|Chapter 15: Alcohols, Diols and Thiols|
(review of Chapter 14)
Reaction type: Electrophilic Addition
MECHANISM FOR REACTION OF ALKENES WITH Hg(OAc)2 / H2O
The C=C p electrons act as the nucleophile with the electrophilic Hg and loss of an acetate ion as a leaving group, forming the mercurinium ion.
Water functions as a nucleophile and attacks one of the mercury substituted carbons resulting in cleavage of the C-Hg bond.
The acetate ion functions as a base deprotonating the oxonium ion to give the alcohol. This completes the oxymercuration part of the reaction.
The hydride reduces the Hg off, creating a C-H bond while breaking the C-Hg bond. This is the demercuration part of the process.
|© Dr. Ian Hunt, Department of Chemistry, University of Calgary|