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3 marksFunctional Group Analysis, Reactions and Mechanisms

CAPE Chemistry Unit 2 · May/June 2019 · Paper 2 · Question 1(a)(iii)

The compound (CH3)2CHCBr(CH3)CH2CH2CH3 reacts with aqueous sodium hydroxide to produce an alcohol.

Outline a mechanism for the reaction, using curved arrows to show the movement of electrons. Show clearly the structure of any intermediates formed as well as the final product.

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Other parts of this question

  1. 1(a)(i)State the name of the starting compound.[1 mark]
  2. 1(a)(ii)State the type of reaction which takes place when the compound reacts with sodium hydroxide.[1 mark]
  3. 1(b)(i)State the reagents and condition(s) used to convert benzene into nitrobenzene.[3 marks]
  4. 1(b)(ii)Outline the mechanism for the reaction described in (b) (i).[5 marks]
  5. 1(c)(i)Write the reagents used for the reactions I, II and III.[3 marks]
  6. 1(c)(ii)State the class of compounds to which E belongs, giving the commercial significance of such compounds.[2 marks]
  7. 1(d)(i)Use the compound ethylamine CH3CH2NH2 and a relevant equation to explain the statement above.[3 marks]
  8. 1(d)(ii)The pKb values for ethanamide, ethylamine and phenylamine are 14.51, 3.27 and 9.38 respectively. Account for the difference in these pKb values.[4 marks]
  9. 1(e)Complete the table by inserting the appropriate observations and reagents.[5 marks]

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