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Question

Arrange increasing order of acidic strength of following dicarboxylic acid.
(i) Oxalic acid
(ii) Succinic acid
(iii) Malonic acid
(iv) Adipic acid

A
iii < ii < i < iv
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B
i < ii < iii < iv
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C
iv < iii < ii < i
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D
iv < ii < iii < i
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Solution

The correct option is D iv < ii < iii < i
The dicarboxylic acids are stronger than monocarboxylic acid becasue it has a electron withdrawing (COOH) group.
The increase in the CH2 group in the compound will decrease the acidic strength of the compound because CH2 is an +I effect group so it will increase the electron density on conjugate base.


Here, oxalic acid doesn't have +I group so it more acidic.
Then, malonic acid has one CH2 and succinic acid has 2 CH2 and adipic acid has 4 CH2.
Therfore the strength of acid follows the order,
Adipic acid<Succinic acid<Malonic acid<Oxalic acid

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