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    Acidity of Aromatic Carboxylic Acid

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    sayyed mohsina
    Aromatic carboxylic acids are slightly stronger acids than aliphatic acids. The acidity of aromatic carboxylic acids depends on both inductive and resonance effects of any substituents on the aromatic ring. Electron-releasing groups in the ortho or para positions increase acidity, while electron-withdrawing groups in the para position increase acidity through resonance stabilization of the carboxylate anion. The proximity and position of substituents determines whether inductive or resonance effects dominate in influencing acidity.

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    Acidity of Aromatic Carboxylic Acid

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    sayyed mohsina
    588 views6 pages
    Aromatic carboxylic acids are slightly stronger acids than aliphatic acids. The acidity of aromatic carboxylic acids depends on both inductive and resonance effects of any substituents on the aromatic ring. Electron-releasing groups in the ortho or para positions increase acidity, while electron-withdrawing groups in the para position increase acidity through resonance stabilization of the carboxylate anion. The proximity and position of substituents determines whether inductive or resonance effects dominate in influencing acidity.

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    Acidic nature of Aromatic Carboxylic Acid

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    Aromatic carboxylic acids are slightly stronger acids than aliphatic acids. The acidity of aromatic carboxylic acids depends on both inductive and resonance effects of any substituents on the aromatic ring. Electron-releasing groups in the ortho or para positions increase acidity, while electron-withdrawing groups in the para position increase acidity through resonance stabilization of the carboxylate anion. The proximity and position of substituents determines whether inductive or resonance effects dominate in influencing acidity.

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    588 views6 pages

    Acidity of Aromatic Carboxylic Acid

    Uploaded by

    sayyed mohsina
    Aromatic carboxylic acids are slightly stronger acids than aliphatic acids. The acidity of aromatic carboxylic acids depends on both inductive and resonance effects of any substituents on the aromatic ring. Electron-releasing groups in the ortho or para positions increase acidity, while electron-withdrawing groups in the para position increase acidity through resonance stabilization of the carboxylate anion. The proximity and position of substituents determines whether inductive or resonance effects dominate in influencing acidity.

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    ACIDITY OF AROMATIC

    CARBOXYLIC ACID
    ACIDITY OF AROMATIC CARBOXYLIC ACID
    Aromatic carboxylic acids with unsubstituted benzene ring are slightly
    stronger acids than the aliphatic acids. Thus benzoic acid is somewhat
    stronger acid than acetic acid.

    The effect of substituent groups in the ring on the acidity of benzoic


    acid (i.e., on ionisation of —COOH) depends not only on the nature
    of the group but also its position with respect to the position of the
    COOH group.
    Acidity of aromatic carboxylic acids, in fact, is determined by
    the inductive effect as also the resonance effect. Electron-
    releasing substituents and ortho-para directors increase the
    electron-density in the ortho and para positions.

    Thus with OH group in thç ortho or para position; the benzene


    ring is unable to delocalize the negative charge of the
    -
    carboxylate anion (COO ).
    With long distances between the electron-releasing OH group, and
    carboxyl group,the inductive effect is important.

    However, with the decreasing distance, the inductive effect dominates


    over the resonance effect. That is why o-hydroxybcnzoic acid is
    stronger (Ka=100x10-5) and p-hydroxybenzojc acid weaker (Ka=2.9 x
    10-5) than benzoic acid (Ka=6.3x10-5).
    Electron-withdrawing substituents and meta directors like NO2 group,
    on the other hand,decrease electron density ortho and para to them.
    Thus the negative charge of the carboxylate anion is delocalized and
    hence it is stabilised.
    That is why p-nitrobenzoic acid (Ka=40x10-5) is stronger than
    benzoic acid (Ka=6.3x l0).

    However, p-nitrobenzoic acid is weaker than o-nitrobenzoic acid


    (Ka=620x10-5), where the strong inductive effect of the NO2, group
    -
    close to COO anion causes additional strong delocalization of the
    negative charge.

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