JEE Main · 2024 · Shift-IhardIEQ-019

Which of the following is the strongest Bronsted base?

Ionic Equilibrium · Class 11 · JEE Main Previous Year Question

Question

Which of the following is the strongest Bronsted base?

Options
  1. a

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  2. b

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  3. c

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  4. d

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Correct Answerd

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Detailed Solution

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

Step 1 — Analyse each compound:

(1) Aniline (C6H5NH2\mathrm{C_6H_5NH_2}): Lone pair on N is delocalized into the benzene ring (resonance) \rightarrow reduced basicity. pKb9.4\mathrm{pK_b} \approx 9.4

(2) Diphenylamine ((C6H5)2NH(\mathrm{C_6H_5})_2NH): Two phenyl groups withdraw lone pair \rightarrow even weaker base than aniline. pKb13.1\mathrm{pK_b} \approx 13.1

(3) Pyrrole: N lone pair is part of the aromatic π\pi system (6 π\pi electrons) \rightarrow essentially non-basic. pKb13.6\mathrm{pK_b} \approx 13.6

(4) Pyrrolidine (cyclic secondary amine): No aromatic ring, no resonance withdrawal \rightarrow lone pair fully available \rightarrow strongest base. pKb2.7\mathrm{pK_b} \approx 2.7

Order of basicity: Pyrrolidine >> Aniline > Diphenylamine > Pyrrole

Answer: Option (4) — Pyrrolidine

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