Which of the following is the strongest Bronsted base?

Question

Canvas Classes · Accepted Answer

Bronsted base strength = ability to accept a proton = availability of lone pair on N.

Step 1 — Analyse each compound:

(1) Aniline (): Lone pair on N is delocalized into the benzene ring (resonance)  reduced basicity.

(2) Diphenylamine (): Two phenyl groups withdraw lone pair  even weaker base than aniline.

(3) Pyrrole: N lone pair is part of the aromatic  system (6  electrons)  essentially non-basic.

(4) Pyrrolidine (cyclic secondary amine): No aromatic ring, no resonance withdrawal  lon

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