A Simple Assignment That Enhances Students' Ability To Solve Organic Chemistry Synthesis Problems and Understand Mechanisms

Abstract

Organic chemistry students typically struggle with the retrosynthetic approach to solving synthesis problems because most textbooks present the chemistry grouped by "reactions of the functional group". In contrast, the retrosynthetic approach requires the student to envision "reactions that yield the functional group". A second challenge is the inability to visualize the bond-forming and bond-breaking events that allow for predictive chemistry on the basis of reaction mechanism. Here we describe an original, easily implemented approach toward simultaneously addressing both problems. Starting in the middle of the first semester of organic chemistry—where reactions are typically first introduced—students begin to construct a "functional group transformation" notebook, or FGT. As reactions are presented in class, the students log these reactions, including the mechanism, in a reverse context, or a reactions that yield context. By the middle of the second semester of organic chemistry, where the retrosynthetic approach is addressed in full, the students have a notebook organized by functional group formed. The students are, in an ongoing sense, learning to think about organic reactions in both the forward and the reverse (retrosynthetic) sense from the middle of the first semester of organic chemistry through the end of the second semester while also recopying all the mechanistic details associated with each reaction.