Reasoning is a critical aspect of chemistry that students must learn to become full participants in the discipline. However, reasoning is inherently complex and science education researchers have struggled to consistently define and, consequently, to capture patterns of reasoning in student discourse and coursework. We seek to understand reasoning to move beyond the teaching of chemistry as a disconnected set of ideas and to improve the outcomes of chemistry instruction. In chemistry broadly, we have examined various types of reasoning that are distinctive of our discipline such as mathematical reasoning,^1,2  reasoning with chemical representations,^3,4  mechanistic reasoning,^5–7  and argumentation.^8–10  Organic chemistry as a subfield of chemistry requires reasoning that is distinct from other subfields. We know that typical organic chemistry instruction often fails to effectively promote reasoning and relies on assessments that emphasize rote memorization rather than an understanding of underlying phenomena. This recognition has led to an emerging focus on reasoning in organic chemistry that is captured in the chapters of this book including studies examining the role of representations, in-depth studies of complex reasoning, classroom teaching practices designed to promote reasoning, and approaches to the formative assessment of reasoning.

The first section of the book covers research on student representational competence. Understanding and interpreting visual complex representations is a primary challenge in organic chemistry learning. The contributions highlight how using representations in learning are perceived and understood by students. While solving organic chemistry tasks students often struggle to understand the underlying meaning of reaction mechanisms and electron-pushing formalism. Little is known about what students visually focus on while evaluating the plausibility of reaction mechanism and how that relates to the types of features they discuss in their reasoning. Weinrich & Britt make use of eye-tracking, followed by think-aloud interviews, to examine how students visually focus on curved arrows and how this relates to the students’ mentions of explicit and implicit features of the given representation. The study demonstrates eye-tracking technology as a valuable tool to examine how a feature (e.g., curved arrows) is focused on while evaluating reaction mechanisms and how these insights can be used to derive implications to support students’ mechanistic reasoning [Section A, Chapter 1]. Keller & Habig qualitatively investigate if students working on tasks involving stereochemistry and pericyclic reactions with augmented-reality support incorporated spatial aspects into their explanations compared to those working without augmented-reality [Section A, Chapter 2]. Learners who used the augmented-reality app tend to be able to involve spatial aspects in their reasoning more often and were able to conduct rotation operations correctly compared to the control group. The work by Ward, Rotich, Hoang & Popova draw on the seminal work from Kozma and Russel (1997) and combined it with Schönborn and Anderson’s model (2008) to characterize how organic chemistry students interpret, translate, generate, and use dash-wedge diagrams and Newman projections [Section A, Chapter 3]. This work demonstrates that the appropriateness of student reasoning can vary across tasks focusing on different representations, different representational competence skills, and whether the student attends to the external features or the conceptual information embedded in the representation.

The second selection of contributions highlights approaches to describe student reasoning about reaction mechanisms expressed in written or verbal contexts. Various frameworks have been used in the last decades that cover aspects of causality and mechanistic reasoning. The chapters in this section illustrate an in-depth analysis of students being engaged with organic chemistry tasks, argumentation, and in-class discourse. Crandell & Cooper provide a synthesis of their research on causal mechanistic reasoning as they have applied it, a description of evidence-based strategies used to engage students in reasoning and modelling, and findings from two longitudinal studies [Section B, Chapter 4]. The longitudinal studies both compare students in traditional introductory courses to those in CLUE courses, designed to elicit causal mechanistic reasoning. Their findings speak to the importance of instruction that is designed to elicit reasoning. Deng, Carle & Flynn illustrate an argumentation framework focusing on reasoning, granularity, and comparisons to characterize students’ arguments in organic chemistry and make use of a constructive alignment approach to guide teaching and assessment [Section B, Chapter 5]. The third chapter by Asmussen, Rodemer, Eckhard & Bernholt investigates undergraduate students’ verbal explanations to a series of case comparisons on nucleophilic substitution reactions and analyses how different concepts were used and related in students’ argumentation [Section B, Chapter 6]. The categorized concepts are transformed into weighted networks to capture the prevalence and centrality of individual concepts across students and tasks and are further compared to sample solutions. Their study illustrates that students experience difficulties when selecting the appropriate concepts relevant for a task at hand, often relying on single concepts, when multiple ones were required. Lieber & Graulich use a detailed process-oriented lens on students’ problem-solving to elicit students’ reasoning processes and their experiences during these processes [Section B, Chapter 7]. By explicitly examining students’ expression of epistemic stances, they could describe how these stances influence students’ judgements on claims and the justification with evidence and reasoning. Two case descriptions of students are used to illustrate (1) how epistemic stances and argument components are linked in students’ reasoning processes and (2) how epistemic stances are related to turning points. Hermans & Keller qualitatively analyze how writing comic captions for single mechanistic steps can engage students in describing the how, what, and why of organic mechanisms [Section B, Chapter 8]. They document that students were mostly focusing on describing the what and how and often neglected to provide causal relationships, describing the why of processes. Walsh, Karch & Caspari-Gnann use practical epistemological analysis to explore how students’ reason about organic chemistry problems and learn in-the-moment in natural settings [Section B, Chapter 9]. Applying practical epistemological analysis (PEA) allows describing how gaps in students’ understanding can be characterized, filled during interaction and how this is related to students’ prior knowledge. They analyze video recording of online active learning sequences facilitated by learning assistants and show how PEA is used as a tool to make student learning during collaborative group discussion visible.

