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The goal of the present work is to extend an online reaction categorization task as a research instrument to a formative assessment tool of students' knowledge organization for organic chemistry reactions. Herein, we report our findings from administering the task with undergraduate students in Organic Chemistry II, at a large, research intensive Canadian university, including the relationship between instrument and exam scores. The online categorization task uses 25 reaction cards that participants were asked to sort first into categories of their choosing ("i.e.," an open sort) then into the mechanistic categories defined in a Patterns of Mechanisms curriculum ("i.e.," a closed sort). We observed a small, significant correlation between how learners "chose" to organize their knowledge ("i.e.," open sort) and their "cued ability" ("i.e.," match with expert sort) at the beginning of the Organic Chemistry II course (N = 65, r = 0.28, p = 0.026). We conducted a correlation analysis between students' scores on the open and closed sort tasks and academic achievement. We found a strong relationship between the scores in the online categorization tasks and Organic Chemistry II exams, especially from the closed sort tasks (N = 43, r = 0.70, p = 0.000). To date, no other discipline specific card-sort tasks have shown such a strong correlation with final assessment grades. We also found an increasing relationship between students' choice and ability over time as students developed their expertise in the domain. This work also added evidence to the validity and reliability of the organic card-sort instrument, through multiple measures. Educators and students could use the card sort task as a self-assessment measure and as part of classroom activities related to mechanistic analysis. Future work is needed to investigate how card sort tasks of this type are connected with expertise in other settings.

Making decisions, reasoning, and constructing arguments with scientific evidence are essential skills for all members of society, especially in a world facing complex socioscientific issues such as climate change and pandemics. Argumentation is a complex linguistic practice but little is known about how students from diverse language backgrounds engage in argumentation. The goal of this study was to identify how students' English language proficiency and history was associated with the reasoning demonstrated in their written arguments. We found that students with lower English proficiency and less English history produced fewer causal responses compared to students with higher English language proficiency and history. Follow-up interviews with fifteen participants revealed that students' comfort communicating in English on assessments was affected by a combination of general and academic language experiences. Findings suggest a need to identify the barriers encountered by students from diverse language backgrounds during argumentation to ensure students from all language backgrounds have equitable supports and opportunities to demonstrate their scientific abilities.

Response process validity evidence can provide researchers with insight into how and why participants interpret items on instruments such as tests and questionnaires. In chemistry education research literature and the social sciences more broadly, response process validity evidence has been used and reported in a variety of ways. This paper's objective is to support researchers in developing purposeful, theory-driven protocols to investigate response processes. We highlight key considerations for researchers who are interested in using cognitive interviews in their research, including the following: the theoretical basis for response process investigations, collection of response process validity evidence through cognitive interviews, and use of that evidence to inform instrument modifications.

Organic chemistry has its own representational language and as with any language, any barrier with the language makes understanding the message difficult. In this article, we describe the design of an open education resource that empowers students to master this language. We also describe the structure and findings of a pilot study designed to measure students' learning and experiences using the module, with a focus on principles, structure, and key findings, rather than on the chemistry-specific elements.

In a world facing complex global challenges, citizens around the world need to be able to engage in scientific reasoning and argumentation supported by evidence. Chemistry educators can support students in developing these skills by providing opportunities to justify how and why phenomena occur, including on assessments. However, little is known about how students' arguments vary in different content areas and how their arguments might change between tasks. In this work, we investigated the reasoning, granularity, and comparisons demonstrated in students' arguments in organic chemistry exam questions. The first question asked them to decide and justify which of three bases could drive an acid--base equilibrium to products (Q1, n = 170). The majority of arguments exhibited relational reasoning, relied on phenomenological concepts, and explicitly compared between possible claims. We then compared the arguments from Q1 with arguments from a second question on the same final exam: deciding and justifying which of two reaction mechanisms was more plausible (Q2, n = 159). The arguments in the two questions differed in terms of their reasoning, granularity, and comparisons. We discuss how course expectations related to the two questions may have contributed to these differences, as well as how educators might use these findings to further support students' argumentation skill development in their courses.

This article focuses on the benefits and barriers to engaging students as partners in educational projects.

