Schmidt Reaction (Rearrangement): definition| Mechanism| example

What is Schmidt Reaction explain?

Schmidt reaction is a acid-catalyzed Rearrangement reaction of hydrazoic acid reactions of electrophiles, like carbonyl compounds, alkenes tertiary and alcohols. The following these substrates include amines, nitriles, amides or imines, rearrangement and extrusion of nitrogen.

Schmidt Reaction for synthesis of amine
Schmidt reaction: synthesis of amine
Schmidt Reaction for synthesis of Nitrile and amide
Schmidt Reaction: Synthesis of Nitrile and Amide

Schmidt Reaction Mechanism:

The mechanism shown is for an aldehyde regent but it can be easily extended to the other regents. The reaction begins with abstraction of a proton from the acid by the aldehyde or other reagent to activate it for future attack. The generated water molecule then abstracts the proton from hydrazoic acid to regenerate the acid and produce an azide anion which then attacks the activated reagent. A series of steps and the release of a molecule of nitrogen gas result in the final product.

Schmidt Reaction Mechanism for synthesis of amine| Schmidt Reaction Mechanism for Producing nitrile
Schmidt Reaction Mechanism for Synthesis of Nitrile |Schmidt Reaction Mechanism for Producing Amides

Related Reaction:

1. Baeyer-Villiger oxidation 2 Beckmann rearrangement
3. Claisen rearrangement 4. Cope rearrangement
5. Curtius rearrangement6. Eschenmoser-Claisen rearrangement
7. Fries rearrangement 8. Hofmann rearrangement
9. Ireland-Claisen rearrangement10. Johnson-Claisen rearrangement
11. Wagner-Meerwein rearrangement12. Wolff rearrangement
Related Reaction to Schmidt Rearrangement Reaction


  1. Schmidt, K. F. Z. Angew. Chem. 1923, 36, 511. Karl Friedrich Schmidt (1887–1971) collaborated with Curtius at the University of Heidelberg, where Schmidt became a Professor of Chemistry after 1923.
  2. Schmidt, K. F. Ber. dtsch. Chem. Ges. 192457, 704–706.

1 thought on “Schmidt Reaction (Rearrangement): definition| Mechanism| example”

Leave a Comment