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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.
Which of the following compound(s) cannot give Hoffman rearrangement:

A

B

`CH_(3)-CH_(2)-overset(O)overset(||)(C)-NH-Ph`

C

D

`Ph-overset(O)overset(||)(C)-NH_(2)`

Text Solution

Verified by Experts

The correct Answer is:
B
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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. Arrange the following amides according to their relative reactivity when reacted with Br_(2) in excess of strong base:

Statement-1 : Electrons releasing group at para position of a migrating aryl group enhances. The rate of reaction in Hofmann's preparation of primary amine from amides. Statement-2: