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Chemistry 330: Advanced Organic Chemistry

Course Level: 
Third Year
Academic Year: 
2014/2015

Chem 330 focuses on current methods of C–C bond formation, primarily through enolate and cycloaddition chemistry, and on other fundamental aspects of modern synthetic organic chemistry.

Instructor & office hours. Dr. Marco A. Ciufolini (office: Chemistry A331) is in charge of the course. This instructor has no fixed office hours. Please make an appointment by e-mail ( ) whenever you need to see him. Sporadic drop-ins are OK.

Website. The course website may be found at: http://groups.chem.ubc.ca/chem330/index.html

Prerequisites. The instructor presumes that you are familiar with fundamental concepts of general chemistry and introductory organic chemistry, especially: general chemistry organic chemistry • oxidation states, formal charges, etc. • elementary organic reactions • thermodynamics: ΔH', ΔG's, etc. • stereochemistry • acid-base equilibria (pKa's, etc.) • fundamental reaction mechanisms
Please take some time to review these important concepts. Useful reviews on oxidation states, formal charges, and pKa's are posted on the course website (click on "handouts" to access these documents).

Book. No book is required for this course. A good deal of material, including summaries of lectures, "handouts," etc., will be placed on the course website. If you wish to read more about the material presented in class, you may consult any good advanced organic chemistry textbook, such as Carey-Sundberg or March. If you wish to purchase a book, I recommend March over Carey-Sundberg. An investment in March will pay off handsomely in the future, especially for those of you who wish to become organic chemists.

Molecular models. We will frequently deal with stereochemical aspects of organic reactions in this course. Therefore, it is essential that you obtain a set of molecular models to help you visualize and understand the stereochemical properties of the molecules / reactions that we will encounter.

Any good set of molecular models will do. However, it is recommended that you obtain a set of Darling models. These inexpensive models are especially suited to the study of organic chemistry.

COURSE OUTLINE

(1) Introduction

(a) Importance of complex chiral molecules in the biopharmaceutical industry

(b) Carbonyl-based transformations as fundamental C-C bond forming processes

(2) Carbonyl-Based C—C Bond Formation

(a) Review of acid/base chemistry

(b) Claisen and Dieckmann ester condensations

(c) Regioselective formation of ketone enolates: thermodynamic and kinetic enolates

(d) Alkylation & intramolecular alkylation of ketones

(e) Alkylation of esters, lactones, nitriles, aldehydes

(f) Stereochemical aspects of enolate alkylation: cyclohexanones, decalones, etc.

(g) Enone synthesis & reactions

(h) Michael reactions and other conjugate additions

(i) Robinson annulation

(i) Aldol & intramolecular aldol

(k) Diastereo- and enantioselective aldols

(3) Formation of C—C Bonds Through Cycloaddition Processes

(a) Intermolecular and intramolecular Diels-Alder reactions

(b) Other cycloaddition reactions of synthetic interest