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Lec 22 Amine Synthesis

This is the 22nd 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 phenethylamines and the Henry reaction in Shulgin's book PiHKAL and on the EROWID web site. I review methods for the synthesis of amines: reduction of nitroarenes to anilines and lithium aluminum hydride reduction of amides and nitriles to amines. I introduce a new method called reductive amination using the reagent sodium cyanoborohydride. I start talking about amines as bases and the varying ionization states of amine functional 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