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The authors describe the construction and use of tactile models for demonstrating intermolecular forces. These models are composed of inexpensive materials and can be used in college chemistry classrooms of varying levels including general and organic chemistry. The models were designed to be paired with an accompanying activity to encourage students to compare and contrast the three types of intermolecular forces (hydrogen bonding, dipole-dipole forces, and London dispersion forces) as well as determine the relationship between intermolecular forces and the physical properties of specific molecules. More importantly, the handheld models allow for visualization of molecular interactions to promote multisensory learning. In this work, the authors discuss the development, implementation, and survey results of a modeling activity for conceptualization and review of intermolecular forces in introductory, general, and organic chemistry classrooms.

An undergraduate laboratory experiment for the synthesis of biologically significant bis-4-hydroxycoumarins using a new catalyst is described here. An experimental setup plan, monitoring the reaction by TLC, isolation of the product, safe laboratory handling procedures, and significance of data reproducibility of the result are the main learning outcomes of this work. The products are characterized by melting point, [superscript 1]H nuclear magnetic resonance (NMR), [superscript 13]C NMR, distortion enhancement by polarization transfer (DEPT) NMR, and Fourier transform infrared (FTIR) spectra. This simple and cost-effective experiment with wide substrate applicability also introduces the concept of research work on multicomponent condensation reaction among the students.

Educational Scaffolding was first mentioned in 1976 by Wood et al. Several examples for scaffolding in chemistry are also known from the literature. As written scaffolds, stepped supporting tools to support students while solving problems in organic chemistry were developed, applied, and evaluated. Although the students rated the tool as very helpful, a think-aloud study showed that the support given by this scaffold was not sufficient. As a further development of stepped supporting tools, task navigators were therefore developed, applied, and evaluated. This new scaffold gives tips on strategy, knowledge, and application of knowledge after the STRAKNAP concept. The evaluation of this tool shows that the students rated the tool as being very helpful. A think-aloud study showed that the scaffold supports the students while they solve a problem. Because of the stepwise construction of the task navigators and the providing of the knowledge needed for the application, the students can solve parts of the task successfully even if they do not solve all parts correctly; the students can always start from scratch. When students use the tool regularly, their knowledge of organic chemistry increases compared to students who did not use the tool at all. The task navigator is not only a scaffold for the content of the task but also for the development of methodological competences on the field of strategies and applying knowledge.

Converting a first-term, accelerated summer organic chemistry course to a flipped format reduced the achievement gap in the flipped course and in the second-term traditional lecture course between Non-Repeaters taking an accelerated course to "get ahead" and Repeaters taking the course to "get back on track". The difference in final exam performance in the second-term course was nearly halved, the GPA gap in both courses was reduced, and the gap in passing rate for the second-term course was eliminated. First-generation students who took the first-term course in the flipped format experienced a final exam score boost in the second-term course regardless of repeater status. While most students responded positively to the flipped course structure, repeating students held a stronger preference for the flipped format. These findings provide guidance on how to create courses that promote equity, access, and retention of diverse students in STEM.

The need for more sustainable practices is in high demand. Green chemistry discusses practices that would lead to less harmful chemical products ending up in the environment. Herein, we describe an outreach activity that introduces minority high school students to the topic of green chemistry. Three hands-on activities were done to illustrate a few of the 12 principles of green chemistry. The students picked suitable solvents, built ball-and-stick models of organic molecules, and made "green" paint during an interactive case-based green chemistry module. The students expressed their enjoyment of the activity and showed gains in green chemistry knowledge and attitude toward chemistry after participating in the module.

Chemical eponyms possess important didactic and axiological potential that can be utilized for implementation of the principles of humanization and historicism manifested in national educational standards. This study focused on students' knowledge and views of eponyms in the light of history of science. 22 general chemistry students of Belarusian State University, 131 students of general and 119 students of organic chemistry of University of Oregon, all different majors, were surveyed on their knowledge and views of eponyms using a 24-item online questionnaire. Mann-Whitney coefficients were calculated to establish significant differences and Pearson chi-square test was applied to find correlations. It was found that students' knowledge and views of eponyms are defined mostly by major: students majoring in teaching chemistry showed higher knowledge and expressed more positive views of eponyms than those majoring in non-teaching, non-chemistry and especially non-science. Other factors include students' learning experience and study intensiveness. While didactic potential of eponyms is utilized anyway, utilization of their axiological potential depends on instructor's willingness and mastery and should not be exaggerated as vehicles for the principles of humanization and historicism.

This study attempts to discover the effectiveness of an e-content package when teaching IUPAC nomenclature of organic chemistry at the undergraduate level. The study consisted of a Pre-test-Post-test Non Equivalent Groups Design, and the sample of 71 (n = 71) students were drawn from two colleges. The overall study was divided into two groups, an experimental group and a control group; and it consisted of (n = 36) students in the experimental group, and (n = 35) in the control group. The experimental group students were taught through an e-content package, whereas the control group students were taught via existing conventional methods of teaching. The initial results of the study revealed that the students in the experimental group achieved more in learning organic chemistry than the students in the control group. The final results of the calculated t-values from the study indicated a higher level of significance. And the research hypothesis, which was based on pre-test and post-test scores of the control group and experimental group in teaching IUPAC nomenclature of organic chemistry was accepted. Our findings showed a significant difference in mean scores between the control group and experimental group in teaching IUPAC nomenclature of organic chemistry.

