Epistemic messages about how and why to learn in organic chemistry lectures

Abstract

Recent reforms in chemistry education aim to shift the goals of learning from knowing chemistry facts toward using chemistry understandings to make sense of natural phenomena (i.e., doing science). Doing so requires that we attend to, and work to shift, how and why students engage in class activities. To accomplish this, we must understand how the structure and enactment of chemistry courses communicate useful ways of knowing and learning – that is, how our courses convey epistemic messages. This study contributes to the larger goal of understanding epistemic messaging in science classes by investigating epistemic messages embedded in introductory organic chemistry lectures on nucleophilic substitution reactions. Specifically, our analysis describes the epistemic operations communicated (i.e., how to engage with knowledge), and the values ascribed to these operations for achieving epistemic aims (i.e., why engage with this knowledge). Analysis of seven lectures revealed that instructors communicated various epistemic operations, with notable variation in types and frequency. Most prominent were operations related to evaluating properties of chemical structures and predicting the pathway or outcome of chemical reactions. In contrast, operations associated with explaining or controlling reactions appeared less often. Some messages also conveyed the value of epistemic operations, either emphasizing their relevance for assessment or for doing science. The findings suggest that epistemic messages in lectures can frame how one should engage with knowledge in organic chemistry and why, although, in many cases, this orientation may not yet be explicit enough to be consequential to students.

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Introduction

Chemistry education has long aimed for students to experience chemistry classes as an opportunity to think like a chemist. In pursuit of this goal, the construct of chemical thinking (Sevian and Talanquer, 2014) and curricula (Cooper and Klymkowsky, 2013) designed to support its various aspects have been developed. In general, chemistry aims to investigate and explain the properties and changes of matter to predict and control chemical transformations. As such, thinking like a chemist would entail engaging with disciplinary knowledge and practices for the purpose of predicting and controlling chemical reactions.

Within this overarching goal of thinking like a chemist, two types of sub-goals can be distinguished. The first type is content goals – the specific concepts students are expected to learn (e.g., ideas related to bonding and energetics), as summarized in lists of such content goals (Gillespie, 1997; Atkins, 1999; Murphy et al., 2012; Cooper et al., 2017). The second type is focused on what it should mean to know and learn chemistry. These goals are answers to questions like: ‘Where should I go for useful knowledge of chemistry?’, ‘How will I know my understandings are trustworthy?’, and ‘What form should my knowledge product take?’. Since sub-goals of this second type refer to useful ways of knowing and learning, scholars in chemistry and science education have referred to them as epistemic or epistemological (Berland et al., 2016; Barzilai and Chinn, 2018). Ideally, epistemic ideas that seem sensible in the classroom overlap with how and why disciplinary professionals construct knowledge (Berland et al., 2016).

However, there is reason to question whether common approaches to teaching science support the adoption of a perspective on knowledge and learning that is useful to achieve those goals outlined. Empirical studies of K-16 science learning indicate that students frequently engage in course activities for reasons very different from those that motivate professional scientific work (Berland and Hammer, 2012; McNeill et al., 2016; Gouvea and Passmore, 2017). For example, Schwarz and colleagues (2025) found that students in a transformed organic chemistry course often constructed knowledge primarily for the purpose of being evaluated by the teacher for correctness (Schwarz et al., 2025). This means that, at least in the class examined by Schwarz et al. (2025), the goal of supporting students in thinking like a chemist was not advanced.

How might the ways of knowing and learning experienced as useful in a chemistry education classroom be shifted to better approximate the epistemic perspectives that underlie doing chemistry? Work by Russ (2018) provides useful insights. Specifically, Russ notes that messages about appropriate ways to know and learn may influence the epistemic ideas students activate in a particular moment. Such epistemic messages† may, for instance, be embedded in teacher talk, assessments, or course materials (Ke and Schwarz, 2021; Schafer et al., 2023; Schwarz et al., 2025). Over time, students’ experiences with epistemic messages may shape students’ broader conceptions of chemistry knowledge and chemistry learning (Sandoval, 2005; Hofer, 2016; Russ, 2018). Therefore, if we want students to genuinely experience a chemistry course as a space for thinking like a chemist, we must understand how appropriate ways to know and learn in and across moments are communicated in this environment.

Understanding epistemic messaging in chemistry courses is a complex endeavour. It requires identifying course components likely to communicate consequential epistemic information, developing a framework to describe such epistemic messages, and investigating if and how students experience, interpret, and respond to these messages.

The present study contributes to understanding epistemic messaging by mapping messages embedded in one crucial part of undergraduate chemistry learning: instructor lectures. Specifically, we present an analysis of how several organic chemistry instructors communicated ways of constructing knowledge (i.e., epistemic operations) and justified the utility of these epistemic operations. This study thus aims at providing insight into the ways of knowing and learning signalled as important by a ubiquitous instructional practice enacted by several instructors and demonstrates a useful method for describing lecture-embedded epistemic messages.

Theoretical framework

Epistemological resources

For many decades, scholars in psychology and education have been interested in epistemic cognition, which refers to how people understand the nature of knowledge and learning (Hofer, 2001, 2016; Chinn and Rinehart, 2016; Elby et al., 2016; DeGlopper and Stowe, 2024). While earlier works often treated epistemic cognition as a rather stable construct, e.g., framed as epistemological beliefs (Schommer, 1990; Hofer and Pintrich, 1997; Conley et al., 2004), personal epistemology (Hofer, 2000; Burr and Hofer, 2002; Schommer-Aikins, 2004), or epistemic beliefs (Bendixen et al., 1998; Mason and Bromme, 2010; Schiefer et al., 2022), current research increasingly models epistemic cognition as the dynamic activation of fine-grained pieces (Minstrell, 1992; diSessa, 1993; Sherin, 2006) of knowledge, or epistemological resources (Hammer and Elby, 2002, 2003) that are compiled in the moment.

There are several important features to the resources model of epistemic cognition. First, epistemic ideas active in a moment are often unconscious and unspoken. As such, scholars frequently infer aspects of one's epistemic cognition from behaviour (Sandoval, 2005). Second, epistemic ideas are dynamic and may change from one moment to the next (Rosenberg et al., 2006). It should thus not be assumed that epistemic ideas will be consistently activated across time and place. Third, there is no overall best compilation of epistemic ideas. All stances on knowing and learning can be useful in some context. Fourth and finally, epistemic ideas exist along multiple dimensions. For example, ideas about the aims motivating knowledge construction and ideas about useful processes for achieving these goals are about different aspects of knowing and learning.

Chinn et al. (2011) synthesized prior work in science education and philosophy into a framework that comprehensively describes different dimensions of epistemic cognition. Two such dimensions are epistemic aims and epistemic values. Epistemic aims are goals that people adopt, related to accomplishing epistemic achievements. These may include acquiring knowledge, understanding, explanations, or true beliefs, as well as avoiding false beliefs. Therefore, epistemic cognition can be considered as ‘directed at epistemic aims and their achievement’ (Chinn et al., 2011, p. 147). Epistemic aims, as with other aspects of epistemic cognition, are context-dependent and may shift in response to cues in learning situations. The reasons for adopting epistemic aims can be attributed to the epistemic value that is related to the resulting epistemic achievements. The value certain knowledge, belief, or understanding holds depends on various factors such as the justification, generality, or utility of acquired knowledge, which may differ in importance for different individuals and in different contexts (Chinn et al., 2011).

