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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