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JEE Advanced 2020Paper 2
Exam
JEE Advanced
Year
2020
Paper
Paper 2
Subject
Chemistry
Chapter
Amines

JEE Advanced 2020 · Paper 2 · Chemistry · Amines

Consider the following four compounds I, II, III, and IV. Choose...

Consider the following four compounds I, II, III, and IV.

Consider the following four compounds I, II, III, and IV. Choose the correct statement(s).

Choose the correct statement(s).

Options

  1. AThe order of basicity is II>I>III>IVII > I > III > IV.
  2. BThe magnitude of pKb{pK}_{b} difference between II and IIII is more than that between IIIIII and IVIV.
  3. CResonance effect is more in IIIIII than in IVIV.
  4. DSteric effect makes compound IVIV more basic than IIIIII.

Correct answer

C. Resonance effect is more in IIIIII than in IVIV.

Step-by-step solution

The correct basic strength order is

(A) Kb:IV>II>∣>III;{K}_{b}: IV > II > ∣ > III;

  • IVIV is strongest base due to SIR effect.
  • IIIIII is weakest base due to−M- M group of three nitro groups present at Ortho and Para positions.
  • IlIl is stronger than II since IIIIII is tertiary and II primary aromatic amine.

(B) IVIV is found to be 40,00040, 000 times more basic than IIIIII. While IandI andIIdifferverylittleinbasicstrength.</p><p>(C,D)DuetoSIReffectindiffer very little in basic strength.</p><p>(C,D) Due to SIR effect inIVbothboth- {NO}_{2}andand- N{\left({CH}_{3}\right)}_{2} will be out of plane hence resonance effect is more in IIIIII than in IVIV.
in III than in V\mathrm{V}.

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