The contributions on classroom practices and student reasoning report about empirical investigation of instructional practices in organic chemistry, either large-class interventions and targeted intervention to support specific aspects of student reasoning. The contributions in this chapter highlight influences of additional factors on student reasoning in organic chemistry, such as the pedagogical content knowledge of teaching faculty and teaching assistants. Traditional teaching methods, particularly those that emphasize lecturing, may not be sufficient to promote student reasoning in organic chemistry. How we design organic chemistry learning environments and what we do as instructors matters. In this section, the authors explore classroom environments and teaching practices designed to promote learning and reasoning in organic chemistry. Learning environments that engage students in discussion, drawing, and writing offer the opportunity for students to practice reasoning. Mooring, Burrows & Gamage examine the influence of a flipped-classroom approach on students’ reasoning in organic chemistry [Section C, Chapter 10]. They present a case study of students’ reasoning as they work together on a group quiz activity. Observing students during such group activities may provide unique insight into how learning environments may be designed to support the development of reasoning. Trabert, Schmitt & Schween describe an experiment-based learning environment designed to foster students’ causal mechanistic reasoning [Section C, Chapter 15]. Students engage in experiment-based case comparison activities purposefully designed to help them reason using experimental evidence in the classroom laboratory environment. Few studies have examined reasoning during organic chemistry lab work, and further research is needed to understand how instructors can relate laboratory coursework to the theory learned in lecture courses. Two chapters in this section explore the use of the Systemic Approach to Teaching and Learning (SATL) to promote reasoning. Sendur provides an overview of SATL and multiple examples of how systemic diagrams and assessment questions can be applied in organic chemistry [Section C, Chapter 11]. Rončević, Rodić & Horvat extend this by focusing on the application of SALT to diagnose conceptual understanding related to students’ reasoning about organic reaction mechanisms [Section C, Chapter 13].

Focusing specifically on teaching, Atieh, Mitchell-Jones, Xue & Stains examine instructors enacted pedagogical content knowledge for teaching resonance in organic chemistry [Section C, Chapter 12]. Their interview study describes how seven organic chemistry instructors plan for teaching, teach, and reflect on teaching resonance. Participating instructors demonstrated a range of knowledge and were organised by the authors into three groups characterizing their knowledge of curriculum, knowledge of students, knowledge of instructional strategies as they relate specifically to the teaching of resonance in organic chemistry. Finally, Stieff, Scopelitis & Lira present a study of how instructors use embodied actions—their use of hands and bodies during instruction—to model spatial thinking in organic chemistry [Section C, Chapter 14]. In this qualitative investigation, the authors describe how instructors used similar gestures to demonstrate how to perceive spatial information and how their actions differed in response to their teaching environment. We need to know more about how instruction in organic chemistry occurs and its relationship to student learning and the development of reasoning.

The third set of contributions report about novel ways of assessing student reasoning, including automated text-analysis, and underscore the importance of assessments that can measure deeper understandings associated with expert mechanistic reasoning. Bhattacharyya reviewed various studies in organic chemistry education which compared typical problems used by instructors to assess students’ reasoning with purposefully designed variations [Section D, Chapter 16]. He illustrates that most of the problems typically used may not adequately assess students’ reasoning and may rather emphasize the use of heuristics or product-oriented approaches. The following chapters provide novel approaches for assessment as well as the use of machine learning to facilitate the assessment. The chapter by Watts, Dood & Shultz, as well as Raker, Yik & Dood illustrate the start to developing education resources that utilize machine learning technology to assess reasoning and other learning objectives in organic chemistry. Watts, Dood & Shultz describe a machine learning model that was applied to longer pieces of writing about three different introductory organic reaction mechanisms [Section D, Chapter 17]. The model successfully predicts most components of reasoning characterized by the Russ framework, except for causal mechanistic reasoning.

Raker, Yik & Dood adds to this topic by describing a generalizable framework for evaluating mechanistic reasoning in student writing [Section D, Chapter 18]. The framework provides an assessment that can differentiate between different aspects of a reaction mechanism (i.e., nucleophiles, proton transfer etc.) and thus could be used by educators to formatively assess a variety of reactions. This framework has the potential to be used to create predictive models that can be used to analyze texts describing a variety of chemical reactions. Schwarz, DeGlopper, Ellison, Esselman & Stowe close this selection of chapters on assessment by providing an overview of assessment in chemistry more generally and assessment associated with practice of chemistry and describe two specific assessments they designed to measure three-dimensional (3D) learning in organic chemistry [Section D, Chapter 19]. 3D learning here includes knowledge of fundamental ideas, the practice of science, and understanding of cross cutting concepts.

A summarizing editorial highlights the advances illustrated in this book on researching student reasoning in organic chemistry and opens the gaps and future directions for research.

Nicole Graulich

Ginger Shultz