Organic Chemistry (8th Edition)

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

Chapter 8 - Reactions of Alkenes - Problems: Problem 8-9 c


The following synthetic conversion can be obtained through acid-catalyzed hydration or oxymercuration-demercuration.

Work Step by Step

The picture shows the process for acid catalyzed hydration. It can be observed that there is a chance of carbocation rearrangement. The resulting product will be a mixture of products. Thus, to obtain the desired product oxymercuration-demercuration should be performed with the following steps: 1) Electrophilic attack of $ ^+Hg(OAc)$ forms a mercurinium ion. 2) $OH^-$ attacks the most substituted carbon and opens the ring to give an organomercurial alcohol. 3) Demercuration with $NaBH_4$ replaces the mercuric fragment with hydrogen to give an alcohol.
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