Organic Chemistry (8th Edition)

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

Chapter 8 - Reactions of Alkenes - Problems: Problem 8-16 a

Answer

The addition is not stereospecific because the Br can attack from either top or bottom.

Work Step by Step

After the double bond attacks the H in HBr, the carbocation at the most substituted carbon forms. The hybridization of this carbon is $sp^2$, which is planar. This planar carbon causes the non-stereoselectivity because the $Br^-$ can attack on either side, top or bottom.
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