [5]
34. June 2024 · Paper 3 · Q2(c)(i) · 1 marks ·
(c) Compound B, shown below, is an antiviral medicine. HO OH O O N O HO N N O H compound B (i) What is the molecular formula of compound B? ..................................................................................................................................................... [1]
35. June 2024 · Paper 3 · Q5(b)(ii) · 6 marks ·
(ii)* The student is provided with further information about compounds F–I. • They all have the molecular formula C5H10O. • One of the compounds is alicyclic. • The other compounds are unbranched. Use this further information and the student’s observations in Table 5.1 to answer the following. • How do the observations provide evidence for the possible functional groups in compounds F–I? • Suggest a possible structure for each of the compounds F–I. Show your reasoning. [6] .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... Extra answer space if required. .......................................................................................................................................................... .......................................................................................................................................................... .......................................................................................................................................................... ..........................................................................................................................................................
36. June 2023 · AS Paper 1 · Q15 · 1 marks · AO1
15 Which formula does not represent 3-methylbut-1-ene? A CH3CHCH3CHCH2 B CH2CHCH(CH3)2 C D Your answer [1]
37. June 2023 · AS Paper 1 · Q16 · 1 marks · AO2
16 How many structural isomers have the molecular formula C4H9Cl ? A 2 B 3 C 4 D 5 Your answer [1]
38. June 2023 · AS Paper 1 · Q25(b) · 2 marks · AO3
(b) Butane reacts with bromine by radical substitution to form a mixture of organic products. The reaction needs UV radiation for the initiation stage. Write equations for the propagation stage that follows to form 2-bromobutane. Use skeletal formulae and ‘dots’ (•) to show the position of any radicals. Propagation [2]
39. 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]
40. June 2023 · Paper 2 · Q3 · 1 marks · AO2
3 Propyne, CH3C≡CH, is a member of the alkynes homologous series with the C≡C functional group. What is the general formula of the alkynes? A CnH2n–4 B CnH2n–2 C CnH2n D CnH2n+2 Your answer [1]
41. June 2023 · AS Paper 2 · Q3(c) · 3 marks · AO1, 2
(c) A student is studying the hydrolysis of haloalkanes. The equation for the alkaline hydrolysis of 2-bromopropane, CH3CHBrCH3, is shown below. CH3CHBrCH3 + OH– CH3CHOHCH3 + Br – Use the curly arrow model to outline the mechanism for the alkaline hydrolysis of 2-bromopropane. Show relevant dipoles and lone pairs, and name the mechanism. name of mechanism .......................................................... [3]
42. June 2023 · Paper 2 · Q5 · 1 marks · AO1
5 Oxymetazoline, shown below, is used as a decongestant in the treatment of colds. HO N HN Oxymetazoline How many H atoms are in one molecule of oxymetazoline? A 23 B 24 C 25 D 26 Your answer [1]
43. June 2023 · AS Paper 2 · Q5(a)(i) · 1 marks · AO2
5 This question is about alkenes. (a) A mixture of alkenes is produced when water is eliminated from alcohol A. OH Alcohol A (i) What is the systematic name of alcohol A? ...................................................................................................................................... [1]
44. 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]
45. June 2023 · Paper 2 · Q7 · 1 marks · AO1
7 What is the systematic name for the compound below? A 3,5-dimethylocta-1,3,6-triene B 3,5-dimethylocta-2,5,7-triene C 4,6-dimethylocta-1,3,6-triene D 4,6-dimethylocta-2,5,7-triene Your answer [1]
46. June 2023 · Paper 2 · Q13 · 1 marks · AO1
13 Which compound(s) is/are aliphatic? 1 2 3 A 1, 2 and 3 B Only 1 and 2 C Only 2 and 3 D Only 1 Your answer [1]
47. June 2023 · Paper 2 · Q16(b)(i) · 6 marks · AO1, 2, 3
(b) 2-methylpentane reacts with bromine by radical substitution. 2-methylpentane A mixture of organic products is formed, including 3-bromo-2-methylpentane, and compounds A and B. (i) Complete the table below to show the mechanism for the formation of 3-bromo-2-methylpentane and three possible equations for termination. In your equations, use structural or skeletal formulae and ‘dots’ (•) for the position of radicals. Equation: ............................................................................................ Initiation Conditions: ......................................................................................... Propagation Termination [6]
48. 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]
49. 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]
50. June 2023 · Paper 2 · Q17(d) · 5 marks · AO2, 3
(d) There are 4 structural isomers of C4H10O that are alcohols. A student predicts that these structural isomers could be distinguished using carbon-13 NMR spectroscopy. Explain whether the student is correct. In your answer, show how the peaks in the carbon-13 NMR spectra are linked to the structure of each alcohol isomer. ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... .............................................................................................................................................. [5]
51. June 2023 · Paper 2 · Q21(b)(i) · 1 marks · AO1
(b) The α-amino acid valine has the R group of –CH(CH3)2. (i) What is the systematic name of valine? ...................................................................................................................................... [1]
52. June 2023 · Paper 2 · Q22(a)(i) · 4 marks · AO1, 2
22 This question is about reactions of acrolein, H2C=CHCHO. (a) Acrolein reacts with sodium cyanide in acidic conditions, NaCN(aq) / H+(aq). (i) Outline the reaction mechanism for this reaction, showing the intermediate and the organic product. The structure of acrolein has been provided. Include curly arrows and relevant dipoles. H H C C H C O H [4]
53. June 2023 · Paper 3 · Q2(c) · 4 marks · AO3
(c) The benzenediazonium ion, shown below, is stable at temperatures below 10 °C. + N N Benzenediazonium Above 10 °C, the benzenediazonium ion reacts with water to form phenol. The reaction proceeds in a three-step mechanism. Step 1 Elimination of nitrogen gas to form a carbocation. Step 2 Nucleophilic attack by water. Step 3 Proton loss to form the organic product. Complete the boxes below with intermediates and curly arrows to show the mechanism for this reaction. + Step 1 N N + ............ Step 2 Step 3 OH + H+ [4]
54. June 2022 · AS Paper 1 · Q15 · 1 marks · AO1
15 What is the number of hydrogen atoms in one molecule of the compound below? O OH A 8 B 10 C 12 D 14 Your answer [1]
55. June 2022 · AS Paper 1 · Q21(a)(i) · 1 marks · AO1
SECTION B Answer all the questions. 21 The alkene, (CH3)3CCH=CH2, is used to make some perfumes. (a) (i) What is the systematic name for (CH3)3CCH=CH2? ...................................................................................................................................... [1]
56. June 2022 · AS Paper 1 · Q21(a)(ii) · 5 marks · AO1, 2
(ii) (CH3)3CCH=CH2 decolourises bromine. Outline the reaction mechanism for the reaction of (CH3)3CCH=CH2 and bromine. The structure of (CH3)3CCH=CH2 has been provided. Include curly arrows and relevant dipoles, the structure of the product and the name of the mechanism. (CH3)3C H C C H H name of mechanism ...................................................................................................... [5]
57. June 2022 · AS Paper 1 · Q26(a) · 3 marks · AO1, 2
26 This question is about haloalkanes. (a) 1-Chloropropane, C2H5CH2Cl , can be hydrolysed with aqueous sodium hydroxide, NaOH. Outline the mechanism for this reaction. The structure of 1-chloropropane has been provided. Show curly arrows, relevant dipoles and product(s). H C2H5 C Cl H [3]
58. June 2022 · AS Paper 2 · Q5(a)(ii) · 2 marks · AO2
(ii) Write two equations for the propagation steps in the mechanism for Reaction 5.1. Use structural formulae for organic species and dots (•) for unpaired electrons on radicals. CH3CH2CH2CH3 + ................ ............................................... + ................ .............................................. + ................ ............................................... + ................ [2]
59. June 2022 · Paper 2 · Q16(a)(i) · 1 marks · AO1
SECTION B 16 This question is about unsaturated hydrocarbons. (a) The unsaturated hydrocarbon A, shown below, is reacted with bromine. H3C CH3 C C CH3CH2CH2 H Hydrocarbon A (i) What is the systematic name of hydrocarbon A? ...................................................................................................................................... [1]
60. June 2022 · Paper 2 · Q16(a)(ii) · 3 marks · AO1, 2
(ii) Outline the mechanism for the reaction of hydrocarbon A with bromine. The structure of hydrocarbon A has been provided. Include curly arrows and relevant dipoles. H3C CH3 C C CH3CH2CH2 H [3]
61. June 2022 · Paper 2 · Q16(b)(i) · 1 marks · AO1
