1559rch22389-40810/19/0517:23Page394 394 chapter 22 CHEMISTRY OF BENZENE SUBSTITUENTS:ALKYLBENZENES,PHENOLS,AND BENZENAMINES 39.(a)One solution,perhaps a bit roundabout: 】CHa.A BrCHCHs NBS./wy K+-OC(CH: (CHaCOH CH=CH2 CH2CH2Br COOH B.a. 一-○-00 0Seven resonance forms make this carbanion especially stable. It is also aromatic, having 14
electrons in an unbroken loop of p orbitals. 39. (a) One solution, perhaps a bit roundabout: (b) (c) (d) CH3 Br Br Na2Cr2O7, H2SO4 product CH3 CH3 SO3H SO3H CH3 Br Br SO3, H2SO4 2 Br2, FeBr3 H2O,  C COOH CH3OH, H O product C CH3 Na2Cr2O7, H2SO4 O CH3 COOH COCl SOCl2 KMnO CH3, AlCl3 4, HO,  CH3 CH3 Cl Cl2, FeCl3 Na2Cr2O7, H2SO4,  COOH Cl 1. SOCl2 2. NH3 product CH2CH2Br HBr, ROOR (Anti-Markovnikov) CH CH2 BrCHCH3 NBS, hv CH2CH3 K OC(CH3)3 (CH3)3COH CH3CH2Cl, AlCl3 394 • Chapter 22 CHEMISTRY OF BENZENE SUBSTITUENTS: ALKYLBENZENES, PHENOLS, AND BENZENAMINES 1559T_ch22_389-408 10/19/05 17:23 Page 394