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Organic reaction mechanisms are often represented by the electron-pushing formalism and reaction coordinate diagrams. These representations pose a challenge to students because valuable information is encoded within each representation, and students must know how to reason about mechanisms using both. Hence, it is important to understand whether and how students consider these two representations when reasoning about reaction mechanisms. We have collected responses to a writing-to-learn assignment administered in a second-semester organic chemistry laboratory course to investigate students’ reasoning. The assignment was designed to elicit students’ reasoning about the most likely of two mechanisms for a catalyzed intramolecular aldol reaction when given the electron-pushing scheme and reaction coordinate diagram for both mechanisms. As part of the assignment, students submitted initial drafts, participated in content-focused peer review, and submitted revised drafts. We analyzed each component using a mixed methods approach to identify students’ reasoning about the most likely reaction pathway and how their reasoning changed after peer review and revision. In this article, we present a quantitative overview of changes students made about their decisions for the most likely reaction pathway and how these changes are related to providing and receiving feedback. Additionally, we present our analysis of the features of representations students used to reason about the likelihood of alternative reaction mechanisms. This study demonstrates how existing research about students’ reasoning with representations was operationalized for classroom practice using writing-to-learn. Furthermore, the analysis illustrates how writing-to-learn to can be used to develop students’ reasoning and offers implications for teaching students to reason about reaction mechanisms using multiple representations.

Student affect is an important factor in the learning process and may be especially important in gateway courses such as organic chemistry. Students’ recognition of the relevance of the content they are learning and interactions with their peers can support their motivation to learn. Herein, we describe a study focused on how Writing-to-Learn assignments situate organic chemistry content within relevant contexts and incorporate social elements to support positive student interactions with organic chemistry. These assignments incorporate rhetorical elements—an authentic context, role, genre, and audience—to support student interest and demonstrate the relevance of the content. In addition, students engage in the processes of peer review and revision to support their learning. We identified how the authentic contexts and peer interactions incorporated into two Writing-to-Learn assignments supported students’ interactions with the assignments and course content by analyzing student interviews and supported by feedback survey responses. Our results indicate that assignments incorporating these elements can support student affect and result in students’ perceived learning, but that there should be careful consideration of the relevance of the chosen contexts with respect to the interests of the students enrolled in the course and the complexity of the contexts.

Many assessments in organic chemistry ask students to produce reaction mechanisms with the electron-pushing formalism. It is well known that students can apply the electron-pushing formalism without engaging in chemical reasoning about the processes underlying mechanisms. Furthermore, engagement in mechanistic and causal reasoning correlates with student performance on organic chemistry tasks. Hence, it is valuable to elicit students' explanations of mechanisms beyond relying on traditional mechanism assessments. One evidence-based approach for encouraging and eliciting students' mechanistic explanations is through writing. However, instructors may hesitate to implement writing in their courses due to a lack of tools available to provide formative feedback on students' mechanistic explanations. To address this challenge, we analyzed students' written explanations of three different organic reaction mechanisms for individual features involved in mechanistic reasoning. In this chapter, we present our adaptation of Russ et al.'s mechanistic reasoning framework specifically for students' written explanations of organic chemistry reaction mechanisms. Additionally, we describe a set of predictive models which we have used to accurately identify features of students' writing involved in mechanistic reasoning in the context of the three different reaction mechanisms. This work has implications for instructors seeking to identify students' reasoning in written explanations of organic reaction mechanisms. Additionally, this work has implications for future research into developing immediate and automated student- and instructor-facing formative feedback to encourage students' development of mechanistic and causal reasoning.

Resonance is a fundamental concept that is necessary for students’ successful learning in organic chemistry. However, there is a need to know more about both (1) what students find important when describing resonance and (2) students’ conceptual understanding. This research seeks to address this discrepancy by examining second-semester organic chemistry students’ responses to a writing-to-learn (WTL) assignment focused on resonance. This work is guided by the cognitive process theory of writing and studies within undergraduate STEM and chemistry courses that indicate the usefulness of WTL assignments for examining how students convey their understanding of fundamental concepts. We analyzed students’ responses to a WTL assignment designed to elicit students’ explanations of resonance and its influence on reactivity to a general, nonscientific audience. The goal of our analysis was to identify the features students found important when explaining resonance and to gain insight regarding their conceptual understanding. The analysis was guided by an analytical framework outlining the learning objectives for resonance at the introductory organic chemistry level. We identified various elements in students’ writing, including (1) the analogies or examples students used to explain resonance, (2) the basic definitions of the concept students included, and (3) the various ways students described the influence of resonance on reactivity. Our findings indicate that students generally described resonance with an operational rather than conceptual definition, focusing on the process of drawing resonance structures rather than providing conceptual explanations. Furthermore, we identified that students tended to associate resonance with stability, with many students often extending this association to make overgeneralized statements about the influence of resonance on reactivity.

