Case study·Standard multi-step (3/5)·No calculator

Difficulty guide

The label describes the problem, not your ability.

1/5 - Foundational

Warm-up setup; checks one basic idea.

2/5 - Routine exam skill

Normal syllabus skill; usually one main rule or interpretation.

3/5 - Standard multi-step

Exam-style problem with multiple steps or a common trap.

4/5 - Hard exam skill

High-end exam problem; combines methods carefully.

5/5 - Challenge

Stretch problem beyond normal exam pressure.

Question

A laboratory has three starting materials: CH3COCl\mathrm{CH_3COCl}, CH3CN\mathrm{CH_3CN} and CH3CCH\mathrm{CH_3C{\equiv}CH}. A student must prepare carbonyl compounds under controlled conditions.
Total: 3 marks

(a) Which starting material can give ethanal by Rosenmund reduction? (1 mark)

(b) Which starting material gives ethanal by Stephen reduction followed by hydrolysis? (1 mark)

(c) Which starting material gives propanone on mercuric-ion catalysed hydration? (1 mark)

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