(b) Compounds B and C are branched hydrocarbons that are structural isomers of C6H12. Compounds B and C both have stereoisomers. • Compound B has cis and trans isomers but does not have optical isomers. • Compound C has optical isomers but does not have cis and trans isomers. (i) What is meant by the term structural isomers? ........................................................................................................................................... ........................................................................................................................................... ...................................................................................................................................... [1]
62. June 2022 · Paper 2 · Q16(b)(iii) · 2 marks · AO1, 2
(iii) Draw structures for the cis and trans isomers of the branched hydrocarbon B. cis isomer trans isomer [2]
63. June 2022 · Paper 2 · Q16(b)(iv) · 2 marks · AO2
(iv) Draw 3D structures for the optical isomers of compound C. Optical isomers [2]
64. June 2022 · Paper 2 · Q16(c)(ii) · 1 marks · AO3
(ii) The mechanism for ozonolysis takes place in several steps. The curly arrows in the first step in the ozonolysis of methylbut-2-ene are shown below. In the box, draw the structure(s) for the product(s) of this step. + O O O.. – H3C H C C H3C CH3 [1]
65. June 2022 · Paper 2 · Q19(c)(i) · 2 marks · AO1, 2
(c) This part is about polymers derived from carboxylic acid monomers. (i) Poly(pent-3-enoic acid) is an addition polymer. Draw the structure of pent-3-enoic acid and two repeat units of this polymer. Pent-3-enoic acid Two repeat units of poly(pent-3-enoic acid) [2]
66. 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]
67. June 2022 · Paper 3 · Q6(c)(i) · 2 marks · AO3
(c) Vitamin C, C6H8O6, is a weak acid (Ka = 7.94 x 10–5 (mol dm–3)), which is often referred to as ascorbic acid. (i) In aqueous solution, vitamin C donates a proton to water: C6H8O6 + H2O C6H7O6 – + H3O+ Add curly arrows to the diagram to suggest the mechanism for this process. H2O: O O H O O H H H H + H3O+ O O – O O O O O O H H [2]
68. November 2021 · AS Paper 1 · Q13 · 1 marks · AO2
13 What is the number of unsaturated isomers (structural and stereoisomers) that have the molecular formula C4H8? A 3 B 4 C 5 D 6 Your answer [1]
69. November 2021 · AS Paper 1 · Q14 · 1 marks · AO1
14 What do curly arrows always show in reaction mechanisms? A Movement of one electron. B Movement of a pair of electrons. C Movement of a lone pair of electrons. D Movement of the electrons in a covalent bond. Your answer [1]
70. November 2021 · AS Paper 1 · Q17 · 1 marks · AO1
17 What is the systematic name of the compound below? OH A 3-methylhex-5-en-4-ol B 4-methylhex-1-en-3-ol C 2-ethylpent-4-en-3-ol D 4-ethylpent-1-en-3-ol Your answer [1]
71. November 2021 · AS Paper 1 · Q18 · 1 marks · AO2
18 The ‘dienes’ are a homologous series of non-cyclic compounds with two double bonds. The simplest diene is shown below. What is the general formula of the dienes homologous series? A CnH2n+2 B CnH2n C CnH2n–2 D CnH2n–4 Your answer [1]
72. November 2021 · AS Paper 1 · Q21(d)(i) · 1 marks · AO2
(d) Halothane, C2HBrCl F3, (Mr = 197.4) is used as a general anaesthetic in medicine. (i) The systematic name for halothane is 2-bromo-2-chloro-1,1,1-trifluoroethane. Draw the structure of a halothane molecule. [1]
73. November 2021 · AS Paper 1 · Q24(a) · 4 marks · AO1, 2
24 A student reacts methylpropene with hydrogen bromide, HBr, as shown in Reaction 1. CH3 H H3C H Reaction 1 C C + HBr H3C C C H H3C H Br H Methylpropene Compound A (a) Outline the reaction mechanism for Reaction 1. The structures of methylpropene and compound A have been provided. Include curly arrows and relevant dipoles. CH3 H H3C H C C H3C C C H H3C H Br H name of mechanism ............................................................................................................ [4]
74. November 2021 · AS Paper 1 · Q24(b)(i) · 1 marks · AO1
(b) When reacting methylpropene with HBr, a small amount of compound B also forms. Compound B is a structural isomer of compound A. (i) Explain the term structural isomer. ........................................................................................................................................... ........................................................................................................................................... ...................................................................................................................................... [1]
75. November 2021 · AS Paper 1 · Q24(b)(ii) · 1 marks · AO2
(ii) Show the structure for compound B. [1]
76. November 2021 · AS Paper 1 · Q26 · 5 marks · AO3
26 An organic compound E contains C, H and O only. The mass and infrared spectra of organic compound E are shown below. Mass spectrum 100 80 60 relative intensity 40 20 0 10 20 30 40 50 60 70 80 90 m / z Infrared spectrum 100 transmittance (%) 50 0 4000 3000 2000 1500 1000 500 wavenumber / cm–1 Analyse this information to suggest two different possible structures for compound E. Explain your reasoning. ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... Structures [5]
77. November 2021 · Paper 2 · Q1 · 1 marks ·
1 2-Methylbutane is reacted with chlorine by radical substitution. What is the number of structural isomers with the molecular formula C5H11Cl that could be formed? A 2 B 3 C 4 D 5 Your answer [1]
78. November 2021 · AS Paper 2 · Q2(a) · 1 marks · AO1
2 Alkane A, shown below, reacts with bromine in a radical substitution reaction. CH3 H3C C H CH3 Alkane A (a) What is meant by a radical? .............................................................................................................................................. [1]
79. November 2021 · AS Paper 2 · Q2(b) · 1 marks · AO1
(b) Name the type of bond breaking that occurs in a radical substitution reaction. .............................................................................................................................................. [1]
80. 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]
81. 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]
82. 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]
83. November 2021 · Paper 2 · Q16(b)(i) · 4 marks · AO1, 2
(b) But-1-ene is reacted with hydrogen bromide, forming a mixture of two saturated organic products. One of the organic products is formed in a much greater quantity than the other organic product. (i) Outline the reaction mechanism for the formation of this major organic product. The structure of but-1-ene has been provided. Include curly arrows and relevant dipoles. H CH2CH3 C C H H [4]
84. November 2021 · Paper 2 · Q16(b)(iii) · 1 marks · AO1
(iii) Buta-1,3-diene is reacted with an excess of hydrogen bromide, forming a mixture of saturated organic products. How many saturated organic products could be present in this mixture? ...................................................................................................................................... [1]
85. November 2021 · Paper 2 · Q16(d)(i) · 2 marks · AO2
(d) ‘Diels-Alder’ reactions are used in the synthesis of many important organic compounds. The Diels-Alder reaction of buta-1,3-diene with ethene is shown below. + (i) Add curly arrows to the diagram below to complete the mechanism for this Diels-Alder reaction. [2]
86. November 2021 · Paper 2 · Q17(c) · 4 marks · AO1, 2
(c) A polymer can be made from the monomers: • 1,4-diaminobutane • benzene-1,4-diacyl dichloride. Draw the structures of these monomers and one repeat unit of the polymer. 1,4-diaminobutane benzene-1,4-diacyl dichloride one repeat unit of polymer [4]
87. November 2021 · Paper 2 · Q18(c)(i) · 1 marks · AO2
(c) Ibuprofen, shown below, is used as a painkiller. O OH ibuprofen (i) What is the molecular formula of ibuprofen? ...................................................................................................................................... [1]
88. November 2021 · Paper 2 · Q19(a)(i) · 1 marks · AO1
19 This question is about organic synthesis. (a) Prenal, shown below, is used in the synthesis of some pharmaceuticals. O prenal (i) What is the systematic name for prenal? ...................................................................................................................................... [1]
89. November 2021 · Paper 2 · Q20(a)(i) · 6 marks · AO1, 2
20 This question is about reactions of phenol. (a) Salicylic acid can be prepared from phenol as shown below. OH O– O– OH Stage 1 Stage 2 Stage 3 NaOH CO2 HCl COO– COOH phenol salicylic acid (i) Complete the mechanism below for Stage 1 and Stage 2. Show curly arrows, the structure of the intermediate and the missing formulae on the dotted lines. Stage 1 O O– H + ................... – OH Stage 2 O– O C O intermediate O– + ................... COO– [6]
90. November 2021 · Paper 3 · Q1(f) · 3 marks · AO1, 2
(f) The ester, methyl ethanoate, can be synthesised by reacting a haloalkane with a carboxylate ion. The mechanism is nucleophilic substitution. Outline the mechanism for this reaction. [3]
91. November 2021 · Paper 3 · Q3(b) · 7 marks · AO2, 3
(b) The student prepares a 100.0 cm3 solution containing 3.215 g of acid D. The student titrates 25.0 cm3 samples of the solution of D with 0.150 mol dm–3 Ba(OH)2(aq) in the burette. 1 mol Ba(OH)2 reacts with 2 mol of D. The mean titre of Ba(OH)2(aq) is 23.50 cm3. Analyse the titration results to determine two possible structures for the cis stereoisomer of organic acid D. Structures of 2 possible cis stereoisomers of acid D [7]
