Revision Notes for Chemical Science: Schmidt Reaction! (Download PDF)

By Renuka Miglani|Updated : December 6th, 2021

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Candidates preparing for their CSIR NET exam might need to get some short study notes and strategies to apply while preparing for the key exam of their life. At this point, We at Byjus Exam Prep come up with short notes on the Schmidt Reaction, which comes under the Organic Chemistry section of the Chemical Science syllabus.

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SCHMIDT REACTION

The organic reaction in which hydrogen azide (HN3) reacts with electrophiles, such as aldehyde, ketone, carboxylic acid, tertiary alcohols, or alkenes in presence of an acid (i.e., acid catalyzed reaction) to give amines, amides, nitriles, or imines with and expulsion of Nitrogen (N2).

In this reaction mechanism, rearrangement occurs.

Notes-

1. The Schmidt reaction is used to convert substituted ketone to amides or lactams.

2. Schmidt reaction with aldehydes is not very much successful because of C – migration to form amide or H – migration to form nitrile.

3. In the case of tertiary alcohols, they give substitution by azide, via carbenium ion which gives alkyl azide that rearranges to yield an imine.

General Reaction -

Reaction mechanism-

For an acid: The reaction with carboxylic acid produces acyl azides, which rearranges to form isocyanates, which is further either solvolyzed to carbamates or hydrolyzed to carbamic acid; decarboxylation of which successfully gives amines with carboxylic acids.