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Which of the following compounds can undergo Hofmann degradation (Hofmann bromamide reaction)?

1. CH3-C(=O)-NH-C(=O)-CH3
2. CH3-C(=O)-NH-CH3
3. CH3-C(=O)-NH2
4. Both (A) and (C)

Correct answer: CH3-C(=O)-NH2

Solution

Hofmann degradation works only on primary amides (RCONH2) where Br2/NaOH converts RCONH2 to RNH2 (amine with one fewer carbon). Option C (CH3CONH2) is the only primary amide; A is an imide and B is a secondary amide — neither undergoes Hofmann degradation.

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