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This is the 23rd lecture from the course Chem 51C Organic Chemistry taught by David Van Vranken at UC Irvine in Spring 2020. At the beginning of the lecture I talk about Bill Gates' experience in his organic chemistry course. I talk about the partitioning of amines between organic solvents and either unbuffered aqueous acid or unbuffered aqueous base and the chemistry of free-basing of cocaine. I introduce the non-basicity of amide nitrogens and the reduced basicity of anilines, particularly when resonance acceptors are ortho or para. I talk about the differential basicity of two types of nitrogens in aromatic heterocycles. Finally, I present the synthesis of arenediazonium ions from anilines and the subsequent substitution of diazonium ions with activated arenes, HO, F, I, and CN groups. Course Coverage: Organic Chemistry 5th Ed., J. Gorzynski-Smith Chapter 18: Electrophilic Aromatic Substitution Chapter 19: Carboxylic Acids and the Acidity of the O-H Bond Chapter 20: Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction Chapter 21: Aldehydes and Ketones--Nucleophilic Addition Chapter 22: Carboxylic Acids and Their Derivatives--Nucleophilic Acyl Substitution Chapter 23: Substitution Reactions of Carbonyl Compounds at the α Carbon Chapter 24: Carbonyl Condensation Reactions Chapter 25: Amines