Bromination can occur in a 1,4 fashion across conjugated double bonds, as shown here for cyclohexa-1,3-diene. One mechanism that has been proposed involves a five-membered ring, bromonium ion intermediate, as shown below. (a) According to this mechanism, what should the stereochemistry be for the products-namely, all cis, all trans, or a mixture of both? (b) Observations from experiment show that both cis and trans products are formed. Does this support or discredit the proposed mechanism shown here? Br Br2 Cyclohexa-1,3-diene Br :Br: Br: Br:
Bromination can occur in a 1,4 fashion across conjugated double bonds, as shown here for cyclohexa-1,3-diene. One mechanism that has been proposed involves a five-membered ring, bromonium ion intermediate, as shown below. (a) According to this mechanism, what should the stereochemistry be for the products-namely, all cis, all trans, or a mixture of both? (b) Observations from experiment show that both cis and trans products are formed. Does this support or discredit the proposed mechanism shown here? Br Br2 Cyclohexa-1,3-diene Br :Br: Br: Br:
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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