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Question

Rank in the order of increasing acidity :


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

The correct option is D II<I<III
More the stability of conjugate base formed, more is the acidity.
The conjugate base so formed after removal of H+ for each of the following compounds are :

III (phenoxide ion) is resonance stabilized, whereas there is no resonance in I and II.
So III is the most stable conjugate base and most acidic.
Comparing I and II
In I the negative charge is on more electronegative atom (oxygen), as compared to II where the negative charge is on less electronegative atom (nitrogen).
So, I is more stable than II, and consequently a stronger acid .
The correct order of increasing acidity is :
II<I<III

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