The achievement of an epistemic aim may require certain knowledge-related activities or a set of activities, called reliable processes in the framework by Chinn et al. (2011). These processes can be understood as composed of different epistemic operations and practices such as explaining, arguing, modelling, or predicting (Mason, 1996; Christodoulou and Osborne, 2014; Casas-Quiroga and Crujeiras-Pérez, 2020). Here, we think of a reliable process as composed of nested epistemic operations, which could also be composed of different steps. Arguing, for instance, involves a sequence of different operations, including making a claim, deriving evidence and justifying the evidence with reasoning to construct a sound argument (Toulmin, 2003; Osborne and Patterson, 2011; Lieber and Graulich, 2022). These operations may themselves depend on other operations, for instance, identifying and evaluating relevant data. Similarly, mechanistic reasoning requires different epistemic operations, like identifying the entities, evaluating their properties, coordinating their activities, and inferring their interactions to explain a phenomenon (Russ et al., 2008; Krist et al., 2019; Haskel-Ittah, 2023). In the context of organic chemistry, epistemic operations to achieve epistemic aims like predicting or controlling chemical transformations, could include identifying stereocenters in a molecule, predicting which mechanism a reaction follows, or explaining why a particular reaction yields certain side products. These epistemic operations may be applied at different levels of granularity, for instance, when analysing electron distribution within a single molecule versus reasoning about complex reaction systems, e.g., in the context of synthesis.

Accordingly, epistemic operations may vary in their grain size: several smaller operations (e.g., evaluating the properties of chemical structures) may be integrated into broader ones (e.g., inferring the likely progression of a chemical reaction based on those properties). In this way, more fine-grained operations can scaffold more complex cognitive processes, thereby supporting students in progressing toward epistemic aims (e.g., predicting a reaction outcome).

Epistemic messages

Observing that instructors’ epistemic ideas are often tacit, dynamic, and context-dependent does not immediately suggest useful implications for chemistry teaching. To arrive at such implications, we need to theorize about how features of a context influence students’ epistemic cognition in a certain way. This understanding could inform changes to instructional contexts that support productive epistemic ideas in students while learning chemistry. Russ’ construct of epistemological messaging (Russ, 2018), which we refer to here as epistemic messaging, gives us the theoretical lens we need to connect features of a course to students’ epistemic ideas. She argues that, during instruction, teachers tacitly communicate to students the type of knowledge or the knowledge processes that are valued at that moment. For example, encouragement to ‘start with what you know’ when constructing a model may communicate that students’ past experiences are a useful source of knowledge for engaging in the present activity (Rosenberg et al., 2006). Students may shift how and why they engage in class activities in response to epistemic messages they experience from a course.

The conceptual model shown in Fig. 1 illustrates how instructors’ goals for knowing and learning might relate to course-embedded epistemic messages. These, in turn, may help shape how and why students engage in class activities. Importantly, connections between instructors’ goals, course-embedded messages, and students’ experiences with these messages are likely to be complex and context-dependent. Instructors’ stated goals for knowing and learning may differ from the epistemic ideas they tacitly prioritize in their courses. Additionally, students’ experiences with course-embedded messages may be influenced by past experiences in similar courses, understandings of content, messages experienced from peers.

Fig. 1 Conceptual model illustrating the role of epistemic messages in the organic chemistry lecture classroom. The epistemic messages potentially conveyed by instructors represent the core of this study, with a focus on epistemic operations and their value. Dashed lines indicate additional potential influences and relationships, warranting further empirical investigation.

Empirical and theoretical work in science education makes it clear that instructors' views on knowing and learning (i.e., instructor's epistemic cognition) affect their approach to teaching (e.g., Kane et al., 2002; Windschitl, 2002; Windschitl et al., 2008; Long et al., 2013; Idsardi et al., 2023). Specifically, perspectives on knowledge and learning underlie what instructors build (i.e., curricula) and how they enact those course designs. Epistemologies available to instructors are potentially affected by their social environment, past experiences as students, and the affordances of the respective discipline (Fig. 1, upper part).

Instructors’ tacit epistemic commitments show up in classrooms as messages about valued knowledge and ways of knowing (Fig. 1, central part; Russ 2018). These might be embedded in student–teacher dialogue, as noted previously, or in other aspects of the course such as curricula or assessments (Schwarz et al., 2025). Epistemic messages might pertain to goals aiming at knowledge construction (i.e., epistemic aims), the relative importance of goals in a moment (i.e., epistemic values), criteria for goal achievement (i.e., epistemic ideals), or epistemic processes that enable progress toward goals (i.e., reliable processes) (Berland et al., 2016; Russ, 2018). For example, an activity that opens space for students to negotiate plausible claims from spectroscopic data of a crude product mixture may communicate messages such as ‘knowledge is justified by aligning with data’ or ‘observations are a useful source of knowledge’. Some scholars in science education have focused attention on epistemic messages that support productive engagement in scientific knowledge-building practices (e.g., Berland and Reiser, 2011; Hammer and Berland, 2012; Manz, 2015; Berland et al., 2020).

Epistemic messages students experience may affect which epistemic resources are activated in a given moment of learning (Hammer and Elby, 2002). In doing so, course epistemic message landscapes affect how and why students engage in class activities (Fig. 1, lower part). For instance, whether students perceive knowledge as transmitted by authorities or as something they construct themselves makes a difference in how they engage with a learning subject (Russ, 2018). Scherr and Hammer (2009) could show how students who treat the knowledge task as completing a worksheet with known information engage differently from those who treat the task as discussing ideas. Through their epistemic messages, instructors can thus play a central role in framing students’ learning (Ke and Schwarz, 2021).

The critical role of epistemic messaging in connecting course design and enactment to students’ epistemologies has led many scholars to employ and elaborate on this theoretical construct. Most of this work has focused on epistemic messages in interactive teacher–student discourse, especially in elementary to high school settings (Christodoulou and Osborne, 2014; Berland et al., 2016; Russ, 2018; Ke and Schwarz, 2021; Oh et al., 2022; Schafer et al., 2023). Russ (2018) described in her study, that all observed teachers conveyed epistemic messages while teaching. However, the messages differed, depending on, for instance, if they focused on the content, the form, or the production of ideas. (Oh et al., 2022) documented in a modelling-based classroom that the messages about the nature of knowledge and the process of knowing emphasized students’ own construction of knowledge, whereas in a traditional classroom, the focus was primarily on conveying messages about learning canonically correct knowledge (Oh et al., 2022). In their investigation, Schafer et al. (2023) characterized epistemic messages embedded in a high school curriculum and investigated how these might influence teachers’ reflections on what knowledge products or processes could be considered valuable at a given moment. This study found that epistemic ideas underlying teachers’ reflections were consistent with the emphasis of the curriculum they had adopted. Specifically, the curriculum and teachers’ reflections emphasized acquiring true beliefs (i.e., learning about content). The authors stated that curriculum-embedded epistemic messages may constrain ways of knowing and learning available to teachers who enact that curriculum.

Instruction-embedded epistemic messages can guide students’ epistemic ideas in learning activities. For instance, Ke and Schwarz (2021) showed that students’ approaches to modelling were related to epistemic messages their teacher conveyed about the nature and appropriate use of models. Students whose teacher encouraged them to ‘include everything’ in their model approached a modelling activity differently from students whose teacher emphasized that models should ‘explain how and why’ phenomena happen (Ke and Schwarz, 2021). Similarly, Oliveira et al. (2012) analysed the discourse of elementary teachers and their students in science classrooms. One key finding was that the way teachers implicitly communicated about the certainty of knowledge, e.g., through the use of terms like ‘maybe’ or ‘absolutely’, in turn significantly influenced how their students communicated about knowledge (Oliveira et al., 2012).

The nature of the epistemic messages that students experience can lead them to shift the ways they engage in and think about class activities. For instance, in Rosenberg and colleagues’ (2006) analysis of a group of middle school students working to construct a model for the Rock Cycle, these students begin approaching their task by transcribing vocabulary words from worksheets. Noticing that the students do not understand a lot of the copied terms, the teacher encourages the group to rely on their own knowledge instead of the worksheet to construct the model. This prompts a shift in the students behaviour from compiling scientific terms to constructing a causal mechanism based on prior experience with the topic (Rosenberg et al., 2006).

