Question:medium

Which of the following compounds is obtained when acetamide is warmed with bromine and excess KOH (aq) solution?

Show Hint

In the Hofmann rearrangement, the reaction of an amide with bromine and KOH leads to the formation of a primary amine by removing the carbonyl group.
Updated On: Jun 30, 2026
  • \( \text{CH}_4 \)
  • \( \text{CH}_3\text{CH}_2\text{NH}_2 \)
  • \( \text{CH}_3\text{COOH} \)
  • \( \text{CH}_3\text{NH}_2 \)
Show Solution

The Correct Option is D

Solution and Explanation

Step 1: Understanding the Question:
The reaction involves an amide (acetamide) reacting with bromine and aqueous KOH, which is the reagent set for the Hoffmann bromamide degradation.
Step 2: Detailed Explanation:
Hoffmann bromamide degradation converts a primary amide into a primary amine with one fewer carbon atom.
Acetamide (\( \text{CH}_3\text{CONH}_2 \)) contains 2 carbon atoms.
Upon reaction with \( \text{Br}_2/\text{KOH} \), the carbonyl group is removed as carbonate, leaving methylamine (\( \text{CH}_3\text{NH}_2 \)), which contains 1 carbon atom.
\[ \text{CH}_3\text{CONH}_2 + \text{Br}_2 + 4\text{KOH} \xrightarrow{\Delta} \text{CH}_3\text{NH}_2 + 2\text{KBr} + \text{K}_2\text{CO}_3 + 2\text{H}_2\text{O} \]
Step 3: Final Answer:
The product obtained is methylamine (\( \text{CH}_3\text{NH}_2 \)).
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