|Chapter 17: Aldehydes and Ketones. Nucleophilic Addition to C=O|
The Baeyer-Villager Reaction
Reaction type: Oxidation-reduction via Nucleophilic addition
|In this example the primary ethyl group migrates in preference to the methyl group so we end up with an ethyl ester.|
In this example the O ends up on the more substituted side.
Count C atoms!
THE BAEYER-VILLAGER REACTION
An acid/base reaction. Protonation of the carbonyl activates it while creating a more reactive nucleophile, the percarboxylate.
Now the nucleophilic O attacks the carbonyl C with the electrons from the C=O π bond going to the positive O.
Electrons from the O come back (this reforms the π bond of the C=O) and we migrate the C-C electrons to form a new C-O bond displacing the carboxylate as a leaving group.
Finally an acid/base reaction reveals the C=O and therefore the ester product.
|© Dr. Ian Hunt, Department of Chemistry, University of Calgary|