Reaction of Substituted Benzenes and Chloral. VI

Influence of Substituents on Reactivity

Abstract

Various substituent groups were introduced into anisole and acetanilide and their reactivity was compared by reacting with chloral in conc. sulfuric acid. The order of reactivity was OCH₃>CH₃>Cl>NHCOCH₃>COOH>NO₂ (in H₂SO₄). It is assumed that the reason why the acetamido group is placed lower than chlorine is because its polarization to Ar-NH⁺=C(CH₃)-O^- increases in conc. sulfuric acid.