Much of the research on epistemic messages focused on the role of these messages in short time frames within instructional settings. While it can be assumed that many factors influence the activation of epistemic resources throughout a lecture session or a semester, repeated exposure to specific messages over time might shape students’ perception of the discipline and their approach to learning in classes related to that discipline (Russ, 2018; Krist, 2020). Recently, Schwarz et al. (2025) built on this idea to investigate how the sum of such epistemic messages unfolds over a semester. They examined epistemic messages regarding the value, construction, and evaluation of knowledge transmitted through assessments and related materials in a college chemistry course. Their findings revealed that these messages aggregated to communicate that learning in organic chemistry meant constructing knowledge products on exams that map onto the instructor-authored key (Schwarz et al., 2025).

The prospect of course-embedded epistemic messages influencing students’ epistemic cognition raises a host of questions for chemistry education research to explore. These include: what sources of epistemic messages are consequential to students? How well do instructors’ often tacit epistemic messages align with their goals for the course, and how do messages synthesize across the timescale of a course to affect more macro-level understandings of chemistry learning? Addressing these and other questions requires to simultaneously map the epistemic messaging landscape of our courses and explore how students experience, negotiate, and respond to that landscape. Here, we describe part of this work. Specifically, we describe epistemic messages embedded in lectures of several organic chemistry instructors.

For this study, we focus on a specific message source (lecture) and a particular course context (organic chemistry). Organic chemistry courses often serve as a gatekeeper to determine who may be able to continue their studies (Reingold, 2001; Schwarz et al., 2024), these courses and associated assessments lay the foundation of how students think about organic chemical knowledge (Stowe and Cooper, 2017). Additionally, instructors often have substantial say over the ways in which they run whole-class meetings (Wang et al., 2024). Thus, the results of this study might be actionable for instructors’ professional development. As research indicates that students typically approach college STEM courses with the epistemic aim of acquiring authorized facts and skills (Jiménez-Aleixandre et al., 2000; Schwarz et al., 2025), we focused our investigation on epistemic messages related to epistemic operations that might be helpful in acquiring such knowledge as well as on the values associated with these operations.

Research questions

Our work toward describing lecture-embedded epistemic messages in organic chemistry was structured to address the following research questions:

RQ1|What epistemic messages conveying epistemic operations can be identified in organic chemistry lectures focusing on substitution reactions?

RQ2|What types of added value are communicated in connection with epistemic operations?

RQ3|How do epistemic messages function as structuring elements throughout the lectures?

Methods

Context and data collection

Because of the exploratory nature of this study, a convenience sampling of university-level introductory organic chemistry lectures was conducted. Instructors of organic chemistry were contacted via e-mail or in person and recruited on a voluntary basis. In this manner, instructors from various universities in Germany and the USA provided video recordings of their lecture courses for the purpose of this study. All instructors gave their consent for using the provided recordings for analysis and publication purposes. For the analysis, all lectures were pseudonymized to avoid reidentification of the participating instructors. No IRB approval was required for data collection for this study. Nevertheless, ethical guidelines were followed during the research process. The analysed lecture courses were targeted at undergraduate students majoring in chemistry (i.e., bachelor programs in chemistry and food chemistry, chemistry student teachers) or related STEM majors (i.e., medicine, engineering), who had already completed their first semester of studies, including at least one general chemistry course. The lecture sections relevant to this study focused on nucleophilic substitution (S_N) reactions. This content area was chosen due to its ubiquity across organic chemistry courses and its substantial complexity. Students learning about S_N reactions are frequently asked to consider the possibility of multiple competing reactions and to design systems biased to produce one of several possible products. This complexity led us to suspect that instructors might express a diverse array of epistemic operations during recorded lectures. Additionally, in many introductory courses, S_N reactions are one of the first topics, where students are prompted to think about potential mechanisms of a reaction. Due to the importance of thinking in mechanisms for understanding organic chemistry, lectures on S_N reaction may lay an important foundation for how students think and reason about organic chemical reactions and mechanisms in their future studies.

From the seven collected video-recorded introductory lecture courses on organic chemistry, those sections (single lectures or sections of multiple lectures) that focused on S_N reactions were isolated. For each instructor, the isolated lecture sections first introduced general principles of S_N reactions and then discussed different influencing factors in varying depth, although the general order and topics of presented content knowledge were similar. The lecture sections on S_N reactions were considered finished when the instructors introduced a new topic with no apparent focus on S_N reactions in their lecture course. Depending on the instructor, the lecture sections on S_N reactions ranged from a single lecture to a series of several lectures on this topic (Number of respective (parts of) lecture sessions: Meyer (3), Fischer (2), Hoffmann (1), Jones (1), Becker (3), Peters (6), Miller (2)). This resulted in a variety in the duration of the lecture videos on this topic ranging from 45 to 303 minutes. This variation across instructors in the number of lecture sessions and, therefore in the duration of the video recordings focusing on S_N reactions can, for instance, be attributed to the fact that some instructors already included elimination reactions in these lecture sessions, as well as to significant differences in the extent to which exercises and off-topic talk were included. Importantly, the focus of the present study demonstrates the feasibility of an approach to characterizing lecture-embedded epistemic messages. It is not an attempt to assemble an exhaustive list of all messages one might infer from each lecture. As such, the variation in time dedicated to S_N reactions across recorded enactments was not an issue. Since the distinction between lecture sections in terms of duration and organisational structure, including whether an instructor covers S_N reactions in a single lecture or across several lectures, is not central for this study, the term lecture is here used in a generalised sense for reasons of readability. It encompasses both, single lectures and sets of lectures by the respective instructor analysed for this study. Further clarification is given where a more precise distinction is considered useful.

Data analysis

Preparation of the data for coding. The video recordings were transcribed with the help of an AI-based audio-to-text converter. After a first transcription with the AI tool, all transcripts were checked and revised manually until a verbatim transcription was reached. Each instructor was given a pseudonym, and other information in the transcripts that might have allowed identification of the instructors, like names or places, was also changed or removed. Transcripts of German lectures were translated into English for this publication. The cleaned transcripts of the lecture recordings were transferred to the coding software MAXQDA for qualitative analysis. To structure the analysis and to see if the occurrence and quality of epistemic messages differed between functionally different sections of a lecture, the transcripts were divided into three structural types, based on the function of disciplinary knowledge within the respective part of the lecture: content presentation, exercises, and miscellaneous topics (e.g., course organization). Additionally, concerning the presented and discussed content, the lectures were segmented into broader units that reflected the conceptual focus of each lecture part.

Coding of epistemic operations. The transcripts were analysed through inductive coding (Saldaña, 2016) of epistemic operations communicated within the lecture. After an initial coding of around 15% of the data set to establish the granularity and basic categories of epistemic messages in the lecture, the categories were discussed among the two authors (EH, NG), who performed the coding independently, resulting in an initial codebook. Iterative rounds of coding bigger sets of the data and updating the possible categories of epistemic messages as well as discussing different perspectives on the wording of the coding followed until agreement. This process included the discussion with other group members to integrate a broader perspective for an appropriate coding of the data. Two authors then coded the whole data set separately. Remaining differences were resolved to reach a consensus on the coded data.

In the end, two criteria were essential for assigning the code epistemic operation to a statement of an instructor: the message had to explicitly express the cognitive operation in which students are expected to engage. This might, for instance, include explaining why a chemical reaction proceeds in a certain way or comparing chemical structures in terms of their properties. Secondly, this cognitive operation had to be aimed at knowledge elements relevant to organic chemistry.

These criteria aim to distinguish epistemic messages that explicitly emerge from the general epistemic background noise of lectures, where most statements are to some extent related to knowledge and learning. For instance, statements that merely announced a new topic or indicated that certain knowledge elements are important were not coded as epistemic operations if they did not specifically indicate how students should interact with a certain knowledge element. This focus on explicit messages about how to engage with organic chemistry knowledge was meant to increase the trustworthiness of our coding process. The statements coded as epistemic operations were further grouped into categories based on the type of practices involved and the disciplinary content knowledge elements they referred to (Table 1).