92. November 2021 · Paper 3 · Q5(b)(iii) · 3 marks · AO2, 3
(iii) In the Schmidt reaction, hydrazoic acid, HN3, reacts with carboxylic acids to form primary amines. For example, HN3 reacts with RCOOH to form RNH2 and two gases that are found in the atmosphere. Write the equation for the reaction of HN3 with 2-methylbutanoic acid. Show structures for organic compounds. [3]
93. November 2020 · AS Paper 1 · Q14 · 1 marks · AO1
14 Which statement is correct for the two structures below? A They have the same empirical formula. B They have different relative molecular masses. C They are structural isomers. D They have different functional groups. Your answer [1]
94. November 2020 · AS Paper 1 · Q25(b) · 4 marks · AO1, 2
(b) Propene also reacts with bromine. Outline the mechanism for the reaction of propene with bromine, Br2. The structure of propene has been provided. Show curly arrows, relevant dipoles and product(s). H CH3 C C H H [4]
95. November 2020 · AS Paper 1 · Q25(c)(i) · 2 marks · AO1
(c) The ‘alkynes’ is a homologous series of hydrocarbons. The table shows three alkynes. Alkyne Structural formula Molecular formula ethyne HC≡CH C2H2 propyne CH3C≡CH C3H4 but-1-yne CH3CH2C≡CH C4H6 (i) Explain what is meant by the term: homologous series. ........................................................................................................................................... ........................................................................................................................................... ...................................................................................................................................... [2]
96. November 2020 · AS Paper 1 · Q25(c)(ii) · 1 marks · AO3
(ii) Suggest the general formula of the alkynes. ...................................................................................................................................... [1]
97. November 2020 · AS Paper 1 · Q25(c)(iii) · 2 marks · AO2
(iii) Propyne reacts with bromine to form a saturated compound. Write an equation for the reaction, showing the structure of the organic product. [2]
98. November 2020 · AS Paper 1 · Q25(c)(iv) · 2 marks · AO3
(iv) But-1-yne is a structural isomer of C4H6. Draw the structures of 2 other structural isomers of C4H6. [2]
99. November 2020 · AS Paper 1 · Q25(c)(v) · 1 marks · AO2
(v) Draw the structure of 2,5-dimethylhept-3-yne. [1]
100. November 2020 · Paper 2 · Q1 · 1 marks · AO1
1 What is the name of the compound below? H3C CH2CH3 C C H Br A E-3-bromopent-2-ene B E-3-bromopent-3-ene C Z-3-bromopent-2-ene D Z-3-bromopent-3-ene Your answer [1]
101. November 2020 · AS Paper 2 · Q5(c) · 1 marks · AO1
(c) What is the systematic name of alcohol B? .............................................................................................................................................. [1]
102. November 2020 · AS Paper 2 · Q5(d)(ii) · 3 marks · AO1, 2
(ii) Outline the mechanism for the alkaline hydrolysis of (CH3)2CHCH2CH2Br. The structure of (CH3)2CHCH2CH2Br has been provided. Show curly arrows, relevant lone pairs and dipoles, and the products. H (CH3)2CHCH2 C Br H [3]
103. November 2020 · Paper 2 · Q9 · 1 marks · AO1
9 What is the structural formula of ethyl 3-methylbutanoate? A CH3CH2COOCH2CH2CH(CH3)2 B CH3CH2COOCH(CH3)CH2CH3 C CH3CH2CH(CH3)COOCH2CH3 D (CH3)2CHCH2COOCH2CH3 Your answer [1]
104. November 2020 · Paper 2 · Q10 · 1 marks · AO2
10 What is the number of alicyclic structural isomers of C5H10? A 3 B 4 C 5 D 6 Your answer [1]
105. November 2020 · Paper 2 · Q12 · 1 marks · AO2
12 What is the molecular formula of the steroid molecule below? OH HO A C18H24O2 B C18H26O2 C C18H28O2 D C18H30O2 Your answer [1]
106. November 2020 · Paper 2 · Q16(a) · 1 marks · AO1
SECTION B Answer all the questions. 16 The structure of hydrocarbon A is shown below. A (a) Hydrocarbon A can be reacted with bromine in the presence of ultraviolet radiation to prepare (CH3)3CCHBrCH3. What is the systematic name for (CH3)3CCHBrCH3? .............................................................................................................................................. [1]
107. November 2020 · Paper 2 · Q16(c) · 3 marks · AO1, 2
(c) Complete the table to show the mechanism for the reaction of hydrocarbon A with Br2 to form (CH3)3CCHBrCH3. Use skeletal formulae for all organic compounds. Use ‘dots’ (●) to show the position of unpaired electrons. Initiation ...................................................................................................................................... Propagation + .............................. .............................. + .............................. .............................. + .............................. .............................. + .............................. [3]
108. November 2020 · Paper 2 · Q19(a)(i) · 2 marks · AO1
19 The carbonyl compounds, F and G, shown below, contribute to the flavour of coffee. O CH3 H CH C H3C C O H2 F G (a) Compound F is a member of a homologous series. (i) Explain the term homologous series. ........................................................................................................................................... ........................................................................................................................................... ........................................................................................................................................... ...................................................................................................................................... [2]
109. November 2020 · Paper 2 · Q19(a)(ii) · 1 marks · AO2
(ii) Predict the molecular formula for the member of this homologous series containing 24 carbon atoms. ...................................................................................................................................... [1]
110. November 2020 · Paper 2 · Q19(c)(i) · 5 marks · AO1, 2
(c) Compound F reacts with HCN using NaCN(aq) and H+(aq). (i) Outline the mechanism for the reaction of F with NaCN(aq) and H+(aq) and state the name of the mechanism. The structure of F has been provided. Include relevant dipoles, lone pairs and the structure of the organic product. CH3 H CH C H3C C O H2 Name of mechanism: ................................................................................................... [5]
111. November 2020 · Paper 2 · Q19(c)(ii) · 2 marks · AO1
(ii) Explain why the mechanism in (c)(i) involves heterolytic fission. ........................................................................................................................................... ........................................................................................................................................... ........................................................................................................................................... ...................................................................................................................................... [2]
112. November 2020 · Paper 3 · Q6(c) · 4 marks · AO3
(c) Carboxylic acids and sulfonic acids both form esters. Sulfonic acid esters can be hydrolysed by aqueous alkali. The equation shows the alkaline hydrolysis of a sulfonic acid ester. CH3SO2OCH3 + OH− → CH3SO2O− + CH3OH In the 3 boxes below, add curly arrows to show the mechanism for this reaction. In the first box, the hydroxide ion acts as a nucleophile. O O – H3C S OCH3 H3C S OCH3 O O OH – OH O H H3C S O – OCH3 O O H3C S O – + HOCH3 O [4]
113. June 2019 · AS Paper 1 · Q15 · 1 marks · AO1
15 Which compound is unsaturated, alicyclic and contains an alkyl group? A B C D Your answer [1]
114. June 2019 · AS Paper 1 · Q25(a)(ii) · 1 marks · AO1
(ii) Write the systematic name for alcohol C. ...................................................................................................................................... [1]
115. June 2019 · AS Paper 1 · Q25(b)(i) · 3 marks · AO1, 2
(b) Under suitable conditions, butane, C4H10, reacts with chlorine by radical substitution. A mixture of organic compounds is formed, including C4H9Cl , and compounds D and E. (i) Complete the table below to show the mechanism for the initiation and propagation stages of the reaction of C4H10 with chlorine to form C4H9Cl . In your equations, use molecular formulae and ‘dots’ (•) with any radicals. Equation .................................................................................................... Initiation Conditions .................................................................................................. ..................................................... → ..................................................... Propagation ..................................................... → ..................................................... [3]
116. June 2019 · Paper 2 · Q3 · 1 marks · AO1
3 What is the name of the compound below? H CH3 C C H3C CH2 CH2 CH2 CH3 A 3-Propylpent-2-ene B 3-Propylpent-3-ene C 3-Ethylhex-2-ene D 4-Ethylhex-4-ene Your answer [1]
117. June 2019 · AS Paper 2 · Q3(a)(i) · 3 marks · AO2
3 This question is about 1-iodopentane, CH3CH2CH2CH2CH2I. (a) 1-Iodopentane can be hydrolysed by aqueous sodium hydroxide. (i) Outline the mechanism for this reaction. Include curly arrows, relevant dipoles and the final product(s). H CH3CH2CH2CH2 C I H [3]
