Hoffmann Bromamide Degradation
Hoffmann bromamide reaction converts:
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About This Question
- Subject
- chemistry
- Chapter
- organic compounds containing nitrogen
- Topic
- hoffmann bromamide degradation
- Difficulty
- Medium
- Year
- 2025
Solution
Correct Answer:
Amide to amine with one less carbon
The Hoffmann Bromamide Degradation is used to prepare primary amines from amides.
- Reaction: R−CONH2+Br2+4NaOH→R−NH2+Na2CO3+2NaBr+2H2O
- The reaction involves the migration of an alkyl/aryl group from the carbonyl carbon to the nitrogen atom.
- The carbonyl carbon is lost as carbonate ion, resulting in an amine that has one less carbon atom than the starting amide.
- Intermediate: An alkyl isocyanate (R−N=C=O) is formed during the mechanism.
This medium difficulty chemistry question is from the chapter organic compounds containing nitrogen, covering the topic of hoffmann bromamide degradation. It appeared in the 2025 exam.
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