1559T_ch20_358-37210/18/054:24Page363 EQA Soutionso Problems363 0 36.(a)CH.CH,CH,CH,CO,H(b)CH,CH.CH,CH,COCH.CH,CH(CH) OH (e)CH;CH:CH2CH-CN(CH2CHs)2 (d)CH;CH:CH2CH2CCH, 0 (e)CHaCH2CH2CH2CH2OH (f)CH,CH2CH2CH2CH OH 37.(a)CH,CHCH2CH2CO2H (b)CH,CHCH,CH,COCH2CH,CH(CH3)2 OH OH OH (e)CH,CHCH,CH,CN(CH,CH2(d)CH,CHCH,CH.CCH, OH (e)CH CHCH CH,CHOH OH ⊕ HC、0、OH (f)CHCHCHCH-CH.which forms the cyclic hemiaceta 0 38.(a (b) (c)y CH:CH2 0 (d)NH e D R -CH 0 COH 39.(.C,(CH)..CH :0-H H 0: (CH)CHCGCHCH,(CH).CHC CH-CH; Solutions to Problems • 363 O B 36. (a) CH3CH2CH2CH2CO2H (b) CH3CH2CH2CH2COCH2CH2CH(CH3)2 O OH B A (c) CH3CH2CH2CH2CN(CH2CH3)2 (d) CH3CH2CH2CH2CCH3 A CH3 O B (e) CH3CH2CH2CH2CH2OH (f) CH3CH2CH2CH2CH OH OH O A AB 37. (a) CH3CHCH2CH2CO2H (b) CH3CHCH2CH2COCH2CH2CH(CH3)2 OH O OH OH AB AA (c) CH3CHCH2CH2CN(CH2CH3)2 (d) CH3CHCH2CH2CCH3 A CH3 OH A (e) CH3CHCH2CH2CH2OH OH O A B (f) CH3CHCH2CH2CH, which forms the cyclic hemiacetal 38. (a) (b) (c) (d) (e) (f) 39. H, CH3CH2OH (CH3)2CHC (CH3)2CHCOCH3 CH2CH3 OCH3 O O  O H H H H (CH3)2CHCOCH2CH3 H CH3 O O  H H (CH3)2CHCOCH2CH3 OH  (CH3)2CHCOCH2CH3 O CH3OH 
 O N CH3   O CH3 NH O
 NH  
O O CH3CH2 O O H3C O
 O H3C O OH 1559T_ch20_358-372 10/18/05 4:24 Page 363