How do electron-donating groups change the acidity of carboxylic acids?
Electron-donating groups decrease the acidity of carboxylic acids by destabilizing the carboxylate ion.
When a carboxylic acid loses a proton, it forms a negatively charged carboxylate ion. The stability of this resulting anion is a primary determinant of the parent acid's strength. Electron-donating groups (also referred to as electron-repelling groups, such as alkyl groups) increase the electron density near the carboxylate group, which destabilizes the negative charge and makes the loss of a proton less favorable.12
For example, acetic acid (CH₃COOH) is approximately 10 times weaker than formic acid (HCOOH) because the methyl group acts as an electron-donating substituent compared to the hydrogen atom in formic acid. In contrast, electron-withdrawing groups increase acidity by dispersing the negative charge and stabilizing the carboxylate ion.12