Question

Predict the product of the given rearrangement reaction.

• A.
• B.
• C.
• D.

Answer 1

The correct option is A

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 $N_2$ and aryl group migration leads to the formation of isocyanate intermediate.

Step 4: Formed isocyanate gets hydrolysed to form amine and $C{O}_2$.

Hence, option (a) is correct.