Table 1 Codes for epistemic operations present in organic chemistry lectures on S_N reactions

Code	Related content	Code description	Examples
Identify chemical structures	Chemical structures	Operations related to the identification of (parts of) chemical structures	‘[…] important being able to identify […] stereoisomers.’
			‘[…] very important identifying acids and bases […]’
Evaluate properties		Operations related to the evaluation of the properties of chemical structures	‘So, what makes one nucleophile better than another? You always have to compare […].’
			‘The first thing you need to assess is the leaving group.’
Predict reactions	Chemical reactions	Operations related to predicting how a chemical reaction proceeds, or which products are formed	‘[…] which mechanism a reaction follows. After all, you want to be able to predict […].’
			‘[…] you have to figure out likely products based on a variety of different system parameters.’
Control reactions		Operations related to manipulating chemical systems to achieve certain reaction products	‘This means that if you want to shift a reaction from SN2 to SN1 […].’
			‘[…] if you want to favour an E2 elimination […].’
Investigate reactions		Operations related to finding things out about mechanisms (using experimental evidence)	‘[…] you can immediately determine which reaction mechanism is operative […].’
			‘This is one of the best experimental methods to study a mechanism in the first place.’
Explain reactions		Operations related to explaining why a chemical reaction proceeds in a certain way	‘[…] different product outcomes, and our task is going to be to explain why […].’
			‘[…] make a little bit more sense of why this backside approach happens the way that it does.'

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In terms of the knowledge elements, the epistemic operations were either related to chemical structures or chemical reactions. In the context of chemical structures, the related operations could be grouped into two categories, depending on their focus on either identifying chemical structures or evaluating their properties. In the context of chemical reactions, epistemic operations could be allocated into one of four groups, depending on whether these practices were aimed at investigating, explaining, controlling, or predicting chemical reactions. In all cases, the overarching epistemic aim in the lectures was acquiring authorized knowledge of chemistry content.

Coding of added values. In a second step, the transcripts were inductively coded for messages that conveyed achievements or applications enabled by engaging in epistemic operations, thereby highlighting what the respective epistemic operations, i.e., the knowing/knowledge resulting from engaging in these operations, are valuable for. Values of interest needed to be more specific than simply useful for knowing or useful for understanding – these somewhat generic values were ubiquitous in all recorded lectures and (we suspect) do little to shift students toward thinking like a chemist. As such, we focused our attention on explicit value statements that extended beyond useful for knowing. To be coded, such explicit value statements needed to be clearly linked to an epistemic operation in the transcript. For example, ‘[…] you have to figure out likely products […]. You will have it on exams […] to come.’ In this example, the epistemic operation of figuring out products (predict reactions) is connected to an indication of its value for future assessments. Similar values were grouped, resulting in two distinct categories for added values, transporting the value of epistemic operations as either for the assessment or for doing science (Table 2).

Table 2 Codes for added values conveyed in association with epistemic operations in organic chemistry lectures on S_N reactions

Code	Code description	Examples
For the assessment	Messages that indicate the value of a certain epistemic operation for assessments	‘[…] in the exam, it will be clear which effects are decisive. With this, you can then decide how the reaction will proceed.’ (epistemic operation = predict reactions)
		‘[…] and you have to figure out likely products […]. You will have it on exams and quizzes to come.’ (epistemic operation = predict reactions)
For doing science	Messages that indicate the value of a certain epistemic operation for application in a scientific or professional context	‘You can convert various functional groups into one another. […] This is important when you think about the significance of synthetic chemistry […].’ (epistemic operation = control reactions).
		‘What we discuss here about the chemical reactivity of compounds is also reflected in their toxicity. […] it is important that when you see a molecular structure, you can estimate that caution is required.’ (epistemic operation = evaluate properties)

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For a better overview of the prevalence of each category of epistemic operations and added values, their absolute and relative occurrences were plotted. To illustrate the distribution and relationship between epistemic operations and values for RQ3, the lecture sections were represented as barcodes, using a method proposed by Colley and Windschitl (2021).

Results

RQ 1|What epistemic messages conveying epistemic operations can be identified in organic chemistry lectures focusing on substitution reactions?

Various messages conveying useful epistemic operations could be identified in all lectures. Those messages that stood out beyond the epistemic background noise of the lecture typically involved linking a knowledge element with a practice, indicating how students should interact with these knowledge elements. Across the seven lecture sections, 61 such messages explicitly focusing on epistemic operations were found. These epistemic operations could be grouped into six categories: (1) explain reactions, (2) investigate reactions, (3) control reactions, (4) predict reactions, (5) evaluate properties, (6) identify chemical structures (see Table 1). The number of epistemic operations as well as the categories varied between the different instructors (Fig. 2). The total number of messages conveying epistemic operations per instructor across all their respective lecture sessions on S_N reactions ranged from three in the case of instructor Hoffmann to 18 in the lecture of instructor Fischer. The number of different categories ranged from one category covered in instructor Hoffmann's lecture section (in this case evaluate properties) to five in instructor Peters’ lecture, while most of the lecture sections included two or three categories in general. In none of the lectures did all six categories appear. Every lecture section included at least one epistemic operation focusing on chemical structures (Fig. 2, codes: identify chemical structures and evaluate properties). Except for instructor Hoffmann's lecture, each lecture section contained at least two epistemic operations related to chemical reactions (codes: explain reactions, investigate reactions, control reactions, or predict reactions).

Fig. 2 Absolute number of epistemic operations communicated in each of the seven investigated lectures on S_N reactions by category.

Considering the density of epistemic operations per lecture time, the highest density can be found in instructor Fischer's lecture with about 12 epistemic operations per 60 minutes of lecture time (18 epistemic operations in 91 min total lecture time), followed by instructor Meyer with close to 6 (10 in 87 min) and instructor Jones with slightly above 4 operations per 60 minutes (6 in 96 min) (Fig. 3). The four other instructors conveyed between 2 and 4 epistemic operations per 60 minutes of the respective lecture (Hoffmann: 3 in 45 min; Becker: 6 in 137 min; Peters: 12 in 303 min; Miller: 4 in 87 min).

Fig. 3 Density of messages conveying epistemic operations communicated in each of the seven lecture sections on S_N reactions separated by category.

Comparison of epistemic operations across lectures. The results reveal marked differences in both the quantity and diversity of epistemic operations emphasized in messages across the lectures. While some instructors, such as Fischer and Meyer, articulate a high number of messages conveying epistemic operations, others, such as Miller and Hoffmann, convey a much smaller number. As shown by comparing Fig. 2 and 3, this variation can only be partly accounted for by differences in lecture length.

Additionally, the lectures differ in the extent to which they focus on particular epistemic operations, for instance, in instructor Jones's lecture, the messages conveying epistemic operations primarily include identifying chemical structures, while instructor Hoffmann's lecture revolves around evaluating properties (Fig. 2). In addition to the number of epistemic operations, the variety in epistemic operations seems especially important when comparing different lectures. For instance, the lectures of instructors Becker and Peters show a rather low density of epistemic operations (Fig. 2), but convey a broader variety, including a relatively high proportion of more complex epistemic operations when compared to the lectures of, e.g., instructors Jones or Hoffmann.

Typically, all lectures started with an introduction to the general principles of S_N reactions and then addressed factors influencing these reactions. The depth of this analysis differed across different instructors: while some instructors mainly focused on highlighting trends, e.g., in nucleophilicity and leaving-group quality, others already included more complex evaluations of several influencing factors while discussing the competition between different types of substitution and elimination reactions in later lecture segments. However, no systematic relation could be observed between this variation in the discussion of disciplinary content and the number or type of epistemic operations conveyed.