Interactive learning is one of the approaches that is very important to explore in higher education. Chemistry students own smartphones, laptops, and tablets and could use appropriate apps to complement traditional forms of learning. Here we introduce a new app, MILAGE LEARN+, which integrates several teaching strategies, such as mobile learning, autonomous learning, peer review, blended learning, and gamification. These strategies were evaluated by the student users through an electronic survey form containing 15 statements with responses graded on a Likert-type scale. Students rate the usage of novel teaching/learning strategies in the MILAGE LEARN+ app as something very positive. There is a positive correlation between the relative grades obtained using MILAGE LEARN+ and the final exam grades. Thus, in this experience, students with better results in MILAGE LEARN+ also had better results in the final exam.

The practical two-step synthesis of 1-phenylthiourea is reported here as an undergraduate experiment for the organic synthesis laboratory. The reactions involved in 1-phenylthiourea preparation are very useful didactic examples to illustrate concepts relating to carbonyl substitution and addition, the effect of pH on solubility of organic compounds, and many laboratory techniques, such as isolation, purification, and product analysis. The products were purified through precipitation, which involves changing the pH value, followed by recrystallization. The products were identified by melting point and infrared and NMR spectroscopy.

The dehydration of 2- or 4-methylcyclohexanol to obtain isomers of methylcyclohexene is a classic organic chemistry experiment. Students perform a distillation, collecting samples to analyze the progress of the reaction. The reaction produces a major product that can be explained on the basis of the regiochemistry of the [pi] bond formation for the [alpha]-[beta] elimination process. Minor products can be attributed to the possible rearrangement of the carbocation through a hydride shift. We have added computational analysis to this classic experiment to help students understand alkene stability. The experiment was performed early in the sophomore organic chemistry laboratory, before students were introduced to the mechanistic perspectives that govern the reaction. The iSpartan analysis of the possible methylcyclohexene products combined with gas chromatography data provides students with an inquiry-based laboratory experience. A novice student can analyze the computational information about the products to determine the trend in product stability and determine if a double-bond is formed at an unexpected location in the molecule. The integration of computational tools provides more information to students than performing the experiment in isolation.

This three-part laboratory experiment investigates key aspects of the Buchwald-Hartwig amination cross-coupling reaction through guided-inquiry learning strategies. The first part of this experiment utilizes high-throughput experimentation techniques to reinforce, explore, and extend fundamental concepts that are represented in the classroom, including the use of air-free Schlenk techniques and heteronuclear NMR analysis. The second component challenges students to evaluate their results to design, set up, and perform a preparative-scale Buchwald-Hartwig amination. Finally, students purify and isolate their products using column chromatography allowing them to fully characterize their target molecules through a variety of analytical techniques. This experiment represents one of the final experiments performed in the fourth-year undergraduate chemistry curriculum and serves as a capstone learning experience for students.

In this paper the development, use, and evaluation of tasks based on the construct of school-related content knowledge are described. The tasks were used in seminars on organic chemistry for bachelor and master preservice chemistry teachers at a German university. For the evaluation a questionnaire with open and closed items was used. The tasks were rated by the preservice chemistry teachers as relevant for their future profession as a chemistry teacher if the content of the tasks is part of the school curriculum. If the content does not belong to the school curriculum, they rated the nature of the tasks still as relevant; they seem to recognize the importance of conceptual knowledge for their future profession. However, the master's preservice teachers argued with this conceptual knowledge more often than the bachelor's preservice teachers. Although the study is cross-sectional, a certain shift from the focus on the content to conceptual knowledge from bachelor's to master's preservice teachers can be observed.

Herein, we describe an accessible and safe organic chemistry lab experiment that can be completed at home. Liquid-liquid extraction is a fundamental organic chemistry lab experiment that touches on topics such as chemical structure, density, solubility, and acid-base chemistry. Given the increased demand for safe organic chemistry experiments that can be performed in the at-home environment, we have adapted the conventional wet lab liquid-liquid extraction experience by using food colorants. Students are first guided through sample questions to establish a basic understanding of solubility, acid-base chemistry, and separation via extraction techniques. Next, they are given unknown dye mixtures which they subject to liquid-liquid extraction using a plastic soda bottle with vegetable oil, water, white vinegar, and sodium bicarbonate. All materials are readily available and food-safe, making the experiment amenable to the at-home environment while still allowing students to physically engage in a foundational lab experiment.

