Characterization of student problem solving and development of a general workflow for predicting organic reactivity

A central practice in the discipline of organic chemistry is the ability to solve certain fundamental problems, including predicting reactivity, proposing mechanisms, and designing syntheses. These problems are encountered frequently by both students and practitioners, who need to utilize vast amounts of content knowledge in specific ways to generate reasonable solutions. To gain insight into how one of these major problem types can be solved, we have investigated student approaches to complex predict-the-product problems through the detailed analysis of think-aloud interviews. This work led to the creation of a general workflow model that describes the reasoning pathways of students with varying levels of expertise when attempting to predict organic reactivity. The problems used in this study were designed to be non-trivial and potentially ambiguous to elicit "true" problem solving and discourage a purely memorization-based approach, even from more experienced organic chemists. Rich descriptions of undergraduate and graduate student interviews are provided, and student thought processes are characterized in terms of common problem-solving actions. These actions were developed into the workflow model using an iterative method that combined results from our analysis with the experiences of instructors and feedback from both undergraduate focus groups and graduate students. The workflow serves as both a potential instructional tool and a model for student thinking. This model is general enough to be applied to both successful and unsuccessful solution pathways by both novice undergraduates and more expert-like graduate students. Characteristics of more successful and more experienced problem solvers are investigated, and concrete strategies that can be recommended to students are discussed. The results of this study complement existing work on other fundamental problem types in organic chemistry and suggest a variety of teaching interventions to develop students into more successful organic problem solvers.