Evaluate the following diverse collection of nitrogenous organic bases: p-Toluidine, p-Nitroaniline, — GOC and Organic Chemistry Basics Chemistry Question

💡 Solution & Explanation

To be more basic than aniline, a compound must lack extended delocalization or possess electron-donating groups. p-Toluidine (methyl $+I/+H$ effect increases basicity). Cyclohexylamine and Benzylamine (aliphatic amines, lone pairs localized, no resonance with ring, highly basic). Pyridine (lone pair localized in $sp^2$ orbital, doesn't participate in ring resonance, stronger base than aniline). Conversely, p-Nitroaniline ($-M$ group), Diphenylamine (delocalization over two rings), and Pyrrole (lone pair consumed by aromaticity) are substantially weaker bases than aniline. Total = 4.