1559T_ch06_099-11210/22/0520:19Pa9e105 EQA Solutions to Problems.105 Product is(15.35)-3-hydroxycyclohexylacetate HO (d)Starting material is (15.3S)-3-chlorocyclohexanol 0 CH Product is(1R.35)-3-hydroxycyclohexyl acetate. HO Notice that in the product for (c),exchanging the OH and OCCH groups does not change the molecule. However,in the product for (d).such an exchange turns the molecule into its enantiomer. 38.(36a)::-CH-CH2-CH2Br (36b)NC CH)CH-CH, (36)(CH.CHO-CHC (36d)CH,CH,S: CH;-CH2-Br (3e)(CHCH i, 60)(CHN:CHCH COSOCH CH2CH3 CIH B年Hea (d) Starting material is (1S,3S)-3-chlorocyclohexanol. Notice that in the product for (c), exchanging the OH and groups does not change the molecule. However, in the product for (d), such an exchange turns the molecule into its enantiomer. 38. (36a) (36b) (36c) (36d) (36e) (36f) (37a) (37b) H3C CH3 H Br Cl H I I “ “ Cl CH2CH3 Br CH3 H (CH3)3N (CH3)2CH OSO2CH3 (CH3CH2)2Se CH2 Cl CH3CH2S CH3 CH2 Br (CH3)2CHO CH3 I N C (CH3)2CH CH2 I I CH3 CH2 CH2 Br OCCH3 O OCCH3 O 1 2 3 HO Product is (1R,3S)-3-hydroxycyclohexyl acetate. OCCH3 O HO Product is (1S,3S)-3-hydroxycyclohexyl acetate. Solutions to Problems • 105 1559T_ch06_099-112 10/22/05 20:19 Page 105