Reaction of HBr with 3-methylcyclohexene yields a mixture of four products: CH3 .CH3 „CH3 HBr `Br Br cis & trans cis & trans However, similar reaction of HBr with 3-bromocyclohexene produces a single product, trans-1,2-dibromocyclohexane: Br Br HBr 'Br Propose a structure for an ionic intermediate that is responsible for the unique regiochemistry and stereochemistry of the reaction of 3-bromocyclohexene with HBr.

Reaction of HBr with 3-methylcyclohexene yields a mixture of four products: CH3 .CH3 „CH3 HBr `Br Br cis & trans cis & trans However, similar reaction of HBr with 3-bromocyclohexene produces a single product, trans-1,2-dibromocyclohexane: Br Br HBr 'Br Propose a structure for an ionic intermediate that is responsible for the unique regiochemistry and stereochemistry of the reaction of 3-bromocyclohexene with HBr.

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

Chapter6: Reactions Of Alkenes

Section: Chapter Questions

Problem 6.38P: Reaction of -pinene with borane followed by treatment of the resulting trialkylborane with alkaline...

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