Question

Effects of substituents on acidic strength of carboxylic acid

Answer 1

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In the case of carboxylic acids, if the electrophilic character of the carbonyl carbon is decreased the acidity of the carboxylic acid will also decrease. Similarly, an increase in its electrophilicity will increase the acidity of the acid. ... Electronegative substituents increase acidity by inductive electron withdrawal.

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Answer 2

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(1). The electrical-releasing group such as, __CH3, __OH, __NH2 etc ., Tend to decrease the acid strength of benzoic acid. The electron - withdrawing group such as, __Cl, __NO2 etc., tend increase the strength of benzoic acid.

(2). Ortho isomer of benzoic acid is the strongest of all the isomers irrespective of the nature of the substituents. This is called ortho effect. This effect may be due to a combination steric and electronic factores.

(3). The acid - strengthening effect of electron - withdrawing group (e.g., __Cl, __NO2 etc.) Is more pronounced at p - position than at m - position.

(4). The acid - weakening effect of an electron - releasing substituents (e.g., __OH, __CH3, __NH2 etc) is more pronounced at p - position than at m - position.

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