In undergraduate chemistry curricula that include computational modeling, students may gain first-hand experience in both introductory and advanced applications of this technique. However, although students can be exposed to the predictive power of computational work, its capabilities are often limited to determining the intrinsic properties of the molecules being modeled, rather than potential applications of functional materials intended for devices. To address this disconnect, we have designed and implemented a computational module for upper-year undergraduate and graduate students within an organic materials chemistry course. The module is conducted over 7 weeks and is based on an increasingly important phenomenon in organic photochemistry known as thermally activated delayed fluorescence (TADF). TADF emitters are ideal for display technologies (organic light emitting diodes). Students connect molecular structure with predicted properties and function by performing computational modeling on known TADF emitters, before correlating their results with the experimental performance of the emitters. They also address potential limitations of density functional theory (DFT) that they have not encountered previously, attempt to rationalize outlying data points based on content presented in class, and summarize their calculations and conclusions in a communications-style manuscript. Overall, students learn how DFT can be used to inform molecular materials chemistry and engineering as well as identify some limitations of "in silico" design.

The effects of kinetic vs thermodynamic control on "endo"/"exo" stereoisomer ratios can be observed in a simple Diels-Alder reaction between "N"-phenylmaleimide and furan. The use of microwave-promoted synthesis affords the cycloadducts in yields ranging from 65-100%, employing reaction times of 1-10 min at temperatures of 55-130 °C. Short reaction times enable screening of numerous reaction conditions (time and temperature) within a single lab period, where "endo":"exo" product ratios follow the primary facets of kinetic and thermodynamic control. Analysis of product ratios obtained under kinetic control allows for the evaluation of activation parameters ([delta][delta]"H"[thermodynamic] ([approximately equal to] [delta]"E"[subscript a]), [delta][delta]"S"[thermodynamic], and [delta][delta]"G"[thermodynamic]) by means of the Arrhenius and Eyring equations. Values of [delta][delta]"H"[thermodynamic], [delta][delta]"S"[thermodynamic], and [delta][delta]"G"[thermodynamic] were found to be 6.4 ± 0.3 kJ mol[superscript -1], 16.5 ± 0.9 J mol[superscript -1] K[superscript -1], and 1.5 ± 0.4 kJ mol[superscript -1] ([delta][delta]: "exo"-"endo"), respectively. Experimentally determined activation parameters correlate well with quantum-chemical calculations. Several key teaching points are also addressed, including frontier molecular orbital analysis, reversibility of the Diels-Alder reaction, column chromatography, and the use of [superscript 1]H nuclear magnetic resonance spectroscopy to assess both stereoisomeric yield and purity.

Nuclear magnetic resonance (NMR) spectroscopy is the tool of choice for organic chemists to determine the molecular structure of organic molecules and, as a result, is a fundamental topic in the organic chemistry curriculum. A novel laboratory module has been developed to expand the scope of NMR spectroscopy beyond structure validation at the undergraduate level to include how organic chemistry and FT-NMR spectroscopy are directly related to contrast-assisted magnetic resonance imaging (MRI). This laboratory module allows students to synthesize commercially available MRI contrast agents and exposes students to the important concepts of longitudinal relaxation time ("T"[subscript 1]) and relaxation rate ("r"[subscript 1]), and how both properties can be enhanced by paramagnetic contrast agents. By using an NMR spectrometer for inversion recovery experiments, students will be able to bridge the concepts of NMR and MRI, while understanding how organic chemistry plays a vital role in a technology that revolutionized diagnostic and therapeutic medicine.

An augmented reality (AR) application and an activity worksheet have been developed to support students in visualizing the concepts involved when solving [superscript 1]H NMR problems. This instructional resource was designed to encourage conceptual problem-solving and prevent memorization by eliminating the use of chemical shift tables. It uses the compare-predict-observe-explain (CPOE) cycle and contrasting cases to guide students to abstract principles about how proton equivalency, nuclear spin, electronegativity, and anisotropy impact the number, intensity, splitting, and shift of signals on a spectrum. The AR resource aids students in visualizing 3D structures, molecular orbitals, and electrostatic potential maps. Results from the user experience questionnaire revealed that students had a positive user experience and ranked the novelty of the application as its best feature. We also provide evidence using the Behavioral Observation of Students in Schools protocol that merits the use of this instructional resource in the laboratory setting on the basis of the minimal need for instructor's assistance that was observed. This paper describes how the application H NMR MoleculAR, now freely available in Android and iOS stores, was incorporated as an in-lab app for the [superscript 1]H NMR laboratory at our institution. It has also been administered remotely and has been proven to be a useful complement to organic chemistry instruction.

As green chemistry and engineering are being integrated into chemical processes in academia and industry, it becomes equally important to equip students with the relevant tools in the fields of sustainable chemistry and processes. In this context, continuous flow technology has been identified as one of the promising strategies. Herein, we describe an approach which unites flow chemistry, undergraduate research, and chemical education research. Teams of undergraduate students designed, developed, validated, and implemented batch and flow experiments for an upper-level organic chemistry laboratory. The research to develop the experiment, which was part of an undergraduate research course (Vertically Integrated Project course, VIP), the pedagogic implementation, and the outcome in the instruction laboratory are reported.

