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:

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Question

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:

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