Teaching Organic Synthesis: A Comparative Case Study Approach

摘要

There are myriad possible approaches (1) to an advanced organic course for undergraduate or graduate students. Formats could include traditional lectures, group problem sets, class discussions, or student presentations Course content could focus on a catalog of reaction types, detailed analysis of reaction mechanisms, a selection of literature syntheses, or the development of student-proposed syntheses. I construct my upper-division synthesis course around group presentations (2) on several literature syntheses of complex, bioactive molecules. The course culminates in individual synthesis proposals of student-selected compounds. To develop students' understanding of synthetic strategy, I contextualize the literature syntheses by juxtaposing different approaches to related or identical molecules. I then challenge the students to articulate the strengths and weaknesses of the synthetic strategies in preparation for their critical analysis of their own synthetic plans at the end of the semester (3). In this model, the chalk and laser pointer are not in my hands but in the hands of the students, I serve as a guide and resource (4), particularly between class meetings.