1559T_ch22_389-40810/19/0517:23Pa9e405 ⊕ EQA Soutions to Problems405 OH HNO:H.O.OC 上8,9C8nc CucN.product 2+C (CHa)2CH (CHaCH [From(b)] COOH COOH 2899H8c 风 N2+CI- Note concering the first step:Nitration of methylbenzene gives mostly ortho product.The larger alkyl group favors para substitution. NOz 2 NaNO:HCHOC CI N2 CaBr.product N2"CI- o,Haot Br From (a (d) (e) Note concerning the first step: Nitration of methylbenzene gives mostly ortho product. The larger alkyl group favors para substitution. (f) (g) 2. NaNO2, HCl, H2O, 0 C CuBr,  1. Fe, HCl product Cl Cl NO2 NO2 Cl Cl ClN2 N2 Cl Cl Cl CuCl,  Excess HNO3, H2SO4,  N2 Cl N2 Cl NO2 NO2 2. NaNO2, HCl, H2O, 0 C Excess 1. H2, Ni, CH3CH2OH HNO3, H2SO4,  COOH NO2 COOH N2 Cl KI H2O,  product 2. NaNO2, HCl, H2O, 0 C 1. H2, Ni, CH3CH2OH (CH3)2CH [From (b)] (CH3)2CH NO2 HNO3, H2SO4 H2SO4 Na2Cr2O7, NO2 OH OH N2 Cl CuCN,  product 2. NaNO2, HCl, H2O, 0 C 1. H2, Ni, CH3CH2OH OH 2. NaOH,  HNO3, H2O, 0 C 1. SO3, H2SO4 Solutions to Problems • 405 Br2, H2O NaNO2, HCl, H2O, 0 C NH2 [From (a)] Br Br Br N2 Cl Br Br Br NH2 1. CuCN,  2. H, H2O,  product 1559T_ch22_389-408 10/19/05 17:23 Page 405