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Question
Predict the product of the given schmidt rearrangement.
Predict the product of the given schmidt rearrangement.
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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.
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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