Highly efficient microwave-assisted organic synthesis is now commonplace in both industry and academia. Recently, a conductively heated sealed-vessel reactor was introduced that acts very similarly to a microwave reactor and is more affordable. Application of such reactors in teaching laboratories is advantageous because of the restricted window of time available to perform experiments and because it avoids long reaction times that are unpopular with students. These reactors thus allow reactions that were previously considered impractical for the teaching laboratory, such as the Fischer indole synthesis, to now be very feasible. We designed a clean and efficient Fischer indole synthesis to introduce advanced undergraduate students to this important method in heterocycle synthesis, which has been highly under-represented in the curriculum. It also introduces it in the context of a more complex ketone of biological relevance (a steroid). This laboratory exercise can be used to teach about Green Chemistry Principles, product analysis (TLC, NMR, MS, UV-vis), and a complex multistep mechanism. It can also act as a starting point to teach terpenoid biosynthesis, some key concepts in medicinal chemistry such as pharmacophores and pro-drugs, and even to open discussions on the societal impacts of steroids.

This study explores the importance of general chemistry as a prerequisite for organic chemistry lecture courses. The students taking organic chemistry were categorized into three groups: (1) those who had finished the prerequisite before starting organic chemistry, (2) those who had not finished the prerequisite before starting organic chemistry, and (3) those who were repeating the course. Most students in group 2, however, took general chemistry during the same semester. The general chemistry prerequisite was found to have a positive but minimal impact on student performance, yielding a slightly improved average and pass rate. However, the difference between groups 1 and 2 was not statistically significant. These results raise the question of whether or not general chemistry should be viewed as a required prerequisite. A few more responses to the implications of these results are offered including using placement exams and AP/IB scores to evaluate whether students require the prerequisite and using intended learning outcomes strategically when designing curricula. Lastly, these results can remind us, as instructors, of being aware of the assumptions we make about our students' knowledge and academic preparedness.

This article highlights the multianalytical study of exuded liquid from an ancient Egyptian sealed alabaster vase by Master's students in an applied chemistry for cultural heritage course. Master students are introduced to the field of Archaeometry that see the collaboration of experts in different areas of research such as conservators, curators of museums, physicists, chemists, etc. The sample is a residue exuded on the linen strip sealing an ancient Egyptian alabaster vase (inventory number S.8448) from the collection of the Museo Egizio in Turin (Italy). The students start to plan the noninvasive investigation by X-ray fluorescence (XRF), transmission electron microscopy (TEM), and energy-dispersive X-ray spectroscopy (EDS) for the inorganic compounds characterization, followed by the extraction of the organic components (such as oils, fats, and waxes) to be analyzed by high-resolution [superscript 1]H and [superscript 13]C nuclear magnetic resonance (NMR) spectroscopy and 2D NMR correlation spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), and long-range heteronuclear correlation (HMBC) techniques and by gas chromatography coupled with mass spectrometry (GC/MS). Reference standards, spectral databases, and published data on similar artifacts served as the basis for the interpretation of the instrumental results. The approach was introduced in the course of Applied Chemistry for Cultural Heritage for Master students in Archaeology (University of Palermo, Italy), where the need is to know how to approach the scientific investigation together with the conservation scientists and how to manage with a very low amount of sample. Pedagogically, the approach introduces students to the main techniques currently used in the field of Archaeometry while reinforcing fundamental concepts in sample collecting and multicomponent microsample analysis. This interdisciplinary approach provides a unique experience that demonstrates chemistry's broad applicability outside of the traditional laboratory. Students are guided to identify the inorganic and organic components of the exudate liquid: the first one is ascribable to clay minerals iron oxides, which could impart the brown color to the sample; the second one is ascribed to triglycerides of various kinds, which probably comes from vegetable oil.

The laboratory experiment regarding esterification of ethylene glycol with acetic acid to ethylene glycol diacetate using resin catalysts in a continuous flow was designed to carry out the reaction in a flow through an inquiry-guided approach. Incorporating the burgeoning field of continuous flow chemistry into the educational infrastructure, the experiment showed the practical application of heterogeneous catalysts in continuous flow synthesis. In a discussion of the importance of continuous flow chemistry and heterogeneous catalysis, students were encouraged to seek effective, sustainable, and environmentally friendly approaches to synthesize compounds.

Undergraduate organic chemistry students, as they study conformational analysis and stereochemistry, frequently have trouble manipulating three-dimensional structures on a two-dimensional page or screen. The inability to accurately convert three-dimensional bond-line representations into Fischer projections is one example of this. While some students can utilize traditional approaches, other students require another way to visualize the molecule in order to perform the conversion. This text describes a method for converting bond-line structures of varying chain lengths and conformations into corresponding Fischer projections.

Polymerization reaction media can have a profound effect on the physical properties of the resultant polymer. This phenomenon is showcased in a new experiment for the organic chemistry and polymer science teaching laboratories wherein the radical copolymerization of biobased [beta]-myrcene and dibutyl itaconate is performed using a nonhazardous aqueous emulsion solvent and compared to a bulk reaction. Both procedures demonstrate multiple green chemistry principles and application to sustainable polymer synthesis. The emulsion copolymerization produces a tacky, elastomeric cross-linked material, capable of swelling to many times its original volume in organic solvents, setting the stage for the exploration of the relationship between solvent polarity and swelling capacity. Conversely, the polymerization of [beta]-myrcene and dibutyl itaconate in the bulk yields a viscous non-cross-linked polymer whose [superscript 1]H NMR spectrum is suitable for student analysis and estimation of polymer number-average molar mass (M[subscript n]), monomer conversion, and copolymer composition. This inexpensive experiment models the use of renewable feedstocks, the effect of reaction medium on polymer architecture, the unique properties of cross-linked organogels, and the quantitative analysis of polymer structure using [superscript 1]H NMR spectroscopy.

