|Chapter 16: Ethers, Epoxides and Sulfides|
Cleavage of Ethers by HI or HBr
Reaction type: Nucleophilic Substitution
An acid/base reaction. Protonation of the alcoholic oxygen to make a better leaving group. This step is very fast and reversible. The lone pairs on the oxygen make it a Lewis base.
The bromide ion functions as the nucleophile and attacks to displace the good leaving group, neutral alcohol molecule, by cleaving the C-O bond. This results in the formation of an alkyl bromide and an alcohol.
|© Dr. Ian Hunt, Department of Chemistry, University of Calgary|