Science is rapidly changing with vast amounts of new information and technologies available. However, traditional instructional formats do not adequately prepare a diverse population of learners who need to evaluate and use knowledge, not simply memorize facts. Moreover, curricular change has been glacially slow. One starting goal for curricular change can be identifying the features of a current curriculum, including potential areas for improvement, but a model is needed to accomplish that goal. The vast majority of studies related to curricular change have been conducted in K-12 environments, with an increasing number in post-secondary environments. Herein, we describe a model for science curriculum evaluation that we designed by integrating a number of different approaches. That model evaluates the intended, enacted, and achieved components of the curriculum, anchored by analyzing learning outcomes through five lenses: (1) a scientific "Framework" reported by the US National Research Council; (2) systems thinking; (3) equity, diversity, and inclusion; (4) professional skills; and (5) learning skills. No curriculum evaluation models to date have used the five learning outcomes lenses that we describe herein. As a proof of principle, we applied the evaluation model to one organic chemistry course, which revealed areas of strength and possible deficiencies. This model could be used to evaluate other science courses or programs. Possible deficiencies may be addressed in other courses, in the course at hand, or may not be deemed necessary or important to address, demonstrating the potential for this evaluation to generate areas for discussion and ultimately, improvements to post-secondary science education.

The concept of delocalization (i.e., resonance) is fundamental concept in organic chemistry but essential learning outcomes (LOs) have not previously been proposed nor has there been an analysis of how resonance is taught, despite indications in the literature that students have many non-canonical ideas about the concepts. To address this deficit, we first developed a set of ten learning outcomes believed to be essential to the concept of delocalization in organic chemistry, especially for students' later success. Next, we analyzed how these learning outcomes are being taught, practiced and assessed in common textbooks and in a sample of exams. Five themes emerged from the analysis: (1) several of the essential intended LOs we identified are not represented in the textbooks' teaching explanations, practice questions, or professors' assessments; (2) the concepts related to delocalization are often taught, practiced, and assessed without associated justifications; (3) there is a large gap between when delocalization is taught and when it is used in context; (4) the link between delocalization and other concepts (e.g., reactivity) is not explicitly explained in most teaching materials; and (5) the language used around delocalization may be misleading (e.g., resonance, stability). Our analysis identified areas in which delocalization education could be improved, including with respect to teaching, practice opportunities, and assessing the concepts.

In chemistry, novices and experts use mental models to simulate and reason about sub-microscopic processes. Animations are thus important tools for learning in chemistry to convey reaction dynamics and molecular motion. While there are many animations available and studies showing the benefit of learning from animations, there are also limitations to their design and effectiveness. Moreover, there are few experimental studies into learning chemistry from animations, especially organic reaction mechanisms. We conducted a mixed-methods study into how students learn and develop mental models of a reaction mechanism from animations. The study (N = 45) used a pre-/post-test experimental design and counterbalanced static and animated computerized learning activities (15 min each), plus short think-aloud interviews for some participants (n = 20). We developed the tests and learning activities in a pilot study; these contained versions of an epoxide opening reaction mechanism either as static (using the electron-pushing formalism) or animated representations. Participants' test accuracy, response times, and self-reported confidence were analyzed quantitatively (a = 0.05) and we found that, while participants showed a learning effect, there were no significant differences between the static and animated learning conditions. Participants' spatial abilities were correlated to their test accuracy and influenced their learning gains for both conditions. Qualitative framework analysis of think-aloud interviews revealed changes in participants' reasoning about the test questions, moving toward using rule- and case-based reasoning over model-based reasoning. This analysis also revealed that dynamic and transitional features were incorporated into participants' working mental models of the reaction mechanism after learning from animations. The divergence of participants' mental models for reasoning and visualization could suggest a gap in their mental model consolidation.

We developed an online learning module called ''Organic Mechanisms: Mastering the Arrows'' to help students learn part of organic chemistry's language--the electron-pushing formalism. The module guides students to learn and practice the electron-pushing formalism using a combination of interactive videos, questions with instant feedback, and metacognitive skill-building opportunities. This module is part of OrgChem101.com, an open educational resource (OER) that houses a series of learning modules. To evaluate the mechanism module's effects on students' learning and experiences, we offered a workshop during which undergraduate students used the module. We investigated their learning gains via a pre-test and post-test format and their experiences using a survey. Analysis of responses revealed significant learning gains between the pre- and post-test, especially with questions that asked students to draw the products of a reaction. After using the learning tool, students used more analysis strategies, such as mapping, attempted more questions, and made fewer errors. The students reported positive experiences and a belief that the module would help them in their organic chemistry courses. Previous work also identified greater metacognitive skills after using the module, related to the module's intended learning outcomes. Herein, we describe the module, evaluation study, findings, and implications for research and practice.

