"It Gets Me to the Product": How Students Propose Organic Mechanisms

The ability to use the curved-arrow or electron-pushing formalism is one of the most vital skills in the organic chemist's repertoire. Their introduction to this formalism occurs when they first encounter reaction mechanisms. As they gain experience, the arrow-pushing formalism eventually becomes the primary technique organic chemists use to do retrosynthetic analysis, to predict the chemoselectivity of a reaction, and to create novel methodologies. Because practicing organic chemists use the arrow-pushing formalism in situations that are far removed from the simple contexts in which they are first presented, this study probed how students enrolled in a first-semester, graduate-level organic chemistry course approached the task of writing the mechanisms for two- to four-step reactions that lacked the typical cues that bring common mechanisms to mind. This article focuses on the students' solutions and discusses possible limitations of their strategies.