To compare the acidity of substituted benzoic acids:
- Electron-withdrawing groups (-NO$_2$, -CN, -X) increase acidity (lower pK$_a$).
- Electron-donating groups (-OH, -OR, -NH$_2$, -R) decrease acidity (higher pK$_a$).
- The effect is generally stronger at the para position for resonance effects. Carboxylic acids are almost always stronger than phenols.