Among the following given compounds: Aniline, p-Nitroaniline, N-Methylaniline, Benzylamine, and Etha — Amines Chemistry Question
Question
Among the following given compounds: Aniline, p-Nitroaniline, N-Methylaniline, Benzylamine, and Ethanamine; how many are intrinsically weaker bases than standard ammonia in an aqueous medium?
💡 Solution & Explanation
Ammonia is a stronger base than aromatic amines where the lone pair is resonance delocalized. Aniline, p-Nitroaniline (further weakened by the -R/-I effect of $-NO_2$), and N-Methylaniline have their nitrogen lone pair conjugated with the benzene ring and are weaker bases than $NH_3$. Benzylamine and Ethanamine are aliphatic amines (nitrogen localized on an $sp^3$ carbon) benefiting from the +I effect of the alkyl chain, making them stronger bases than ammonia. Total = 3.