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Chemistry 330: Advanced Organic Chemistry

Course Level: 
Third Year
Academic Year: 
2017/2018

Instructor: Gregory Dake, A341

Prerequisites:

Chemistry 203/233; Chemistry 213.

Students are expected to be comfortable with the material contained in their second year level undergraduate organic chemistry courses. Materials to assist students’ review (videos, notes, problem sets) are uploaded onto Connect.

Textbook and reference materials:

There is no formal textbook for this course. Handouts will contain references to the primary literature. Sections of texts will be scanned and uploaded onto Connect.

If a student desires a book to augment their academic studies, an excellent textbook is “Organic Chemistry” by Clayden, Greeves, and Warren. This book can serve as a reference text for all third and fourth year organic courses (330, 313, 460, 413, 411). 

Other (more advanced) reference materials are: “Comprehensive Organic Synthesis”, Trost, B. M., Ed or the “Encyclopedia of Reagents in Organic Synthesis”, Paquette, L. A., Ed. These can be found in the Science Division of the Woodward Library.

Problem sets:

Problem sets will be distributed throughout the term. Topics covered in these problem sets will complement the lecture material AND in some cases introduce new concepts not explicitly covered within the lecture notes. 

Outline of Course Material:

A. Inspiration: prostaglandins! Introduction. Polarization of bonds in organic molecules. Examples of how organic chemists exploit the periodic table to modify reactivity: silicon, cerium, zinc, copper. (~5-6 hours)

B. Inspiration: the steroids, testosterone, estrone, cortisone! Cyclization reactions. Robinson annulation. Decalin synthesis and properties. Regiocontrolled formation of enolates and enolate equivalents. (~ 6 hours)

C. Inspiration: oxytocin, pepsin, b-lactam antibiotics, microcoxxin A! Amino acids. Amide bond formation in complex settings. (~ 4 hours)

D. Inspiration: Viagra, pharmaceuticals! Heterocycles. Heteroaromatics. Properties and reactions of common heterocycles. Fischer indole synthesis. (~ 5-6 hours)

E. Inspiration: UBC research! Exploiting organometallic reactions. Standard cross-couplings. Metathesis. Hydroamination. Hydrothiolation. p-Acid catalysis. (~ 5 hours)

F. Inspiration: Tamiflu! The Venerable Diels-Alder reaction (~4-5 hours)

G. Inspiration: UBC research! Case studies in molecule functionalization, enzymology, and PET bioimaging (~3-4 hours)

H. Interspersed As Needed! Case studies in selectivity: chemoselectivity, regioselectivity and stereoselectivity.