Inductive Effect
Which of the following α-halo carboxylic acids is the strongest acid due to the inductive effect of the halogen substituent?
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About This Question
- Subject
- chemistry
- Chapter
- some basic principles of organic chemistry
- Topic
- inductive effect
- Difficulty
- Medium
- Year
- 2025
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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