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1 markFunctional Group Analysis, Reactions and Mechanisms

CAPE Chemistry Unit 2 · 2013 · Paper 2 · Question 4(b)(iv)

Figure 5 shows the 3-step synthesis of 3-bromoaniline from benzene (Step I: nitration; Step II: bromination; Step III: reduction).

Explain why the bromo substituent enters the 3-position (meta-position) relative to the nitro group in Step II.

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Other parts of this question

  1. 4(a)(i)State the reagent needed to convert phenol into sodium phenoxide (reaction (i)).[1 mark]
  2. 4(a)(ii)Draw the structure of the organic product formed when phenol reacts with Br2(aq) (reaction (ii)).[1 mark]
  3. 4(a)(iii)Identify the reagent needed to convert phenol into phenyl propanoate (reaction (iii)).[1 mark]
  4. 4(b)(i)State the reagents and conditions required for each of Steps I, II, and III.[3 marks]
  5. 4(b)(ii)Outline the electrophilic substitution mechanism for the nitration of benzene in Step I, using curved arrows to show electron movements.[3 marks]
  6. 4(b)(iii)State the name of the reaction mechanism outlined in (b)(ii).[1 mark]
  7. 4(c)(i)Arrange benzene, nitrobenzene, and methylbenzene in order of increasing ease of reactivity towards electrophilic chlorination.[1 mark]
  8. 4(c)(ii)Draw the major mono-substituted aromatic chlorinated product formed from the reaction of chlorine with benzene, nitrobenzene, and methylbenzene, respectively.[3 marks]

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