Boron tribromide (BBr3) cleaves ethers to give alkyl halides and alcohols.R¬O¬R′ + BBr3 ¡ R¬O¬BBr2 + R′BrR¬O¬BBr2 + 3 H2O ¡ ROH + B(OH)3 + 2 HBrThe reaction is thought to involve attack by a bromide ion on the Lewis acid–base adductof the ether with BBr3 (a strong Lewis acid). Propose a mechanism for the reaction ofbutyl methyl ether with BBr3 to give (after hydrolysis) butan-1-ol and bromomethane.
Boron tribromide (BBr3) cleaves ethers to give alkyl halides and alcohols.R¬O¬R′ + BBr3 ¡ R¬O¬BBr2 + R′BrR¬O¬BBr2 + 3 H2O ¡ ROH + B(OH)3 + 2 HBrThe reaction is thought to involve attack by a bromide ion on the Lewis acid–base adductof the ether with BBr3 (a strong Lewis acid). Propose a mechanism for the reaction ofbutyl methyl ether with BBr3 to give (after hydrolysis) butan-1-ol and bromomethane.
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter10: Alcohols
Section: Chapter Questions
Problem 10.49P
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Boron tribromide (BBr3) cleaves ethers to give
R¬O¬R′ + BBr3 ¡ R¬O¬BBr2 + R′Br
R¬O¬BBr2 + 3 H2O ¡ ROH + B(OH)3 + 2 HBr
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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