In this study, we investigated how students organized their knowledge about organic chemistry reactions in a transformed curriculum, including their choices, abilities, and changes over time. This transformed curriculum focuses on interpreting the underlying mechanistic patterns of chemical reactions and emphasizes the principles of reactivity in organic chemistry. Data from this study were collected at beginning and end of an Organic Chemistry II course using an open and closed online categorization task with a set of organic chemistry reactions. In the open task, participants organized the set of reactions as they chose, giving us insight into how the participants preferred to organize their knowledge. In the closed task, participants were asked to organize the set of reactions in a specific way--by each reaction's governing mechanism--which would provide a measure of the students' ability to categorize the reactions in that way. We investigated the similarities and differences of the open and closed categorizations at each time of administration and analyzed the changes over time. Findings from this study emphasized the efficacy of the transformed curriculum for: (a) promoting a focus on process-oriented features of reactions over static features of a reaction and (b) increasing the students' abilities to categorize a set of reactions according to the mechanism governing the reaction. Findings revealed implications for the transformed curriculum, which addresses key areas for improvements, potential implications for research, and also limitations of the current study. We further describe possible extensions of this study to how the open and closed categorization tasks may be used for research and instruction in other science, technology, engineering, and math disciplines.

Systems thinking approaches underscore a holistic view of the components comprising a dynamic system, including their connections and interdependencies as well as their interactions with other systems. Compelling international calls have been made recently to infuse chemistry education with systems thinking so as to not only better illustrate chemistry's connection to other disciplines, but also explain and address emerging global challenges. Doing so presents exciting opportunities for chemistry educators to incorporate creative new activities into their courses. However, to employ systems thinking effectively in the chemistry classroom, we argue that considering "the learner" must take precedent. Relatively little is known regarding how chemistry learners interact with systems thinking, or the knowledge and skills necessary for chemistry learners to productively engage in systems thinking. In this article, we begin to address the discipline's knowledge gap about learning using a systems thinking approach. Our goal is to explore systems thinking from the perspective of the chemistry learner using current learning frameworks relevant to chemistry education (i.e., information processing theory, meaningful learning, sociocultural theory, and three-dimensional learning). Using this analysis, we highlight opportunities and challenges for employing systems thinking in chemistry education, to encourage further educational research and development using this approach.

The International Union of Pure & Applied Chemistry (IUPAC) launched a global project in 2017 to infuse systems thinking into chemistry education, motivated in part by the desire to help equip chemists and citizens to better address the complex, global challenges our society currently faces. One important early outcome of the IUPAC Systems Thinking in Chemistry Education (STICE) project is this special issue of the "Journal of Chemical Education," which provides a key reference point for the rapidly emerging literature on the incorporation of systems thinking into chemistry education, including its application to green and sustainable chemistry. The STICE project outcomes to date include reviewing systems thinking approaches in other STEM fields, articulating a framework for STICE, identifying aspects of learning theories relevant to learning systems thinking skills in chemistry, using systems thinking approaches to integrate green and sustainability chemistry concepts into university-level chemistry classrooms, and identifying considerations for assessing systems thinking in chemistry education. The authors of this article, who, with others, have provided leadership to the STICE project, conclude this "Journal's" special issue by briefly reviewing progress to date and identifying three main areas of future work for the application of systems thinking in chemistry education: (1) developing systems thinking resources for chemistry educators and students, (2) identifying chemistry education research needed to investigate and improve systems thinking approaches, and (3) investigating opportunities to apply chemistry-related systems thinking approaches in broader educational contexts. Our intention is to recommend potential opportunities, stimulate conversations, and motivate actions required to successfully equip learners with systems thinking skills in chemistry, such that these learners, citizens of our countries and our planet, are better positioned to interpret and address complex global challenges.

