CHEMISTRY 412
Topics in Organic Chemistry

In CHEM 412, students will study a variety of topics that are of current interest to organic chemists. Whenever possible, these topics will be related to one another and to topics wheich have been introduced in other organic chemistry courses.  Details of topics to be covered in a given semester will be posted on the Chemistry department website approximately one year before the course is offered.

CHEM 311 or CHEM 312.

Introduction:

• What is a reaction mechanism?
• Why study reaction mechanisms?
• Reaction mechanisms and the "scientific method."

• Bond fission, nucleophiles and electrophiles, curly arrows, thermodynamic vs. Kinetic control.

Some common reaction types:

• Substitution, addition, elimination, rearrangements, oxidation, reduction, decarboxylation.

• Carbocations, carbanions, free radicals, carbenes, other intermediates.

• A "case study" approach to the investigation of reaction mechanisms; for example, the benzyne mechanism, nucleophilic aromatic substitution via Meisenheimer complexes, the rearrangement of N-chloroacetanilide (the Orton rearrangement), the von Richter reaction, Saytzeff vs. Hofmann elimination, Hofmann degradation, Baeyer-Villiger rearrangement, and ester hydrolysis. In each case, the methods used to elucidate the accepted mechanism will be studied; these methods will include, but will not be limited to: product analysis; the use of isotopes, including the primary kinetic isotope effect; stereochemistry; substituent effects, including linear free energy relationships; solvent effects; etc.

• A survey of catalytic mechanisms and a detailed study of selected enzyme-catalyzed reactions, including reactions catalyzed by chymotrypsin, lysozyme, glutathione reductase, and liver alcohol dehydrogenase.

Quantitative structure activity relationships in biological systems:

• The application of QSAR to enzymology and pharmacology.