Q11 / 54 · JEE Advanced 2020 (Paper 2) · Chemistry

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

Figure

Choose the correct statement(s).

  • A
    The order of basicity is II>I>III>IV.
  • B
    The magnitude of pKb difference between I and II is more than that between III and IV.
  • Correct answer
    C
    Resonance effect is more in III than in IV.
  • Correct answer
    D
    Steric effect makes compound IV more basic than III.

Solution

The correct basic strength order is

(A) Kb:IV>II>∣>III;

  • IV is strongest base due to SIR effect.
  • III is weakest base due to-M group of three nitro groups present at Ortho and Para positions.
  • Il is stronger than I since III is tertiary and I primary aromatic amine.

(B) IV is found to be 40,000 times more basic than III. While I and II differ very little in basic strength.

(C,D) Due to SIR effect in IV both -NO2 and -NCH32 will be out of plane hence resonance effect is more in III than in IV.
in III than in $\mathrm{V}$.

Hence, the correct answer is options: 'C', 'D'.

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