Lec 26 Review: Carboxylic Acid Derivatives, Enolates, Amines

This is the 26th lecture from the course Chem 51C Organic Chemistry taught by David Van Vranken at UC Irvine in Spring 2020. I begin by talking about 2-chlorobenzylidenemalononitrile, the active agent in CS gas that forms a covalent bond with the TRPA1 ion channel. Then I continue reviewing material from the course. I talk about the various transformation of carboxylic acid derivatives. I introduce the chemistry of enolates, particularly as nucleophiles in SN2 reactions. I introduce the powerful and selective base lithium diisopropylamide. I then talk about the addition of enolates to carbonyl groups in directed aldol reactions and aldol condensations. After showing the Michael addition of stabilized enolates to enones, I introuce the Robinson annulation. Finally I talk about the synthesis of amines through various reductive process. Finally. I review the various substitution reactions of arenediazonium ions. 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