31. Preparing Single Enantiomers and Conformational Energy

Freshman Organic Chemistry (CHEM 125)

After mentioning some legal implications of chirality, the discussion of configuration concludes using esomeprazole as an example of three general methods for producing single enantiomers. Conformational isomerism is more subtle because isomers differ only by rotation about single bonds, which requires careful physico-chemical consideration of energies and their relation to equilibrium and rate constants. Conformations have their own notation and nomenclature. Curiously, the barrier to rotation about the C-C bond of ethane was established by measuring its heat capacity.

00:00 - Chapter 1. Introduction: Legal Implications of Chirality
03:36 - Chapter 2. Methods for Isolating Esomeprazole into a Single Enantiomer
15:14 - Chapter 3. Conformational Isomerism: An Introduction
31:36 - Chapter 4. Newman Projections and Nomenclature for Conformations
37:30 - Chapter 5. Understanding the Barrier to Rotate about the C-C Bond of Ethane

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

This course was recorded in Fall 2008.