Organic Chemistry (8th Edition)

Published by Pearson
ISBN 10: 0321768418
ISBN 13: 978-0-32176-841-4

Chapter 6 - Alkyl Halides: Nucleophilic Substitution and Elimination - Problems - Page 229: Problem 6-10 c

Answer

The mechanism is shown in the attached image.

Work Step by Step

The mechanism is shown in the attached image. The bromination of this compound will replace the hydrogen, resulting in the most stable intermediary radical. So, the hydrogen next to the benzene ring is replaced so that the radical is stabilized by resonance.
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