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Postgraduate engagement in delivering outreach activities is more commonplace than it once was. However, the impact on postgraduate students (typically studying for a Ph.D. degree) of participating in the delivery of these outreach activities has rarely, if ever, been recorded. The Bristol ChemLabS Outreach program has been running for ca. 17 years, and in that time, many postgraduate students have been involved (approximately 500), with around 250 typically for up to 3 years. We sought to investigate the impact of outreach engagement on postgraduate alumni who were involved in the program for over 3 years (32) and how the experiences and training of the outreach program had impacted on their careers postgraduation. Thirty of the 32 postgraduates engaged and ~70% reported that their outreach experience had influenced their decision making on future careers. Many respondents reported that the skills and experiences gained through outreach participation had contributed to success in applying for and interviewing at their future employers. All respondents reported that outreach had helped them to develop key skills that were valued in the workplace, specifically, communication, teamwork, organizational skills, time planning, event planning, and event management. Rather than a pleasant distraction or an opportunity to supplement income, all participants noted that they felt there were many additional benefits and that this was time well spent. Outreach should not be viewed as a distraction to science research but rather an important enhancement to it provided that the program is well constructed and seeks to develop those delivering the outreach activities.

Researchers and educators have been exploring systems thinking (ST) in chemistry education to better equip citizens for 21st century challenges; however, little is known about students' perspectives and experiences. In this study, we investigated students' perspectives of ST and their experiences with ST activities. We designed and implemented a ST intervention, performed individually and collaboratively, as well as follow up interviews. Twenty-four university undergraduate and graduate students participated in this study and reported a variety of experiences and perspectives. For students' experiences, we found that (1) while collaborating, participants recognized and appreciated different perspectives, (2) participants included chemistry concepts and connections in their system maps despite having difficulties, (3) system maps emphasized problems/solutions and causes/effects and differed in terms of organization and intended purpose, and (4) limitations to system map construction included time, knowledge, and technology skills. Students also expressed positive perspectives of a ST approach based on their experience engaging with the ST intervention and believed a ST approach (1) is beneficial to learning, (2) captures interest and engagement, (3) allows perspectives to be shared and gained, and (4) provides personal, social, and professional relevance. Based on these findings, we suggest aspects to consider when planning and implementing ST activities and identify future research required to better understand the impacts of ST in chemistry education.

New resources have recently been emerging for educators to implement systems thinking (ST) in chemistry education, including a proposed set of ST skills. While these efforts aim to make ST implementation easier, little is known about how to assess these skills in a chemistry context. In this study, we investigated ST skills employed by students who constructed system maps of a topic related to climate change. Eighteen undergraduate chemistry students from first- to third-year participated in this study. We designed and implemented a ST intervention to capture how students engaged with three ST tasks, performed individually and collaboratively. In our analysis, we focused on 11 ST skills that aligned with five characteristics proposed in a recent study. We found that participants demonstrated most of these ST skills when engaging with the ST tasks, with nuances. Participants' system maps:(1) lacked concepts and connections at the submicroscopic level; (2) included multiple types of connections but few circular loops and causal connections; (3) lacked causal reasoning, although participants did predict how their system maps changed over time; (4) demonstrated the breadth of connections but did not describe human connections to the underlying chemistry of climate change topics. These findings identify aspects of ST where chemistry educators need to place emphasis when teaching ST skills to chemistry students and when guiding learning activities and other assessments. Using our findings, we created an adaptable ST rubric for the chemistry community as a tool for assessing ST skills.

Having a shared language such as English facilitates the globalization of science, but it can also limit science by posing barriers for those who have learned English-as-an-additional language (Eng+). Research on the experiences of Eng+ graduate students and postdoctoral researchers ("trainees") is needed as our scientific community becomes more diverse and continues working toward improving equity and inclusion; without such research, we risk losing out on perspectives and expertise that might otherwise strengthen scientific progress. We investigated three research questions: (1) What are Eng+ chemistry trainees' language experiences before entering English-dominant research programs? (2) What language barriers have trainees faced in learning, communicating, and doing chemistry? and (3) What strategies and supports have been helpful or needed? In focus groups and interviews with 18 Eng+ trainees, participants described having diverse language experiences before entering English-dominant research programs and faced challenges working in an English research environment. Participants reported avoiding interactions with colleagues, exacerbated feelings of imposter syndrome, needing extra time to learn or communicate, and not being able to fully express their knowledge. Participants expressed an ongoing desire to learn English and described various independent strategies to navigate challenges. All participants believed that research supervisors and institutions needed to play a larger role in supporting Eng+ trainees, such as supervisors who offer personal and professional support, and institutional supports that provide chemistry-specific knowledge-building and networking opportunities. Based on the findings, we recommend approaches that supervisors and institutions can enact that may improve linguistic equity in the chemical sciences.

In an effort to further develop critical thinking and problem solving skills, a guided-inquiry-based, multioutcome organic chemistry synthesis and characterization experiment was developed. Students were provided with the protocol for a time-saving microwave-assisted acetanilide synthesis reaction from acetic anhydride and an unknown primary aryl amine. They developed their own protocol for thin-layer chromatography to determine their unknown reactant and assess the completion of the acetanilide reaction. The microwave-catalyzed reaction allowed time for characterization of the acetanilide product, including thin-layer chromatography, melting point, and [superscript 1]H NMR spectroscopy during a single laboratory period. Determination of the unknown reactant was accomplished using these data. This experiment was successful in both science majors and health science majors organic chemistry courses.

