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 a


The following synthetic conversion can be obtained through oxymercuration–demercuration of alkenes.

Work Step by Step

1) Electrophilic attack of $ ^+Hg(OAc)$ forms a mercurinium ion. 2) Methoxide attacks the most substituted carbon and opens the ring to give an organomercurial ether. 3) Demercuration with $NaBH_4$ replaces the mercuric fragment with hydrogen to give an ether.
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