A-LevelChemistryOrganic synthesis9701/12 · Oct/Nov 2009 · Q281 Mark

The characteristic odour of rum is attributed to the compound 2-ethyl-3-methylbutanoic acid. [Figure 28.1] Which compound will produce 2-ethyl-3-methylbutanoic acid by heating under reflux with alcoholic sodium cyanide and subsequent acid hydrolysis of the reaction product?

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ACH3CH(CH3)CH2CH(Br)CH3

BCH3CH(CH3)CH(Br)CH2CH3

CCH3CH(C2H5)CH(CH3)CH2Br

DCH3CH(CH2Br)CH2CH(CH3)CH3

✓ Correct answer

B: CH3CH(CH3)CH(Br)CH2CH3

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Topic: Organic synthesis, A-Level Chemistry (syllabus 9701). Multiple choice, 1 mark.
Source: A-Level Chemistry, Oct/Nov 2009 Paper 1 Variant 2, question 28.

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