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

Answer

The following synthetic conversion can be obtained through acid-catalyzed hydration or oxymercuration-demercuration.
1477871227

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.
Small 1477871227
Update this answer!

You can help us out by revising, improving and updating this answer.

Update this answer

After you claim an answer you’ll have 24 hours to send in a draft. An editor will review the submission and either publish your submission or provide feedback.