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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc177

An amide X () undergoes Hofmann bromamide degradation to give amine Y. When Y is treated with / dil. at 273-278 K, nitrogen gas is evolved vigorously and an alcohol is formed. X is

  1. Aacetanilide
  2. B2-phenylacetamide,
  3. CN-methylbenzamide
  4. D4-methylbenzamide

Answer: B

Vigorous N2 evolution at 273-278 K shows that Y is an aliphatic primary amine (aromatic ones give stable diazonium salts). Y must therefore be benzylamine, from 2-phenylacetamide (loss of one carbon). 4-Methylbenzamide would give p-toluidine (diazonium salt, no N2), while N-methylbenzamide and acetanilide are N-substituted and do not undergo Hofmann degradation.
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