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ExamsJEE MainChemistry

A compound 'X' on treatment with Br2/NaOH, provided C3H9N, which gives positive carbylamine test. Compound 'X' is: (1) CH3CH2CH2CONH2 (2) CH3CON(CH3)2 (3) CH3CH2COCH2NH2 (4) CH3COCH2NHCH3

  1. CH3CH2CH2CONH2
  2. CH3CON(CH3)2
  3. CH3CH2COCH2NH2
  4. CH3COCH2NHCH3

Correct answer: CH3CH2CH2CONH2

Solution

Br2/NaOH (Hofmann bromamide degradation) converts a primary amide RCONH2 to RNH2 with one fewer carbon. To obtain C3H9N that gives a positive carbylamine test (a primary amine, propan-1-amine), X must be butanamide CH3CH2CH2CONH2. The other choices are not primary amides and cannot undergo this reaction to give a primary amine.

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