Intermediate Organic Chemistry - Part 1

Organic chemistry course covering intermediate topics in structure and reactivity with emphasis on electronic structure, pericyclic reactions and aromatic heterocycles.

About the Course

This course covers intermediate topics on the structure and reactivity of organic compounds with an emphasis on electronic structure, pericyclic reactions and the chemistry of heteroaromatic compounds. Mechanistic concepts and models of reactivity are developed to build intuition about how organic compounds undergo their chemical transformations. An emphasis will be placed on developing problem-solving skills using frontier molecular orbitals to prepare students to think critically about the organic chemistry of living systems (e.g., nucleic acids, aromatic and heteroaromatic amino acids, etc.). This course and Part 2 are equivalent to a second-semester organic chemistry course, and these courses are especially suited for students in agricultural, nutritional and biological sciences, as well as premedical, predental, and preveterinary programs.

About the Instructor(s)

Michael Evans received a Bachelor's degree in Chemistry from the University of Kentucky in 2008. He is currently a graduate student in the Chemistry department at the University of Illinois, Urbana-Champaign, studying chemical education and educational technology. The goal of his research is the design, development, and evaluation of web-based tools for organic chemical education. He is also a Graduate Affiliate at UIUC's Center for Teaching Excellence and the webmaster of OrganicReactions.org, the website of the secondary reference Organic Reactions. In his spare time he enjoys running, cooking, and playing chess.
Professor Moore received his B.S. degree in Chemistry in 1984 and his Ph.D. in Materials Science in 1989 from the University of Illinois. Thereafter, he was an NSF Postdoctoral Fellow at Caltech and an assistant professor at the University of Michigan before joining the faculty in 1993. Professor Moore is the author of over 300 publications, a Fellow of the American Chemical Society, a Member of the American Academy of Arts and Sciences and an Associate Editor of the Journal of the American Chemical Society.

Course Syllabus

Week 1: Structural Fundamentals; The Curved-arrow Formalism; Introduction to Orbital Theory Week 2: Constructing & Interpreting Molecular Orbitals; Frontier Molecular Orbital Theory; Non-traditional Resonance Week 3: π Delocalization & Color; Aromaticity & Cyclic, π-type Molecular Orbitals; Aromatic Heterocycles Week 4: Cycloaddition Reactions; Cycloaddition Theory; Other Pericyclic Reactions Week 5: Organic Reaction Mechanisms & Proton Transfer; Strategies for Drawing Mechanisms; Patterns in Electron Flow & Reactivity Week 6: Reaction Intermediates, Transition States & Stability Trends; Radical Chemistry
Week 7: Photochemical Reactions; Kinetics & Thermodynamics; Catalysis
Week 8: Stereotopic Relationships; Stereochemistry & Symmetry; Facial Stereotopic Relationships

Recommended Background

One semester of organic chemistry is strongly recommended. Prior exposure to Lewis structures, basic stereochemistry, acid-base reactions, substitution reactions, and elimination reactions will be helpful.

Course Format

Each week of the course includes three lessons. A lesson is a set of short videos (webcasts) and reading materials centered on a particular topic. Each lesson includes several webcasts, but videos are generally less than ten minutes in length. Watch the webcasts and look over the reading materials for each lesson—this includes tackling the interactive problems linked from these materials! If you have questions or concerns about the content of a lesson, or if you’d like to help your peers, visit the discussion forums. Once you feel comfortable with all three lessons for a week, attempt the week’s quiz.
Because training effective problem solvers is one of our primary goals, we strongly emphasize tackling and understanding all of the quiz problems.

FAQ

Will I get a certificate for this course?
Yes. Students who successfully complete the class will receive a certificate signed by the instructor.

What technology is required/recommended for this course?An up-to-date web browser and Internet connection will be necessary to engage with the course content. We recommend Mozilla Firefox or Google Chrome (steer clear of Internet Explorer). A current version of Java will be necessary to complete most of the quizzes.

If you'd like to draw your own structures and keep your own files as you progress through the course, download MarvinSketch from ChemAxon. This free Java program is a rich, fully featured chemical structure editor for any operating system that runs Java (including Windows, Mac OS X, and Linux).

In one sentence, what is the primary learning goal of this course?
The student of this course will learn how to study, understand, and predict the features of new organic structures and reactions by drawing analogies to past experiments.

Provided by:

University: University of Illinois at Urbana-Champaign

Instructor(s): Michael Evans, Jeffrey S. Moore