Question Details

Arrange the following acids in increasing order of their acidic strengths:


HCOOH, FCH₂COOH, NO₂CH₂COOH, ClCH₂COOH

Options

A

HCOOH < FCH₂COOH < NO₂CH₂COOH < ClCH₂COOH

B

HCOOH < NO₂CH₂COOH < ClCH₂COOH < FCH₂COOH


C

NO₂CH₂COOH < HCOOH < ClCH₂COOH < FCH₂COOH

D

HCOOH < ClCH₂COOH < FCH₂COOH < NO₂CH₂COOH

Show Answer

Correct Answer :

Option D

HCOOH < ClCH₂COOH < FCH₂COOH < NO₂CH₂COOH

Solution :

The correct option is:
HCOOH < ClCH₂COOH < FCH₂COOH < NO₂CH₂COOH

Step-by-Step Explanation:

Acidic strength of carboxylic acids depends on the stability of the carboxylate anion formed after losing a proton (H+). Electron-withdrawing groups increase acidic strength by dispersing the negative charge on the carboxylate group through the inductive effect (-I effect) or resonance effect. Conversely, electron-donating groups decrease acidic strength by destabilizing the carboxylate anion.

Let us analyze the structures and substituents of the given acids:
1. Formic acid (HCOOH): It has no electron-withdrawing groups attached to the carboxyl carbon. The hydrogen atom has negligible inductive effect.
2. Monochloroacetic acid (ClCH₂COOH): It contains a chlorine (Cl) atom, which is moderately electronegative and exerts a moderate electron-withdrawing inductive effect (-I effect).
3. Monofluoroacetic acid (FCH₂COOH): It contains a fluorine (F) atom. Since fluorine is more electronegative than chlorine, its electron-withdrawing inductive effect (-I effect) is stronger than that of chlorine (-I of F > -I of Cl).
4. Nitroacetic acid (NO₂CH₂COOH): It contains a nitro group (-NO₂). The nitro group is a very strong electron-withdrawing group and exerts a significantly stronger -I effect compared to both halogens (-NO₂ > -F > -Cl).

Comparing the electron-withdrawing strength of the substituents, we have the order:
-H < -Cl < -F < -NO₂

Since a stronger electron-withdrawing group stabilizes the conjugate base more effectively, the acidic strength increases in the same order.

Therefore, the increasing order of acidic strength is:
HCOOH < ClCH₂COOH < FCH₂COOH < NO₂CH₂COOH

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