Construction by De-construction


The research on how students solve electron-pushing tasks in organic chemistry suggests that students tend to memorize entire electron-pushing mechanisms as singular, indivisible units of knowledge. The research also indicates that those who can conceptualize mechanisms as collections of paradigmatic steps are more likely to solve the most challenging tasks, thus creating a need to help students learn to deconstruct these mechanisms. Individuals learning new languages exhibit an analogous behavior in which they memorize by rote entire phrases as unanalyzed chunks. Groups of words are considered unanalyzed chunks when learners can grasp the meanings of the whole phrases without necessarily understanding the constituent words. This phenomenon is most commonly associated with learning idiomatic expressions during second-language acquisition. Analyzing the chunks (i.e., breaking them down into "productive units") is called "syntacticization", which in the context of electron-pushing mechanisms would amount to decomposing the pathways into their constituent, paradigmatic steps. The goal of this commentary is neither to assert a definitive method for instruction in electron-pushing nor to offer an exhaustive list of strategies to help students deconstruct organic reaction mechanisms. Rather, my hope is to propose that the concepts of unanalyzed chunks and syntacticization may present a fruitful perspective to better understand how students make sense of the electron-pushing formalism.


Chemistry and Biochemistry

Document Type





Collaborative/Cooperative Learning, Communication/Writing, Constructivism, Mechanisms of Reactions, Organic Chemistry, Second-Year Undergraduate

Publication Date


Journal Title

Journal of Chemical Education