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Hofmann rearrangement In the Hofmann r...

Hofmann rearrangement
In the Hofmann rearrangement an unsubstitued amide is treated with sodium hydroxide and bromine to give a primary amine that has one carbon lesser than starting amide.
Gneral reaction:
If the migrating group is chiral then its configuration is retained. Electron releasing effects in the migrating group increase reactivity of Hofmann rearangement.
Arrange the following amides according to their relative reactivity when reacted with `Br_(2)` in excess of strong base:

A

`IV gt I gt II gt III`

B

`II gt I gt III gt IV`

C

`II gt IV gt III gt I`

D

`II gt I gt IV gt III`

Text Solution

Verified by Experts

The correct Answer is:
D
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Hofmann rearrangement In the Hofmann rearrangement an unsubstitued amide is treated with sodium hydroxide and bromine to give a primary amine that has one carbon lesser than starting amide. Gneral reaction: If the migrating group is chiral then its configuration is retained. Electron releasing effects in the migrating group increase reactivity of Hofmann rearangement. Which of the following compound(s) cannot give Hoffman rearrangement:

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Hofmann's Bromamide reaction