Nuclear magnetic resonance (NMR) spectra are among the most common visualizations used by chemists in both academic and industrial settings, where they serve as both representations of submicroscopic entities and tools that support social discourse. The ability to use words to communicate about features within NMR spectra is thus an essential aspect of chemists’ representational competence. Collectively, these words constitute a highly specialized language specific to this technique. To adequately prepare chemists, the undergraduate curriculum must therefore cultivate students’ ability to use this lexicon. We developed the NMR Lexical Representational Competence (NMR-LRC) instrument, a formative assessment to measure students’ ability and perceived ability to use words to communicate the identification, analysis, and interpretation of features within 1H NMR spectra. Following development, we administered the NMR-LRC in Spring 2020 to a total of N = 678 second-semester organic chemistry students at a large Midwestern university. We analyzed the responses using the Rasch model to collect statistical evidence of validity and reliability, and we used cluster analysis to evaluate whether the instrument could detect the Dunning–Kruger effect (i.e., students’ illusions of competence). Supporting evidence of response process, content, and associative validity was also collected. The results suggest that data obtained from the NMR-LRC can be interpreted as a measure of students’ lexical representational competence and associated perceived competence in 1H NMR spectroscopy and that the NMR-LRC can detect students’ illusions of such competence. Results further suggest that instructors can use the NMR-LRC to formatively assess their students’ lexical ability and associated perceived ability following instruction, allowing instructors to provide feedback that promotes students’ competence and perceived competence.

Writing is an important skill for communicating knowledge in science, technology, engineering, and mathematics (STEM) and an aid to developing students' communication skills, content knowledge, and disciplinary thinking. Despite the importance of writing, its incorporation into the undergraduate STEM curriculum is uneven. Research indicates that understanding faculty beliefs is important when trying to propagate evidence-based instructional practices, yet faculty beliefs about writing pedagogies are not yet broadly characterized for STEM teaching at the undergraduate level. Based on a nationwide cross-disciplinary survey at research-intensive institutions, this work aims to understand the extent to which writing is assigned in undergraduate STEM courses and the factors that influence faculty members' beliefs about, and reported use of, writing-based pedagogies. Faculty attitudes about the effectiveness of writing practices did not differ between faculty who assign and do not assign writing; rather, beliefs about the influence of social factors and contextually imposed instructional constraints informed their decisions to use or not use writing. Our findings indicate that strategies to increase the use of writing need to specifically target the factors that influence faculty decisions to assign or not assign writing. It is not faculty beliefs about effectiveness, but rather faculty beliefs about behavioral control and constraints at the departmental level that need to be targeted.

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

Students enroll in biochemistry courses for many reasons, whether it be to build a strong foundation in biochemistry content for health science-related careers or to better understand the world around them. Learning is enriched when students can identify the relevance of the content, such as through connecting course content to authentic applications. One way that students can make these connections is by practicing science communication, an increasingly important skill for students to master. Drawing upon the advantages of writing, we designed an assignment that tasked students with writing a summary of a biochemistry-related seminar in which they explained the research and related biochemistry content in the form of a scientific news article targeted for a general audience. In this article, we discuss the design of the assignment and its implementation into an introductory biochemistry course. Results from a feedback survey and our evaluation of student writing assignments suggest that students saw value in communicating science to the general public and reported being able to connect the course content to authentic applications. This assignment is applicable in other chemistry or biology courses as a means to help students develop their skills in science communication and cultivate their appreciation of science content.

