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Electrophilic substitution mechanisms: Edexcel International A Level Chemistry questions

Edexcel International A Level Chemistry past-paper questions on 18.1.3 Electrophilic substitution mechanisms, 2019–2025, with mark schemes and examiner’s reports where available.

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  1. Q20(d)(i)

    June 2025 · Unit 5

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  2. Q20(d)(ii)

    June 2025 · Unit 5

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  3. Q10

    June 2025 (A) · Unit 5

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  4. Q18(a)

    June 2025 (A) · Unit 5

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  5. Q23(b)(ii)

    January 2025 · Unit 5

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  6. Q19(b)(i)

    October 2024 · Unit 5

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  7. Q19(b)(ii)

    October 2024 · Unit 5

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  8. Q8

    June 2024 · Unit 5

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  9. Q17(a)

    June 2024 · Unit 5

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  10. Q14(a)(i)

    January 2024 · Unit 5

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  11. Q14(a)(ii)

    January 2024 · Unit 5

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  12. Q20(a)(i)

    October 2023 · Unit 5

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  13. Q25(d)(i)

    June 2023 · Unit 5

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  14. Q19(a)(i)

    January 2023 · Unit 5

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  15. Q23(c)(i)

    October 2022 · Unit 5

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  16. Q23(c)(ii)

    October 2022 · Unit 5

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  17. Q12(a)(i)

    June 2022 · Unit 5

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  18. Q12(a)(ii)

    June 2022 · Unit 5

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  20. Q19(f)(iii)

    October 2021 · Unit 5

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All 23 questions on Electrophilic substitution mechanisms, as a list
  1. June 2025, Unit 5, Q20(d)(i) (1 mark): Concentrated nitric and sulfuric acid are used to produce NO 2 to initiate the reaction. + Write the equation for the production of NO 2 . (1)
  2. June 2025, Unit 5, Q20(d)(ii) (5 marks): Complete the reaction mechanism to form 5-nitrosalicylic acid, naming the reaction mechanism. (5) Reaction mechanism O OH OH NO2 +
  3. June 2025 (A), Unit 5, Q10 (1 mark): Benzene is nitrated using a mixture of concentrated nitric and sulfuric acids. In this reaction, the sulfuric acid A dissolves both benzene and nitric acid B fo
  4. June 2025 (A), Unit 5, Q18(a) (4 marks): Draw the mechanism for the reaction in Step 1 to produce J, including the formation of the electrophile. (4)
  5. January 2025, Unit 5, Q23(b)(ii) (5 marks): For Step 2, draw the mechanism for this reaction, including the formation of a suitable electrophile and the regeneration of the catalyst. Include curly arrows.
  6. October 2024, Unit 5, Q19(b)(i) (5 marks): Draw the mechanism for this reaction, using appropriate curly arrows. Include equations showing the formation of the electrophile and the regeneration of the ca
  7. October 2024, Unit 5, Q19(b)(ii) (1 mark): Give a reason why the yield of the raspberry ketone by this method is not high. (1)
  8. June 2024, Unit 5, Q8 (1 mark): The formation of nitrobenzene requires benzene and concentrated nitric and sulfuric acids. Which is an equation for the reaction to form the electrophile? A HNO
  9. June 2024, Unit 5, Q17(a) (3 marks): The first step of the synthesis is the formation of methylbenzene, from benzene and chloromethane. Draw the mechanism of this reaction. Equations for the format
  10. January 2024, Unit 5, Q14(a)(i) (2 marks): Identify, by name or formula, the second reagent and the electrophile. (2)
  11. January 2024, Unit 5, Q14(a)(ii) (3 marks): Draw the mechanism for the reaction between the electrophile and benzene to form nitrobenzene. (3)
  12. October 2023, Unit 5, Q20(a)(i) (4 marks): Draw the mechanism for this reaction, including the formation of the electrophile. (4)
  13. June 2023, Unit 5, Q25(d)(i) (4 marks): Give the mechanism for Step 1. Include an equation for the formation of the electrophile. (4)
  14. January 2023, Unit 5, Q19(a)(i) (3 marks): Draw a mechanism for the reaction to form 2-nitrophenol. + is the electrophile. Assume that NO2 (3)
  15. October 2022, Unit 5, Q23(c)(i) (1 mark): Write an equation for the formation of the electrophile from methanoyl chloride. Use displayed formulae. (1)
  16. October 2022, Unit 5, Q23(c)(ii) (3 marks): Draw the mechanism of the formation of benzaldehyde from benzene using the electrophile from (c)(i). (3)
  17. June 2022, Unit 5, Q12(a)(i) (2 marks): Identify two errors in the mechanism by circling them. (2)
  18. June 2022, Unit 5, Q12(a)(ii) (2 marks): State how the errors identified in (a)(i) should be corrected. Justify your answer in terms of the structures involved. (2)
  19. January 2022, Unit 5, Q6(b) (1 mark): What type of reaction takes place? (1) A nucleophilic addition B nucleophilic substitution C electrophilic addition D electrophilic substitution
  20. October 2021, Unit 5, Q19(f)(iii) (4 marks): Complete the diagram, including curly arrows, to show the mechanism for the formation of compound X in this reaction. Include an equation for the regeneration o
  21. June 2021, Unit 5, Q20(b) (4 marks): Bromine reacts with cyclohexene to form 1,2-dibromocyclohexane, and with benzene to form bromobenzene. Compare and contrast these reactions, considering the typ
  22. January 2021, Unit 5, Q24(c)(i) (5 marks): A student suggested that caffeic acid could be synthesised by an electrophilic substitution of 1,2-dihydroxybenzene. Draw the mechanism of this electrophilic su
  23. October 2020, Unit 5, Q22(a)(i) (3 marks): Benzene is converted into nitrobenzene in Step 1 using a mixture of concentrated nitric acid and concentrated sulfuric acid. The electrophile is NO2 + . A stude

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