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Dissociation constants of benzoic acid, ...

Dissociation constants of benzoic acid, p-nitrobenzoic acid and p-hydroxybenzoic acid are `6.3xx10^(-5)`, `36xx10^(-5)" and "2.5xx10^(-5)` respectively. Explain.

Text Solution

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(i) `NO_(2)` group is an electron withdrawing group and tends to stabilise the carboxylate anion more than the benzoate ion after the release of `H^(+)` ion. Thus, p-nitrobenzoic acid is a stronger acid than benzoic acid.
(ii) OH group is an electron releasing group and tends to destabilise the carboxylate anion more than benzoate ion after the release of `H^(+)` ion. Thus p-hydroxybenzoic acid is a weaker acid than benzoic acid. The relative order of of acidic strengths is , thus, justified.
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Knowledge Check

  • Decreasing order of acidity of p-methoxy benzoic acid (A), p-nitrobenzoic acid (B) and benzoic acid (C) is-

    A
    B,C,A
    B
    A,B,C
    C
    C,A,B
    D
    None

  • Decreasing order of acidity of p-methoxy benzoic acid (A), p-nitrobenzoic acid (B) and benzoic acid (C) is –

    A
    B, C, A
    B
    A, B, C
    C
    C, A, B
    D
    None

  • The dessociation cosntants of acetic acid and propionic acid are 1.0 xx 10^(-5) and 1.0 xx 10^(-6) respectively. The value of P^(K_(a)) (propionic acid) - P^(K_(a)) (Acetic acid) is

    A
    10
    B
    `10^(-1)`
    C
    1
    D
    `-1.0`