Identify the major product C formed in the following reaction sequence:

• A

  butylamine
• B

  butanamide
• C

  $\alpha$-bromobutanoic acid
• Correct answer
  D

  propylamine

Solution

- Step-I is $\mathrm{S}_{\mathrm{N}}$ reaction with $\stackrel{\ominus}{\mathrm{C}} \mathrm{N}$ nucleophile. - Step-Il will give amide. - Step-III is Hoffmann bromamide degradation reaction.

Hence, the correct answer is option: 'D'.