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Carboxylic Acid

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Carboxylic acid

Acidic strength of carboxylic acid

HCOOH is more acidic than benzoic acid due to +M effect of ring while inorganic acids like HCl, HI, HBr and HClO₄ are strong acids than organic acids due to complete ionisation of these acids. Benzene sulphonic acid is highly acidic than carboxylic acid due to more number of intermediate resonanting structure of benzene sulphonate ion than acetate ion.

Acidic nature depends upon stability of anion

if G is electron withdrawing group it gives strength to acids while releasing nature of G decreases acidic nature. For example :

CCl₃COOH > HCOOH > CH₃COOH

Due to +R effect or +I effect acidic nature decreases while – R and – I effect increases acidic power. Benzoic acid is weaker than formic acid due to +R effect of phenyl group in benzoic acid, but C₆H₅CH₂COOH is stronger than CH₃COOH because here phenyl group give – I effect

Some important acidic strength order are given below :

(i) FCH₂COOH > ClCH₂COOH > BrCH₂COOH > ICH₂COOH > CH₃COOH

(ii) CCl₃COOH > Cl₂CHCOOH > ClCH₂COOH > HCOOH > CH₃COOH

(iii) CH₃CH₂CH(Cl)COOH > CH₃CH(Cl)CH₂COOH > ClCH₂CH₂CH₂COOH > CH₃CH₂CH₂COOH

(iv) CH₃COOH > CH₃CH₂COOH > (CH₃)₂CHCOOH > (CH₃)₃CCOOH

(v) NO₂CH₂COOH > NCCH₂COOH > ClCH₂COOH > CH₃COOH

(vi) OHCH₂COOH > ClCH₂COOH > CH₃COOH

Any ortho substituted (electron releasing or electron attracting) group at benzoic acid always increase acidic nature. This is due to steric inhibition resonance by ortho group, known as ortho effect.

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