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E/Z and cis–trans isomerism: OCR A‑Level Chemistry A questions

OCR A-Level Chemistry A past-paper questions on 4.1.3.2 E/Z and cis–trans isomerism, 2016–2025, with mark schemes and examiner’s reports where available.

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  2. Q16(c)(i)

    June 2025 · Paper 2

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  3. Q16(c)(ii)

    June 2025 · Paper 2

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  4. Q15

    June 2025 · AS Paper 1

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  5. Q3(c)

    June 2025 · AS Paper 2

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  6. Q16(e)

    June 2024 · Paper 2

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  7. Q5(a)(iii)

    June 2023 · AS Paper 2

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  8. Q16(b)(ii)

    June 2022 · Paper 2

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  9. Q16(b)(iii)

    June 2022 · Paper 2

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  10. Q17

    June 2022 · AS Paper 1

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  12. Q16(c)(i)

    November 2021 · Paper 2

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  13. Q16(c)(ii)

    November 2021 · Paper 2

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  16. Q1

    November 2020 · Paper 2

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  18. Q4

    June 2019 · Paper 2

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  19. Q16(b)(iv)

    June 2019 · Paper 2

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All 31 questions on E/Z and cis–trans isomerism, as a list
  1. June 2025, Paper 2, Q10 (1 mark): How many stereoisomers does the compound CH3CH(Br)CH=CHCH(Cl )CH3 have? A 2 B 4 C 6 D 8 Your answer [1]
  2. June 2025, Paper 2, Q16(c)(i) (2 marks): Draw the structures of the E and Z stereoisomers of compound B. E Z [2]
  3. June 2025, Paper 2, Q16(c)(ii) (2 marks): Explain why compound B can form E and Z stereoisomers. [2]
  4. June 2025, AS Paper 1, Q15 (1 mark): 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
  5. June 2025, AS Paper 2, Q3(c) (2 marks): The structure of malic acid is shown below. OH H HOOC C C COOH H H When malic acid is heated with an acid catalyst, a mixture of cis and trans stereoisomers is
  6. June 2024, Paper 2, Q16(e) (2 marks): Explain why hydrocarbon D is a Z-stereoisomer. [2]
  7. June 2023, AS Paper 2, Q5(a)(iii) (2 marks): The skeletal formulae of alkenes B and C are shown below. Alkene B Alkene C Skeletal formula Isomer Z E Use the Cahn-Ingold-Prelog priority rules to explain why
  8. June 2022, Paper 2, Q16(b)(ii) (1 mark): What is meant by the term stereoisomers? [1]
  9. June 2022, Paper 2, Q16(b)(iii) (2 marks): Draw structures for the cis and trans isomers of the branched hydrocarbon B. cis isomer trans isomer [2]
  10. June 2022, AS Paper 1, Q17 (1 mark): Which alkene is an E stereoisomer? CH3CH2 CH3 C C A H H H3C CH2CH3 C C B H CH3 H CH3 C C C CH3CH2 C(CH3)3 H3C CH3 C C D H CH(CH3)2 Your answer [1]
  11. November 2021, Paper 2, Q2 (1 mark): Which type(s) of stereoisomerism is/are shown by 2,4-dimethylhex-2-ene? A E / Z isomerism only. B Optical isomerism only. C Both E / Z isomerism and optical iso
  12. November 2021, Paper 2, Q16(c)(i) (1 mark): Explain the term stereoisomerism. [1]
  13. November 2021, Paper 2, Q16(c)(ii) (1 mark): Explain, with a reason, whether the student is correct or incorrect. [1]
  14. November 2021, Paper 3, Q3(b) (7 marks): 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(a
  15. November 2021, AS Paper 1, Q13 (1 mark): 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]
  16. November 2020, Paper 2, Q1 (1 mark): 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
  17. November 2020, Paper 2, Q6 (1 mark): Which alcohol reacts with an acid catalyst to form a mixture of stereoisomers? A 3-methylbutan-2-ol B pentan-1-ol C 2-methylhexan-2-ol D heptan-4-ol Your answer
  18. June 2019, Paper 2, Q4 (1 mark): The structure of a stereoisomer is shown below. H3C CH(CH3)2 C C CH3CH2 CH2CH2CH3 Which term correctly describes this stereoisomer? A cis- B trans- C E- D Z- Yo
  19. June 2019, Paper 2, Q16(b)(iv) (1 mark): Explain the term stereoisomerism. [1]
  20. June 2019, Paper 2, Q16(b)(v) (4 marks): The structures of geraniol and citronellal are repeated below with the carbon atoms numbered. 1 1 7 7 5 4 3 5 3 2 4 8 OH 8 2 6 O 6 Geraniol Citronellal Explain
  21. June 2019, Paper 3, Q4(b)(ii) (4 marks): α-Terpineol meets the requirements for E / Z isomerism. However, only one E / Z isomer of α-terpineol exists. Explain • why α-terpineol meets the requirements f
  22. June 2018, Paper 2, Q20(a) (2 marks): Methylcinnamaldehyde is an E stereoisomer. Explain this statement in terms of the Cahn-Ingold-Prelog (CIP) rules. [2]
  23. June 2018, AS Paper 1, Q19 (1 mark): The molecule below has two double bonds, labelled 1 and 2. 1 2 The arrangement around each double bond can be identified as E or Z. Which row in the table is co
  24. June 2017, Paper 2, Q4 (1 mark): Which molecule is a Z-isomer? H3C H Cl F F CH3 H CH3 C C C C C C C C H F H CH3 Cl H H F A B C D Your answer [1]
  25. June 2017, Paper 2, Q16(b)(ii) (1 mark): Define the term stereoisomers. [1]
  26. June 2017, Paper 2, Q16(b)(iii) (2 marks): Draw the structures of the cis and trans stereoisomers of compound C. cis trans [2]
  27. June 2017, AS Paper 1, Q14 (1 mark): 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 Yo
  28. June 2017, AS Paper 1, Q18 (1 mark): Which alcohol reacts with an acid catalyst to form E and Z stereoisomers? A pentan-3-ol B pentan-1-ol C 2-methylbutan-2-ol D 2,2-dimethylpropan-1-ol Your answer
  29. June 2016, AS Paper 1, Q15 (1 mark): Which compound has non-polar molecules? A E-1,2-dichlorobut-2-ene B E-2,3-dichlorobut-2-ene C Z-2,3-dichlorobut-2-ene D Z-1,4-dichlorobut-2-ene Your answer [1]
  30. June 2016, AS Paper 2, Q3(a)(ii) (1 mark): Explain why compound A does not have E/Z isomers. [1]
  31. June 2016, AS Paper 2, Q3(a)(iii) (2 marks): 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]

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