(a) Give a mechanism for this reaction, showing how the two products arise as aconsequence of the resonance-stabilized intermediate.(b) The bromination of cyclohexene using NBS gives only one major product, as shown onthe previous page. Explain why there is no second product from an allylic shift.

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 6.27P: Reaction of this bicycloalkene with bromine in carbon tetrachloride gives a trans dibromide. In both...
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(a) Give a mechanism for this reaction, showing how the two products arise as a
consequence of the resonance-stabilized intermediate.
(b) The bromination of cyclohexene using NBS gives only one major product, as shown on
the previous page. Explain why there is no second product from an allylic shift.

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