Please help me out with these question In ortho effect of a substituted benzoic acid we say that the COOH loses planarity with the ring and the conjugate base becomes more stable due to equivalent resonating structure of COO- group but in case of benzyl amines (where the substituent is at ortho position) due to ortho effect the amine group loses planarity but after losing planarity the lone pair of nitrogen is not involved in resonance so it becomes more available for donation therefore the basicity should increase but the correct answer is it decreases so how can the basicity of ortho substituted benzyl amine in comparison with meta and para substituted decrease

James Macmillan , 10 Years ago

Grade 12th Pass