Q.

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

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Choose the correct statement(s)

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a

The order of basiciy is II > I > III > IV

b

The magnitude of pKb diference between I and II is more than that between III and IV

c

Steric effect makes compound IV more basic than III

d

Resonance effet is more in III than in IV

answer is C, D.

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Detailed Solution

The correct basic strength order is
(A) Kb : IV > II > I > III
i) IV is strongest base due to SIR effect
ii) III is weakest base due to –M group of three nitro groups present at Or tho and Para positions

iii) II 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 & II differ very little in basic strength.
(C, D) Due to SIR effect in IV both –NO2 and –N(CH3)2 will be out of plane hence resonance effect is more in III than in IV

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