Treatment of (S)-(+)-5-methyl-2-cyclohexenone with lithium dimethylcuprate gives, after protonolysis, a good yield of a mixture containing mostly dextrorotatory ketone A and a trace of optically inactive isomer B. Treatment of A with zinc amalgam and HCl affords optically active, dextrorotatory hydrocarbon C. Identify compounds A. B, and C, including stereochemical configurations. Be sure to explicitly draw H and both wedge and dash bonds at any configuration center. Draw compound A. Draw compound B.

Treatment of (S)-(+)-5-methyl-2-cyclohexenone with lithium dimethylcuprate gives, after protonolysis, a good yield of a mixture containing mostly dextrorotatory ketone A and a trace of optically inactive isomer B. Treatment of A with zinc amalgam and HCl affords optically active, dextrorotatory hydrocarbon C. Identify compounds A. B, and C, including stereochemical configurations. Be sure to explicitly draw H and both wedge and dash bonds at any configuration center. Draw compound A. Draw compound B.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.55P

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