The acidic strength of carboxylic acids is influenced by several factors.

These factors can be categorized

into structural and environmental factors. Below are some key factors affecting the acidic strength of
carboxylic acids:

Electronegativity of the substituents: The presence of more electronegative substituents in the

carboxylic acid molecule increases its acidic strength. The electron-withdrawing effect of these
substituents pulls electron density away from the carboxylic acid group, making it more acidic. For
example, a carboxylic acid with a chloro substituent (Cl) is more acidic than the same acid with a methyl
substituent (CH3).

Resonance stabilization: If the carboxylic acid group is involved in resonance with other groups in the
molecule, it stabilizes the negative charge on the carboxylate ion (RCOO-) formed after deprotonation.
Resonance delocalizes the negative charge, making the carboxylic acid more acidic. For example, benzoic
acid (C6H5COOH) is more acidic than acetic acid (CH3COOH) due to resonance stabilization in the
benzoate ion (C6H5COO-).

Inductive effect: The inductive effect refers to the electron-withdrawing or electron-donating influence
of adjacent atoms or groups on the acidity of a compound. Electron-withdrawing groups (e.g., halogens)
adjacent to the carboxylic acid group increase its acidity by pulling electron density away from it.

Hybridization of the carbon atom attached to the carboxylic acid group: Carboxylic acids with a sp-
hybridized carbon atom (e.g., ethynoic acid - HC≡COOH) are more acidic than those with sp2- (e.g.,
acetic acid - CH3COOH) or sp3-hybridized carbon atoms (e.g., propionic acid - CH3CH2COOH). This is
because the greater s-character in sp-hybridized carbon results in more effective overlap with the s-
orbital of the hydrogen, facilitating the release of the proton.

Solvent effects: The choice of solvent can affect the acidic strength of carboxylic acids. In polar solvents,
carboxylic acids tend to dissociate more easily into carboxylate ions and protons, increasing their
apparent acidity.

Temperature: Higher temperatures generally favor the dissociation of carboxylic acids, resulting in higher
acidity.

Molecular size and structure: Bulkier carboxylic acids may have decreased acidity due to steric
hindrance, which hinders the effective dissociation of protons.
It's important to note that these factors interact with each other, and the overall acidic strength of a
carboxylic acid is determined by the combined influence of these factors.