3.2 Ranking Acids and Bases | Organic Chemistry

Chad gives a comprehensive lesson on how to rank acids and bases. This is presented in the context of the ARIO mnemonic which stands for Atom, Resonance, Induction, and Orbitals which helps students remember the most important factors affecting acidity and basicity in the most common order of importance. The Atom Rule for ranking acids and bases shows how the size and electronegativity of the basic atom affect its strength as a base. Of second importance is the effect of resonance on acidity and basicity as resonance can stabilize a base resulting in a weaker base. Typically of third importance is the effect of induction on acidity and basicity. Electron-withdrawing groups such as electronegative atoms near the atom acting as a base will help stabilize it resulting in a weaker base. Finally, the Orbital Rule describes the role that the hybridization of the atom acting as a base affects its basicity. Generally and all else being equal the order of stability with regard to hybridization is sp / sp2 / sp3 and the order of base strength is the opposite: sp3 / sp2 / sp. Chad provides numerous examples of how to rank acids and bases to demonstrate how each rule is applied, and concludes the lesson with several additional examples of ranking acids.

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00:00 Lesson Introduction
00:33 Ranking Acids and Bases (ARIO mnemonic)
03:31 The Effect of Charge on Acidity and Basicity of Organic Compounds
06:10 The Atom Rule for Ranking Acids and Bases of Organic Compounds
12:27 How Resonance Affects Acidity and Basicity of Organic Compounds
16:20 How Induction Affects Acidity and Basicity of Organic Compounds
25:12 How Hybridization Affects Acidity and Basicity of Organic Compounds
29:09 Examples of Ranking Acids

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