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Inductive Effect

Mediumchemistry

Which of the following α-halo carboxylic acids is the strongest acid due to the inductive effect of the halogen substituent?

Select the correct option:

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About This Question

Subject
chemistry
Chapter
some basic principles of organic chemistry
Topic
inductive effect
Difficulty
Medium
Year
2025
Tags
Inductive EffectAcid StrengthSubstituent Effects

Solution

Correct Answer:

FCH₂COOH

Acid strength of carboxylic acids increases when electron-withdrawing groups (–I inductive effect) are present on the α-carbon, as they stabilize the carboxylate anion by dispersing negative charge through the chain. Halogens attached to the α-carbon exert a –I effect. The strength of the –I effect follows electronegativity: F > Cl > Br. Therefore, fluorine withdraws the most electron density from the carboxylate, providing the greatest stabilization of the conjugate base. FCH₂COOH (fluoroacetic acid, Ka ≈ 2.6 × 10⁻³) is the strongest acid among the options. Plain CH₃COOH (Ka = 1.8 × 10⁻⁵) is the weakest.

This medium 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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