Organic Chemistry (8th Edition)

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

Chapter 8 - Reactions of Alkenes - Problems: Problem 8-11 a

Answer

Alkenes can be converted to alcohols through the hydroboration-oxidation synthesis pathway. In hydroboration-oxidation, a hydrogen atom is added to the less substituted vinylic carbon while OH$^-$ will be added to the less substituted vinylic carbon. This is a non-Markovnkov regiochemistry result because of the presence of peroxide.
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Work Step by Step

In the first step, BH$_2$ is added to the carbon on the end of the double bond, which is the less substituted vinylic carbon. H is added to the more substituted vinylic carbon. After this inital reaction, H$_2$O$_2$ and OH$^-$ are used in a reaction that substitutes BH$_2$ with OH$^-$, bearing the final product, Butan-2-ol.
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