Chapter 16: Ethers, Epoxides and Sulfides |
Using Halohydrins to
Synthesise Epoxides
(review of Chapter 6 and 8)
Summary
QUESTIONS
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ANSWER |
Related reactions
MECHANISM
OF HALOHYDRIN TO EPOXIDE |
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Step 1:
An acid/base reaction. The base deprotonates the alcohol forming an alkoxide intermediate that has enhanced nucleophilicity. |
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Step 2:
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. |
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© Dr. Ian Hunt, Department of Chemistry |