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

Answer

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