118. June 2019 · AS Paper 2 · Q3(c)(i) · 1 marks · AO1
(c) 2-Iodo-2-methylbutane is an isomer of 1-iodopentane. (i) Draw the structure of 2-iodo-2-methylbutane. [1]
119. 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]
120. June 2019 · Paper 2 · Q16(a)(i) · 4 marks · AO1, 2
SECTION B Answer all the questions. 16 This question is about unsaturated aldehydes and alcohols. (a) 3-Methylbut-2-enal, shown below, is used as a food flavouring. H3C CHO C C H3C H 3-methylbut-2-enal 3-Methylbut-2-enal is reacted with hydrogen bromide, forming a mixture of two organic products. One of the organic products forms in a much greater quantity than the other organic product. (i) Outline the reaction mechanism for the formation of one of the organic products. Include curly arrows and relevant dipoles. [4]
121. June 2019 · Paper 2 · Q16(b)(ii) · 1 marks · AO1
(ii) What is the molecular formula of geraniol? ...................................................................................................................................... [1]
122. June 2019 · Paper 2 · Q16(b)(iii) · 1 marks · AO1
(iii) Explain why geraniol and citronellal are structural isomers of each other. ........................................................................................................................................... ........................................................................................................................................... ...................................................................................................................................... [1]
123. June 2019 · Paper 2 · Q18(a)(i) · 1 marks · AO1
18 This question is about esters. (a) The structure of ester A is shown below. O Br O Ester A (i) What is the systematic name of ester A? ...................................................................................................................................... [1]
124. June 2019 · Paper 2 · Q18(c) · 1 marks · AO3
(c) Compound B is a structural isomer of ester A. • Compound B reacts with aqueous sodium carbonate. • The 13C NMR spectrum of B has 4 peaks. Draw a possible structure for compound B. [1]
125. June 2019 · Paper 2 · Q19(b)(iii) · 5 marks · AO1, 2, 3
(iii) In the synthesis of compounds D and E, benzene is first reacted with ethanoyl chloride, CH3COCl, to form phenylethanone, shown below. H3C O C phenylethanone The reaction takes place in the presence of aluminium chloride, Al Cl 3, which acts as a catalyst. In the mechanism for this reaction, • ethanoyl chloride first reacts with aluminium chloride to form the CH3–C+=O cation • the CH3–C+=O cation then behaves as an electrophile. Complete the mechanism for the reaction. Include equations to show the role of the Al Cl 3 catalyst, relevant curly arrows and the structure of the intermediate. Formation of electrophile ................................................................................................... + H3C C O Intermediate H3C O C + H+ Regeneration of catalyst ................................................................................................... [5]
126. June 2019 · Paper 2 · Q20(a)(i) · 1 marks · AO1
20 This question is about reaction mechanisms. (a) Chemists use curly arrows in reaction mechanisms. (i) What does a curly arrow show in a reaction mechanism? ........................................................................................................................................... ...................................................................................................................................... [1]
127. June 2019 · Paper 2 · Q20(a)(ii) · 2 marks · AO3
(ii) Draw structures to show the products in the reaction mechanism below. H H + O [2]
128. June 2019 · Paper 2 · Q20(a)(iii) · 2 marks · AO1
(iii) Use the mechanism in (ii) to explain what is meant by heterolytic fission. ........................................................................................................................................... ........................................................................................................................................... ...................................................................................................................................... [2]
129. June 2019 · Paper 2 · Q20(b)(i) · 4 marks · AO3
(b) An incomplete reaction mechanism is shown below. (i) Complete the mechanism by adding curly arrows and any missing species. – O O H3C C H3C C Cl Cl OH – OH O H3C C + ………… OH [4]
130. 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]
131. June 2018 · AS Paper 1 · Q17 · 1 marks ·
17 The structure of naphthalene is shown below. What is the molecular formula of naphthalene? A C10H8 B C10H10 C C12H10 D C12H12 Your answer [1]
132. June 2018 · AS Paper 1 · Q18 · 1 marks ·
18 A student reacts pent-2-ene with bromine in the laboratory. Which compound is formed? A 1,1-dibromopentane B 1,2-dibromopentane C 2,2-dibromopentane D 2,3-dibromopentane Your answer [1]
133. June 2018 · AS Paper 1 · Q24(a) · 5 marks ·
24 This question is about saturated hydrocarbons. (a) Compounds A, B and C are saturated hydrocarbons. The structures and boiling points of A, B and C are shown below. Isomer Boiling point / °C A 36 B 28 C 9 • Use the structures to explain what is meant by the term structural isomer. • Explain the trend in boiling points shown by A, B and C in the table. ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... .............................................................................................................................................. [5]
134. June 2018 · AS Paper 1 · Q24(b)(ii) · 2 marks ·
(ii) Complete the table to show the number of structural isomers of C5H11Cl that could be formed from the reaction of chlorine with A and B. A B Number of structural isomers ...................... ...................... [2]
135. June 2018 · AS Paper 1 · Q25(a)(ii) · 1 marks ·
(ii) What is the systematic name of alcohol E? ...................................................................................................................................... [1]
136. June 2018 · AS Paper 1 · Q25(b)(i) · 3 marks ·
(b) An alcohol can be prepared by hydrolysing the haloalkane C2H5CHBrCH3 with aqueous sodium hydroxide. (i) Outline the mechanism for this reaction. Show curly arrows and relevant dipoles. [3]
137. June 2018 · AS Paper 2 · Q1(d)(ii) · 1 marks ·
(ii) A is an organic acid, containing C, H and O only. One molecule of A contains two COOH groups. Suggest the structure of A. [1]
138. June 2018 · Paper 2 · Q4 · 1 marks ·
4 Which structure represents an alicyclic compound? A B C D Your answer [1]
139. June 2018 · AS Paper 2 · Q6(b)(i) · 1 marks ·
(b) In reaction 2, compound C reacts with bromine to form compound D. (i) Give the systematic name of compound D. ...................................................................................................................................... [1]
140. June 2018 · AS Paper 2 · Q6(b)(ii) · 3 marks ·
(ii) Outline the mechanism for reaction 2. Include curly arrows, charges and relevant dipoles. [3]
141. June 2018 · AS Paper 2 · Q6(c)(i) · 2 marks ·
(c) Compound C forms an addition polymer E. (i) Write a balanced equation for this reaction. Show displayed formulae. [2]
142. June 2018 · Paper 2 · Q11 · 1 marks ·
11 How many straight-chain structural isomers of C7H15Cl contain a chiral carbon atom? A 1 B 2 C 3 D 4 Your answer [1]
143. June 2018 · Paper 2 · Q16(a)(i) · 1 marks ·
SECTION B Answer all the questions. 16 This question is about reactions of organic compounds containing carbon, hydrogen and oxygen. (a) A chemist investigates two reactions of alcohol A, shown below. OH alcohol A (i) What is the systematic name of alcohol A? ...................................................................................................................................... [1]
144. June 2018 · Paper 2 · Q16(a)(ii) · 1 marks ·
(ii) What is the structural formula of alcohol A? ...................................................................................................................................... [1]
145. 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]
146. June 2018 · Paper 2 · Q19(b) · 3 marks ·
(b) Chlorocyclohexane is hydrolysed with aqueous sodium hydroxide. Outline the mechanism for this reaction. Show curly arrows, relevant dipoles and the products. Cl [3]
147. June 2018 · Paper 2 · Q19(c)(ii) · 3 marks ·
(ii) Analyse the information to identify E, F and G. Show your working. [3]
148. June 2018 · Paper 2 · Q20(d) · 6 marks ·
(d)* Methylcinnamaldehyde reacts with iodine monochloride, ICl, by electrophilic addition. The reaction produces a mixture containing two different organic products. CHO methylcinnamaldehyde The electronegativity values of chlorine and iodine are given in the table below. Pauling electronegativity value Cl 3.0 I 2.5 Outline the mechanism, using the ‘curly arrow’ model, for the formation of one of the organic products and explain which of the two possible organic products is more likely to be formed. In your mechanism, you can show the phenyl group as C6H5. [6] ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... Additional answer space if required. ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ...................................................................................................................................................