The course design "Training OC" for training the application of basic concepts consists of four topics: formula language, structure-property relations, reaction mechanisms, and complex tasks that the students should solve with the conceptual knowledge they acquired in the first three topics. A main goal of the course was to enable the students to solve reaction mechanisms. To achieve the goals of the course, several games were specially designed and used. The course was conducted at a German university with ca. 30 students who participated voluntarily. The course was evaluated by several tools: students' products were collected in the course, there were two pre/post-tests, and additionally, interviews on the strategy of designing reaction mechanisms were conducted. The performance of the teacher and the self-assessment of the students were also part of the evaluation. The results of the written exam were compared with the results of the bachelor chemistry major students. The course "Training OC" was rated very well by the students. They were of the opinion that they learned the application of basic concepts taught in this course. This is supported by the results of the evaluation and the written exams. The course concept of Training OC will therefore become a permanent part of the course "Organic Chemistry I" which will be redesigned for the next round in 2020-21.

Large, multisection laboratory courses are particularly challenging when managing grading with as many as 35 teaching assistants (TAs). Traditional grading systems using point-based rubrics lead to significant variations in how individual TAs grade, which necessitates the use of curving across laboratory sections. Final grade uncertainty perpetuates student anxieties and disincentivizes a collaborative learning environment, so we adopted an alternative grading system, called specifications grading. In this system each student knows exactly what level of proficiency they must demonstrate to earn their desired course grade. Higher grades require demonstrating mastery of skills and content at defined higher levels. Each students' grade is solely dependent on the work they produce rather than the performance of other students. We piloted specifications grading in the smaller, third quarter course of the lower division organic chemistry laboratory series held during a summer term. Open-ended questions were chosen to gather student and TA perceptions of the new grading system. TAs felt that the new grading system reduced the weekly grading time because it was less ambiguous. Responses from students about the nature of the grading system were mixed. Their perceptions indicate that initial buy-in and multiple reminders about the bigger picture of the grading system will be essential to the success of this grading system on a larger scale.

Visualizing molecular conformations and complex compound structures and chemical transformations in 3D is one of the most difficult tasks for undergraduate chemistry students. Modern computational technologies have revolutionized every aspect of our lives, including education. As a result, many researchers and educators are working on enhancing student learning and improving construction of knowledge by employing technologies that better illustrate theoretical concepts, such as the visualization of molecular geometry in chemistry. Here, to aid students in understanding molecular structures and chemical reaction mechanisms at the molecular level, we initially developed several 3D animations of fundamental chemical transformations aimed at organic chemistry courses for second- and third-year undergraduate level. These animations became the basis for the 3D augmented reality tool called ARchemy. A comprehensive survey was conducted to gather student feedback on the effectiveness of these tools and their perception of the subject matter using these technologies, which will be presented in this project.

Research in science education agrees that one of the key challenges of learners in the discipline is certainly connecting domain-specific representations to the underlying concepts. One way of supporting students to make applicable connections is using purposefully designed highlighting techniques in multimedia instructions. In order to examine the influence of different highlighting techniques on learning, 171 chemistry undergraduate students were provided with tutorial videos either with static, dynamic or without highlighting. The results show that students viewing tutorial videos with dynamic highlighting gave more sophisticated answers in direct retention tasks. Furthermore, results indicate that low prior knowledge is compensated by both static and dynamic highlighting techniques. This finding is supported by causal mediation analysis, which indicates that the effect of prior knowledge is moderated by the different highlighting techniques. Besides student learning outcomes, students' evaluation of the different tutorial videos shows significant benefits of the highlighted instructions in terms of perceiving higher comprehensibility. The results support the use of appropriate highlighting techniques in instructional formats to foster a stronger link between conceptual knowledge and representations.

Purpose: This paper aims to report a case study in flexible learning with multicomponent blended learning mode in an undergraduate chemistry course. Traditional chemistry courses usually include lectures, tutorials and laboratory sections. For a course "Advances in Organic Synthesis" at undergraduate level, it consists of advanced information in organic chemistry such as reaction mechanisms, asymmetric catalysis, retrosynthesis and applications in synthesis of natural products. This course is a difficult subject and requires deep understanding of contents. After learning this course, students should have comprehensive knowledge in advanced strategies of organic synthesis and have an ability to apply them to real cases. This "flexible learning with multicomponent blended learning mode" was implemented by the authors to enhance student engagement and self-motivation in their studies. Design/methodology/approach: The authors hoped to enhance students' engagement in "flexible learning" -- a mixed concept with "blended learning" and "flipped classroom" -- and called this approach as "multicomponent blended learning mode." Blended learning combines face-to-face and e-learning components with interactive Web-based components and technical experimental videos were developed. The knowledge integrated in different components provides a natural environment to link the different synthetic methods together, which help students to get a better understanding of the complicated knowledge and strengthen their skills. For flipped classroom, students participated in the case studies of the organic synthesis and shared their findings to other classmates in oral presentations. Findings: In this study, both course evaluation score and students' academic performance in the "multicomponent blended learning mode" were increased significantly when comparing with traditional teaching methods in 2011. It was found that students' engagement and their self-motivation in learning were enhanced. Originality/value: The positive feedback from the students and the enhancement of their academic performance supported the value in this research. Besides, most universities in Hong Kong have suspended all face-to-face classes and conducted all teaching in online mode during COVID-19 outbreak. As the multicomponent blended learning mode of this course has already been conducted for eight cohorts, the authors are confident that this feature can minimize the sudden change in the learning habits for the students. As social factors and individual variations in students' learning and study mode may affect the learning outcomes, these interactive multicomponent e-learning components in this special period make students excited when they can study and digest the knowledge according to their own pace.

