Proposing reaction mechanisms using the electron-pushing formalism is central to the teaching and practice of organic chemistry. It is also, arguably, among the more useful of the transferrable skills taught in typical undergraduate organic chemistry courses (Organic One and Organic Two), in which the vast majority of students tend to have interests in the biomedical sciences and allied fields. Many of the core topics in these disciplines are mechanism-based, such as, the mechanism of action of drugs or the processes by which organisms respond to physiological changes at the cellular, tissue, organ, and system levels. Helping students learn and use electron-pushing mechanisms, therefore, could support their shorter- and longer-term professional goals.<br/><br/>Despite significant effort to ground instruction in electron-pushing mechanisms in conceptual frameworks, such as acids and bases and nucleophiles and electrophiles, the nearly two decades of research on student use of electron-pushing indicates that they persist in their tendencies to memorize mechanisms rather than to learn them “logically”. Careful review of this research suggests that the students’ superficial approach is most likely due to a variety of factors, including their epistemic development and their understanding of key concepts in organic chemistry. In this talk I review some of the key research done by several groups, including ours. I further propose, based on our recent interest in the application of foreign-language learning to organic chemistry instruction, that memorization may be an inevitable phase en route to a deeper understanding of electron-pushing in organic chemistry. Finally, I discuss the changes to instruction that may be required to accommodate this perspective of student memorization.

Student memorization of electron-pushing mechanisms in organic chemistry: Poor attitude or cognitive stepping stone?

ACS Spring Meeting 2021

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