Book Cover Organic Chemistry 4e Carey
Online Learning Center

Chapter 14: Organometallic Compounds



Overview of Reactions | Overview of Grignard Reactions | Addition of RLi and RMgX to Aldehydes and Ketones | Addition of RCCM to Aldehydes and Ketones | Addition of RLi and RMgX to Esters | Alkane synthesis using R2CuLi | Reactions of RZnX | Oxymercuration-Demercuration of Alkenes |


Oxymercuration-Demercuration of Alkenes

Chapter 14: Organometallic Compounds

Oxymercuration-Demercuration of Alkenes

alkene alkoxymercuration-demercuration to give an alcohol
Reaction type:  Electrophilic Addition

Summary

a mercurinium ion
alkoxymercuration-demercuration to give an ether
Questions: Related reactions
 
MECHANISM FOR REACTION OF ALKENES WITH Hg(OAc)2 / H2O
Step 1:
The p electrons act as the nucleophile with the electrophilic Hg and loss of an acetate ion as a leaving group, forming the mercurinium ion.
oxymercuration / demercuration of C=C
Step 2:
Water functions as a nucleophile and attacks one of the mercury substituted carbons resulting in cleavage of the C-Hg bond.
Step 3:
The acetate ion functions as a base deprotonating the oxonium ion to give the alcohol. This completes the oxymercuration part of the reaction.
Step 4:(mechanism not shown)
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.


 


HOME UP PREVIOUS

Begin a search: Catalog | Site | Campus Rep

MHHE Home | About MHHE | Help Desk | Legal Policies and Info | Order Info | What's New | Get Involved


Copyright ©2000 The McGraw-Hill Companies. All rights reserved. Any use is subject to the Terms of Use and Privacy Policy.
McGraw-Hill Higher Education is one of the many fine businesses of The McGraw-Hill Companies.
For further information about this site contact mhhe_webmaster@mcgraw-hill.com.


Corporate Link