The bicyclic alkene car-3-ene, a constituent of turpentine, undergoes catalytic hydrogenation to give only one of the

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The bicyclic alkene car-3-ene, a constituent of turpentine, undergoes catalytic hydrogenation to give only one of the two possible stereoisomeric products. The product has the common name cis-carane, indicating that the methyl group and the cyclopropane ring are on the same face of the cyclohexane ring. Suggest an explanation for this stereochemical outcome.

CH3 H3C H H3C H 100 atm H2, PtO2, CНCH,ОH, 25°C H not H3C H3C H;C- CH3 CH3 CH3


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Organic Chemistry structure and function

ISBN: 978-1429204941

6th edition

Authors: K. Peter C. Vollhardt, Neil E. Schore

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