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2 marksFunctional Group Analysis, Reactions and Mechanisms

CAPE Chemistry Unit 2 · 2017 · Paper 2 · Question 4(b)(ii)

Two isomeric phenyl alcohols, A and B (C8H10O), when reacted with concentrated sulfuric acid produce Compound D, which decolourizes bromine in an organic solvent. Acidified potassium dichromate(VI) oxidises both isomers to Compounds E and F respectively, which both produce a yellow precipitate with 2,4-DNP. Only Compound F forms a silver mirror with Tollens' reagent.

Explain the reactions which led to the production of Compounds E and F.

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Other parts of this question

  1. 4(a)Define the terms 'primary', 'secondary', and 'tertiary' as applied to alcohols, providing relevant examples using structural formulae for each.[6 marks]
  2. 4(b)(i)State the type of reaction producing Compound D and write its structural formula.[2 marks]
  3. 4(c)(i)Deduce the structural formulae of Compounds E and F.[2 marks]
  4. 4(c)(ii)Deduce the structural formulae of Compounds A and B.[2 marks]
  5. 4(d)Comment on the reaction of Compounds A and B to plane polarized light.[1 mark]

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