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Question

The carboxylic acids react with hydrazoic acid in presence of H2SO4 to form a primary amine. This reaction is called as :

A
Curtius rearrangement
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B
Lossen rearrangement
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C
Schmidt reaction
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D
Schotten-Boumann reaction
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Solution

The correct option is C Schmidt reaction
The above reaction is called Schmidt reaction which involves alkyl migration over the carbon–nitrogen chemical bond in an azide with expulsion of nitrogen. The carboxylic acid Schmidt reaction starts with acylium ion obtained from protonation and loss of water. Reaction with hydrazoic acid forms the protonated azido ketone, which goes through a rearrangement reaction with the alkyl group R, migrating over the CN bond with expulsion of nitrogen. The protonated isocyanate is attacked by water forming carbamate, which after deprotonation loses carbon dioxide to the amine.
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