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 c


The following transformation can be obtained through dehydration and hydroboration.

Work Step by Step

The dehydration removes the OH and forms a double bond on which hydroboration can be performed. Since the OH is attached on the least substituted carbon, it is hydroboration. 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. There will also be an enantiomer of the product.
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