Question:

The decreasing order of acid strength of the following is} \[ \text{FCH}_2\text{COOH,\ \ NCCH}_2\text{COOH,\ \ NO}_2\text{CH}_2\text{COOH,\ \ ClCH}_2\text{COOH} \]

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Chemistry Tip: Stronger electron-withdrawing group near COOH means stronger acid because conjugate base becomes more stable.
Updated On: Apr 27, 2026
  • FCH$_2$COOH > NCCH$_2$COOH > NO$_2$CH$_2$COOH > ClCH$_2$COOH
  • NCCH$_2$COOH > NO$_2$CH$_2$COOH > FCH$_2$COOH > ClCH$_2$COOH
  • NO$_2$CH$_2$COOH > NCCH$_2$COOH > FCH$_2$COOH > ClCH$_2$COOH
  • NO$_2$CH$_2$COOH > FCH$_2$COOH > NCCH$_2$COOH > ClCH$_2$COOH
  • ClCH$_2$COOH > FCH$_2$COOH > NCCH$_2$COOH > NO$_2$CH$_2$COOH
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The Correct Option is C

Solution and Explanation

Concept:
Acid strength of substituted carboxylic acids depends on the stability of the conjugate base: \[ RCH_2COOH \rightleftharpoons RCH_2COO^- + H^+ \] Electron-withdrawing groups stabilize the carboxylate ion by -I effect, increasing acidity. Stronger $-I$ effect $\Rightarrow$ stronger acid.
Step 1: Compare electron-withdrawing groups.
Given substituents:
  • $-NO_2$ : very strong $-I$ effect
  • $-CN$ : strong $-I$ effect
  • $-F$ : strong electronegative halogen
  • $-Cl$ : weaker than F
General order here: \[ -NO_2>-CN>-F>-Cl \]
Step 2: Apply to acids.
Therefore acidity decreases as: \[ NO_2CH_2COOH>NCCH_2COOH>FCH_2COOH>ClCH_2COOH \]
Step 3: Match option.
This exactly matches: $$\boxed{\text{Option (C)}}$$ :contentReference[oaicite:2]{index=2}
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