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Aldehydes, Ketones and Carboxylic Acids
Acidity of Carboxylic Acids
3 questions from 3 papers, each with its answer.
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Appears in
Concepts tested
- Inductive effect and acid strength 2
- Inductive Effect on Carboxylic Acid Acidity
All Questions
2025 1 question
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The correct order of decreasing acidity of the following aliphatic acids is:
Alkyl groups are electron-donating ($+I$) which destabilize the carboxylate anion, decreasing acid strength: $\text{HCOOH} > \text{CH}_3\text{COOH} > (\text{CH}_3)_2\text{CHCOOH} > (\text{CH}_3)_3\text{CCOOH}$.
Acidity of carboxylic acids depends on the stability of the conjugate carboxylate anion ($\text{RCOO}^-$). Electron-donating inductive groups ($+I$) intensify the negative charge on the carboxylate group and destabilize it, thereby reducing acid strength. Formic acid (HCOOH) has no alkyl group and is the strongest acid. Acetic acid has one $+I$ methyl group, isobutyric acid has an isopropyl group (two methyls), and pivalic acid has a tert-butyl group (three methyls), making it the weakest acid. The decreasing order of acidity is $\text{HCOOH} > \text{CH}_3\text{COOH} > (\text{CH}_3)_2\text{CHCOOH} > (\text{CH}_3)_3\text{CCOOH}$.
2012 AIPMT-PRE 1 question
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The correct order of decreasing acid strength of trichloroacetic acid (A), trifluoroacetic acid (B), acetic acid (C) and formic acid (D) is:Electron-withdrawing groups (–I effect) stabilise the carboxylate ion and increase acid strength; electron-releasing groups (+I) decrease it.
F is more electronegative than Cl, so $CF_3COOH > CCl_3COOH$.
The $CH_3$ group in acetic acid has a +I effect, so HCOOH > $CH_3COOH$.
Order: $CF_3COOH$ (B) > $CCl_3COOH$ (A) > HCOOH (D) > $CH_3COOH$ (C)
2007 AIPMT-PRE 1 question
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Which of the following represents the correct order of the acidity in the given compounds?An electron withdrawing substituent increases the acidity of a carboxylic acid: by its $-I$ (inductive) effect it increases the polarity of the O-H bond and stabilises the carboxylate anion formed.
The halogen atoms are electron withdrawing, so all three haloacetic acids are stronger than acetic acid, in which $CH_3$ is an electron releasing group.
Electronegativity decreases in the order: F > Cl > Br
Hence the $-I$ effect also decreases in the same order.
Therefore the correct order of acidity is: $FCH_2COOH \gt ClCH_2COOH \gt BrCH_2COOH \gt CH_3COOH$
(The $pK_a$ values are about 2.6, 2.9, 2.9 and 4.8 respectively.)
