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Arrange the following carboxylic acids in decreasing order of acidic strength: (A) CH3-CH2-CH(F)-COOH (F at alpha carbon) (B) CH3-CH(F)-CH2-COOH (F at beta carbon) (C) F-CH2-CH2-CH2-COOH (F at gamma carbon)

1. A > B > C
2. B > A > C
3. C > B > A
4. A > C > B

Correct answer: A > B > C

Solution

Fluorine is strongly electron-withdrawing by induction. Its stabilisation of the carboxylate anion is greatest when it is on the alpha carbon (closest), making compound A the most acidic, followed by B (beta) and C (gamma).

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