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Question

The order of basicity among the following compound is:



A
II > I > IV > III
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B
IV > II > III > I
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C
IV > I > II > III
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D
I > IV > III > II
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Solution

The correct option is C IV > I > II > III

Conjugate acid of structure IV has three equivalent canonical forms it is stabalised by resonance with two nitrogen lone pair so due to efficient resonance stabilisation of charge it is most basic.

Conjugate acid of structures I, II, III have two equivalent canonical forms respectively.

I is more basic than II because conjugate acid formed is more stablised by +I effect of CH3

But III is least basic because of electron withdrawing effect of CH=CH group. Also, the lone pairs of one of the nitrogen is involved in resonace and hence aromaticity and the other nitrogen is sp2 hybridised which makes it least basic amongst all .

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