How to Sort Acids and Bases by Strength
1. Charge – Positively charged compounds are typically more acidic, negatively charged compounds are typically more basic.
2. Atom – The more electronegative/larger the atom with a negative charge, the more acidic the hydrogen is.
3. Resonance – The more resonance-stabilized the conjugate base, the stronger the acid.
4. Dipole Induction – Electron withdrawing groups increase acidity, electron donating groups decrease acidity.
5. Orbitals – The more s-character an atom has, the more electronegative it is, and the more acidic hydrogen’s bonded to it will be. i.e. sp > sp2 > sp3