About

Alan Shusterman

weekly schedule shows S’21 (online) OFFICE HOURS, alan@reed.edu, 503-517-7699

Syllabus 2021

time and location – MWF 10:05-10:55 AM, see syllabus for zoom meeting

text – none, just handouts and web posts

attendance – required

Description

Chemistry 324 is a half-unit course in advanced organic chemistry. Chemistry 201 and 202 (or instructor’s consent) are prerequisites, which means 324 is normally taken by Reed College juniors and seniors majoring in chemistry. Chem 333 (quantum mechanics) provides background that is helpful in places, but it is not required.

The course emphasizes the following areas:

  • Description of pericyclic* reactions from a physical (mechanistic) organic chemistry perspective
  • Application of the most widely used theories of chemical reactivity (Woodward-Hoffmann, Fukui FMO, Dewar-Zimmerman) that chemists rely on for the description of pericyclic reactions*
  • Using molecular modeling to study critical species in chemical reactions

*A pericyclic reaction is a concerted  reaction in which the transition state contains a cyclic array of forming and breaking bonds. Some of the pericyclic reactions covered in this class include electro(de)cyclizations, cycloadditions (e.g., Diels-Alder, 3+2, “click”, photochemical 2+2), and sigmatropic migrations (e.g., H migrations) and rearrangements (e.g., Claisen, Ireland-Claisen, Cope, oxy-Cope, anion oxy-Cope).

In addition to the above, we will also set aside time for reading and discussing the research literature, particularly intersections of chemical structure, reactivity/selectivity, and molecular modeling.

Chemistry 324 differs from Chemistry 345 (Adv. Synthetic Organic Chemistry) in that chemical reactions are studied from the physical side, rather than the synthetic. Instead of learning lists of reagents and experimental conditions, our focus is on thermodynamics, kinetics, isotope effects, reactivity models, and so on.

Assignments

See appropriate web page (Homework, Papers) for details. The number of assignments varies from year-to-year, so take the following parameters as rough indicators of workload and type of work.

  • 6-12 homework sets
  • 2-6 journal articles to read at home and discuss in class (written work may also be attached to these articles)