To the Literature and Beyond: Teaching Advanced Organic Chemistry at a Primarily Undergraduate Institution

Offering an advanced organic chemistry course at a primarily undergraduate institution poses a challenge of condensing graduate organic synthesis into one course. This course was designed so students choose and read recent total synthesis papers from the literature in lieu of relying on a textbook or other preexisting course materials. Following the reading, students are required to propose a reasonable arrow-pushing mechanism for each step in the paper. The professor guides students on how to develop the ability to use resources (e.g., the primary literature, books, search engines, etc.) to propose mechanisms for reactions that are new to the students. In-class group work is implemented to promote active learning of complex topics. All mechanism proposals are presented to the entire class so that students become competent at communicating complex topics to others. Students not only learn many new reagents, reactions, and mechanisms relevant to modern organic synthesis but more importantly become proficient in finding detailed information on unfamiliar topics, a skill valuable to any scholar. As the course does not require the creation of materials such as problem sets or lecture notes, it can be taught with minimal preparation and work during the week by an instructor holding a PhD in synthetic organic chemistry or a closely related field.