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Question

A carbonyl compound gives a positive iodoform test but does not reduce Tollen's reagent or Fehling's solution. It forms a cyanohydrin with HCN, which on hydrolysis gives a hydroxy acid with a methyl side chain. The compound is:
  1. propionaldehyde
  2. acetaldehyde
  3. crotonaldehyde
  4. acetone

A
acetaldehyde
B
crotonaldehyde
C
propionaldehyde
D
acetone
Solution
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Acetone gives a positive iodoform test as it is a methyl ketone. It does not reduce Tollen's reagent or Fehling's solution which are the test's characteristics of aldehydes.

Acetone forms a cyanohydrin with HCN (characteristic of a carbonyl group) which on hydrolysis gives a hydroxy acid with a methyl side chain.

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