Organic Chemistry (8th Edition)

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

Chapter 8 - Reactions of Alkenes - Study Problems - Page 391: 8-70 a

Answer

The proposed mechanism is shown in the picture.

Work Step by Step

Electrophilic attack forms a mercurinium ion. Then internal OH attack happens on the most substituted carbon. Then the H from OH is deprotonated using $AcO^-$. Then $NaBH_4$ replaces $Hg(OAc)$ with a hydrogen.
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