15597.eh22.389-40810/19/0517:23Pag0398 398 chapter 22 CHEMISTRY OF BENZENE SUBSTITUENTS:ALKYLBENZENES,PHENOLS,AND BENZENAMINES NO [From Problem 48(d)] OH OCH-COOCH 风 NOH.H:O 2.4-D OH OCH.CH OCH-CH CH:CH:OH NO: OH 00H Br(d) 49. (a) (b) (c) CO2, pressure, KHCO3, H2O OH Br Br OH Br Br COOH CH3COCCH3, H,  O O product 1. HNO3, H2SO4 2. Br2, FeBr3 1. Fe, HCl 2. NaNO2, HCl, 0 C 3. H2O,  4. Br2, CCl 4, 0 C NO2 Br 1. HNO3, H2SO4 2. H2, Ni CH3CH2OH OCH2CH3 OCH2CH3 CH3COCCH3,  NH2 O O product 1. SO3, H2SO4 2. NaOH,  1. NaOH, CH3CH2OH 2. CH3CH2Br OH 1. NaOH, CH3CH2OH 2. ClCH2COOCH3 OH NaOH, H2O Cl Cl OCH2COOCH3 (Williamson ether synthesis) Cl Cl 2,4-D 1. NaNO2, HCl, H2O, 0 C 2. CuCl,  NO2 OH NO2 NH2 NH2 OH H2, Ni, CH3CH2OH [From Problem 48(d)] Cl2, FeCl3 NO2 OH NO2 Cl NO2 NO2 OH Excess HNO3, H2SO4,  NaOH, H2O,  (Nucleophilic aromatic subst.) NO2 Cl Cl NO2 398 • Chapter 22 CHEMISTRY OF BENZENE SUBSTITUENTS: ALKYLBENZENES, PHENOLS, AND BENZENAMINES 1559T_ch22_389-408 10/19/05 17:23 Page 398