Systems thinking in chemistry education (STICE) has been proposed as an approach that could better equip students with abilities to connect their chemistry knowledge with other disciplines and with the skills needed to tackle complex global issues. However, educational change in chemistry is a complex effort that involves many interconnected factors that enable or hinder chemistry educators' adoption of new pedagogical approaches. Using an adapted version of the Teacher-Centered Systemic Reform (TCSR) model, we investigated factors that connect with chemistry educators' willingness and ability to implement a STICE approach in their courses. We surveyed a group of 56 secondary and postsecondary chemistry educators from ten different countries, to capture chemistry educators' perspectives toward a STICE approach. Through thematic analysis of responses, we identified four key themes as follows. Theme 1: Educators' willingness and ability to implement STICE is influenced by their knowledge, beliefs, experiences, contextual and personal factors; Theme 2: Educators report experiences with aspects of STICE without knowing or specifically calling it ST; Theme 3: Some educators implement limited aspects of STICE when teaching chemistry in context; and Theme 4: The ratings of barriers can guide priorities for educational change efforts. This paper discusses specific aspects of the reform model that experts and administrators can address to reduce barriers to implement and engage with STICE. We also highlight future chemistry education research that is needed to explore specific aspects of educators' perspectives and STICE more broadly.

There is a wide variety of ways for instructors to seek to improve diversity, equity, inclusion, and respect (DEIR) in chemistry through their instruction. One way is to talk with students explicitly about equity and injustice in science. We propose a curricular framework for teaching about equity as a way to improve DEIR in science classes at the high school and college levels. The framework has six parts, including expansive framing, buy-in, active and collaborative learning, action, flexible content, and science as a context for learning. We also present the Underrepresentation Curriculum as an example of the framework for teaching about equity in science in action. The Underrepresentation Curriculum (underrep.com) is a flexible set of lesson plans that aims to help students learn about and take action to improve equity in science.

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.

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.

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."

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.

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.

A discovery-based Grignard experiment that emphasizes several important concepts in organic chemistry is reported. The Grignard reagent from 1- bromo-4-chlorobenzene was prepared and reacted with dimethylformamide (DMF) to synthesize 4-chlorobenzaldehyde. Students were tasked with predicting halogen reactivity in the formation of the Grignard reagent, predicting the final product, and drawing a reasonable mechanism for the reaction with DMF. The Grignard reaction with tertiary amides is typically not discussed in the organic chemistry curriculum, so the students have an opportunity to apply concepts covered in lecture to a new situation. Lastly, the students experimentally verified the identity of the product using thin layer chromatography, melting point analysis, gas chromatography, IR and NMR spectroscopy, and mass spectrometry.

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.

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.

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.

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.)

One of the major focuses of biochemistry courses is metabolic pathways. Although certain aspects of this content may require a rote approach, more applied techniques make these subject areas more interesting. This article describes the use of an assignment, "Design Your Own Disease" to teach students metabolic regulation and biosignaling mechanisms. Concepts related to peer review and scientific literacy are emphasized in the context of disease processes. There are three phases that are associated with this assignment. In the first phase, students choose a biosignaling mechanism from the textbook. In the second phase, the students use this mechanism to propose a new disease process that is associated with one of the regulatory steps of a metabolic pathway and present the information as a paper. Finally in the third stage, the students peer review three student papers using three biosignaling mechanisms that they did not use in their own paper. Possible modifications to the assignment include the use of guest speakers, refinement of the peer-review process, and removal of the biosignaling mechanism requirement. A grading rubric makes assigning grades more straightforward and helps students conduct their peer reviews. Student comments and interest concerning the assignment and areas related to the assignment are positive and reflect its applied nature. (Contains 3 tables.)

Microscopy Camp program is designed to introduce acceptable representations of crystalline particles and their atomic structure to twelve-year-old middle school students at a developmental and educational stage.

A low-cost biochemistry experiment is described that demonstrates current techniques in the use of catalytic DNA molecules and introduces a nonradioactive, nonfluorescent, inexpensive, fast, and safe method for monitoring these nucleic acid reactions. The laboratory involves the exploration of the 10-23 DNA enzyme as it cleaves a specific RNA substrate, and the reaction is visualized qualitatively following gel electrophoresis. This experiment provides the students with hands-on experience manipulating nucleic acids using polyacrylamide gel electrophoresis to visually follow the kinetics of the reaction and introduces the student to a novel postelectrophoretic stain, cresyl violet, for detection of the nucleic acids. These DNA enzyme catalysts have potential applications in both biotechnology and medicine and therefore should be of great interest to upper-level undergraduate students. (Contains 4 figures.)

"Science days" is a project to encourage school students interest at an early age and to ensure that students experience the benefit out of this opportunity. It is found that majority of outreach program focused on chemistry alone as an important science subject, and young students interest in general, and it stated that science should be fostered in a better way through general science outreach program.