66201 - Advanced Organic Chemistry M

Learning outcomes

When the course ends, the students know the basics of stereochemistry: symmetry elements and operations, and how to classify an enantiopure molecule by standard nomenclature (D/L, R/S and M/P). Some example of axial chirality and helicity will be shown The students also know the theory of optical activity, and the techniques employed for the measurement of the optical activity, like the ORD spectroscopy, Electronic and Vibrational Circular Dichroism. The students are trained in the use of these techniques for the assignment of the absolute configuration of organic molecules (octant rule and spectra comparison), and for the determination of the enantiomeric excess of reaction mixtures. In addition to the chiroptical techniques, the students will grow a basic knowledge about the determination of the absolute configuration by anomalous dispersion X-ray crystallography. The last part will deal with the separation of racemic mixtures by crystallization of conglomerates or by chromatographic techniques.

Course contents

Preliminary requirements to follow and understand the course:

basic knowledge in organic chemistry: reactivity, stereochemistry, reaction mechanisms.

Contents:

The course deals primarily with organic chemical reactions for the creation of C-C bonds emphasizing enolate chemistry and asymmetric catalysis.  The course gives also advanced knowledge in oxidations and reduction reactions in organic chemistry. The emphasis is on the different chemo-, regio- and stereoselectivity of the different reaction types. Fundamental retrosynthetic analysis of target molecules is taught as means to design multistep synthesis. The course is focused on applying a mechanistic approach to understand the outcome of chemical reactions.

Readings/Bibliography

Lecture handouts. Available on the web.

Assessment methods

Written/oral exam

Teaching tools

Class lectures with videoprojections

Office hours

See the website of Luca Bernardi