Book Cover Organic Chemistry 4e Carey
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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


a mercurinium ion
alkoxymercuration-demercuration to give an ether
Questions: Related reactions
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.



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