149. June 2018 · Paper 2 · Q21(c)(ii) · 3 marks ·
(ii) A general structure for esters J, L and M is shown below. O C R O HO Where ‘R’ is an alkyl group. Use the mass spectrometry results to deduce possible structures for esters J, L and M. J L M [3]
150. June 2018 · Paper 2 · Q22(c)(i) · 5 marks ·
(c) Fuel additives are often used to improve the combustion of a fuel. (i) Compound N is a fuel additive containing carbon, hydrogen and oxygen only. Complete combustion of 1.71 g of compound N produces 2.97 g of CO2 and 1.62 g of H2O. The relative molecular mass of compound N is 76.0. Calculate the molecular formula of N and suggest a possible structure for the compound. compound N [5]
151. June 2018 · Paper 3 · Q4(a)(ii) · 2 marks ·
(ii) Cis-platin is prepared in a ligand substitution reaction which takes place in multiple steps. The equation for the final step forming cis-platin is shown below. [PtCl3(NH3)]– + NH3 → PtCl2(NH3)2 + Cl– cis-platin In the box, outline the mechanism for the formation of cis-platin from [PtCl3(NH3)]–. Use curly arrows and lone pairs where appropriate. Cl Cl _ Pt + Cl H3N NH3 cis-platin [2]
152. June 2018 · Paper 3 · Q5(b)(iii) · 1 marks ·
(iii) Draw the skeletal formula of the ester present in the equilibrium mixture. [1]
153. June 2018 · Paper 3 · Q6(a)(i) · 1 marks ·
6 This question is about organic reactions. (a) Compound A is formed when ethanal is mixed with OH–(aq) ions, which act as a catalyst. The balanced equation is shown in reaction 6.1 below. H O H O H OH H O H C C + H C C H C C C C Reaction 6.1 H H H H H H H H Compound A (i) Give the systematic name for compound A. ...................................................................................................................................... [1]
154. June 2017 · AS Paper 1 · Q14 · 1 marks ·
14 What is the systematic name of the compound below? Br A E-2-bromobut-2-ene B Z-2-bromobut-2-ene C E-1,2-dimethyl-1-bromoethene D Z-1,2-dimethyl-1-bromoethene Your answer [1]
155. June 2017 · AS Paper 1 · Q15 · 1 marks ·
15 The skeletal formula of an organic compound is shown below. O OH What is the molecular formula of the organic compound? A C6H10O2 B C6H11O2 C C6H12O2 D C6H13O2 Your answer [1]
156. June 2017 · AS Paper 1 · Q16 · 1 marks ·
16 How many structural isomers have the molecular formula C5H12? A 2 B 3 C 4 D 5 Your answer [1]
157. June 2017 · AS Paper 1 · Q25(b) · 5 marks ·
(b) An alkene D is a liquid at room temperature and pressure but can easily be vaporised. When vaporised, 0.1881 g of D produces 82.5 cm3 of gas at 101 kPa and 373 K. Determine the molar mass and molecular formula of alkene D. Show all your working. molar mass = .................................................. g mol−1 molecular formula = .......................................................... [5]
158. June 2017 · Paper 2 · Q2 · 1 marks ·
2 How can the molecule below be described? OH A Aromatic and alicyclic B Aliphatic and unsaturated C Aromatic and unsaturated D Alicyclic and saturated Your answer [1]
159. June 2017 · AS Paper 2 · Q4(b)(i) · 1 marks ·
(b) Alcohol C is analysed using mass spectrometry. OH alcohol C (i) Give the systematic name of alcohol C. ...................................................................................................................................... [1]
160. June 2017 · AS Paper 2 · Q5(a) · 1 marks ·
5 Propanoic acid, CH3CH2COOH, is a member of the homologous series of carboxylic acids. (a) Suggest the general formula for a carboxylic acid. .............................................................................................................................................. [1]
161. June 2017 · AS Paper 2 · Q5(c) · 4 marks ·
(c) Compound D is a neutral compound which is a structural isomer of propanoic acid, CH3CH2COOH. The infrared spectrum of compound D is shown below. Item removed due to third party copyright restrictions. Suggest two possible structures of compound D. Explain all your reasoning. ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... .............................................................................................................................................. [4]
162. June 2017 · AS Paper 2 · Q5(d)(iii) · 1 marks ·
(iii) The first step in the reaction mechanism involves homolytic fission of a chlorine molecule to form two chlorine radicals. Why is this step an example of homolytic fission? ........................................................................................................................................... ........................................................................................................................................... ...................................................................................................................................... [1]
163. June 2017 · AS Paper 2 · Q5(d)(iv) · 2 marks ·
(iv) Write two equations to show the propagation steps in the mechanism for this reaction. Use dots,•, to show the unpaired electrons on radicals. ........................................................................................................................................... ...................................................................................................................................... [2]
164. June 2017 · AS Paper 2 · Q5(d)(v) · 1 marks ·
(v) Draw the displayed formula of the radical formed in the first propagation step. Use a dot,•, to show the position of the unpaired electron. [1]
165. June 2017 · Paper 2 · Q9 · 1 marks ·
9 What is the molecular formula of the compound below? A C7H10 B C7H12 C C7H14 D C7H16 Your answer [1]
166. June 2017 · Paper 2 · Q14 · 1 marks ·
14 Ethane reacts with chlorine by radical substitution to form chloroethane. Which radical(s) is/are present in the mechanism? 1 H 2 Cl 3 C2H5 A 1, 2 and 3 B Only 1 and 2 C Only 2 and 3 D Only 1 Your answer [1]
167. June 2017 · Paper 2 · Q15 · 1 marks ·
15 Which compound(s) is a/are structural isomer(s) of C6H12O2? 1 hexanoic acid 2 ethyl butanoate 3 propyl propanoate A 1, 2 and 3 B Only 1 and 2 C Only 2 and 3 D Only 1 Your answer [1]
