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Question

Consider the acidity of the carboxylic acids:
(i) C6H5COOH (ii) ONO2C6H4COOH
(iii) pNO2C6H4COOH (iv) mNO2C6H4COOH
Which of the following order is correct?

A
(i) > (ii) > (iii) > (iv)
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B
(ii) > (iv) > (iii) > (i)
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C
(ii) > (iv) > (i) > (iii)
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D
(ii) > (iii) > (iv) > (i)
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Solution

The correct option is D (ii) > (iii) > (iv) > (i)

NO2 at o-position stabilizes by both - I and - R
NO2 at p-position stabilizes only by - R
NO2 at m-position stabilizes by - I only

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