Learning to reason through organic reaction mechanisms is challenging for students because of the volume of reactions covered in introductory organic chemistry and the complexity of conceptual knowledge and reasoning skills required to develop meaningful understanding. However, understanding reaction mechanisms is valuable for students because they are useful for predicting and explaining reaction outcomes. To identify the features students find pertinent when explaining reaction mechanisms, we have collected students’ written descriptions of an acid-catalysed amide hydrolysis reaction. Students’ writing was produced during the implementation of Writing-to-Learn assignments in a second semester organic chemistry laboratory course. We analysed students’ written responses using an analytical framework for recognizing students’ mechanistic reasoning, originally developed with attention to the philosophy of science literature. The analysis sought to identify the presence of specific features necessary for mechanistic reasoning belonging to four broad categories: (1) describing an overview of the reaction, (2) detailing the setup conditions required for the mechanism to occur, (3) describing the changes that take place over the course of the mechanism, and (4) identifying the properties of reacting species. This work provides a qualitative description of the variety of ways in which students included these features necessary for mechanistic reasoning in their writing. We additionally analysed instances of co-occurrence for these features in students’ writing to make inferences about students’ mechanistic reasoning, defined here as the use of chemical properties to justify how electrons, atoms, and molecules are reorganized over the course of a reaction. Feature co-occurrences were quantified using the lift metric to measure the degree of their mutual dependence. The quantitative lift results provide empirical support for the hierarchical nature of students’ mechanistic descriptions and indicate the variation in students’ descriptions of mechanistic change in conjunction with appeals to chemistry concepts. This research applies a framework for identifying the features present in students’ written mechanistic descriptions, and illustrates the use of an association metric to make inferences about students’ mechanistic reasoning. The findings reveal the capacity of implementing and analysing writing to make inferences about students’ mechanistic reasoning.

What students write about when students write about mechanisms: analysis of features present in students’ written descriptions of an organic reaction mechanism

Teaching organic chemistry requires supporting learning strategies that meaningfully engage students with the challenging concepts and advanced problem-solving skills needed to be successful. Such meaningful learning experiences should encourage students to actively choose to incorporate new concepts into their existing knowledge frameworks by appealing to the cognitive, affective, and psychomotor domains of learning. This study provides a qualitative analysis of students’ meaningful learning experiences after completing three Writing-to-Learn (WTL) assignments in an organic chemistry laboratory course. The assignments were designed to appeal to the three domains necessary for a meaningful learning experience, and this research seeks to understand if and how the WTL assignments promoted students’ meaningful learning. The primary data collected were the students’ responses to open-ended feedback surveys conducted after each assignment. These responses were qualitatively analyzed to identify themes across students’ experiences about their meaningful learning. The feedback survey analysis was triangulated with interviews conducted after each assignment. The results identify how the assignments connected to students’ existing knowledge from other courses and indicate that assignment components such as authentic contexts, clear expectations, and peer review supported students’ meaningful learning experiences. These results inform how assignment design can influence students’ learning experiences and suggest implications for how to support students’ meaningful learning of organic chemistry through writing.

Students’ meaningful learning experiences from participating in organic chemistry writing-to-learn activities

Writing is a key disciplinary practice in STEM used to construct scientific knowledge and communicate research findings. With its role in the scientific process, writing is often incorporated into STEM classrooms to train students in scientific writing. The importance of incorporating writing in STEM classrooms is heightened by the role it can play in supporting student learning of disciplinary knowledge and thinking. However, the characteristics of a writing assignment can shape how and what students are learning. Although faculty recognize the value of writing in instruction, they often face barriers that constrain the amount and types of writing they incorporate into their classes. This article describes the design and propagation of Writing-to-Learn assignments in introductory STEM courses at the University of Michigan through the MWrite program. Our aim is to present a framework that could inform similar efforts from the classroom to institutional levels. The Writing-to-Learn assignment design described herein incorporates a context-driven prompt followed by content-focused peer review and revision. We also describe the structures incorporated into the MWrite program to support the large-scale implementation of writing in high-enrollment introductory STEM courses.

