Which of the following is the schmidt rearrangement reaction?
A
RCOClNaN3−−−→ΔRNH2
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B
RCONHOOCR′−OH−−−→RNH2
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C
RCOOH+N3HH2SO4−−−−→R−NH2
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D
RCONH2Br2+4NaOH−−−−−−−−→RNH2
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Solution
The correct option is CRCOOH+N3HH2SO4−−−−→R−NH2 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 alkyl/aryl group migration leads to the formation of isocyanate intermediate.
Step 4: Formed isocyanate gets hydrolysed to form amine and CO2.