168. June 2017 · Paper 2 · Q16(b)(i) · 1 marks ·
(b) Compound C, CH3CH2CH=CHCH2CH2OH, exists as cis and trans stereoisomers. (i) Name compound C. ..................................................................................................................................... [1]
169. June 2017 · Paper 2 · Q16(d)(iii) · 3 marks ·
(iii) Outline the mechanism of the reaction between compound D and hydrogen bromide to form either compound E or compound F. Include curly arrows and relevant dipoles. [3]
170. June 2017 · Paper 2 · Q16(e)(ii) · 4 marks ·
(ii) β-Carotene is a naturally occurring unsaturated hydrocarbon found in carrots. A β-carotene molecule contains 40 carbon atoms, has two rings, and a branched chain. 0.0200 mol of β-carotene reacts with 5.28 dm3 of hydrogen gas to form a saturated hydrocarbon. Using molecular formulae, construct a balanced equation for this reaction. Include relevant calculations and reasoning. Equation ...................................................................................................................... [4]
171. June 2017 · Paper 2 · Q18(a)(i) · 3 marks ·
18 This question is about organic compounds containing nitrogen. (a) Sodium cyanide, NaCN, can be reacted with many organic compounds to increase the length of a carbon chain. (i) 1-Chloropropane, CH3CH2CH2Cl, reacts with ethanolic sodium cyanide by nucleophilic substitution. Outline the mechanism for this reaction. Include curly arrows, relevant dipoles and the structure of the organic product. [3]
172. 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]
173. 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]
174. June 2017 · Paper 2 · Q19(c)(ii) · 1 marks ·
(ii) What is the name of compound K? ..................................................................................................................................... [1]
175. June 2017 · Paper 3 · Q3(c)(i) · 1 marks ·
(c) Peroxycarboxylic acids are organic compounds with the COOOH functional group. Peroxyethanoic acid, CH3COOOH, is used as a disinfectant. (i) Suggest the structure for CH3COOOH. The COOOH functional group must be clearly displayed. [1]
176. June 2017 · Paper 3 · Q5(a)(iii) · 1 marks ·
(iii) When beer is exposed to light, 3-methylbut-2-ene-1-thiol is formed, which gives an unpleasant smell and flavour to the beer. Draw the skeletal formula for 3-methylbut-2-ene-1-thiol. [1]
177. June 2016 · AS Paper 1 · Q13 · 1 marks ·
13 The skeletal formulae of four alcohols, E, F, G and H, are shown below. OH OH E F HO OH G H Which pair of alcohols are structural isomers of each other? A E and F B E and G C E and H D F and G Your answer [1]
178. June 2016 · AS Paper 1 · Q14 · 1 marks ·
7 14 What is the name of the following compound? Cl Cl H3C C C CH3 H CH3 A 1,2-dichloro-1,2-dimethylpropane B 2,3-dichloro-2,3-dimethylpropane C 2,3-dichloro-2-methylbutane D 2,3-dichloro-3-methylbutane Your answer [1]
179. June 2016 · AS Paper 1 · Q26(a)(i) · 1 marks · AO1
22 26 Compound B, shown below, can be used to synthesise organic compounds with different functional groups. H CH3 C C H CH3 Compound B (a) (i) Compound B is a member of a homologous series. Name the homologous series and state its general formula. Homologous series ........................................................................................................... General formula ............................................................................................................ [1]
180. June 2016 · AS Paper 2 · Q3(a)(iii) · 2 marks ·
(iii) A structural isomer of compound A has E/Z isomers. Draw the structure of the Z isomer and then name this isomer. structure of Z isomer name ........................................................................ [2]
181. June 2016 · AS Paper 2 · Q3(c) · 6 marks ·
8 (c)* Compound A reacts with hydrogen bromide to form a mixture of two different organic products. H3C CH3 C C H CH3 compound A Give the structures of the two possible organic products of the reaction. Outline the mechanism, using the ‘curly arrow’ model, for the formation of one of the organic products from compound A. Explain which of the two organic products is more likely to be formed. ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... ................................................................................................................................................... .............................................................................................................................................. [6]

Mark schemes

1. June 2025 · AS Paper 1 · Q14
Mark scheme June 2025 Paper 1 Q14
2. June 2025 · AS Paper 1 · Q15
Mark scheme June 2025 Paper 1 Q15
3. June 2025 · AS Paper 1 · Q17
Mark scheme June 2025 Paper 1 Q17
4. June 2025 · AS Paper 1 · Q24(a)(i)
Mark scheme June 2025 Paper 1 Q24(a)(i)
5. June 2025 · AS Paper 1 · Q24(c)(i)
Mark scheme June 2025 Paper 1 Q24(c)(i)
6. June 2025 · AS Paper 1 · Q25(b)
Mark scheme June 2025 Paper 1 Q25(b)
7. June 2025 · Paper 2 · Q1
Mark scheme June 2025 Paper 2 Q1
8. June 2025 · Paper 2 · Q3
Mark scheme June 2025 Paper 2 Q3
9. June 2025 · AS Paper 2 · Q4(b)(iv)
Mark scheme June 2025 Paper 2 Q4(b)(iv)
10. June 2025 · AS Paper 2 · Q4(c)
Mark scheme June 2025 Paper 2 Q4(c)
11. June 2025 · AS Paper 2 · Q4(d)(ii)
Mark scheme June 2025 Paper 2 Q4(d)(ii)
12. June 2025 · AS Paper 2 · Q4(d)(iii)
Mark scheme June 2025 Paper 2 Q4(d)(iii)
13. June 2025 · Paper 2 · Q16(a)
Mark scheme June 2025 Paper 2 Q16(a)
14. June 2025 · Paper 2 · Q16(b)
Mark scheme June 2025 Paper 2 Q16(b)
15. June 2025 · Paper 2 · Q19(a)(i)
Mark scheme June 2025 Paper 2 Q19(a)(i)
16. June 2025 · Paper 2 · Q21(a)
Mark scheme June 2025 Paper 2 Q21(a)
17. June 2025 · Paper 2 · Q23(a)
Mark scheme June 2025 Paper 2 Q23(a)
18. June 2025 · Paper 3 · Q2(a)(i)
Mark scheme June 2025 Paper 3 Q2(a)(i)
19. June 2025 · Paper 3 · Q5(a)(i)
Mark scheme June 2025 Paper 3 Q5(a)(i)
20. June 2025 · Paper 3 · Q5(a)(iv)
Mark scheme June 2025 Paper 3 Q5(a)(iv)
21. June 2024 · AS Paper 1 · Q14
Mark scheme June 2024 Paper 1 Q14
