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 c


To achieve this reaction, the alkane must first be converted into an alkene which is then converted into an alcohol.

Work Step by Step

To convert an alkylhalide, in this case, into an alkene we perform dehydrohalogenation. In dehydrohalogenation, in the presence of a strong base such as KOH, the Br atom will attack the K atom as it is partially positive in the KOH molecule. After abstracting the K atom, KBr leaves the molecule. Due to the leaving of KBr, an empty pi orbital now exists, this is a carbocation. To become more stable, a Hydrogen atom from a neighboring carbon donates its electrons between the C-C bond, creating a double bond. We now have an alkene. To this alkene we can perform hydroboration with BH$_3$,THF and H$_2$O$_2$/OH$^-$ as our reactants. This will follow non-Markovnikov regiochemistry, resulting in OH$^-$ beign added to the less substituted vinylic carbon while H is added to the more substituted vinylic carbon. The end result is our alcohol: 2,4-dimethylpentan-ol.
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