Q17 / 150 · MHT CET 2025 (21 Apr Shift 2) · Chemistry
Which from following compounds is obtained when acetamide is warmed with bromine and excess conc. $\mathrm{KOH}_{(\mathrm{aq})}$ solution?
- A$\mathrm{CH}_4$
- B$\mathrm{CH}_3 \mathrm{COOH}$
- C$\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{NH}_2$
- Correct answerD$\mathrm{CH}_3 \mathrm{NH}_2$
Solution
The Hofmann bromamide degradation reaction converts primary amides to primary amines with one fewer carbon atom. For acetamide, $\mathrm{CH}_3\mathrm{CONH}_2$, the reaction proceeds as follows: $\mathrm{CH}_3\mathrm{CONH}_2 + \mathrm{Br}_2 + 4\mathrm{KOH} \xrightarrow{\text{warm}} \mathrm{CH}_3\mathrm{NH}_2 + \mathrm{K}_2\mathrm{CO}_3 + 2\mathrm{KBr} + 2\mathrm{H}_2\mathrm{O}$, yielding methylamine.
Examining the options:
A) $\mathrm{CH}_4$
B) $\mathrm{CH}_3\mathrm{COOH}$
C) $\mathrm{CH}_3\mathrm{CH}_2\mathrm{NH}_2$
D) $\mathrm{CH}_3\mathrm{NH}_2$
Only methylamine, with one carbon, matches the product structure and carbon count reduction. The correct answer is $\boxed{\text{D}}$.
Hence, the correct answer is option: 'D'.