Return to Contents Chapter 16: Ethers, Epoxides and Sulfides Ch 16 contents

Epoxidation of Alkenes
(review of Chapter 6)

epoxidation of alkenes

Reaction type: Electrophilic Addition

Summary

QUESTION What other addition reactions convert an alkene into a product with a three membered ring ? ANSWER

Related reactions

MECHANISM FOR REACTION OF ALKENES WITH PERACID
A single step reaction involving several changes. Start at the C=C as the nucleophile, make a bond to the slightly electrophilic O, break the weak O-O bond and form a C=O, break the original C=O to make a new O-H bond, break the original O-H to form the new C-O bond ! (phew !) formation of an epoxide by reaction of a peracid with an alkene

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© Dr. Ian Hunt, Department of Chemistry, University of Calgary