Ch15: Epoxides

Chapter 15: Alcohols, Diols and Thiols

Ring Opening of Epoxides

reaction of epoxide with organometallic reagents

Reaction type: Nucleophilic Substitution

Summary

Grignard reagents, organolithiums or acetylides (all C nucleophiles) react with epoxides to give alcohols.
The reactions are essentially S_N2 reactions.
Ring strain makes epoxides more reactive than simple ethers.
Epoxide chemistry will be discussed more in Chapter 16.

QUESTION
Lithium aluminum hydride, LiAlH₄ reacts as a source of nucleophilic H, what would the product of the reaction of LiAlH₄ with ethylene oxide ? ANSWER

Related Reactions

Reaction of RLi and RMgX with aldehydes and ketones
Reaction of RLi and RMgX with esters
Reaction of RLi and RMgX with carbon dioxide