Treatment of (S)-(+)-5-methyl-2-cyclohexenone with lithium dimethylcuprate gives

Question

Treatment of (S)-(+)-5-methyl-2-cyclohexenone with lithium dimethylcuprate gives, after protonolysis, a good yield of a mixture containing mostly a dextrorotatory ketone A and a trace of an optically inactive isomer 8. Treatment of A with zinc amalgam and HCI affords an optically active, dextrorotatory hydrocarbon C. Identify compounds A, B, and C, including stereochemical configurations. Be sure to explicitly draw H and both wedge/dash bonds at any configuration center. In each reaction box, place the best reagent and conditions from the list below. Supply the reagents and intermediates for the following reaction by dragging compounds to the appropriate boxes.

Explanation / Answer

Li/CuI (CH3)2Li CH3-O-C(O)-CH3 FOR NEXT Mg/Et2O NaCN KMnO4/H3O+

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