Freshman Organic Chemistry II with Michael McBride - 34. Acids and Acid Derivatives

Freshman Organic Chemistry II (CHEM 125B) Reactions of carboxylic acids and their salts include nucleophilic substitution and decarboxylation to leave enols, free radicals, or alkyl halides. A review of the IR spectroscopy of acid derivatives includes the use of vibrational coupling in the structure determination of anhydrides and imides. Many acid derivatives can be interconverted by substitution through a tetrahedral intermediate, and differences in acidity can be used to drive such reactions toward completion. Reduction of acid derivatives illustrates the challenge of designing selective reactions. Acidic and basic mechanisms allow conversion of nitriles to carboxylic acids. Ketenes provide routes to several acid derivatives. The Baeyer-Villiger oxidation of ketones to esters illustrates atom insertion into acyl-R bonds. 00:00 - Chapter 1. Reducing Carboxylic Acids to Carbonyl Groups 02:21 - Chapter 2. Decarboxylation Reactions 12:02 - Chapter 3. Acid Derivatives and their IR Spectra 18:18 - Chapter 4. Interconversion of Acid Derivatives, Saponification 27:16 - Chapter 5. Selective Reduction of Acid Derivatives 40:45 - Chapter 6. Nitriles and Ketenes 47:35 - Chapter 7. Insertion into the Acyl-R Bond: Baeyer-Villiger Oxidation Complete course materials are available at the Open Yale Courses website: http://oyc.yale.edu This course was recorded in Spring 2011.