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Q. Consider the acidity of the carboxylic acids
(i) PhCOOH (ii) $o-NO_2C_6H_4COOH$ (iii) $p-NO_2C_6H_4COOH$ (iv) $m-NO_2C_6H_4COOH$
Which of the following orders is correct?

Jharkhand CECEJharkhand CECE 2008Aldehydes Ketones and Carboxylic Acids

Solution:

$-NO_2$ group at any position shows electron withdrawing effect, thus acid strength is increased, but o-nitro benzoate ion is stabilised by intramoiecuiar H-bonding like forces, hence its acid strength is maximum.
Thus, the order of acid strength is (ii) > (iii) > (iv) > (i).

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