Creating and using models are essential skills in chemistry. Novices and experts alike rely on conceptual models to build their own personal mental models for predicting and explaining molecular processes. There is evidence that chemistry students lack rich mental models of the molecular level; their mental models of reaction mechanisms have often been described as static and not process-oriented. Our goal in this study was to characterize the various mental models students may have when learning a new reaction mechanism and to explore how they use them in different situations. We explored the characteristics of first year organic chemistry students' (N = 7) mental models of epoxide-opening reaction mechanisms by qualitative analysis of transcripts and written answers following an audio-recorded interview discussion. We discovered that individual learners relied on a combination of both static (with a focus on symbolism and patterns) and dynamic (reactivity as process or as particles in motion) working mental models, and that different working mental models were used depending on the task. Static working mental models were typically used to reason generally about the reaction mechanism and products that the participants provided. Dynamic working mental models were commonly used when participants were prompted to describe how they pictured the reaction happening, and in attempting to describe the structure of a transition state. Implications for research, teaching, and learning from these findings are described herein.

Citizens in all roles need to be able to construct causal explanations of scientific phenomena and engage in coherent argumentation, supported by evidence and sound reasoning. These skills are needed in many contexts, from making everyday decisions to addressing complex global issues. One goal of instruction in this area is to get past assessment questions that can be answered using only memorized rules (e.g., S[subscript N]1 reactions are favored with tertiary halide substrates), toward answers that require reasoning with evidence (why is an S[subscript N]1 pathway favored under certain conditions?). Previous work has suggested that these reasoning skills may not be effectively taught, practiced, or learned in organic chemistry courses or directly assessed on exams. In this study, we explored students' ability to construct scientific arguments using evidence in the context of organic reaction mechanisms, specifically when comparing two proposed reaction mechanisms, making a claim as to which was most plausible, and providing reasoning. We used a qualitative coding scheme to analyze (1) the features and concepts students discussed in their arguments on exams, including the concept of granularity, (2) the connections (links) made between features and concepts, (3) the modes of reasoning revealed in the arguments, and (4) how the ideas and claims were explicitly compared. We found that 60% of arguments with correct claims established causal relationships between the relative stability of the carbocation intermediates and the relative activation energy barriers to the formation of these intermediates. However, the vast majority of students did not go to sufficient granularity to meet the expectations in the course, which they could have done by invoking Hammond's postulate and hyperconjugation in their arguments. Incorrect claims were often supported by causal arguments but these arguments were incorrectly based on drawing a causal relationship between the relative steric hindrance of the starting materials and activation energy. Over 60% of students provided a linear causal mechanistic argument to justify their claim, independent of whether their claims were correct. Over 90% of arguments at least partially compared key concepts explicitly, with over 20% doing so completely. The findings suggest that the majority of students in this study understood the need to provide cause-and-effect relationships to justify their answer, beyond identifying reaction features and their effects; however, students may have struggled to identify which features of those molecules were "relevant."

An instructional method is described that was used in a large, introductory organic chemistry course to ask online, post-class questions and to use the students' answers to design the lesson and learning activities for the following class. Additional goals of this method were to provide relevant, regular, and prompt feedback to students and the instructor, to emphasize the value of time on task (i.e., that learning takes time) and to connect in- and out-of-class learning. Herein, the results of formative project evaluation and preliminary results of an educational evaluation of the method are also described.

Research has shown that within a traditional organic chemistry curriculum, organic chemistry students struggle to develop deep conceptual understanding of reactions and attribute little meaning to the electron-pushing formalism. At the University of Ottawa, a new curriculum was developed for organic chemistry in which students are taught the language of the electron-pushing formalism prior to learning about specific reactions. Reactions are then organized by governing pattern of mechanism rather than by functional group and are taught in a gradient of complexity. To investigate how students are making connections across reactions within the new curriculum, a card sort task was developed. The card sort task consisted of 25 cards, each depicting the reactants and solvent for a reaction taught during the two-semester organic chemistry sequence. The first part of the task asked participants to sort 15 of 25 cards into categories. Then, participants were given the 10 remaining cards to incorporate into categories with the previous 15. Participants were asked to explain the characteristics of each category and their sorting process. Students (N = 16) in an organic chemistry course were interviewed while enrolled in the second semester course. We analyzed the students' sorts based on which cards were sorted frequently together, the underlying characteristics used to form the categories, and the participants' sorting processes. Participants created categories based on different levels of interpreting the reactions on the cards, with levels ranging from recognizing identical structural features to identifying similar types of mechanisms. Based on this study, if we want students to develop mechanistic thinking, we think students need to be more explicitly directed to the patterns present in organic reaction mechanisms and given opportunities to uncover and identify patterns on their own, during both summative and formative assessments.

