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326 Chapter 16 ELECTROPHILIC ATTACK ON DERIVATIVES OF BENZENE: SUBSTITUENTS CONTROL REGIOSELECTIVITY 1. HNO3. H₂SO₄ 2. Ni A D Br Br HNO3. H₂SO₄ NH₂ H₂SO₄ 2. H₂-Ni H₂O. A C Removes SO₃H SO₃H mainly Br NH₂ (again) H₂SO₄ A C Blocks position para to amine Br NH₂ FeBr₃ 1 B Removes HO₃S Br Pd-C 49. + 2H₂ 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. 50. Reaction should occur on the most activated (or least deactivated) ring, directed by the groups present. CH₃ NO₂ (a) (b) Major: CH₃ NO₂ CH₃O is sterically hindered NO₂ X CI NO₂ NO₂ (c) 3 5