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Account for the following : Cl – CH2COOH is a stronger acid than CH3COOH. - Chemistry

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ConceptCarboxylic Acids Chemical Reactions of Carboxylic Acids - Substitution Reactions in the Hydrocarbon Part

Question

Account for the following : Cl – CH2COOH is a stronger acid than CH3COOH.

Solution 1

Monochloroacetic acid is stronger than acetic acid. This is due to –Cl as a – I group.

Solution 2

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.

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Solution Account for the following : Cl – CH2COOH is a stronger acid than CH3COOH. Concept: Carboxylic Acids - Chemical Reactions of Carboxylic Acids - Substitution Reactions in the Hydrocarbon Part.
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