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Inductive Effect

Easychemistry

Replacing a hydrogen of acetic acid with a strongly electron-withdrawing chlorine atom changes its acid strength in which observable direction?

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About This Question

Subject
chemistry
Chapter
some basic principles of organic chemistry
Topic
inductive effect
Difficulty
Easy
Year
2025
Tags
inductive effectminus I effectcarboxylic acid strengthconjugate base stabilityelectron withdrawal

Solution

Correct Answer:

Acidity increases

The inductive effect is the permanent polarisation of sigma bonds caused by an electronegativity difference, transmitted through the chain with diminishing strength. A chlorine atom is electron-withdrawing and exerts a -I effect, pulling electron density away from the carboxyl group of the resulting chloroacetic acid. This stabilises the conjugate base, the carboxylate anion, by dispersing its negative charge, so the acid loses its proton more readily and acidity increases. The option that acidity decreases is wrong because only electron-donating (+I) groups would destabilise the anion and weaken the acid. The claim that acidity stays the same ignores the clear electronic perturbation introduced by chlorine. The idea that it becomes a base is incorrect since a carboxylic acid retains its acidic -COOH group regardless of substitution. This trend matches the NCERT ordering where chloroacetic acid is markedly stronger than acetic acid. Plausibility check: greater stabilisation of the negative conjugate base always corresponds to a stronger acid, consistent with increased acidity.

This easy difficulty chemistry question is from the chapter some basic principles of organic chemistry, covering the topic of inductive effect. It appeared in the 2025 exam.

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