Messages about identifying chemical structures and evaluating their properties were common across all observed lectures. This is reasonable from a disciplinary perspective since epistemic operations of both categories can be considered disciplinary prerequisites for engaging in reasoning about chemical reactions. In the context of determining substitution reactions and choosing between competing S_N1 and S_N2 pathways, identifying chemical structures or reasoning about their properties can be seen as foundational skills. For instance, accurately predicting or explaining reaction products requires identifying the nature of the chemical structures, e.g., the nature of the substrate or the leaving group.

We observed messages about epistemic operations along a spectrum of granularity, with small-grain epistemic operations potentially supporting or facilitating large-grain epistemic operations. For instance, effectively evaluating properties often requires one to first identify salient aspects of chemical structures. Thus, identify chemical structures may serve as a small grain epistemic operation that scaffolds engagement in the larger-grain epistemic operation of evaluating properties. In turn, effective reasoning about S_N reactions necessitates key comparisons on, e.g., a molecular or electronic level—such as evaluating the strength of nucleophiles, the quality of the leaving group, substrate structure, and the influence of different solvents on reaction intermediates.

Since these aspects involve relative properties, identifying structures alone may be insufficient; it is essential to compare and assess properties. Such comparative evaluation is, thus, an important facet of evaluating properties. With 24 messages coded across seven lectures, evaluating properties was the most prevalent category of epistemic operations, absent only from the lectures by instructors Jones and Miller—interestingly, the only two who included epistemic operations explicitly related to identifying structures. This suggests that small grain epistemic operations embedded in larger-grain epistemic operations may be challenging to detect using our method of directly coding explicit messages.

In contrast to the categories identify chemical structures and evaluate properties, which focused on chemical structures, the epistemic operations in the four remaining categories targeted S_N reactions themselves. Among these, epistemic operations to predict reactions were the most abundant, with 17 messages coded and absent only in the lecture of instructor Hoffmann (Fig. 2). For the other instructors, the number of messages in the category predict reactions ranged from two to four. We observed three major variations of messages related to predicting reactions. One type covers the question of whether a certain reaction proceeds at all or how fast it is in qualitative comparison to other reactions. Other messages highlighted the ability to predict which mechanism a certain reaction follows, while the third theme shifted the focus to predicting the products or the properties of the products of a chemical reaction.

A total of four messages included epistemic operations related to controlling or manipulating chemical reactions (code: control reactions). These messages occurred only in the lectures by instructors Fischer and Peters (two each) (Fig. 2). Additionally, five epistemic messages, found in lectures by the instructors Fischer, Becker, Peters, and Miller, pertained to investigating and discovering aspects of chemical reactions and their mechanisms (code: investigate reactions). Both categories (control reactions and investigate reactions) reflect a hoped-for connection between disciplinary knowledge and its practical application.

Finally, messages explicitly pointing out the importance of the ability to explain chemical reactions were found exclusively in instructor Peters’ lecture, with five messages coded (Fig. 2). These messages highlighted a distinct emphasis on explanatory understanding within this teaching context, which can be considered as one of the central competencies in organic chemistry (Cooper, 2015). While having the lowest density of epistemic operations overall (Fig. 2), this focus on explaining reactions makes instructor Peters’ lecture one of the lectures with the highest density of the higher level epistemic operations focusing on chemical reactions. Additionally, in contrast to the other lectures, in instructor Peters’ lecture, a wide range of epistemic operations is emphasized. This raises the question of the extent to which a broader variety of epistemic operations is productive for student learning and the epistemic aims they adopt, or whether a more focused approach, repeating a smaller number of epistemic operations more frequently, might be more effective. Beyond the variety and frequency of epistemic messages, their coherence both internally and in relation to other elements of the learning environment, such as assessments or laboratory courses, may affect what ways of knowing and learning seem useful to students.

On the one hand, a more focused and consistent emphasis on a limited number of epistemic operations in the conveyed messages may provide students with a clearer orientation and enable them to concentrate on what is considered central in the respective lecture. For example, the strong focus on evaluate properties in instructor Hoffmann's lecture might encourage students to initially prioritize assessing relevant properties, such as the quality of the nucleophile, when dealing with S_N reactions, thereby establishing a foundation for their further or future reasoning about chemical reactions. A large variety of epistemic operations may make it challenging for students to decide which epistemic operations should be applied.

On the other hand, a greater diversity of epistemic operations in messages may more authentically represent the multifaceted nature of epistemic processes, while deciding about reaction pathways in organic chemistry. Indeed, scholars who conceptualized the resources model of epistemology see evidence of epistemic sophistication when ‘students explore and discuss the differences between knowledge in multiple contexts’ (Elby and Hammer, 2001, p. 564). This means that epistemic sophistication amounts to having a diverse array of epistemic resources and a finely tuned mechanism for deciding which will be helpful when. Perhaps students in instructor Peters’ class had a greater chance of developing epistemic sophistication, due to the many different epistemic ideas they were expected to use. In contrast to other instructors, instructor Peters overall spends significantly more lecture time on S_N reactions, thereby also leaving enough time between epistemic messages, potentially making it easier for students to progress from lower to higher level epistemic operations. By illuminating the diverse cognitive practices employed in organic chemistry, an approach like in this lecture may promote a more differentiated understanding of learning in this field, possibly one that values the application of knowledge over mere reproduction.

RQ2|What types of added value are communicated in connection with epistemic operations?

In some cases, epistemic operations are accompanied by messages conveying an associated value. Specifically, we coded messages that explicitly communicated a value going beyond the underlying value of ‘knowing something’, e.g., to acquire fundamental knowledge in organic chemistry, often expressed by the instructors by ‘Topic XY is important’. In most lectures, such added values (i.e., indications of why engaging in certain epistemic operations may be useful) that went beyond this implicit baseline value could be identified, with 17 total messages coded. Every lecture, except for the lecture by instructor Jones, had at least one statement that explicitly expressed added value associated with an epistemic operation. The highest number of messages indicating the value of an epistemic operation can be found in the lecture by instructor Fischer with six messages, followed by instructor Peters’ lecture with five, and instructor Meyer's with three. Instructor Hoffmann, instructor Becker, and instructor Miller expressed the added value of an epistemic operation in one case each.

Interestingly, the instructors differed in the kinds of added value they communicated. Only in the lectures of instructors Fischer and Peters, both coding categories of added value, for the assessment and for doing science, could be found. The lectures of the five other instructors included only values of a single category or none at all.

The added value for the assessment indicates that the value of an epistemic operation or the associated epistemic product lies in its usefulness in, for instance, passing the exam, collecting points on tests, or for assessment-related contexts (see Fig. 4 for an example). Eight messages of this category could be found in three of the seven lectures. The added value for the assessment was most common in instructor Fischer's and instructor Meyer's lectures, with three messages each, followed by instructor Peters’ lecture with two. The occurrence of this value may not be surprising, as instructors typically use this to draw students ' attention to important aspects that prepare them for the exam (Stowe et al., 2021). Nevertheless, it sets the scene for what and why knowledge elements are important.

Some of the messages coded as for the assessment affirmed that the complexity of the knowledge about certain mechanisms would be reduced for the exam. This could entail that the wording of the value would frame what students should be able to do in the assessment (e.g., Fig. 4(a)).

Fig. 4 Examples of epistemic messages conveying added value related to epistemic operations: (a) for the assessment; (b) for doing science.

The added value for doing science was assigned to messages associated with an epistemic operation if the message expressed the importance of this operation for scientific practices, be it in the laboratory, in everyday life, or in a professional context. Given our field's goal of engaging students in knowledge building that would be meaningful to professional chemists (Raker and Towns, 2012; Sevian and Talanquer, 2014; Cooper et al., 2015; Berland et al., 2016; Talanquer, 2018a, b; Neiles et al., 2020), it makes sense to capture lecture-embedded epistemic messages that attest to the utility of epistemic operations in non-school settings. Nine such messages could be found across five of the seven lectures, absent only in the lectures given by instructors Meyer and Jones. They were most abundant in the lectures by instructor Fischer and instructor Peters, with three statements each. The lectures by instructor Hoffmann, instructor Becker, and instructor Miller each included one such message.