In this study, we continue our efforts to address students' difficulties understanding organic chemistry, particularly in connecting structure to function and using the language of chemistry to explain how and why reactions occur. For the first time, we have characterized students' work and problem-solving strategies on familiar and unfamiliar mechanism questions in a new course format: a patterns of mechanisms organic chemistry curriculum and flipped course format. This study began with analysis of students' exam answers then more deeply explored the features to which they attend and their strategies using a think-aloud interview protocol. Success rates were higher on both the familiar and unfamiliar mechanism questions in the new course format with medium effect sizes, although we cannot conclude a causal link with the new format. Interview analysis revealed that all used the electron-pushing formalism correctly and as an initial and routine part of their problem-solving strategy. Most participants regularly used concepts of nucleophiles, electrophiles, electronegativity, and charges (full and partial) in their problem-solving process. Participants used dipoles and charges (full and partial) to reveal nucleophilic and electrophilic portions of molecules, often expanding structures to do so. In difficult questions or steps, successful strategies involved expanding and mapping in combination with chemistry reasoning. Every participant struggled with an acronym in one question, LDA, wanting to draw its structure and identify its role but not being sure they could remember it. That difficulty drawing the structure became a barrier to analyzing the reactivity. To emphasize the importance of connecting structure and reactivity over memorizing, we recommend drawing out structures and not only acronyms on assessments. In this article, we describe the context, methods, findings, and implications for research and instruction.

With feelings of great pleasure, joy, and respect, tinged with the sadness of loss, we introduce this special issue dedicated to Dr. Margaret-Ann Armour. Margaret-Ann Armour was born in Glasgow, [...]

To explore the differences between how organic chemistry students and organic chemistry professors think about organic chemistry reactions, we administered a card sort task to participants with a range of knowledge and experience levels. Beginning students created a variety of categories ranging from structural similarities to process oriented categories. Professors and more experienced graduate students created their categories only for process-oriented reasons. Professors discussed different features of the reactions than the students did, suggesting that students need guidance and opportunities to develop skills to identify mechanistically relevant features in a reaction. More specifically, at the University of Ottawa, a transformed organic chemistry curriculum has been designed and implemented where students are first taught the language of mechanisms before learning about specific reactions. Then, students are taught reactions in order of their governing pattern of mechanism, rather than by functional group. We developed a card sort task to investigate how students perceive the organization of the reactions in the curriculum as well as to explore how graduate students and professors think about organic chemistry reactions. There were 25 cards designed with reactants and reagents for reactions taught within the first two semesters of organic chemistry. The card sort task is composed of two parts: first, participants are asked to sort 15 cards into categories; second, the participants are given 10 additional cards and asked to incorporate them into their existing categories. During the fall 2017 semester, second semester organic chemistry students (N = 16), organic chemistry graduate students (N = 10), and professors who either teach and/or conduct research in organic chemistry (N = 7) were interviewed using the card sort task. We analyzed the participants' categories for cards that were frequently sorted together and the reasons they gave for creating the categories and then compared the findings across the different participant groups.

Research on mechanistic thinking in organic chemistry has shown that students attribute little meaning to the electron-pushing (i.e., curved arrow) formalism. At the University of Ottawa, a new curriculum has been developed in which students are taught the electron-pushing formalism prior to instruction on specific reactions--this formalism is part of organic chemistry's language. Students then learn reactions according to the pattern of their governing mechanism and in order of increasing complexity. If students are fluent in organic chemistry's language, they should have lower cognitive load demands when learning new reactions, and be better positioned to connect the three levels of chemistry's triplet (i.e., Johnstone's triangle). We developed a qualitative research protocol to explore how students use and interpret the mechanistic language. Twenty-nine first-semester organic chemistry students were interviewed, in which they were asked to (1) explain a mechanism, given all the starting materials, intermediates, products, and electron-pushing arrows, (2) draw in arrows for a reaction mechanism, given the starting materials and products of each step, and (3) predict the product of a reaction step, given the starting materials and electron-pushing arrows for that step. To investigate the students' ideas about mechanistic language rather than their knowledge of specific reactions, we selected reactions for the interview guide that had not yet been taught. Following transcription, we analyzed the interviews using constant comparative analysis to explore how students used and interpreted the mechanistic language. Four categories of student thinking emerged with electron movement underlying students' thinking throughout the interviews. Herein, we discuss these categories, students' interpretation of the symbolism, connections to learning theory, and implications for teaching, learning, and research.

