Grade 11Organic Chemistry

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

Swapnil Saxena

14 Years agoGrade 11

2 Answers

Aman Bansal

14 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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