Many recent studies document the difficulties that students experience when learning organic chemistry, often due to the complex visualization and reasoning skills required to successfully understand the ways molecules interact in specific environments. Many of these studies call on instructors to improve their teaching strategies to support students’ learning of organic chemistry mechanisms, but few have focused on instructors’ knowledge of organic chemistry and how they use their knowledge to teach this topic. To investigate university instructors’ knowledge for teaching organic chemistry mechanisms, we utilized a task-based think-aloud interview protocol where graduate teaching assistants (GTAs) and faculty instructors assessed authentic undergraduate student responses to three organic chemistry mechanism questions. We describe this knowledge for a substitution, an acid–base, and an addition reaction. For all mechanisms, we describe how GTA participants’ knowledge for teaching related to their content knowledge. This result revealed differences between GTA and faculty participants’ knowledge for teaching mechanisms that were specific to features of each mechanistic task. For example, in a substitution reaction question, all faculty participants recognized and explained issues with a student's drawing of a transition state and apparent understanding of partial bonds. These features of the student's drawing were not recognized by any GTA participants, who focused instead on the student's prior knowledge about ionic bonding. These findings qualitatively illuminate strengths and weaknesses in graduate students’ knowledge for teaching which can guide how they are supported as instructors.

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

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

Advancements in organic chemistry depend upon chemists' ability to interpret NMR spectra, though research demonstrates that cultivating such proficiency requires years of graduate-level study. The organic chemistry community thus needs insight into how this expertise develops to expedite learning among its newest members. This study investigated undergraduate and doctoral chemistry students' understanding and information processing during the interpretation of 1H NMR spectra and complementary IR spectra. Eighteen undergraduate and seven doctoral chemistry students evaluated the outcome of a series of syntheses using spectra corresponding to the products. Eye movements were measured to identify differences in cognitive processes between undergraduate and doctoral participants, and interviews were conducted to elucidate the chemical assumptions that guided participants' reasoning. Results suggest five areas of understanding are necessary for interpreting spectra, and progress in understanding corresponds to increasing knowledge of experimental and implicit chemical variables. Undergraduate participants exhibited uninformed bidirectional processing of all information, whereas doctoral participants exhibited informed unidirectional processing of relevant information. These findings imply the community can support novices' development of expertise by cultivating relevant understanding and encouraging use of informed interpretation strategies, including preliminary evaluation of relevant variables, prediction of expected spectral features, and search for complementary data across spectra.

Course-based undergraduate research experiences (CUREs) are purported to support a range of learning objectives and outcomes for students. Pedagogical approaches are needed to promote these learning objectives as students engage in classroom research activities. The goal of this article is to describe a series of five writing assignments designed to contribute to the learning objectives of a CURE by introducing students to a wider variety of scientific practices, specifically analyzing data, constructing explanations, and communicating findings. Two writing assignments are data-based explanations requiring students to describe and reason about the results of laboratory experiments. Three writing assignments require students to respond within particular rhetorical contexts—a blog post, a scientific news article, and a grant preproposal. The assignments were implemented in a single semester during an introductory organic chemistry CURE focused on polymer chemistry. In this article, we describe the assignments, how they were implemented, and provide an overview of students’ responses. Additionally, we present results from specific questions on a student assessment of learning gains survey that indicate that students found the writing assignments to promote the specific learning goals of the CURE. While the described assignments were implemented in a CURE, we envision the possibility for future adaptation and application in other instructional laboratory settings to support students’ engagement with the aforementioned scientific practices.

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

An understanding of acid–base reactions is necessary for success in chemistry courses and relevant to careers outside of chemistry, yet research has demonstrated that students often struggle with learning acid–base reaction mechanisms in organic chemistry. One response to this challenge is the development of educational applications to support instruction and learning. The development of these supports also creates an opportunity to probe students’ thinking about organic chemistry reaction mechanisms using multiple modalities—i.e., using an app interface or the traditional paper–pencil. This study used think-aloud interviews conducted with undergraduate students in their first semester of organic chemistry to understand how they worked through two acid–base reactions using either paper–pencil or an app. Analysis of the interviews indicates that students from both groups recognize the steps of acid–base reactions, but do not always apply the underlying concepts, such as assessment of pKa values or resonance, when determining how a reaction will proceed. The modality seemed to somewhat influence students’ thinking, as the app prevented students from making chemically unreasonable mistakes. However, some students relied on the cues it provided, which could potentially be problematic when they are required to respond to assessments that do not provide these cues. Our results suggest that instructors should emphasize the conceptual grounding for the steps that govern acid–base reactions to promote chemical thinking about the relationships between the reaction components and how those influence reaction outcomes, as well as support students to think critically about the chemical information contained within the modalities they are using.

