Draw a reaction-energy diagram for the propagation steps of the free-radical addition of HBr to isobutylene. Draw curves representing the reactions leading to both the Markovnikov and the anti-Markovnikov products. Compare the values of ∆G° and Ea for the rate-limiting steps, and explain why only one of these products is observed.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter10: Organohalides
Section10.SE: Something Extra
Problem 18MP: Draw the electron-pushing mechanism for the propagation steps of the allylic bromination reactions...
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Draw a reaction-energy diagram for the propagation steps of the free-radical addition of HBr to isobutylene. Draw curves representing the reactions leading to both the Markovnikov and the anti-Markovnikov products. Compare the values of ∆G° and Ea for the rate-limiting steps, and explain why only one of these products is observed.

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