Single correct · +4 / −1

The product of reaction of acetone with HCN is:

  1. (a) Acetaldehyde cyanohydrin
  2. (b) Acetone cyanohydrin
  3. (c) Lactic acid
  4. (d) No reaction
Answer and solution

Answer (b) Acetone cyanohydrin

Solution

Chemistry ma’am · 3 steps

Cyanide adds to the carbonyl carbon of acetone, so the cyanohydrin keeps both methyl groups.

  1. Nucleophile forms. A trace of base pulls H⁺ off HCN and gives CN⁻, the real nucleophile. The carbonyl carbon of acetone carries a partial positive charge, so CN⁻ attacks it.
  2. Addition happens. The C=O π bond breaks and oxygen takes a negative charge. This alkoxide then picks up H⁺ from HCN, so -OH and -CN end up on the same carbon.

    (CH₃)₂C=O + HCN → (CH₃)₂C(OH)CN

  3. So. The product is 2-hydroxy-2-methylpropanenitrile, called acetone cyanohydrin, which is option (b).

The idea to keep. Aldehydes and most ketones add HCN across C=O: the CN goes to carbon and the H goes to oxygen. The starting carbon skeleton stays, plus one extra carbon from CN.

Answer from the NTA final answer key. Solution by PrepWiser.

Study Aldehydes & Ketones

Asked about 130 times in JEE Main since 2020.