Organic Chemistry (8th Edition)

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

Chapter 8 - Reactions of Alkenes - Problems: Problem 8-7 a

Answer

The mechanism used is Oxymercuration–demercuration.
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Work Step by Step

The reagents used are ethanol and $NaBH_4$. The mechanism is Oxymercuration–demercuration. Steps: 1) The arrow goes from the double bond to the Hg and back from Hg to the carbon. This electrophilic attack forms a mercurinium ion. 2) Ethanol opens the ring to give an organomercurial alcohol. It attacks on the most substituted carbon. 3) Deprotonation of the ethanol happens, leaving behind a organomercurial alcohol.
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