12. Alcohols, Ethers, Epoxides and Thiols
Ether Cleavage
Problem 14.16
Textbook Question
Textbook QuestionBoron tribromide (BBr3) cleaves ethers to give alkyl halides
and alcohols.
R-O-R′ + BBr3 → R-O-BBr2 + R′Br
R-O-BBr2 + 3H2O → ROH + B(OH)3 + 2HBr
The reaction is thought to involve attack by a bromide ion
on the Lewis acid–base adduct of the ether with BBr3
(a strong Lewis acid).
Propose a mechanism for the reaction of butyl methyl ether
with BBr3 to give (after hydrolysis) butan-1-ol
and bromomethane.
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