Some of the messages coded as for doing science emphasized finding things out about chemical reactions in an experimental setting or from empirical data (5), while another message framed the value as acquiring a realistic view of what to expect of chemical reactions in an authentic laboratory context (1), (e.g., Fig. 4(b)). In other cases, for instance, the value of the application of organic chemistry knowledge for synthetic chemistry (2) or for evaluating hazards of chemicals (1) was emphasized.

Associations between epistemic operations and added values. 17 out of the 61 observed messages on epistemic operations were associated with some indication of added value. With 5 out of 12, instructor Peters has the highest portion of messages on epistemic operations with an explicit indication of an added value across all the lectures, followed by instructor Fischer (6 out of 18) and instructor Hoffmann (1 out of 3) with an equal ratio, instructor Meyer with 3 out of 10, instructor Miller with 1 out of 4, and instructor Becker with 1 out of 7. No statements conveying added value were found in the lecture by instructor Jones.

In the lectures investigated, each of the two kinds of added values observed was associated with certain categories of epistemic operations (Fig. 5). For doing science was primarily associated with investigating or controlling reactions. Furthermore, this added value was in two cases associated with evaluating properties of chemical compounds. For the assessment was mainly associated with predict reactions (five messages) and with instances of evaluate properties (two messages) and explain reactions (one message). No added values could be found for the category identify chemical structures.

Fig. 5 Association of the added values for doing science and for the assessment with the categories of epistemic operations.

It is not surprising that epistemic operations were linked to epistemic values in our data, as both relate to the importance and achievement of particular epistemic aims. Epistemic aims that are especially valuable for doing science likely include data-supported causal explanations and models. These can be achieved via careful analysis of data from well-designed experiments (Esselman et al., 2023). Although explicit epistemic messages about developing explanations appeared only in one of the investigated lectures, several instances of epistemic operations highlighting knowledge generation through experimentation (e.g., for investigating chemical reactions) were observed.

By contrast, epistemic aims useful for succeeding on course assessments include authorized facts and skills. These are efficiently learned via different epistemic operations, such as recognizing patterns between reactants, reagents and expected products for ‘predict the product’ questions (Bhattacharyya, 2022). These two examples of values conveyed in connection with epistemic operations showcase how different epistemic messages could frame learning situations very differently (Russ, 2018). This way, depending on the epistemic communication in the moment, different, potentially conflictive, approaches to learning might be portrayed as useful in relation to a certain epistemic aim.

Proportional to the total number of epistemic operations in the different categories, the highest concentration of messages conveying added values was associated with the categories investigate reactions and control reactions, with 4 out of 5 and 3 out of 4, respectively. In all other categories, less than a third of the epistemic operations were associated with an explicitly added value. These results show that the observed instructors tended to associate different values with different epistemic operations. Only epistemic operations related to investigating or controlling chemical reactions are, in most cases, associated with the value for doing science. The relation to investigating and controlling reactions is sensible as both are closely related to doing experiments and other forms of scientific inquiry work – tasks that are uncommon on assessments given in a lecture course. However, the total absence of the value for doing science with some categories of epistemic operations, especially concerning explaining reactions is striking, as it is in contrast to rhetoric in chemistry education that advocates for reasoning about causes for chemical phenomena, e.g., to explain reactions and build arguments purposefully (Sevian and Talanquer, 2014; Berland et al., 2016; Talanquer, 2018a, b, 2021; Cooper et al., 2019, 2024).

In comparison, the added value for the assessment is mainly found in conjunction with epistemic operations concerning the prediction of reactions (Fig. 5). Therefore, messages around predicting the mechanism and the products of chemical reactions may, in some lectures, send the notion that this operation is a prerequisite to pass the exam, but not necessarily that this is an important practice of scientific inquiry (Bhattacharyya, 2022). This observation suggests that students who approach organic chemistry learning as an opportunity to perform disaggregated skills may, in fact, be learning in ways that instructors (tacitly) seem to value (Bhattacharyya and Bodner, 2005; Anderson and Bodner, 2008; Schwarz et al., 2025). Additionally, in the lectures investigated, the added values of epistemic operations tend to be communicated only in isolated instances, often linked to a small variety of epistemic operations, associated with specific knowledge elements. Rarely do such value-related messages appear in a general or overarching form.

Overall, it can be assumed that the strong orientation on assessment in some lectures may lead students to perceive epistemic processes as merely a means to pass exams rather than essential scientific practices. Even though assessments still present a central component of contemporary instruction in organic chemistry, a more conscious conveyance of the value for doing science could help promote a notion of chemistry knowledge useful beyond the exam context (Nayyar et al., 2025) and, therefore, contribute to the shift from learning about science to learning by doing science (Berland et al., 2016). Although the epistemic messages conveying the value of epistemic operations are not too abundant, the observation of these messages supports the perspective that instructors convey views about valued ways of engaging with knowledge, thereby indicating how to appropriately learn in a discipline and why (Russ, 2018).

RQ3|How do epistemic messages function as structuring elements throughout the lectures?

Contrasting cases in the occurrence of epistemic operations were and added values. In line with the substantial variation in the number and density of messages emphasizing certain epistemic operations across the seven instructors, there are also clear differences in how these messages appear throughout each lecture section. These differences in epistemic messaging may reflect different epistemic frames adopted by teachers (Russ and Luna, 2013). Differences become particularly evident when comparing the contrasting cases of instructor Jones (Fig. 6) and instructor Fischer (Fig. 7).

Fig. 6 Structure of the lecture by instructor Jones including the distribution of messages with epistemic operations and added values and a selection of examples of such messages.

Fig. 7 Structure of the lecture by instructor Fischer including the distribution of messages with epistemic operations and added values and a selection of examples of such messages.

In instructor Jones’ lecture, explicit communication on epistemic operations can be found only occasionally (Fig. 6). While some conveyed epistemic operations appear to frame the presentation of disciplinary knowledge, large parts of the section are devoid of such messages. At the beginning of segment 1, shortly after the start of the lecture, instructor Jones communicates the ability to predict the stability of reaction products as an overarching aim of the lecture (Fig. 6(a)). This message is directly followed by other messages that convey the importance of epistemic operations related to identifying chemical structures as a prerequisite for correctly predicting reaction product stability. These are picked up again in segment 2, where foundational aspects for S_N and elimination reactions, such as nucleophiles and leaving groups, are introduced.

The next explicit communication on epistemic operations occurs at the end of the content presentation in segment 4, after an extended portion of the lecture with no such messages. At this point, after a basis of knowledge on S_N reactions has been presented in segments 1–4, two epistemic operations are emphasized (Fig. 6(b) and (c)), framing the following exercise on the influence of different substrates on the reaction rate. In the exercise, students are asked to predict which substrate of a given selection would undergo the fastest S_N2 reaction and to assign chemical roles to various substances (e.g., nucleophile, substrate, solvent). Here, the epistemic operations framing the exercise align with the task (in contrast to the absence of messages framing the exercise of segment 3), thereby serving as a link between conceptual knowledge and its application in problem-solving contexts. After this segment, no further communication on epistemic operations was identified in instructor Jones’ lecture.

In contrast to instructor Jones’ lecture, in the lecture of instructor Fischer (Fig. 7), epistemic operations were frequently emphasised and sometimes associated with added values.

