SCHMIDT REACTION

CONTENTS: INTRODUCTION MECHANISM APPLICATIONS

INTRODUCTION: Rearrangement reaction is also called Molecular It is a type of Named Rearrangement reaction. Rearrangement reaction is also called Molecular Rearrangement. This rearrangement involves migration of an alkyl or aryl group with its bonding electrons from carbon to the adjacent nitrogen atom.

DEFINITION: Carboxylic acids and hydrazoic acids react in presence of concentrated sulphuric acids to give amines. Schmidt reaction also occur in ketones

FOR ALDEHYDES: This reaction closely releated to Hofmann and Curtius reaction, of all which involves formation of isocyanate intermediate through the migration of group from carbon to nitrogen. the rearrangement closely resemble the Beckmann rearrangement.

MECHANISM FOR ACIDS:

FOR STERICALLY HINDERED ACIDS: EXAMPLE 2,4,6 TRI METHYL BENZOIC ACIDS 2,4,6 Trimethyl benzoic acid

REACTION WITH KETONES:

MECHANISM FOR ALDEHYDES:

IF ‘H’ MOVES:

APPLICATIONS: Example 1: PREPARATION OF PRIMARY AMINES: Example 1: It is a direct method for the preparation of primary amines from carboxylic acid and give usually better yield than the hofmann or curtius reaction.

Example 2:

PREPARATION OF a AMINOACIDS:

Preparation of lactones: Cyclic ketones react to give lactones

If excess of hydrazoic acid used: cyclic ketones tetrazoles

THANK YOU