This study investigated students' successes, strategies, and common errors in their answers to questions that involved the electron-pushing (curved arrow) formalism (EPF), part of organic chemistry's language. We analyzed students' answers to two question types on midterms and final exams: (1) draw the electron-pushing arrows of a reaction step, given the starting materials and products; and (2) draw the products of a reaction step, given the starting materials and electron-pushing arrows. For both question types, students were given unfamiliar reactions. The goal was for students to gain proficiency--or fluency--using and interpreting the EPF. By first becoming fluent, students should have lower cognitive load demands when learning subsequent concepts and reactions, positioning them to learn more deeply. Students did not typically draw reversed or illogical arrows, but there were many other error types. Scores on arrows questions were significantly higher than on products questions. Four factors correlated with lower question scores, including: compounds bearing implicit atoms, intramolecular reactions, assessment year, and the conformation of reactants drawn on the page. We found little evidence of analysis strategies such as expanding or mapping structures. We also found a new error type that we describe as picking up electrons and setting them down on a different atom. These errors revealed the difficulties that arose even before the students had to consider the chemical meaning and implications of the reactions. Herein, we describe our complete findings and suggestions for instruction, including videos that we created to teach the EPF.

Skill in organic chemistry nomenclature is fundamental for communicating more complex concepts. Interpreting and using functional group names is particularly important. With nomenclature101.com, students can create tailored interactive quizzes according to their learning needs; the tool is free and available in English and French. The present study investigated students' nomenclature learning in three different learning environments to determine (1) what learning gains participants make when using nomenclature101.com independently, when guided, or taught nomenclature through a traditional classroom tutorial and (2) students' perceptions of the usefulness, ease of use, and overall learning experience in each of the settings. We invited students from first and second semester organic chemistry courses at a large, research-intensive Canadian university to participate in a nomenclature workshop. When participants arrived, they were randomly sorted into one of three treatment groups: classroom tutorial, independent use of nomenclature101, or guided use of nomenclature101. Before the session, participants completed a pre-test; at the end, they completed a post-test and a questionnaire related to affective aspects of their experience. We analyzed participants' scores and questionnaire responses, and qualitatively analyzed their test answers, including errors. Learning gains were significant with large effect sizes for all three groups although there were no significant differences in learning gains between groups. The largest gains were observed in the ability to correctly identify and draw functional groups. Exploratory factor analysis showed that the post-workshop questionnaire about nomenclature101.com reliably measured participants' perceptions about two latent factors: usefulness and ease of use. Based on questionnaire results, most participants liked the learning tool and found it useful and easy to use. Participants in all groups reported enjoying their learning experience. Few participants postdicted their quiz grades accurately, suggesting that metacognitive skillfulness was lacking among workshop participants. The large learning gains observed after using nomenclature101.com or learning in a classroom setting for just one hour shows the potential that instruction has to help students learn functional group identification skills, which ideally will mitigate barriers to communication and understanding. These results offer flexibility to educators as they make instructional choices such as teaching nomenclature in a course period or tutorial setting or asking students to learn nomenclature independently with nomenclature101.com. Students have the flexibility to work outside of class in the manner of their choosing.

Organic synthesis problems require the solver to integrate knowledge and skills from many parts of their courses. Without a well-defined, systematic method for approaching them, even the strongest students can experience difficulties. Our research goal was to identify the most successful problem-solving strategies and develop associated teaching models and learning activities. Specifically we asked: (1) What problem-solving strategies do undergraduate students use when solving synthesis-type problems? Are these strategies used correctly/as intended? (2) What strategies have the highest association with successful answers? (3) What relationships exist between these strategies? We analyzed more than 700 responses to synthesis problems from the final exams of undergraduate organic chemistry courses at a large, research-intensive institution. We analyzed the data using an open-coding system and a theoretical framework based on meaningful learning and representational systems in problem-solving. Our analysis found that successful answers demonstrated six key strategies: (1) identified newly formed bonds in the target molecule, (2) identified atoms added to the starting molecule to form the target, (3) identified key regiochemical relationships, (4) mapped the atoms of the starting material onto the target, (5) used a partial or complete retrosynthetic analysis, and (6) drew reaction mechanisms. The vast majority of successful answers demonstrated the use of multiple strategies in concert. This higher degree of success is logical in the context of meaningful learning and of representational systems in problem-solving. These strategies were often absent from unsuccessful answers, possibly because students did not know these strategies, did not believe them to be useful, or did not write them down. For teaching, our results suggest that students should be taught, encouraged, and given opportunities to use multiple key strategies; sample problems are included herein.