Praxis of Writing-to-Learn: A Model for the Design and Propagation of Writing-to-Learn in STEM

Organic chemistry reaction mechanisms are central to the discipline of organic chemistry but challenging for students to learn and for instructors to teach. Due to the unique challenges surrounding the topic, reaction mechanisms have been the focal point of many studies within organic chemistry education research. This article provides a scoping review of the existing research on students’ descriptions and explanations of organic chemistry reaction mechanisms and synthesizes the results and implications of the body of literature. The first half of the article provides an overview of the various reasoning frameworks researchers use to characterize students’ reasoning with reaction mechanisms, including synthesizing the literature on students’ approach to reaction mechanisms using a range of teleological, anthropomorphic, mechanistic, and causal reasoning. The second half of the article synthesizes the findings in the literature regarding students’ explanations of features and concepts common across reaction mechanisms (i.e., the electron-pushing formalism, nucleophiles and electrophiles, acid–base theories, resonance, leaving groups, and carbocations). Findings across the literature regarding approaches for supporting students’ reasoning with each feature and concept are described within each section. The review concludes with a synthesis of the implications for instruction and provides an overview of directions for future research. 

Mechanistic Reasoning in Organic Chemistry: A Scoping Review of How Students Describe and Explain Mechanisms in the Chemistry Education Research Literature

Reasoning about organic chemistry reaction mechanisms requires engagement with multiple concepts and necessitates balancing the relative influence of different chemical properties. A goal of organic chemistry instruction is to support students with engaging in this type of reasoning. In this study, we describe our use of case comparison problems to elicit students’ reasoning about acyl transfer reaction mechanisms across a semester. Using an instrumental case study methodology, we analysed three students’ reasoning across three time points: in a pre-interview at the beginning of the semester, on their written responses to one implementation of an in-class scaffold activity, and in a post-interview near the middle of the semester. Through the theoretical lens of Hammer's resources framework, we analysed the resources that students activated when approaching the case comparison problems. We characterized how students used each resource to support their reasoning, alongside characterizing how students weighed the different resources they activated. Our findings indicate that the case comparison problems activated a number of resources for each student across the time points by encouraging students to relate the surface-feature differences between reactions with the associated underlying properties. Students generally used resources, such as resonance and steric effects, in similar ways to support their reasoning across the time points. The study also illustrates the range in students’ abilities to weigh multiple conceptual influences and how this ability might change across the semester. This case study has implications for future research exploring how students reason with multiple concepts and for instructors seeking to implement activities that support students’ reasoning with case comparison problems.

Investigating students’ reasoning over time for case comparisons of acyl transfer reaction mechanisms

Acid–base chemistry is a foundational topic that is taught in courses across the chemistry curriculum. Students often have difficulty distinguishing between the different theories of acid–base chemistry—Bronsted–Lowry and Lewis acid–base chemistry—and applying these two definitions correctly in unfamiliar scenarios. To help students learn these definitions and be able to apply them, an acid–base Writing-to-Learn assignment was developed and evaluated. The Writing-to-Learn assignment involved a three-step process where students constructed an initial draft in response to a writing prompt, participated in peer review, and made revisions based on peer review feedback, before submitting a final draft. This process is informed by sociocultural theory applied to writing, which states that student learning of concepts increases through engagement with their peers’ work and receiving peer feedback on their own writing. To test the efficacy of the acid–base writing assignment, an external assessment, comprised of conceptual questions related to acid–base chemistry and students’ confidence when responding to them, was administered in two groups; a treatment group who completed the Writing-to-Learn assignment, and a comparison group who completed a separate assignment. Additionally, students who completed the Writing-to-Learn assignment were interviewed about their experiences. Regression analysis revealed that students in the treatment group had a greater increase in their conceptual understanding and confidence as compared to the students in the comparison group. The results demonstrate the students could successfully write about the Bronsted–Lowry and Lewis acid–base models separately, but were less successful with connecting these two concepts together in their writing. These results demonstrate the efficacy of Writing-to-Learn as an approach for promoting conceptual learning of acid–base chemistry.

Analysis of the role of a writing-to-learn assignment in student understanding of organic acid–base concepts

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Analysis of the role of a writing-to-learn assignment in student understanding of organic acid–base concepts