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Why only THF (tetrahydro furan) or cyclic ethers are used as solvents in oxymercuration demercuration???

Swapnil Saxena , 13 Years ago
Grade 11
anser 2 Answers
Aman Bansal

Last Activity: 13 Years ago

Daer Swapnil,

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.

 

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:
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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Swapnil Saxena

Last Activity: 13 Years ago

Still dont get it .

Why only THF is used not any other solvents like straight chain ethers ? ? ? Does THF play any specific role in the reaction???

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