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 387: 8-47 p

Answer

The major product is shown in the picture.

Work Step by Step

1) Electrophilic attack of the double bond forms a mercurinium ion. 2) Water attacks the most substituted carbon and opens the ring to give an organomercurial alcohol (intermediate). 3) Demercuration with $NaBH_4$ replaces the mercuric fragment with hydrogen to give the alcohol.
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