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 b

Answer

The following synthetic conversion can be obtained through adding a strong base (KOH) and then oxymercuration-demercuration of alkene.
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Work Step by Step

Since we need a double bond to perform oxymercuration- demercuration, we have to first make alkene from 1-iodo-2-methylcyclopentane. The addition of KOH in presence of heat favors elimination to give an alkene. Then oxymercuration- demercuration is 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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