In this lecture, epistemic messages primarily frame units of content presentation, occurring mostly at their beginning or end. Additionally, such messages can be found when subtopics, like the different factors influencing S_N reactions (e.g., nucleophilicity, leaving group quality) are introduced in segment 2. In these cases, these messages may serve as structuring elements, indicating the start or end point of a topic, or framing what the learning goals of the respective section are. Additionally, repeating epistemic messages may indicate how the presented knowledge can be meaningfully applied and which interactions with knowledge elements are considered especially important.

As in instructor Jones’ lecture, epistemic messages in instructor Fischer's lecture also function as bridges between content presentation and exercises. Before the exercise in segment 2, instructor Fischer elaborates on the evaluation of the quality of nucleophiles by considering basicity trends (Fig. 7(a)). This operation is then applied in the exercise by comparing the basicity of similar molecular structures (e.g., H₂O and H₂S) to infer relative nucleophilicity.

Notably, this section also includes an instance of explicit communication of an epistemic operation within the exercise itself (Fig. 7(b)), reinforcing the earlier message.

In the second half of segment 6, another epistemic operation is emphasized, this time related to controlling chemical reactions and thus how to influence whether they proceed via an S_N1 or S_N2 mechanism. In the following exercise, different examples of S_N reactions are discussed. While the focus lies on predicting the appropriate mechanism, students are also prompted to consider how reaction conditions could be modified to shift between mechanisms, thereby applying the epistemic operation emphasized before.

In summary, epistemic messages conveying epistemic operations predominantly appear in two key contexts across the lectures: (1) within the presentation of content knowledge, particularly at the beginning or end of conceptual knowledge units, and (2) at the transition between content presentation and exercises. This way, messages conveying epistemic operations structure the lecture, to varying degrees, by framing transitions between different topics or subtopics as well as by serving as a link between disciplinary knowledge and its application in the context of exercises.

Nested hierarchy of epistemic operations. In some cases, messages conveying epistemic operations appear nested with certain concepts serving as prerequisites for more complex operations. For example, before introducing the various factors influencing S_N reactions in segment 2 (Fig. 7), instructor Fischer frames this introduction in segment 1 with the overarching aim of enabling the students to predict reactions with a particular focus on the reaction rate (Fig. 7(c)). In segment 2, where different factors influencing S_N reactions are presented, additional epistemic operations, i.e., evaluate properties, are emphasized at several points. These operations are framed as sub-operations supporting the overarching aim of predicting chemical reactions. The first of these messages occur at the beginning of the segment, emphasising the role of the leaving group (Fig. 7(d)).

Subsequent messages elaborate on this by addressing specific operations in the context of examples and specific cases (e.g., Fig. 7(e)). This example illustrates that epistemic operations can be found at different grain sizes: epistemic operations framed more generally are supported by more specific sub-operations at lower levels. In instructor Fisher's case, the prediction of reactions is facilitated by different nested epistemic operations on subordinate levels of granularity, contributing different aspects to the achievement of this aim. Epistemic operations from different categories may thus complement one another to fulfil higher-level epistemic operations and achieve associated aims. However, this is rather a rare case, and the connection between these operations is not always made explicit by the instructors.

Examples of nesting can also be found in other lectures. For instance, in instructor Becker's lecture, the epistemic operation of evaluating properties is conveyed as an overarching aim. After a first focus on nucleophile characteristics (such as charge or particle size), the epistemic operation of evaluating properties is revisited through specific examples, each accompanied by related sub-operations of the same category. In these sections, the subordinate epistemic operations of evaluating the properties of specific molecules jointly reinforce the broader focus of evaluating chemical properties. Another example can be found in instructor Meyer's lecture, where initially the weighing of main effects is emphasized as an essential epistemic operation for reasoning about S_N reactions, which forms the basis for the subsequently conveyed broader operation of predicting how the reaction is likely to proceed overall.

From a disciplinary perspective, such nesting of epistemic operations appears well justified. As demonstrated in instructor Fischer's lecture, for instance, evaluating molecular properties, and, thus, the reactivity of organic molecules is a crucial basis for reasoning effectively about the kinetics of chemical reactions. Similarly, identifying chemical structures and patterns, as well as evaluating properties, can serve as prerequisites for engaging in more complex cognitive operations related to chemical reactions and their mechanisms.

These observations suggest that, when connected across different grain sizes, epistemic operations could function as a scaffold in organic chemistry lectures, systematically connecting knowledge elements in pursuit of some sort of content understanding. For instance, predicting which mechanism a certain reaction follows may require several different epistemic operations on lower levels of granularity, like identifying relevant molecular structures, evaluating their properties, assessing potential interactions, and weighing competitive reaction pathways. How such an interplay of epistemic operations forms a process reliable for achieving an epistemic aim is seldom articulated explicitly, and may, thus, remain opaque to students. Indeed, most lectures (or lecture sections) that convey epistemic operations lacked a clear hierarchical organization of epistemic operations useful for achieving a particular aim. Instead, the lectures sought to establish coherence by announcing topics.

Limitations

In this study, the status quo of communication about epistemic operations and the value of knowledge and understanding in introductory organic chemistry lectures was captured without evaluating the teaching quality of the lectures. Therefore, the disciplinary content presented in the lectures was not assessed in depth, nor were perspectives of students and instructors or exam results included in the analysis. The analysis of the amount and kinds of epistemic operations and added values in the lectures thus serves as a contribution to understanding how epistemic messages in the context of organic chemistry knowledge unfold. While substitution reactions are fundamental for learning organic chemistry, the present analysis is confined to lecture sections covering this topic. Other sections of a lecture course may exhibit different characteristics in terms of epistemic communication. In addition, there is no guarantee that students experienced the messages we coded, or that their experience aligned with our description. For example, students who have no experience engaging in scientific research may not experience doing science epistemic messages in the ways we expect. We would need to observe or interview students to get a sense for how the differing epistemic messaging landscapes we described affected appropriate ways to know and learn across contexts.

Conclusion

This study aims to contribute to a better understanding of epistemic aspects of science learning by characterizing the epistemic messages present in organic chemistry lectures. The investigation revealed that epistemic operations are emphasized to varying degrees by the instructors in introductory organic chemistry lectures and are associated with different added values.

The findings show that epistemic operations related to evaluating properties and predicting reactions, which can be considered disciplinary prerequisites essential for advanced reasoning about reaction mechanisms (Talanquer, 2018a, b), were most prevalent. However, epistemic operations such as investigating, controlling, and explaining reactions were less frequently mentioned, even though they are closely tied to core practices of scientific inquiry, like testing of hypotheses, development of experiments, or causal reasoning, and therefore can be associated with core questions of disciplinary knowledge generation (Sevian and Talanquer, 2014). Their limited presence in the lectures may indicate a reduced emphasis on communicating how scientific knowledge emerges and is justified.

Additionally, instructors differed not only in the number of epistemic messages but also in whether and how these operations were explicitly connected to an added value beyond acquiring knowledge. The messages from the two identified value categories—for the assessment and for doing science—emerged with varying frequencies. The value for the assessment was commonly associated with operations related to predicting reactions, suggesting a strong orientation toward preparing for exams, which are typically dominated by predict the product or predict the mechanism tasks (Bhattacharyya, 2022).

The value for doing science, which aligns more closely with authentic scientific practice, was rarely and unevenly communicated and mainly occurred with operations related to controlling or investigating reactions. Strikingly, some instructors did not mention any messages linking epistemic operations to broader scientific or societal relevance, thus missing the opportunity to illustrate the epistemic value of knowledge in this context of organic chemistry. Even if instructors make rhetorical claims about the value of certain scientific knowledge, it is far from certain that students will experience this knowledge as useful in their daily lives. Scholars in science and technology studies (e.g., Feinstein, 2011) have shown that the facts and skills covered in science classes are rarely used to solve the practical problems of people and communities.

