1559T_ch19_344-35710/17/0513:51Pa9e349 ⊕ EQA Solutions to Problems.349 CH;-0-C-CH2-CH2 CH3-0-C-CH2-CHz ◇2品q0 .MOO入oH CHO CO2H .G ○o 2KOC -0 CHCH-O 27.(a)(CHa)CHaCHCOCI(alkanoyl chloride) 00 (b)(CH3)2CHCH2C-O-CCH3(mixed anhydride) >COONHa (ammonium salt) (e)CH,0- -CONH2 (carboxylic amide) (cyclic anhydride) Solutions to Problems • 349 equivalent OCH2O’s (  1.7). The splitting between the upfield signals suggests that the sets of CH2’s are connected, so a reasonable answer is (d) (e) How about (f) 27. (a) (CH3)2CH2CH2COCl (alkanoyl chloride) O O B B (b) (CH3)2CHCH2COOOCCH3 (mixed anhydride) (c) (d) (e) (f) O O O (cyclic anhydride) CH3O CONH2 (carboxylic amide) COO CH3O NH4 (ammonium salt) CO2CH2CH3 (ethyl ester) H2SO4, OH LiAlH4 (CH3CH2)2O 1. O3, CH2Cl2 2. Zn, H, H2O CH2 O LiAlH4 (CH3CH2)2O 1. PBr3, (CH3CH2)2O 2. KOC(CH3)3 CO2H CH2OH 1. PBr3, (CH3CH2)2O 2. Mg OH 1. CO2, (CH3CH2)2O 2. H, H2O MgBr CO2H 1. O3, CH2Cl2 2. Zn, H, H2O Na2Cr2O7, H2SO4, H2O CHO CHO H, CH3OH CO2H G CO2H C CH2 O O CH2 CH2 CH3 CH3 O C CH2 O 1559T_ch19_344-357 10/17/05 13:51 Page 349