22. June 2024 · AS Paper 1 · Q15
Mark scheme June 2024 Paper 1 Q15
23. June 2024 · AS Paper 1 · Q24(b)
Mark scheme June 2024 Paper 1 Q24(b)
24. June 2024 · AS Paper 1 · Q25(b)
Mark scheme June 2024 Paper 1 Q25(b)
25. June 2024 · AS Paper 1 · Q25(d)(i)
Mark scheme June 2024 Paper 1 Q25(d)(i)
26. June 2024 · AS Paper 2 · Q5(b)(i)
Mark scheme June 2024 Paper 2 Q5(b)(i)
27. June 2024 · Paper 2 · Q16(a)
Mark scheme June 2024 Paper 2 Q16(a)
28. June 2024 · Paper 2 · Q16(b)
Mark scheme June 2024 Paper 2 Q16(b)
29. June 2024 · Paper 2 · Q16(c)
Mark scheme June 2024 Paper 2 Q16(c)
30. June 2024 · Paper 2 · Q18(a)(i)
Mark scheme June 2024 Paper 2 Q18(a)(i)
31. June 2024 · Paper 2 · Q19
Mark scheme June 2024 Paper 2 Q19
32. June 2024 · Paper 2 · Q20(b)(i)
Mark scheme June 2024 Paper 2 Q20(b)(i)
33. June 2024 · Paper 2 · Q21(a)(ii)
Mark scheme June 2024 Paper 2 Q21(a)(ii)
34. June 2024 · Paper 3 · Q2(c)(i)
Mark scheme June 2024 Paper 3 Q2(c)(i)
35. June 2024 · Paper 3 · Q5(b)(ii)
Mark scheme June 2024 Paper 3 Q5(b)(ii)
36. June 2023 · AS Paper 1 · Q15
Mark scheme June 2023 Paper 1 Q15
37. June 2023 · AS Paper 1 · Q16
Mark scheme June 2023 Paper 1 Q16
38. June 2023 · AS Paper 1 · Q25(b)
Mark scheme June 2023 Paper 1 Q25(b)
39. June 2023 · AS Paper 1 · Q26
Mark scheme June 2023 Paper 1 Q26
40. June 2023 · Paper 2 · Q3
Mark scheme June 2023 Paper 2 Q3
41. June 2023 · AS Paper 2 · Q3(c)
Mark scheme June 2023 Paper 2 Q3(c)
42. June 2023 · Paper 2 · Q5
Mark scheme June 2023 Paper 2 Q5
43. June 2023 · AS Paper 2 · Q5(a)(i)
Mark scheme June 2023 Paper 2 Q5(a)(i)
44. June 2023 · AS Paper 2 · Q5(a)(ii)
Mark scheme June 2023 Paper 2 Q5(a)(ii)
45. June 2023 · Paper 2 · Q7
Mark scheme June 2023 Paper 2 Q7
46. June 2023 · Paper 2 · Q13
Mark scheme June 2023 Paper 2 Q13
47. June 2023 · Paper 2 · Q16(b)(i)
Mark scheme June 2023 Paper 2 Q16(b)(i)
48. June 2023 · Paper 2 · Q17(a)
Mark scheme June 2023 Paper 2 Q17(a)
49. June 2023 · Paper 2 · Q17(c)(i)
Mark scheme June 2023 Paper 2 Q17(c)(i)
50. June 2023 · Paper 2 · Q17(d)
Mark scheme June 2023 Paper 2 Q17(d)
51. June 2023 · Paper 2 · Q21(b)(i)
Mark scheme June 2023 Paper 2 Q21(b)(i)
52. June 2023 · Paper 2 · Q22(a)(i)
Mark scheme June 2023 Paper 2 Q22(a)(i)
53. June 2023 · Paper 3 · Q2(c)
Mark scheme June 2023 Paper 3 Q2(c)
54. June 2022 · AS Paper 1 · Q15
Mark scheme June 2022 Paper 1 Q15
55. June 2022 · AS Paper 1 · Q21(a)(i)
Mark scheme June 2022 Paper 1 Q21(a)(i)
56. June 2022 · AS Paper 1 · Q21(a)(ii)
Mark scheme June 2022 Paper 1 Q21(a)(ii)
57. June 2022 · AS Paper 1 · Q26(a)
Mark scheme June 2022 Paper 1 Q26(a)
58. June 2022 · AS Paper 2 · Q5(a)(ii)
Mark scheme June 2022 Paper 2 Q5(a)(ii)
59. June 2022 · Paper 2 · Q16(a)(i)
Mark scheme June 2022 Paper 2 Q16(a)(i)
60. June 2022 · Paper 2 · Q16(a)(ii)
Mark scheme June 2022 Paper 2 Q16(a)(ii)
61. June 2022 · Paper 2 · Q16(b)(i)
Mark scheme June 2022 Paper 2 Q16(b)(i)
62. June 2022 · Paper 2 · Q16(b)(iii)
Mark scheme June 2022 Paper 2 Q16(b)(iii)
63. June 2022 · Paper 2 · Q16(b)(iv)
Mark scheme June 2022 Paper 2 Q16(b)(iv)
64. June 2022 · Paper 2 · Q16(c)(ii)
Mark scheme June 2022 Paper 2 Q16(c)(ii)
65. June 2022 · Paper 2 · Q19(c)(i)
Mark scheme June 2022 Paper 2 Q19(c)(i)
66. June 2022 · Paper 3 · Q3(b)
Mark scheme June 2022 Paper 3 Q3(b)
67. June 2022 · Paper 3 · Q6(c)(i)
Mark scheme June 2022 Paper 3 Q6(c)(i)
68. November 2021 · AS Paper 1 · Q13
Mark scheme November 2021 Paper 1 Q13
69. November 2021 · AS Paper 1 · Q14
Mark scheme November 2021 Paper 1 Q14
70. November 2021 · AS Paper 1 · Q17
Mark scheme November 2021 Paper 1 Q17
71. November 2021 · AS Paper 1 · Q18
Mark scheme November 2021 Paper 1 Q18
72. November 2021 · AS Paper 1 · Q21(d)(i)
Mark scheme November 2021 Paper 1 Q21(d)(i)
73. November 2021 · AS Paper 1 · Q24(a)
Mark scheme November 2021 Paper 1 Q24(a)
74. November 2021 · AS Paper 1 · Q24(b)(i)
Mark scheme November 2021 Paper 1 Q24(b)(i)
75. November 2021 · AS Paper 1 · Q24(b)(ii)
Mark scheme November 2021 Paper 1 Q24(b)(ii)
76. November 2021 · AS Paper 1 · Q26
Mark scheme November 2021 Paper 1 Q26
77. November 2021 · Paper 2 · Q1
Mark scheme November 2021 Paper 2 Q1
78. November 2021 · AS Paper 2 · Q2(a)
Mark scheme November 2021 Paper 2 Q2(a)
79. November 2021 · AS Paper 2 · Q2(b)
Mark scheme November 2021 Paper 2 Q2(b)
80. November 2021 · AS Paper 2 · Q7(a)
Mark scheme November 2021 Paper 2 Q7(a)
81. November 2021 · AS Paper 2 · Q7(c)(i)
Mark scheme November 2021 Paper 2 Q7(c)(i)
82. November 2021 · AS Paper 2 · Q7(c)(ii)
Mark scheme November 2021 Paper 2 Q7(c)(ii)
83. November 2021 · Paper 2 · Q16(b)(i)
Mark scheme November 2021 Paper 2 Q16(b)(i)
84. November 2021 · Paper 2 · Q16(b)(iii)
Mark scheme November 2021 Paper 2 Q16(b)(iii)
85. November 2021 · Paper 2 · Q16(d)(i)
Mark scheme November 2021 Paper 2 Q16(d)(i)
86. November 2021 · Paper 2 · Q17(c)
Mark scheme November 2021 Paper 2 Q17(c)
87. November 2021 · Paper 2 · Q18(c)(i)
Mark scheme November 2021 Paper 2 Q18(c)(i)
88. November 2021 · Paper 2 · Q19(a)(i)
Mark scheme November 2021 Paper 2 Q19(a)(i)
89. November 2021 · Paper 2 · Q20(a)(i)
Mark scheme November 2021 Paper 2 Q20(a)(i)
90. November 2021 · Paper 3 · Q1(f)
Mark scheme November 2021 Paper 3 Q1(f)
91. November 2021 · Paper 3 · Q3(b)
Mark scheme November 2021 Paper 3 Q3(b)
92. November 2021 · Paper 3 · Q5(b)(iii)
Mark scheme November 2021 Paper 3 Q5(b)(iii)
93. November 2020 · AS Paper 1 · Q14
Mark scheme November 2020 Paper 1 Q14
94. November 2020 · AS Paper 1 · Q25(b)
Mark scheme November 2020 Paper 1 Q25(b)
95. November 2020 · AS Paper 1 · Q25(c)(i)
Mark scheme November 2020 Paper 1 Q25(c)(i)
96. November 2020 · AS Paper 1 · Q25(c)(ii)
Mark scheme November 2020 Paper 1 Q25(c)(ii)
97. November 2020 · AS Paper 1 · Q25(c)(iii)
Mark scheme November 2020 Paper 1 Q25(c)(iii)
98. November 2020 · AS Paper 1 · Q25(c)(iv)
Mark scheme November 2020 Paper 1 Q25(c)(iv)
99. November 2020 · AS Paper 1 · Q25(c)(v)
Mark scheme November 2020 Paper 1 Q25(c)(v)
100. November 2020 · Paper 2 · Q1
Mark scheme November 2020 Paper 2 Q1
101. November 2020 · AS Paper 2 · Q5(c)
