Question

Trearment of (S)-(+)-5methylcyclohex-2-enone with lithium dimethlycuprate gives, after protonolysis, a good yield of a mixture containing mostly dextrorotary Ketone A and a trace of optically inactive isomer B. Treatment of A with zinc amalgam and HCl affords opticlly active hydrocarbon C (C8H16). Compound B, which exhibits only 5 unique signals in its 13C NMR spectrum, undergoes an aldol condensation with NaOEt and benzaldehyde to produce optically active compound D. Identify componds A-Dincluding stereochemical configurations.

Treatment of (S)- (+-5-methylcyclohex-2-enone with lithium dimethylcuprate gives, after protonolysis, a good a mixture containing mostly dextrorotary ketone A and a trace of optically inactive isomer B Treatment of A with zinc amalgam and HCl affords optically active hydrocarbon C (C,tho). Compound B, which exhibits only five unique signals in its 13C NMR spectrum, undergoes an aldol condensation with NaOEt and benzaldehyde to produce optically active compound D. Identify compounds A -D, including stereochemical configurations. (2 pts) Zn(Hg) HCI (S)-(+)-5-methylcyclohex-2-enone [1] (CH3)2Culi [2] H20 hydrocarbon C A (major) B (minor) NaOEt benzaldehyde -H20]

Answer 1

hex--enone CH C) C1 鳥 一 nals in SUNDAY 20 o 6L Cb