Chapter 16: Assessment of Assessment in Organic Chemistry—Review and Analysis of Predominant Problem Types Related to Reactions and Mechanisms

Learning and applying reactions and their electron-pushing mechanisms constitutes the largest part of instruction in organic chemistry courses. Items such as—supplying missing components of reactions, either reagent(s) or product(s); proposing reaction mechanisms given starting material(s), reagent(s), and product(s); and proposing synthetic routes to target molecules—predominate course assessments. Because these problem types reflect the skills routinely used by expert organic chemists, instructors might expect that such items necessitate chemistry-based reasoning, i.e., reasoning based on chemical concepts, principles, and/or theories, by students. However, the research on how students attempt to solve different types of tasks related to reactions and their mechanisms indicate that in many cases students can successfully solve these tasks relying on rote memorization or domain-general reasoning strategies. Furthermore, whether students use chemistry-based reasoning is most often related to the formats in which the tasks are framed. This chapter identifies the types of reaction- and mechanism-based tasks which tend to cue students to chemistry-based reasoning strategies and those that do not. The research reviewed in this chapter suggests that the many of the types of items organic chemistry instructors traditionally use may not adequately assess students' reasoning.