28. Mechanism and Equilibrium of Carbonyl Reactions

Freshman Organic Chemistry II (CHEM 125B)

This lecture aims at developing facility with devising plausible mechanisms for acid- and base-catalyzed reactions of carbonyl compounds, carboxylic acids, and their derivatives. When steric hindrance inhibits the A/D mechanism of Fischer esterification, an acid-catalyzed D/A mechanism can still occur. Substituent influence on the equilibrium constants for carbonyl hydration demonstrates four effects: bond strength, steric, electron withdrawal, and conjugation. Cyclic acetals play an important role in protecting the carbonyl groups of sugars, but acetals also can be used to protect alcohols, as can silyl ethers. Using amines instead of alcohols allows converting carbonyl compounds to imines via carbinolamines.

00:00 - Chapter 1. Fischer Esterification and Steric Hindrance
13:07 - Chapter 2. Carbonyl Hydration
24:34 - Chapter 3. Protecting Carbonyls and Sugars
38:24 - Chapter 4. Protecting Alcohols
45:44 - Chapter 5. Imines

Complete course materials are available at the Open Yale Courses website: http://oyc.yale.edu

This course was recorded in Spring 2011.