Research on student argumentation in chemistry laboratories has mainly focused on evaluating the quality of students' arguments and analyzing the structure of such arguments ("i.e." claims, evidence, and rationale). Despite advances in these areas, little is known about the impact of activity framing on the nature of student argumentation in laboratory settings. In this research study, we analyzed the arguments generated by college organic chemistry students working on a substitution reaction experiment that was framed in two distinct ways: predict-verify and observe-infer. The arguments constructed by students in their post-laboratory reports under each laboratory frame were characterized by paying attention to both domain-specific and domain-general features. Our analysis revealed significant differences in the chemical concepts and ideas that students under the two conditions invoked, as well as in the level of integration, specificity, alignment, and type of reasoning observed within and across different argument components. Our findings highlight the importance of paying attention to how experiments are framed in terms of the goals, procedures, information, and tools available to students as these decisions can have a major impact on the nature of the claims students make, their use of evidence, and the approach to reasoning that they follow.

Understanding ongoing chemical processes in the laboratory requires constant shifting between different representational levels--the macroscopic, submicroscopic, and symbolic levels--and analysis of the various mechanistic features of each of these levels. Thus, the ability to explain observations of chemical phenomena with regard to their submicroscopic levels in the laboratory is a key requirement. Research shows that students have difficulty in discerning and comprehending the meaning and visualization of the submicroscopic level. Traditional laboratory instruction often fails to help students discern the relationship between their observations and the corresponding chemical processes. Consequently, there is a high demand for new teaching strategies which address these issues. Therefore, we developed and implemented a scaffold for the organic laboratory and tested it in a research study using qualitative methods. The scaffold encourages students to purposefully separate and connect the macroscopic and submicroscopic representational levels. The implementation of the scaffold was accompanied by semi-structured pre- and post-interviews with students (N = 22) and an analysis of students' work with the scaffold in the laboratory. We analysed students' sense-making approach while reflecting on organic syntheses before and after working with the scaffold, and characterized changes in their approach. The findings emphasize the need to develop further resources to support students' understanding of the submicroscopic level. Implications of these findings for research and teaching to foster meaningful learning in the organic laboratory are discussed.

Peer-Led Team Learning (PLTL) is a small-group, collaborative problem-solving model that has significantly increased student performance in a variety of chemistry undergraduate courses and other STEM courses. Cyber Peer-Led Team Learning (cPLTL), an online adaptation of PLTL, has been effective in general chemistry courses, but this study was the first to evaluate the impact of implementing cPLTL in an organic chemistry course. Organic chemistry is a pivotal course in the curriculum of several science majors and preparation for health professions schools. Therefore, it is important to assess an academic intervention with the possibility of improving course performance and retention of science, technology, engineering, and mathematics (STEM) majors. In this study, the course performance and student perceptions from four "comparison group" PLTL and cPLTL sections were analyzed. The results of this study support the hypothesis that implementation of PLTL/cPLTL programs increases both students' performance and perceived learning gains in an organic chemistry course. Moreover, this study demonstrates that a typically face-to-face active learning intervention can be successfully transitioned to an online setting.

A method to synthesize biaryls through the Suzuki-Miyaura cross-coupling reaction using a recyclable fluorous precatalyst is described. This laboratory experiment, which demonstrates the safety benefits of green chemistry, is integrated into an upper-division course. Besides simply using the catalyst for a reaction, students can reuse the catalyst which is seldom performed in teaching laboratories. A multioutcome approach was employed for the first reaction where students are provided with different starting materials. Students elucidate the structure of the starting material/product using [superscript 1]H NMR spectroscopy. Subsequently, the precatalyst is recovered using fluorous solid-phase extraction and reused in the synthesis of a precursor to valsartan. Valsartan is a drug commonly used to treat high blood pressure. Students' feedback indicates that the laboratory session helped them better understand and apply the principles of green chemistry.

