Lecture 34 - Acids and Acid Derivatives. 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. (from oyc.yale.edu)
Lecture 34 - Acids and Acid Derivatives
Time
Lecture Chapters
[00:00:00]
1. Reducing Carboxylic Acids to Carbonyl Groups
[00:02:21]
2. Decarboxylation Reactions
[00:12:02]
3. Acid Derivatives and their IR Spectra
[00:18:18]
4. Interconversion of Acid Derivatives, Saponification
[00:27:16]
5. Selective Reduction of Acid Derivatives
[00:40:45]
6. Nitriles and Ketenes
[00:47:35]
7. Insertion into the Acyl-R Bond: Baeyer-Villiger Oxidation
References
Lecture 34 - Acids and Acid Derivatives
Instructor: Professor J. Michael McBride. Resources: Professor McBride's website resource for CHEM 125b (Spring 2011). Transcript [html]. Audio [mp3]. Download Video [mov].