Organic Chemistry (8th Edition)

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

Chapter 8 - Reactions of Alkenes - Problems: Problem 8-15 b

Answer

The following transformation can be obtained with hydroboration of alkene.
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Work Step by Step

Since the OH is attached to the least substituted carbon, this reaction takes place with hydroboration, instead of oxymercuration-demercuration. Borane adds to the double bond in a single step. Boron adds to the less hindered, less substituted carbon, and hydrogen adds to the more substituted carbon. And then $BH_2$ gets replaced by OH. There will be two products because borane can attack from either top or bottom.
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