Chemical information literacy is an essential skillset for navigating, evaluating, and using the wealth of print and online information. Accordingly, efforts are underway to improve students' acquisition and mastery of this skillset. However, less is known about students' abilities related to finding and using chemical information to solve problems. We studied students' abilities in one area of chemical information literacy: finding, estimating, and using pK[subscript a] values in organic acid-base problems. We identified areas of student difficulty related to these skills, implemented instruction aligned with desired learning outcomes, and then studied students' success rates after instruction. Our results revealed improvements in some areas but not in others. In particular, students still struggled when the desired information was not directly available in the literature (i.e., data had to be estimated) or when students had to use the information in more complex contexts.

A significant redesign of the introductory organic chemistry curriculum at the authors' institution is described. There are two aspects that differ greatly from a typical functional group approach. First, organic reaction mechanisms and the electron-pushing formalism are taught before students have learned a single reaction. The conservation of electrons, atoms, and formal charges, how the use of curved arrows helps describe the mechanism, and how to predict reaction mechanisms are emphasized. Second, the reactions taught in the first two semesters of organic chemistry are arranged by their governing mechanism, rather than by functional group. The reactions are taught in order of increasing difficulty, beginning with acid-base reactions, followed by simple additions to p electrophiles, and ending the first semester with addition to p nucleophiles, including aromatic chemistry. The reactions in the second organic semester begin with elimination reactions, then substitutions, and finally more complex p nucleophile mechanisms (e.g., aldol reaction) and p electrophile reactions (e.g., acetals). Ultimately, the goal is for students to learn and interpret reactions based on their patterns of reactivity, allowing them to analyze, predict, and explain new reactions. In principle, a mechanistic method is more general, easier to understand, and provides a better way to achieve a deep understanding of chemical reactivity. Chemical reactions follow patterns, and these patterns can allow a chemist to predict how a chemical will behave, even if they have never seen a particular reaction before. Visualizing reactivity as a collection of patterns in electron movement is a more powerful and systematic way to approach learning in organic chemistry. It still requires some memorization, but because the course organization is directly linked to reaction patterns, deeper learning in the discipline is possible.

The Canadian Journal of Chemistry has expanded its scope to include Chemistry Education Research (CER) and welcomes submissions in this new area. In this editorial, I give an overview of [...]

An outcome-based approach to teaching and learning focuses on what the student demonstrably knows and can do after instruction, rather than on what the instructor teaches. This outcome-focused approach can then guide the alignment of teaching strategies, learning activities, and assessment. In organic chemistry, mastery of organic acid-base knowledge and skills are particularly essential for success. For example, Brønsted acid-base knowledge and skills are required in greater than 85% of the more complex organic and biochemical reactions we analyzed in this study. Despite the importance of mastering acid-base concepts and skills, the literature describes many related student difficulties. We identified essential learning outcomes (LOs) in organic acid-base chemistry by (1) analyzing more complex organic reactions to identify the acid-base-related skills and knowledge that students would need to successfully analyze those reactions and (2) analyzing textbooks' explanations and coverage of acid-base chemistry. We constructed the learning outcomes using the Structure of Observed Learning Outcomes (SOLO) and modified Bloom taxonomies, as well as SMART (specific, measurable, achievable, relevant, and time-bounded) goal-setting principles. We explicitly aligned our courses' learning activities and assessments with those intended learning outcomes, both in the initial introduction of acid-base chemistry and as we analyze more complex reactions. To clearly communicate these LOs to students and other educators, we described them in an educational graphic.

