1559T_ch15_276-29011/03/0520:24Pa9e284 EQA 284.Chapter 15 BENZENE AND AROMATICITY:ELECTROPHILIC AROMATIC SUBSTITUTION 48.Consider a mechanism similar to Friedel-Crafts alkylation.Twice a-s-:Ac-d--c 6C-m ◇o-c℃ 49.(a)Think mechanistically.Then see if what you come up with matches the data. CH-CIO -O 门益门 48. Consider a mechanism similar to Friedel-Crafts alkylation. Twice. 49. (a) Think mechanistically. Then see if what you come up with matches the data. (b) H2, Pd-C, CH3CH2OH O OH NaBH4, CH3CH2OH Conc. H2SO4, 100°C C9H8O O H O C9H9ClO AlCl3 Cl O O AlCl3; think Friedel-Crafts akanoylation S S H AlCl4 S Cl AlCl3 H AlCl4 ClS ClS AlCl3 Cl S Cl AlCl 3 Cl S Cl AlCl3 284 • Chapter 15 BENZENE AND AROMATICITY: ELECTROPHILIC AROMATIC SUBSTITUTION 1559T_ch15_276-290 11/03/05 20:24 Page 284