JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
The reaction of
with bromine and gives as the end product. Which one of the following is the intermediate product formed in this reation?
with bromine and gives as the end product. Which one of the following is the intermediate product formed in this reation?- A

- BR NH Br
- CR N = C = O
- D

View written solutionFree
Correct answer: C
-
The reaction of an amide with bromine and giving is the Hofmann bromamide degradation (also called Hofmann rearrangement).
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General reaction: This converts an amide into a primary amine with loss of one carbon atom.
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Mechanism outline:
- The amide first reacts with bromine in base to form N-bromoamide:
- On treatment with base, rearrangement occurs to give an isocyanate intermediate:
- The isocyanate then hydrolyzes to form the amine:
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Therefore, the key intermediate product formed in this reaction is: which is an isocyanate.
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Checking options:
- Option B: is not the correct rearranged intermediate; the actual initial brominated species is , not simply .
- Option C: ✔ correct, the isocyanate intermediate.
Hence, the correct answer is Option C.
- Comparison with stored correct answer: Stored correct answer = C Derived answer = C They match.
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