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

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

Grade:11

2 Answers

Aman Bansal
592 Points
9 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
102 Points
9 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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