In the Hofmann rearrangement an unsubstituted amide is treated with sodium hydroxide and bromine to give a primary amine that has one carbon lesser than starting amide.
General reaction :
+ NaOH + Br 2 
R–N=C=O 
R–NH 2
isocyanate
Mechanism :
CO 2 + R– 
R–NH 2
If the migrating group is chiral then its cofiguration is retained. Electron releasing effects in the migrating group increases reactivity of Hofmann rearrangement.
(i) Which of the following compound(s) cannot give Hofmann rearrangement :
Text Solution
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(i) Hofmann rearrangement is shown by 1º amide only
(ii) Rate of reaction in hofmann rearrangement among different amide depends on migratory aptitude of group in the amide.
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