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Question

Increasing order of acidic strength of given compounds is:


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

The correct option is B III<I<IV<II
Conjugate base formed after loss of H+ for each of the following compounds is :
Acidic strengthI,H,M1+I,+H,+M


CH3 and OCH3 when attached to benzene ring show +H and +R effect respectively, which destabilizes the conjugate base .
Since, +R effect is more predominant than +H effect so, III is the least stable followed by I.
In compounds II and IV :
IV is stabilized by delocalization of negative charge on benzene ring. The resonating structures so formed are not equivalent resonating structures.
II is stabilized by -R effect of CN group. So, it is more stable than IV
Correct order of stability of conjugate bases is :
III<I<IV<II
More the stablility of conjugate base more is the acidic strength, so the correct acidic strength order is :
III<I<IV<II

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