1559r.ch20.358-37210/18/054:24Page366 366.chapter 20 CARBOXYUC ACID DERIVATIVES 0: 46.、人 in,+ :0-H C-NH2 :OH LOCCecCM (b)N=C一 NH NEC- 入-Cc阳+H N=C一 H一N=c Then continue as in Problem 46 and repeat at the other nitrile group.366 • Chapter 20 CARBOXYLIC ACID DERIVATIVES 46. 47. (a) (CH3CH2CH2CH2)2CuLi; then H, H2O; (b), (d) LiAlH4, (CH3CH2)2O; then H, H2O; (c) LiAl[OC(CH3)3]H; then H, H2O; (e), (f) CH3CH2CH2MgBr, (CH3CH2)2O; then H, H2O 48. (a) (b) (c) Then continue as in Problem 46 and repeat at the other nitrile group. N C NH2  O N C NH2 H O N C NH H  H O H N C NH H O N C C NH  H2O N C  C N H   N C C N H, H2O HO O O OH N C C N H2, PtO2 H2N NH2 N H N H n O O H  C NH3 O OH OH C O H H H H C NH2  O O H H C NH2 O O H NH2 C  H2O O H NH2 C O 1559T_ch20_358-372 10/18/05 4:24 Page 366