1559T_ch16_291-30311/3/0510:02Page300 EQA 300.Chapter 16 ELECTROPHIUC ATTACK ON DERIVATIVES OF BENZENE:SUBSTITUENTS CONTROL REGIOSELECTIVITY 20,s0 .HNO,HaS HO:S H.HO.A Removes SO.H HO-S 4◇+强c Although aromatic.naphthalene does undergo some addition reactions like this one.Addition curs in such a way that one aromatic benzene ring is left fully intact. 45.Reaction should occur on the most activated (or least deactivated)ring.directed by the groups present .oo."o Majo is sterically hindered NO.C 44. Although aromatic, naphthalene does undergo some addition reactions like this one. Addition occurs in such a way that one aromatic benzene ring is left fully intact. 45. Reaction should occur on the most activated (or least deactivated) ring, directed by the groups present. (a) (b) Major: is sterically hindered (c) NO2 NO2 3 5 CH3O NO2 ) )Cl CH3O NO2 Cl CH3 CH3 NO2 Pd-C 2H2 Br2, FeBr3 H, H2O,  Removes SO3H B Br HO3S Br NH2 SO3, H2SO4 Blocks position para to amine (again) A C Br HO3S NH2 SO3, H2SO4 1. HNO3, H2SO4 2. H2 Ni H2O,  Removes SO3H Br A C SO3H Br SO3H NH2 mainly 1. HNO3, H2SO4 A D 2. H2 Ni 300 • Chapter 16 ELECTROPHILIC ATTACK ON DERIVATIVES OF BENZENE: SUBSTITUENTS CONTROL REGIOSELECTIVITY 1559T_ch16_291-303 11/3/05 10:02 Page 300