- A
- BCO
- CHCO
- DCO
View written solutionFree
Correct answer: D
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Identify the reaction
The reaction of an amide with hypobromite is the Hofmann bromamide degradation (or Hofmann rearrangement).
General reaction:
In this reaction, the amide loses one carbon atom and gives a primary amine with one less carbon.
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What happens to the carbonyl carbon?
During the rearrangement, the carbonyl carbon is removed from the amide skeleton. The intermediate formed ultimately gives an isocyanate, which on hydrolysis produces:
Thus, the carbonyl carbon is initially liberated as carbon dioxide.
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Role of hypobromite medium
Since the reaction is carried out in basic medium (hypobromite is generated in alkali), the formed does not remain free for long. It reacts with hydroxide:
Therefore, in the reaction mixture, the carbonyl carbon is finally present as carbonate ion.
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Check the options
- A: — formed initially, but in alkaline medium it is converted further.
- B: — incorrect.
- C: — not the final species in strongly basic medium.
- D: — correct final form in alkaline hypobromite medium.
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Conclusion
Hence, the carbonyl carbon is lost as:
So the correct option is D.
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