Organic Chemistry (8th Edition)

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

Chapter 8 - Reactions of Alkenes - Problems: Problem 8-12

Answer

See the diagram.
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Work Step by Step

Both enantiomers will be formed as products, this process shows how the other product not shown in the textbook is formed. Following the exact same process with the same reactants, hydroboration of 1-methylcyclopentene occurs. First, BH$_3$,THF react and H and BH$_2$ are added in syn regiochemical fashion. The H is added to the carbon with they methyl group attached, the more substituted vinylic carbon. H is coming towards with a wedge while CH$_3$ has a dash and is going "into" the page. Likewise, BH$_2$ is added and since the H on a wedge, BH$_2$ will also be on a wedge while the H attached to the same carbon will be on a dash. After reacting this compound with H$_2$O$_2$/OH$^-$, BH$_2$ is substituted with OH$^-$ and retains the stereochemistry.
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