A systems thinking approach to incorporating green chemistry and safety into laboratory culture is vital, as chemists will be at the molecular level of the innovative solutions to our global challenges. Training chemists to have the skills and culture to accomplish this feat in the safest way possible is pivotal to safe working conditions within the chemical industry and extends to society in a sustainable future for the planet. Today, we know green chemistry to be the framework for conducting chemistry in a manner that is conducive to life. In this article, we emphasize how framing green chemistry through the lens of systems thinking can build a culture of safety in the laboratory. This can shift the focus of safety culture from compliant to proactive, as assessing the risk of performing a reaction gives chemists ownership and control of their safety. The Guide to Green Chemistry Experiment for Undergraduate Organic Laboratories is highlighted as one approach. The guide utilizes the green chemistry metric, DOZN 2.0, which allows for a quantitative method toward recognizing and assessing the risks of hazards in a chemical reaction. Within the research enterprise, green chemistry is a cornerstone of the Green Laboratories movement and helps institutions to meet both safety and sustainability strategies. Yet, in order for these efforts to be successfully implemented, environmental health and safety (EH&S) and sustainability professionals must engage one another and communicate effectively. Understanding how motivational focus affects our perceptions and attitudes can allow stakeholders to better partner on Green Laboratories initiatives and more successfully implement these techniques.

A relatively large number of organic and inorganic chemistry reagents are air- or moisture-sensitive, and undergraduate students should be trained in their use. When handling such reagents, it is important to select the correct syringe and to use that syringe correctly. We have found that the best syringe for use in an undergraduate setting is a fully plastic polypropylene (PP) Luer lock syringe. While generally safe, such a syringe should be treated as a single-use syringe. Repeated exposure to an organic solvent causes progressively more resistance to the movement of the plunger, or its complete freeze. Thus, when drawing in a volume of liquid that is close to the capacity of the syringe, the plunger could be inadvertently pulled out causing a spill.

Self-efficacy has a strong influence on the learning and motivation of science students at the postsecondary level, especially in upper division science classes, which are key to student success in science majors. This empirical mixed methods research study (N = 205) examines the associations between students' participation in an online preparation course and student self-efficacy in organic chemistry. Qualitative content analysis indicated that students benefited from the online preparatory course in the subsequent organic chemistry course series. The analysis of students' clickstream data indicated that students with self-efficacy ratings in the top 10th percentile exhibited more frequent and consistent engagement with relevant course materials compared to students in the bottom 10th percentile. Notably, linear regression models indicated that participation in the online preparatory course was associated with higher long-term self-efficacy for first-generation college students. These results suggest that online preparatory courses may benefit some students' self-efficacy in demanding science courses.

Performing the identification of organic chemical compounds from a set of spectroscopic data gives the opportunity to students to develop critical thinking and problem-solving skills. In this context, we developed a student-centered methodology for teaching molecular structural analysis to first-year undergraduate students. This systematic approach was implemented during classroom-training sessions and complemented by a home-based training program. Home-based activities involved a multiplatform Web-based application (ULg Spectra) combined with guided inquiries. ULg Spectra offers fully interactive tutorial/drill materials relying on mass, infrared, and nuclear magnetic resonance spectra (i.e., one-dimensional [superscript 1]H NMR and [superscript 13]C NMR spectra and two-dimensional [superscript 1]H-[superscript 13]C HSQC spectra). A survey indicates that the vast majority of students valued the ULg Spectra application combined with guided inquiries, especially in terms of usability and usefulness. This approach prompted them to actively engage in problem solving, and student autonomy was improved. Statistical data demonstrated that low-, medium-, and high-training students' groups showed increasing performance in the final exam. Interestingly, a statistically significant increase in final grades and success rate was also observed compared to previous years.

A dual-enrollment course was designed in which the elementary concepts of organic chemistry were introduced to high school students. Students were assessed at the end of the term using an American Chemical Society (ACS) standardized exam. The same exam was given to corresponding traditional on-campus sections of the same class taught by the same professor. Intriguingly, when dual-enrollment students' performance was compared with the performance of the traditional on-campus students studying the same content, no statistical difference was detected. Moreover, the dual-enrollment students have scored at a level significantly higher than the nationwide averages advertised by the Examinations Committee of the ACS.

The development of an enzyme-mediated reaction for the first-year general, organic, and biological chemistry (GOB) teaching laboratory is of significant importance so that the factors that affect enzyme-mediated reactions can be adequately demonstrated, reinforcing the lecture portion of the GOB course. Some of the factors that affect these types of reactions include, but are not limited to, enzyme concentration, substrate concentration, and temperature. The experiment reported herein utilizes porcine pancreatic lipase (PPL) to catalyze the hydrolysis of triglycerides within cream. The amount of time required to afford triglyceride hydrolysis was probed by altering the concentration of PPL and the temperature at which the reaction was performed. In addition, to provide the students with a hands-on demonstration of how bile salts aid in the digestion of triglycerides, various trials were performed to explore the effect of altering bile salt concentration. Finally, the data obtained from the enzyme concentration trials, the temperature trials, and the bile salt concentration trials were graphed to provide a visual representation of how triglyceride hydrolysis, mediated by PPL, is affected by these various factors.

