An optically active alkyne A (C 10 H 14 ) can be catalytically hydrogenated to butylcyclohexane. Treatment

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An optically active alkyne A (C10H14) can be catalytically hydrogenated to butylcyclohexane. Treatment of A with EtMgBr liberates no gas. Catalytic hydrogenation of A over Pd/C in the presence of quinoline poison and treatment of the product with O3 and then H2O2 gives an optically active tricarboxylic acid C8H12O6. (A tricarboxylic acid is a compound with three —CO2H groups.) Give the structure of A, and account for all observations.

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Organic Chemistry

ISBN: 9781936221349

6th Edition

Authors: Marc Loudon, Jim Parise

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