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


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.

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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