Organic chemistry is a traditionally difficult subject with high failure & withdrawal rates and many areas of conceptual difficulty for students. To promote student learning and success, four undergraduate organic chemistry and spectroscopy courses at the first to third year level (17-420 students) were "flipped" in 2013-2014. In the flipped course, content traditionally delivered in lectures is moved online; class time is dedicated to focused learning activities. The three large courses were taught in English, the small one in French. To structure the courses, each course's intended learning outcomes (ILOs) were analyzed to decide which course components would be delivered online and which would be addressed in class. Short (2-15 min), specific videos were created to replace lectures. Online and in-class learning activities were created in alignment with the ILOs; assessment was also aligned with the ILOs. A learning evaluation was undertaken to determine the impact of the new course structure, using Guskey's evaluation model. Analysis of students' grades, withdrawal rates, and failure rates were made between courses that had a flipped model and courses taught in previous years in a lecture format. The results showed a statistically significant improvement in students' grades and decreased withdrawal and failure rates, although a causal link to the new flipped class format cannot be concluded. Student surveys and course evaluations revealed high student satisfaction; this author also had a very positive experience teaching in the new model. The courses' overall design and evaluation method could readily be adapted to other chemistry, science and other courses, including the use of learning outcomes, the weekly course structure, online learning management system design, and instructional strategies for large and small classes.

Fundamental to a student's understanding of organic chemistry is the ability to interpret and use its language, including molecules' names and other key terms. A learning gap exists in that students often struggle with organic nomenclature. Although many resources describe the rules for naming molecules, there is a paucity of resources available to actively and independently practice naming and drawing molecules and receiving feedback; plus, many of these resources are of low quality. Furthermore, students often do not see the real-life applications of the molecules they are naming. Our team created www.nomenclature101.com to respond to the learning gap and the lack of quality resources and to provide a link to real-life applications. This Web site hosts a free, interactive, online, bilingual (English/French) learning tool that draws from a bank of almost 1000 questions. This online learning tool is student-driven; it allows students to tailor their learning to their needs by creating customized nomenclature quizzes and providing immediate feedback. Nomenclature101.com has three key learning objectives; after working through the quizzes and other learning supports, students can (i) identify functional groups in a given molecule, (ii) name a molecule, given its structure, and (iii) draw a molecule, given its name. The learning tool is designed for high school chemistry and introductory organic chemistry courses. Students can use the tool independently or based on specific recommendations from their instructor; additionally, instructors could generate and print quizzes to use as part of their course assessment.

Organic chemistry has the long-standing reputation as a challenging course, and organic synthesis is an aspect of organic chemistry that requires students to make the most links between concepts and requires the highest order of thinking. One-on-one interviews were conducted with students from a second undergraduate organic chemistry course in which participants solved synthesis problems using a think aloud protocol. Those problems had been previously designed to scaffold students' acquisition of synthesis problem-solving skills. The research question for this study asked whether students worked through the synthesis learning activities as designed, toward the intended learning outcomes. The results show that in some questions, students used or tried to use desirable problem solving skills, such as using reaction mechanisms and chemical principles to explore possible solutions. However, with other question types, students (i) relied on familiarity with the reactions in question and lacked a problem-solving strategy when they could not recall the answer or (ii) avoided the purpose of the question and attempted to provide an answer that the professor ''wanted.'' Strategies for promoting desired synthesis skills and addressing other issues are discussed.

A unique method was devised integrating online postclass questions, clickers, a tablet, and active learning strategies in each class. This successful method connected in- and out-of-class learning, provided prompt, regular, and relevant feedback to students and to the instructor, encouraged students to spend time on task, and enabled class time to be focused on topics that students found particularly challenging. The effects on student learning and experience in large organic chemistry courses, as determined from students' assignment, midterm, and exam scores as well as student surveys, is discussed. The results of four years of data identified statistically significant improvements in students' scores at the question level in classes that used the postclass question method as compared to classes that did not. (Contains 5 tables and 10 figures.)

A unique approach to teaching and learning problem-solving and critical-thinking skills in the context of retrosynthetic analysis is described. In this approach, introductory organic chemistry students, who typically see only simple organic structures, undertook partial retrosynthetic analyses of real and complex synthetic targets. Multiple reasonable answers were possible for the questions, which provided a basis for the development of critical-thinking skills. A numbering system, described herein, was developed that enabled students to submit numeric clicker answers to a single or to multiple questions and thereby revealed the many ways that they had devised to disconnect these complex synthetic targets. The predominant student answers were readily gauged using the histogram function of the clicker program, which provided a basis for multiple relevant retrosynthetic analyses and enabled prompt, regular, and relevant feedback to be provided to students, even in moderate to very large classes. (Contains 1 table and 4 figures.)

The article explains the regio- and stereocontrolled synthesis of various tetrasubstituted olefins with four different carbon-linked groups. These olefins are commonly used in the manufacture of various drugs.