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Question

Predict the product of the given schmidt rearrangement.


A
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B
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C
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D
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Solution

The correct option is C
Carboxylic acid reacts with hydrazoic acid to form amines. This reaction is called Schmidt rearrangement.

Mechanism:
Step 1: Here, carboxylic acid was protonated and water gets eliminated to form acylium ion.

Step 2: Hydrazoic acid attacks the acylium ion to form protonated azide.

Step 3: Abstraction of proton followed by elimination of N2 and aryl group migration leads to the formation of isocyanate intermediate.

Step 4: Formed isocyanate gets hydrolysed to form amine and CO2.


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