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 b

Answer

Alkenes can be converted into alchols through the oxymercuration (and demercuration) synthesis pathway. In oxymercuration, OH$^-$ will be added to the more substituted vinylic carbon and H added to the lesser substituted vinylic carbon. This follows Markovnikov's Rule.
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Work Step by Step

In the first reaction, the alkene is treated with mercury acetate. Protonation of the alkene double bond yields a carbocation intermediate. Further reaction with H$_2$, THF causes the carbocation to cease and OH is attached to the more substituted carbon while HgOAc is attached to the lesser. A final reaction is carried out with NaBH$_4$ which causes HgOAc to leave the compound and only an alcohol is left.
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