Thermodynamics and kinetics are key topics in the chemistry curriculum that pose challenges to students across a range of educational levels. These struggles arise from the complexity and mixed representations inherent to the topics. Additionally, while thermodynamics and kinetics are related, students struggle to make conceptually correct connections, sometimes seeing them as two separate topics with no relation and other times conflating their meanings and explanatory powers. Herein we captured student conceptions about thermodynamics and kinetics through a Writing-to-Learn activity that utilized peer review and revision to engage students with the concepts by applying them to a real-world context. This study identified whether students focused on the concepts targeted by the assignment and characterized the chemistry content of the peer review feedback. Students’ descriptions of thermodynamics and kinetics content, as well as the relationship between the two and how they connect to the application given in the assignment, improved during the process and suggests that peer review and revision played an important role in supporting students to describe these concepts. When guided by a content-focused peer review rubric, students provided constructive chemistry content-directed feedback. Specifically, analysis of student writing and comments demonstrated the potential of the assignment to engage students in building connections between complexly related topics, including distinguishing between sponteneity and rate and appropriately relating activation energy and rate. Findings from this study suggest that writing can be used to elicit student-specific conceptions of physical chemistry topics and develop students’ explanatory skills of chemistry content even without direct instructor feedback.

While the paths after graduate school are increasingly varied, the central goal of doctoral programs remains to develop independent researchers. Given the important role of doctoral advisors in the socialization and progress-making of doctoral students, we conducted semi-structured interviews with faculty advisors who regularly advise chemistry doctoral students from three chemistry departments with rotation programs for their first-year students. In contrast to existing studies documenting advisee perspectives of research autonomy, this work focuses particularly on the advisor perspective. After open coding these interviews, we found a breadth of ideas and approaches to developing research autonomy. The faculty advisors conceptualized research autonomy in their first-year doctoral students as enthusiasm or curiosity for their research or research area. The advisor’s approaches to developing and promoting autonomy in doctoral students varied widely, and some went so far as to not develop autonomy in new students but to “screen” for it. Finally, different subdisciplines in chemistry provide unique opportunities as well as constraints for advisors and students. We discuss the implications of these findings for doctoral students, advisors of doctoral students, administrators, and research advisors of undergraduate students.

The development of expertise in chemical information literacy requires practicing these skills in the context of chemistry work. The integration of information literacy in problem-based learning is an instructional strategy that can be used to situate skill development in the chemistry classroom. This work describes a mixed-methods approach to investigate the information seeking behavior of upper-level students working collaboratively on a semester-long inorganic chemistry problem. Audio recordings were collected during problem solving sessions and analyzed to investigate the strategies students used to find outside information required to identify an unknown compound. These students had prior coursework in chemical information literacy, and an information literacy test was used to establish the baseline of their knowledge and skills, and its development through the course. Student written work was analyzed to determine the outcomes of students’ information searching processes. Finally, semistructured int...

Lewis structures are fundamental to learning chemistry, yet many students struggle to develop a complex understanding of its meaning and uses. Writing-to-Learn supports students in developing a deeper conceptual understanding of the topic, making it an ideal pedagogy to apply to student learning of Lewis structures. One difficulty often associated with classroom writing is the capacity of instructors to provide feedback to each student on their written work; however, this practical constraint can be mitigated through incorporating peer review. Peer review and revision are known to support conceptual learning and yet are underutilized in STEM (Science, Technology, Engineering, and Math) classrooms. Additionally, peer review is an authentic, common, and necessary practice in chemistry research, which warrants its incorporation early on in chemistry courses. A major concern regarding the use of peer review-based feedback is the ability of students to provide concept-based feedback that is both correct and de...

Graduate students play a critical role in undergraduate education at doctoral-granting institutions and yet their training is often brief and overgeneralized. Little is known about how they develop knowledge for teaching chemistry in this context. To further understand how graduate students develop knowledge for teaching, we used a questionnaire to measure pedagogical content knowledge of solution chemistry concepts. These concepts are revisited frequently in the undergraduate curriculum, particularly in laboratory courses where graduate students commonly teach. Questions were included to measure both the pedagogical content knowledge and content knowledge of graduate students with a range of teaching experience. Analysis revealed that graduate students’ content knowledge is stronger than their pedagogical content knowledge, which increases modestly with teaching experience. Interviews were performed with a subset of respondents to determine whether they interpreted the questions as intended and the source of knowledge they used in responding. The interviews revealed that graduate students relied heavily on their own experience as students rather than direct experience teaching solution chemistry concepts.

