1559Tch22389-40910/19/0517:23Page392 392 chapter 22 CHEMISTRY OF BENZENE SUBSTITUENTS:ALKYLBENZENES,PHENOLS,AND BENZENAMINES 33.Several reactions derive from fundamental material presented in earlier chapters. CICHCH CICHCH HOOCCHCH 8 CH=CHz CH.CH.OH ⊕ 6.8-6-6- 0-这-g-0-i-过 2-1-9-68 butor in which a lone pair on o33. Several reactions derive from fundamental material presented in earlier chapters. (a) (b) (c) (d) 34. The cation derived from chloromethylbenzene (benzyl chloride, top) is stabilized by four resonance contributing forms. The cation from 1-(chloromethyl)-4-methoxybenzene (4-methoxybenzyl chloride, middle) is more stable because of the added contributor in which a lone pair on oxygen is delocalized into the ring (second Lewis structure from the right). The cation from 1-(chloromethyl)-4-nitrobenzene ClCH2 CH2 CH2 Cl CH2 CH2 NO2 NO2 NO2 NO2 NO2 Poor ClCH2 OCH3 OCH3 OCH3 OCH3 OCH3 OCH3 CH2 CH2 Cl CH2 CH2 CH2 ClCH2 CH2 CH2 Cl CH2 CH2 CH CH2 MCPBA O ClCHCH3 CH CH2 KOC(CH3)3 1. BH3, THF 2. NaOH, H2O2 CH2CH2OH ClCHCH3 HOOCCHCH3 1. KCN, DMSO 2. H3O,  CH2CH3 ClCHCH3 Cl2 (1 equivalent), hv (Problem 30a) 392 • Chapter 22 CHEMISTRY OF BENZENE SUBSTITUENTS: ALKYLBENZENES, PHENOLS, AND BENZENAMINES 1559T_ch22_389-408 10/19/05 17:23 Page 392