Question Details

The correct order of decreasing acidity of the following aliphatic acids is

Options

A

HCOOH > (CH3)3CCOOH > (CH3)2CHCOOH > CH3COOH

B

(CH3)3CCOOH > (CH3)2CHCOOH > CH3COOH > HCOOH

C

CH3COOH > (CH3)2CHCOOH > (CH3)3CCOOH > HCOOH

D

HCOOH > CH3COOH > (CH3)2CHCOOH > (CH3)3CCOOH

Show Answer

Correct Answer :

Option D

HCOOH > CH3COOH > (CH3)2CHCOOH > (CH3)3CCOOH

HCOOH > CH3COOH > (CH3)2CHCOOH > (CH3)3CCOOH

Solution :

The correct order of decreasing acidity is:

HCOOH > CH3COOH > (CH3)2CHCOOH > (CH3)3CCOOH

Acidity of carboxylic acids is governed mainly by the stability of their conjugate bases. All four acids have the same carboxylate anion core (‑COO⁻) after deprotonation, so differences arise from how the attached alkyl groups influence that anion.

1. Formic acid (HCOOH) has no alkyl substituent attached to the carbonyl carbon. The conjugate base (formate) is not destabilised by electron‑donating groups, making it the most acidic of the series.

2. Acetic acid (CH3COOH) contains a single methyl group. Methyl is weakly electron‑releasing (+I effect), which slightly destabilises the acetate anion compared with formate, thus lowering its acidity.

3. 2‑Methylpropanoic acid ((CH3)2CHCOOH) has two alkyl groups attached to the α‑carbon. The combined inductive (+I) effect of these groups further reduces the stability of the conjugate base, making it less acidic than acetic acid.

4. Pivalic acid ((CH3)3CCOOH) possesses three methyl groups (tert‑butyl). The strongest overall electron‑donating inductive effect among the four compounds most destabilises the conjugate base, giving it the lowest acidity.

Typical pKa values illustrate this trend:

HCOOH ≈ 3.75
CH3COOH ≈ 4.76
(CH3)2CHCOOH ≈ 5.0
(CH3)3CCOOH ≈ 5.5

Higher pKa means weaker acidity, corroborating the order listed above.

Therefore, the decreasing acidity sequence is exactly as stated: HCOOH > CH3COOH > (CH3)2CHCOOH > (CH3)3CCOOH.

Unlock Our Free Library

Access expert-curated educational resources and study materials—completely free.

Ask AI Tutor
5 left
Q1 View Question & Options
AI Tutor is solving this question...
Reading question context & options...