Reaction of a-pinene with borane followed by treatment of

Chapter 6, Problem 6.38

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Reaction of a-pinene with borane followed by treatment of the resulting trialkylborane with alkaline hydrogen peroxide gives the following alcohol. -Pinene 1.BH3 2.H2O2, NaOH OH Of the four possible cis,trans isomers, one is formed in over 85% yield. (a) Draw structural formulas for the four possible cis,trans isomers of the bicyclic alcohol. (b) Which is the structure of the isomer formed in 85% yield? How do you account for its formation? Make a model to help you make this prediction.

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