Promoting students’ ability to engage in discipline-specific practices is a central goal of chemistry education. Yet if instruction is to meaningfully foster such ability, we must first understand students’ reasoning during these practices. By characterizing constraints on chemistry students’ reasoning, we can design instruction that targets this constrained reasoning and ultimately promotes more sophisticated ways of thinking. For this study, we investigated reasoning used by 18 organic chemistry students at a large university in the United States as they evaluated the success of chemical syntheses through IR and1H NMR spectral interpretation, a common task of practicing chemists. Students completed a series of interpretation tasks while having their eye movements tracked and then participated in semi-structured, cued retrospective think-aloud (RTA) interviews about their reasoning during spectral interpretation. RTA interviews were analyzed qualitatively to characterize invalid chemical assumptions and heuristic reasoning strategies used by participants, both of which science education literature identifies as fundamental constraints to learning. The most problematic assumptions and heuristics,i.e., those used more frequently by unsuccessful participants, were then identified through statistical analysis. Findings suggest that the most problematic constraints on students’ reasoning during spectral interpretation constitute a combination of particular invalid chemical assumptions and heuristic reasoning strategies.

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

Science educators recognize the need to teach scientific ways of knowing and reasoning in addition to scientific knowledge. However, characterizing and assessing scientific ways of knowing and reasoning is challenging. Writing-to-learn offers one way of eliciting and supporting students’ reasoning; further, writing serves to externalize and make traceable students’ reasoning. For this reason, it is a useful formative assessment of scientific reasoning. The utility hinges on researchers’ ability to understand what students can do and think from their writing. Given the challenges in assessing students’ writing, this research offers an adapted framework for assessing students’ scientific reasoning evident in writing. This work will introduce an adapted framework and show an application to general chemistry students’ argumentative writing about ocean acidification. We provide evidence that this framework can be used to validly estimate the quality of students’ reasoning. We argue that this framework offers some affordances that overcome challenges reported in the literature. It serves to define scientific reasoning in a domain-general way by breaking it down into its components, but in a way that can produce a composite score that tells us about how students reason using chemistry content. Further, the framework provides a way to characterize the scientific accuracy of students’ reasoning that can inform instructors’ treatment of alternative conceptions.

Providing students in STEM courses the opportunity to write about scientific content can be beneficial to the learning process. However, it is a logistical challenge to provide feedback to students’ written work in large-enrollment courses. Motivated by these reasons, the study presented herein considers a method to identify the depth of students’ scientific reasoning in their written work. A writing-to-learn (WTL) activity was implemented in a large undergraduate general chemistry class. An analytical framework of cognitive operations that characterizes students’ scientific reasoning evidenced in their writing was applied. Engagement in some of the more complex cognitive operations, such as causal reasoning and argumentation, was a sign that students were properly engaging in meaning making activities. This work considers a method to automate coaching of students in using more complex reasoning in their writing with the desired outcome that it may help students better engage with the science content. We consider a series of new natural language processing models to discern types of reasoning in student essays from the WTL activity.

Determination of chemical identity is a fundamental chemistry practice that previously relied on the analysis of properties such as chemical composition, solubility, and reactivity. This practice now depends almost exclusively on the characterization of molecular structure through spectroscopic analysis. This analysis is a day-to-day task of organic chemists, and instruction in modern organic chemistry aims to cultivate such ability. This chapter provides an overview of the literature on teaching and learning spectroscopic structure elucidation, with the aim of presenting the current state of research, empirical insights into teaching and learning this practice, and trends in instructional innovations. A number of studies have investigated reasoning and problem-solving approaches used to evaluate spectroscopic data for organic structural determination, and they provide a foundation for understanding how this ability develops and how instruction may facilitate such learning. These studies consistently suggest that individuals with different amounts of prior coursework and research experience interpret spectra differently. Specifically, individuals with less coursework and experience often possess limited chemical knowledge and restrict their decision making to fewer observations while ignoring relevant spectral information. Practice articles on spectroscopic structure elucidation focus on two general types of instructional innovations: instructional scaffolding and laboratory exercises. These articles notably incorporate few empirical insights, suggesting a gap between the substantial research conducted on the learning of spectroscopic structure elucidation and instructional innovation.

