Analysis of resources applied to rationalize elimination mechanisms

Abstract

This study aimed to analyze second-semester organic chemistry students’ problem-solving strategies, specifically focusing on the resources activated while solving problems on E2, E1, and E1cB elimination reactions. Using the theoretical framework by Elby and Hammer, we defined a resource as a unit of information used in the problem-solving process. The resources activated to solve elimination reaction problems were probed using a mixed-methods approach using survey assessments and think-aloud interviews. The data were analyzed quantitatively and qualitatively following a validated set of scoring criteria. The results align with existing findings that students focus on surface-level structural information and use resources that have been repetitively emphasized over multiple semesters. Resources related to acid–base chemistry were activated more often than reaction-specific resources, such as conformational analyses or carbocation rearrangements. Although acid–base resources aid students in successfully analyzing reaction mechanisms, additional resources must be activated to rationalize specific mechanisms and to explain the products formed. This calls for instructors to provide formative and summative assessments that evaluate the many resources required to elucidate elimination reaction mechanisms and product stereochemistry.