Return to Contents  Chapter 22: Amines  Ch 22 contents
Hofmann Elimination
Reaction type: Elimination

Summary

completely methylate then convert to the ammonium hydroxide salt
1,2-elimination of the ammonium salt gives mainly the less highly substituted alkene
Related reactions
MECHANISM OF THE HOFMANN ELIMINATION
The initial steps are an example of the alkylation of an amine by methyl iodide. The mechanism of the elimination step is shown. 

When heated, the hydroxide removes the more accessible proton, the π bond of the alkene C=C forms and the leaving group, a neutral amine departs.

the Hofmann elimination  of ammonium salts

previous page
next page
Dr. Ian Hunt, Department of Chemistry, University of Calgary