Trials and tribulations: student approaches and difficulties with proposing mechanisms using the electron-pushing formalism

Abstract

The skill of proposing mechanisms of reactions using the electron-pushing formalism (EPF) is not only of value to practicing organic chemists but it is also emphasized to students enrolled in organic chemistry courses at all levels. Several research studies in the past decade have documented the difficulties that undergraduate, and even graduate students, encounter when trying to propose mechanisms using the EPF. An examination of this work suggests the emergence of a preliminary, but coherent, picture of students' strategies and difficulties with using electron-pushing to solve a variety of organic chemistry tasks. The first two sections of this paper, I present (1) two factors that may underlie several of the students' difficulties as presented in the organic chemistry education research literature; and (2) a model of how students approach solving mechanism tasks using the EPF. This paper concludes with a section on potential implications for instruction and a set of research questions arising from this analysis that have yet to be answered.