Mark scheme November 2020 Paper 2 Q5(c)
102. November 2020 · AS Paper 2 · Q5(d)(ii)
Mark scheme November 2020 Paper 2 Q5(d)(ii)
103. November 2020 · Paper 2 · Q9
Mark scheme November 2020 Paper 2 Q9
104. November 2020 · Paper 2 · Q10
Mark scheme November 2020 Paper 2 Q10
105. November 2020 · Paper 2 · Q12
Mark scheme November 2020 Paper 2 Q12
106. November 2020 · Paper 2 · Q16(a)
Mark scheme November 2020 Paper 2 Q16(a)
107. November 2020 · Paper 2 · Q16(c)
Mark scheme November 2020 Paper 2 Q16(c)
108. November 2020 · Paper 2 · Q19(a)(i)
Mark scheme November 2020 Paper 2 Q19(a)(i)
109. November 2020 · Paper 2 · Q19(a)(ii)
Mark scheme November 2020 Paper 2 Q19(a)(ii)
110. November 2020 · Paper 2 · Q19(c)(i)
Mark scheme November 2020 Paper 2 Q19(c)(i)
111. November 2020 · Paper 2 · Q19(c)(ii)
Mark scheme November 2020 Paper 2 Q19(c)(ii)
112. November 2020 · Paper 3 · Q6(c)
Mark scheme November 2020 Paper 3 Q6(c)
113. June 2019 · AS Paper 1 · Q15
Mark scheme June 2019 Paper 1 Q15
114. June 2019 · AS Paper 1 · Q25(a)(ii)
Mark scheme June 2019 Paper 1 Q25(a)(ii)
115. June 2019 · AS Paper 1 · Q25(b)(i)
Mark scheme June 2019 Paper 1 Q25(b)(i)
116. June 2019 · Paper 2 · Q3
Mark scheme June 2019 Paper 2 Q3
117. June 2019 · AS Paper 2 · Q3(a)(i)
Mark scheme June 2019 Paper 2 Q3(a)(i)
118. June 2019 · AS Paper 2 · Q3(c)(i)
Mark scheme June 2019 Paper 2 Q3(c)(i)
119. June 2019 · AS Paper 2 · Q5(b)(ii)
Mark scheme June 2019 Paper 2 Q5(b)(ii)
120. June 2019 · Paper 2 · Q16(a)(i)
Mark scheme June 2019 Paper 2 Q16(a)(i)
121. June 2019 · Paper 2 · Q16(b)(ii)
Mark scheme June 2019 Paper 2 Q16(b)(ii)
122. June 2019 · Paper 2 · Q16(b)(iii)
Mark scheme June 2019 Paper 2 Q16(b)(iii)
123. June 2019 · Paper 2 · Q18(a)(i)
Mark scheme June 2019 Paper 2 Q18(a)(i)
124. June 2019 · Paper 2 · Q18(c)
Mark scheme June 2019 Paper 2 Q18(c)
125. June 2019 · Paper 2 · Q19(b)(iii)
Mark scheme June 2019 Paper 2 Q19(b)(iii)
126. June 2019 · Paper 2 · Q20(a)(i)
Mark scheme June 2019 Paper 2 Q20(a)(i)
127. June 2019 · Paper 2 · Q20(a)(ii)
Mark scheme June 2019 Paper 2 Q20(a)(ii)
128. June 2019 · Paper 2 · Q20(a)(iii)
Mark scheme June 2019 Paper 2 Q20(a)(iii)
129. June 2019 · Paper 2 · Q20(b)(i)
Mark scheme June 2019 Paper 2 Q20(b)(i)
130. June 2018 · AS Paper 1 · Q16
Mark scheme June 2018 Paper 1 Q16
131. June 2018 · AS Paper 1 · Q17
Mark scheme June 2018 Paper 1 Q17
132. June 2018 · AS Paper 1 · Q18
Mark scheme June 2018 Paper 1 Q18
133. June 2018 · AS Paper 1 · Q24(a)
Mark scheme June 2018 Paper 1 Q24(a)
134. June 2018 · AS Paper 1 · Q24(b)(ii)
Mark scheme June 2018 Paper 1 Q24(b)(ii)
135. June 2018 · AS Paper 1 · Q25(a)(ii)
Mark scheme June 2018 Paper 1 Q25(a)(ii)
136. June 2018 · AS Paper 1 · Q25(b)(i)
Mark scheme June 2018 Paper 1 Q25(b)(i)
137. June 2018 · AS Paper 2 · Q1(d)(ii)
Mark scheme June 2018 Paper 2 Q1(d)(ii)
138. June 2018 · Paper 2 · Q4
Mark scheme June 2018 Paper 2 Q4
139. June 2018 · AS Paper 2 · Q6(b)(i)
Mark scheme June 2018 Paper 2 Q6(b)(i)
140. June 2018 · AS Paper 2 · Q6(b)(ii)
Mark scheme June 2018 Paper 2 Q6(b)(ii)
141. June 2018 · AS Paper 2 · Q6(c)(i)
Mark scheme June 2018 Paper 2 Q6(c)(i)
142. June 2018 · Paper 2 · Q11
Mark scheme June 2018 Paper 2 Q11
143. June 2018 · Paper 2 · Q16(a)(i)
Mark scheme June 2018 Paper 2 Q16(a)(i)
144. June 2018 · Paper 2 · Q16(a)(ii)
Mark scheme June 2018 Paper 2 Q16(a)(ii)
145. June 2018 · Paper 2 · Q16(a)(iii)
Mark scheme June 2018 Paper 2 Q16(a)(iii)
146. June 2018 · Paper 2 · Q19(b)
Mark scheme June 2018 Paper 2 Q19(b)
147. June 2018 · Paper 2 · Q19(c)(ii)
Mark scheme June 2018 Paper 2 Q19(c)(ii)
148. June 2018 · Paper 2 · Q20(d)
Mark scheme June 2018 Paper 2 Q20(d)
149. June 2018 · Paper 2 · Q21(c)(ii)
Mark scheme June 2018 Paper 2 Q21(c)(ii)
150. June 2018 · Paper 2 · Q22(c)(i)
Mark scheme June 2018 Paper 2 Q22(c)(i)
151. June 2018 · Paper 3 · Q4(a)(ii)
Mark scheme June 2018 Paper 3 Q4(a)(ii)
152. June 2018 · Paper 3 · Q5(b)(iii)
Mark scheme June 2018 Paper 3 Q5(b)(iii)
153. June 2018 · Paper 3 · Q6(a)(i)
Mark scheme June 2018 Paper 3 Q6(a)(i)
154. June 2017 · AS Paper 1 · Q14
Mark scheme June 2017 Paper 1 Q14
155. June 2017 · AS Paper 1 · Q15
Mark scheme June 2017 Paper 1 Q15
156. June 2017 · AS Paper 1 · Q16
Mark scheme June 2017 Paper 1 Q16
157. June 2017 · AS Paper 1 · Q25(b)
Mark scheme June 2017 Paper 1 Q25(b)
158. June 2017 · Paper 2 · Q2
Mark scheme June 2017 Paper 2 Q2
159. June 2017 · AS Paper 2 · Q4(b)(i)
Mark scheme June 2017 Paper 2 Q4(b)(i)
160. June 2017 · AS Paper 2 · Q5(a)
Mark scheme June 2017 Paper 2 Q5(a)
161. June 2017 · AS Paper 2 · Q5(c)
Mark scheme June 2017 Paper 2 Q5(c)
162. June 2017 · AS Paper 2 · Q5(d)(iii)
Mark scheme June 2017 Paper 2 Q5(d)(iii)
163. June 2017 · AS Paper 2 · Q5(d)(iv)
Mark scheme June 2017 Paper 2 Q5(d)(iv)
164. June 2017 · AS Paper 2 · Q5(d)(v)
Mark scheme June 2017 Paper 2 Q5(d)(v)
165. June 2017 · Paper 2 · Q9
Mark scheme June 2017 Paper 2 Q9
166. June 2017 · Paper 2 · Q14
Mark scheme June 2017 Paper 2 Q14
167. June 2017 · Paper 2 · Q15
Mark scheme June 2017 Paper 2 Q15
168. June 2017 · Paper 2 · Q16(b)(i)
Mark scheme June 2017 Paper 2 Q16(b)(i)
169. June 2017 · Paper 2 · Q16(d)(iii)
Mark scheme June 2017 Paper 2 Q16(d)(iii)
170. June 2017 · Paper 2 · Q16(e)(ii)
Mark scheme June 2017 Paper 2 Q16(e)(ii)
171. June 2017 · Paper 2 · Q18(a)(i)
Mark scheme June 2017 Paper 2 Q18(a)(i)
172. June 2017 · Paper 2 · Q19(a)
Mark scheme June 2017 Paper 2 Q19(a)
173. June 2017 · Paper 2 · Q19(c)(i)
Mark scheme June 2017 Paper 2 Q19(c)(i)
174. June 2017 · Paper 2 · Q19(c)(ii)
Mark scheme June 2017 Paper 2 Q19(c)(ii)
175. June 2017 · Paper 3 · Q3(c)(i)
Mark scheme June 2017 Paper 3 Q3(c)(i)
176. June 2017 · Paper 3 · Q5(a)(iii)
Mark scheme June 2017 Paper 3 Q5(a)(iii)
177. June 2016 · AS Paper 1 · Q13
Mark scheme June 2016 Paper 1 Q13
178. June 2016 · AS Paper 1 · Q14
Mark scheme June 2016 Paper 1 Q14
179. June 2016 · AS Paper 1 · Q26(a)(i)
Mark scheme June 2016 Paper 1 Q26(a)(i)
180. June 2016 · AS Paper 2 · Q3(a)(iii)
Mark scheme June 2016 Paper 2 Q3(a)(iii)
181. June 2016 · AS Paper 2 · Q3(c)
Mark scheme June 2016 Paper 2 Q3(c)