Advancements in organic chemistry depend upon chemists' ability to interpret NMR spectra, though research demonstrates that cultivating such proficiency requires years of graduate-level study. The organic chemistry community thus needs insight into how this expertise develops to expedite learning among its newest members. This study investigated undergraduate and doctoral chemistry students' understanding and information processing during the interpretation of

The introductory chemistry sequence is a common pathway for undergraduates pursuing science, technology, engineering, and math (STEM) and prehealth careers. Student’s academic decision-making has far-reaching consequences for their trajectory, including persistence in the major and ultimate career choice. This phenomenon was studied using a survey and focus group interviews, which were conducted to better understand the factors that influenced student choice. Results were analyzed using exploratory factor analysis, from which personal and institutional factors were identified. Using binary logistic regression, we found that students who placed importance on institutional factors (placement test results, discussion with advisor, academic plans, course load, and confidence in preparation) were more likely to comply with their placement recommendation, whereas students who placed importance on personal factors (family and financial concerns, advice from friends and family, rumors about the course, and nonaca...

Fundamental quantum chemistry concepts—quantization of energy, electronic structure, and light–matter interaction—are essential for understanding chemistry and spectroscopy, an important tool for studying molecules. However, very few studies have investigated how students learn and understand these concepts or how their learning can be supported. Drawing on the capacity of writing to support learning of difficult concepts, we designed an intervention that targeted quantum concepts in the context of the use of spectroscopy for identifying chemical composition of the Orion Nebula. A quasi-experimental design with a pre-post assessment on a control and treatment group was used to identify the gains associated with completing the WTL activity. Results from a three-tiered assessment show that WTL students significantly improved in their explanations of the concept of spectroscopic transitions and their overall confidence in their understanding. Analysis of their writing, follow-up interviews, and feedback served to explain the changes observed on the pre-post assessment.

Nuclear magnetic resonance (NMR) spectroscopy is an essential analytical tool in chemistry, and the technique is routinely included as a topic across the undergraduate chemistry curriculum. As a result of NMR's importance, classroom instruction of this topic has received considerable attention in chemistry education research. However, little is known about instructors’ knowledge for teaching this topic. In order to better understand this knowledge, we investigated topic-specific pedagogical content knowledge in1H NMR spectroscopy among 20 chemistry teaching assistants at a large Midwestern university in the United States. A questionnaire was developed to provide an inferential measure of content knowledge and topic-specific pedagogical content knowledge in1H NMR spectroscopy for participants with a range of teaching experience. Data from the questionnaire were analyzed qualitatively and quantized using a rubric. The quantitative data were transformed using the Rasch model and statistically analyzed. Results from these analyses indicate that pedagogical content knowledge increased with teaching experience in1H NMR spectroscopy, suggesting that knowledge for teaching this topic is developed through practice. Additionally, the development of pedagogical content knowledge was found to depend upon content knowledge required for specific NMR sub-topics and problems. This finding suggests that the ultimate “grain-size,” or domain-specificity, of pedagogical content knowledge may extend to the problem level. Results from this study have implications for how instructors may cultivate knowledge for teaching NMR spectroscopy, as well as for how pedagogical content knowledge may be more effectively incorporated into instructor training programs.

We conducted a study to examine how a writing-to-learn assignment influenced student learning of polymer behavior. In particular, we examined the role of specific content and a rhetorical framework as well as a structured writing process including peer review and revision. The student-generated writing was analyzed via a content-directed rubric. Students’ conceptual understanding of stress–strain behavior was gauged via a multitiered assessment. Finally, interviews were conducted to probe students’ experiences during the writing process. Results indicate that the writing-to-learn assignment was effective in promoting understanding of stress–strain properties, but that further support is needed to help students connect polymer microscopic properties to macroscopic behavior. Specifically, the content requirements and rhetorical framework guided what students included in their writing. Peer review and revision provided students with further opportunities to engage and learn the material.

Research has demonstrated that students often struggle with learning acid-base reaction mechanisms in organic chemistry. One response is the development of educational applications to support instruction and learning. However, research is needed to characterize how the modality influences students’ thinking about acid-base reaction mechanisms. This study used think-aloud interviews conducted with undergraduate students in their first semester of organic chemistry to understand how they worked through acid-base reactions using either paper-pencil or an app. Analysis of the interviews indicates that students recognize the steps of acid-base reactions, but do not always apply the underlying concepts when determining how a reaction will proceed. The modality somewhat influenced students’ thinking, in that the app prevented students from making chemically unreasonable mistakes. However, some students relied on the cues it provided, which could potentially be problematic when they are required to respond to assessments that do not provide these cues. Our results suggest that instructors should emphasize the conceptual grounding for the rules and steps that govern acid-base reactions to promote chemical thinking about the relationships between the reaction components and how those influence reaction outcomes, as well as support students to think critically about the chemical information contained within the modalities they are using.