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JEE Advanced levelSingle correct optionDifficulty 3 of 3g3100

(S)-2-Methylbutanamide, , is treated with and aqueous (Hofmann degradation). The product is

  1. A2-Methylbutan-1-amine
  2. B(S)-Butan-2-amine
  3. C(R)-Butan-2-amine
  4. DRacemic butan-2-amine

Answer: B

In the Hofmann rearrangement the alkyl group migrates from the carbonyl carbon to nitrogen with retention of configuration, losing the carbonyl carbon as . Hence is replaced by on the same carbon. The CIP priority order is unchanged ( and both outrank ethyl, methyl and H), so (S) gives (S)-butan-2-amine.
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