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Question
Account for the following : Cl – CH2COOH is a stronger acid than CH3COOH.
Solution 1
Cl-CH2COOH is a stronger acid than CH3COOH :
Substitution of electron withdrawing group on carboxylic acid affect the acidity of the carboxylic acid. Chlorine is a electron withdrawing group and its increase the acidity of carboxylic acids by stabilising the conjugate base due to delocalisation of the negative charge by resonance effects. Chloroacetic acid ( Cl-CH2COOH) pKa value is equal to 2.7, while pKa value of acetic acid (CH3COOH) is equal to 4.7.
Solution 2
Monochloroacetic acid is stronger than acetic acid. This is due to –Cl as a – I group.
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Reason (R): Acetic acid is a weaker acid than formic acid.
