|Chapter 16: Ethers, Epoxides and Sulfides|
Using Halohydrins to
(review of Chapter 6 and 8)
MECHANISM OF HALOHYDRIN TO EPOXIDE
An acid/base reaction. The base deprotonates the alcohol forming an alkoxide intermediate that has enhanced nucleophilicity.
An intramolecular SN2 reaction where the alkoxide nucleophile attacks the electrophilic C displacing the leaving group, the halide ion. The nucleophile has to attack anti to the C-X bond.
|© Dr. Ian Hunt, Department of Chemistry, University of Calgary|