Chapter 15: Alcohols, Diols and Thiols
Ring Opening of Epoxides
Reaction type: Nucleophilic Substitution
Grignard reagents, organolithiums or acetylides
(all C nucleophiles) react with epoxides to give alcohols.
The reactions are essentially
Ring strain makes epoxides more reactive than simple ethers.
Epoxide chemistry will be discussed more in
Lithium aluminum hydride, LiAlH
reacts as a source of nucleophilic H, what would the product of the reaction of LiAlH
with ethylene oxide ?
Reaction of RLi and RMgX with aldehydes and ketones
Reaction of RLi and RMgX with esters
Reaction of RLi and RMgX with carbon dioxide
Dr. Ian Hunt
, Department of Chemistry, University of Calgary