3.2 Ranking Acids and Bases
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Conjugate Acid / Conjugate Base Pairs
-The stronger the acid the weaker the conjugate base.
-A more stable base is a weaker base and has a stronger conjugate acid.
-A more stable base generally has lower energy electrons.
Rules for Ranking Acids and Bases (ARIO)
| Factors Affecting Stability of the Conjugate Base | |
|---|---|
| Charge | -A negative charge raises the energy of electrons (stronger base). -A positive charge lowers the energy of electrons (weaker base). |
| Atom | The larger the basic atom in a group the more stable the base (weaker base). The more electronegative the basic atom in a period, the more stable the base (weaker base). |
| Resonance | Delocalization lowers the energy of electrons (weaker base). |
| Induction | LondonElectron withdrawing groups (i.e. electronegative atoms) near the basic atom stabilize the base (weaker base). |
| Orbitals | Greater s-character in hybrid orbitals results in lower energy (greater stability) of a base. Trend in stability: sp > sp2 > sp3 |
Charge
Atom
Resonance
Induction
-The closer the electron-withdrawing group the more stable the base (weaker base)
-The more electronegative the group the more stable the base (weaker base)
Orbitals (i.e. Hybridization)
Ranking Acids (Examples)
