Bromination can occur in a 1,4 fashion across conjugated double bonds, as shownhere for cyclohexa-1,3-diene. One mechanism that has been proposed involves afive-membered ring, bromonium ion intermediate, as shown below.(a) According to this mechanism, what should the stereochemistry be for theproducts-namely, all cis, all trans, or a mixture of both?(b) Observations from experiment show that both cis and trans products areformed. Does this support or discredit the proposed mechanism shown here?BrBr2Cyclohexa-1,3-dieneBr:Br:Br:Br:

It is given that to a diene substrate Br2/CCl4 is added and 1,4-bromination has occurred, and the…

Answered: Bromination can occur in a 1,4 fashion…

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

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.31P

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