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Question

Reaction of R−COOH with N3H gives RNH2 as the main product. The intermediate(s) involved in this reacton is/are :

A
RNHNH2
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B
RCON3
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C
RNCO
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D
RCONH2
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Solution

The correct options are
B RCON3
C RNCO
This reaction is called Schmidt reaction. It involves alkyl migration over the carbon-nitrogen bond in an azide with expulsion of nitrogen.
RCOOH+HN3H+RNCOH2ORNH2
The intermediates involved can be seen in the mechanism provided.

115216_31545_ans.png

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