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Question

The decreasing order of acidic characters of the following is:
I. CHCH
II.
III.

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

The correct option is B II > I > III
Conjugate base of I, II and III:
I. HCC(Negative charge onsp C atom)
sp carbons have 50% s character. More the s- character, more will be the electronegativity. Hence it will stabilise the negative charge on carbon.

(II) In this conjugate base, it has 6 π electrons which will obey the 4n+2 rule. Thus it is aromatic in nature. Hence it stabilise the conjugate base more than others.
(III)

In this conjugate base, it has 4 π electrons which will obey 4n π electron rule. Hence it is anti-aromatic and it destabilise the conjugate base more.

Stability of conjugate base acidic character
Hence, the decreasing acidic character follows II > I > III




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