Overall, these findings indicate that acquiring authorized, canonically correct knowledge can be inferred as an overarching epistemic aim for most of the lecture sections, while there are fewer accounts that seemed to emphasise the construction of knowledge meaningful for the students as a significant goal. This finding aligns with a strong focus on content coverage observed in ongoing research on instructors’ perception of their teaching (e.g., Kraft et al., 2023). Additionally, instructors may not always be aware and intentional about how they shape learning processes by their teaching (Jones et al., 2022), suggesting that the focus on authorized knowledge we perceived here might not always be intended.

Furthermore, balancing the demand of preparing students for assessments with cultivating a broader understanding of how science can be used in life might represent a challenge for instructors. While acknowledging the importance of exam preparation, it is crucial not to let assessment-oriented framing dominate the epistemic climate of a classroom. Enhancing students' awareness of how disciplinary knowledge connects to scientific practices and real-world applications could promote a shift from memorization strategies toward mechanistic and conceptual reasoning (Ebenezer, 1992; Novak, 1998; Flynn and Ogilvie, 2015; Hosbein et al., 2021). Nonetheless, the two kinds of added values are not mutually exclusive, for example, when solving exam tasks requires an engagement with disciplinary knowledge that is also valuable for doing science. In contrast, to help students to meaningfully engage in scientific activities, it might be beneficial to not just communicate the value for doing science, but this value should also be reflected and rewarded in the tasks students face on assessments. One aspect of this shift in the construction of courses and assessments might include, for instance, focusing on sensemaking through modelling or reasoning with authentic data (Stowe et al., 2020; Esselman et al., 2023).

The results suggest that, in many cases, the epistemic structuring of lectures to communicate why and how knowledge is acquired often remains implicit. Hierarchical organization of epistemic operations—where subordinate operations support broader epistemic aims or values—was observed only rarely. Intentional epistemic structuring might have the potential to scaffold students' reasoning processes more effectively. Yet often, the absence of explicit connections between epistemic operations and their value might leave students without a clear orientation about what knowledge is valued and why. It is useful for us to consider how to support instructors in more purposefully and coherently embedding epistemic messages in their instruction. To do so, we must first surface instructors’ goals for knowing and learning and foster reflection on how (or whether) these appear in their courses.

Implications for teaching

To better support learning through intentional epistemic structuring, it may be beneficial to more deliberately introduce epistemic operations at key points in a lecture—such as at the beginning or end of sections—and to embed nested operations into the instructional flow. These could be accompanied by statements that clarify how individual operations relate to each other and how they contribute to learning and acquiring insights. In addition, a more explicit integration into exercises could help students apply epistemic operations more actively and meaningfully to build content knowledge or achieve other epistemic aims.

Purposefully including explicit reflection on epistemic aims and the related operations throughout lectures may help students develop a deeper understanding of the epistemic nature of learning, i.e., what it means to ‘know’ in organic chemistry. This could foster a shift in perspective—from memorization to mechanistic and conceptual reasoning. However, in large portions of the lectures analysed, no such communication was identifiable. Without clear communication about epistemic operations relevant to the discipline, it may be unclear how students are expected to learn—and, considering the sparse occurrence of messages about the added value, why they learn what they learn. In this messaging vacuum, it seems likely that students will default to epistemic ideas that have served them well in past STEM courses. Very often, these ideas are misaligned with our field's goal of thinking like a chemist. Therefore, although communication of central, overarching epistemic operations is present in many lectures, which may offer at least a partial indication of how learning is to occur, the connection to why it matters is not often apparent. However, organic chemistry lectures are just one part of the epistemic system students are confronted with. Assessments, laboratory courses, and other lecture courses or course types may reinforce or subvert the epistemic messages found here, or convey further epistemic goals, not found in the lectures investigated.

Implications for research

This study explored an as-yet unmapped part of the epistemic messaging landscape in college chemistry: lecture-embedded messages in organic chemistry. Specifically, we looked at messages conveying epistemic operations and their value in introductory organic chemistry lectures on S_N reactions (Fig. 1). To evaluate whether messages conveying epistemic operations truly function as structuring or scaffolding tools, it is essential to more fully map the epistemic messaging landscape of our courses. This might include describing assessment-embedded epistemic messages (e.g., Schwarz et al., 2025), epistemic messages embedded in peer–peer interactions, as well as curricular design, lecture format, or active learning pedagogies.

Here, it would be valuable to look beyond the focus on verbal utterances. Epistemic messages are also mediated by the ways students engage with materials and course artefacts that shape epistemic activity. Investigating students’ perception and potential shifts may provide a richer picture of how students develop their epistemic stances and can inform the design of environments that foster deeper engagement with scientific knowledge (Schwarz et al., 2025; Silva and Sasseron, 2025). Considering another element of the conceptual model (Fig. 1), it also seems valuable to investigate factors influencing whether and how instructors send epistemic messages. Russ (2014) emphasises that we need to explore how teachers’ own (potentially tacit) epistemic commitments shape their classroom practice and the opportunities they create for students as well as how instructors flexibly respond to the dynamics of students’ epistemic cognition that they bring to the classroom. Ongoing research on teacher noticing has already documented the need for active training in noticing as part of professional development to leverage students’ understanding of science (Geragosian et al., 2024; Zaimi et al., 2024).

For the last element of the conceptual model (Fig. 1), it would be interesting to learn more about whether and how students perceive epistemic messages, and if and how these perceptions aggregate across time and place. While there are some findings from school contexts on behavioural changes in response to epistemic communication (e.g., Rosenberg et al., 2006; Ke and Schwarz, 2021), we still lack a nuanced understanding of how students experience, negotiate, and respond to potentially conflicting epistemic messages experienced from a variety of sources across a semester. This understanding is required for us to make principled decisions about useful ways to connect small- and large-grain epistemic operations to foster meaningful chemistry learning.

This work, then, represents a start. We have mapped epistemic messages embedded in a ubiquitous instructional practice and shown that the frequency and substance of these messages vary across contexts. It remains to be seen how (or whether) these variations affect what students see as appropriate ways to know and learn in organic chemistry. Future work, undertaken by us or others, should delve more deeply into students’ experiences with varied epistemic messaging landscapes. In addition, it may be fruitful to engage instructors in reflection on how their course structure aligns with their epistemic goals for students. Doing so would let us explore how educators reflect on the epistemic dimensions of their teaching and to create tools that facilitate the intentional incorporation of epistemic messages throughout a course system. By intentionally building and refining the epistemic infrastructure of our classes, we can hopefully engage students in thinking like a chemist.

Author contributions

Elias Heinrich: conceptualization, data curation, methodology, project administration, visualization, writing – original draft. Ryan L. Stowe: writing – review and editing. Nicole Graulich: supervision, conceptualization, methodology, project administration, writing – review and editing.

Conflicts of interest

There are no conflicts to declare.

Data availability

The data are not publicly available as participants of this study did not consent for their data to be shared publicly.

Acknowledgements

This publication represents a component of the first author's doctoral (Dr rer. nat.) thesis in the Faculty of Biology and Chemistry at the Justus-Liebig-University Giessen, Germany. We are grateful to all instructors who generously shared their lectures, enabling this study. We also wish to thank all members of the Graulich group for their fruitful discussions, valuable ideas, and continuous support.

Notes and references

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Footnote

† The term ‘epistemological message’ is prevalent in the science education literature (e.g., Russ, 2018; Ke and Schwarz, 2021; Schwarz et al., 2025) when describing communicative elements that convey perspectives on or about knowledge. Although this terminology may be appropriate, for example, when investigating discussions about scientific models in high school classrooms, it was not considered the best choice for the context of this study: the -ology suffix of epistemology implies a theory or knowing and learning. Since we are describing aspects of knowing and learning in a moment, rather than a meta-theory related to overarching epistemological (‘meta-epistemic’ (Kitchener, 2002)) aspects, the term epistemic message seemed to be a more appropriate descriptor to investigate the epistemic communication in organic chemistry lectures.

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