The mechanism maps that guide student instruction in organic chemistry curricula are structural representations of bond-breaking and bond-making events that transform a reactant into a product. For students, these pathways represented by electron pushing formalism (EPF) can be challenging to navigate. For instructors, providing formative feedback to students to support their learning of the EPF arrow system is difficult to provide in a timely manner. The Mechanisms App ("the App") was developed as a method for students to explore the electron movement of organic chemistry through a touch screen interface of a smart phone or tablet with real-time feedback of these moves. In this paper, the pedagogical content of the App and its backend system is described. This system produces a graphical record of a user's move within the App and is called a decision tree. A study of students' use of the App in two different modes was devised to understand whether the in-app experience can facilitate a hypothesis-driven approach to learning EPF. Examples of classroom implementation for the App in a variety of institutions and future research are also described.

This modular, open-framework capstone course delves deeply into the synthesis, separation, and characterization of chiral molecules while teaching critical thinking and writing skills in a research-like setting within a fertile area for discovery. This course has evolved over 30 years and has been in its present form for 5 years at the time of this writing. The studies described can be easily integrated into a curriculum with other related disciplines, including medicinal, synthetic, analytical, and physical chemistry. The first procedure introduces Pasteur's classic resolution of (±)-[alpha]-phenylethylamine by cocrystallization with enantio-pure d-tartaric acid. The enantiomerically enriched [alpha]-phenylethylamine is then characterized using three different methods: polarimetry to measure [alpha][subscript D], high-performance liquid chromatography (HPLC) with a chiral column to determine the enantiomeric ratio (e.r.), and by proton nuclear magnetic resonance ([superscript 1]H NMR) using a chiral shift reagent. In the second experiment, students carry out a stereoselective alkylation of a glycine Schiff base using a cinchonine-derived phase-transfer catalyst and methods first developed by O'Donnell and expanded on by many other chemists around the world. The students are encouraged to read the primary literature and design their own experiments with the guidance of the instructors and graduate student teaching assistants (TAs). In our course, the first experiment is described as a communication and the alkylation experiment is reported in the format of a full paper.

"Cannabis sativa" is a species of plant with a rich, yet controversial history. Although the utility of cannabis has been documented for thousands of years; during the last century, research has led to a more advanced understanding of its mechanism of action and therapeutic potential. Accordingly, there has been an explosion of interest and attention; particularly from researchers, investors, academics, and those in the medical field. The relevance of cannabis spans many educational disciplines; sociology, economics, pharmacology, biology, and especially chemistry. There was a need in the undergraduate science curricula to include and reflect this revolution in cannabis' perception and application by providing a knowledge base to students. Therefore, in an effort to contextualize cannabis' inextricable connection to chemistry, the interdisciplinary undergraduate course "Chemistry of Cannabis" was developed and implemented. The goal was to increase student awareness, enhance the scope of their general education, and present a scientific foundation for potential further study. Due to the 2020 pandemic-related school closures, the second half of the course was presented online. The successful transition from in-person to remote learning illustrates the versatility of the course content and structure. Assessment of student feedback revealed that the course was well received and that students finished the semester with a greater interest and appreciation for both chemistry and cannabis. This article presents the design and delivery for the course "Chemistry of Cannabis."

An interdisciplinary course called "The Chemistry of Poisons" was created, featuring organic chemistry, biology, pharmacology, and toxicology content. This exploratory chemistry elective course was created by an instructor with a background in synthetic organic chemistry and a teaching assistant with a background in pharmacy practice. "The Chemistry of Poisons" features an interdisciplinary, student-centered approach to learning that provides a foundation for future academic initiatives to deliver chemical, pharmacological, and humanistic content in a manner that is both enjoyable for students and demonstrably facilitates knowledge and application level learning. Student course feedback and a retrospective survey were used to gauge student-perceived learning achievement. Survey results and feedback were consistent with knowledge and application level learning of course content and preference for interdisciplinary course design. These results warrant further development and study of interdisciplinary strategies for chemical education.

The synthesis of a commercial fragrance, methyl cinnamate, via Fischer esterification was evaluated for use as a second-year organic chemistry course. The experiment utilizes "trans"-cinnamic acid, a commercial flavoring that possesses a mild honey floral odor, as an inexpensive starting material. Both the starting material and the product are listed as GRAS (Generally Recognized as Safe) for use in foods and fragrances. The high-yielding experiment enables students to explore concepts of flavor and fragrances, transmutation of scent, catalysis, green chemistry, NMR spectroscopy, thin layer chromatography (TLC), and acid-base extractions. In addition to the commonly employed sulfuric acid catalyst, alternative conditions were developed using "p"-toluenesulfonic acid monohydrate as an easier to handle catalyst, and conditions for performing both reactions under microwave irradiation are also reported. The experiment was analyzed in a second-year organic chemistry laboratory over six semesters.

Given student familiarity with electronic cigarettes (e-cigs), this lab uses a student-built smoke collection apparatus to collect e-cig vapors to teach students about gas chromatography-mass spectrometry (GC-MS). Students in a second semester, introductory organic chemistry course spent 1 week collecting e-cig vapors and 1 week qualitatively analyzing the data collected. In the real-world, the amount of nicotine inhaled by the consumer from an e-cig is going to depend on many variables including the vaping device used, inhalation rate, and voltage applied by the e-cig. This experiment allows students to simplify the vaping process and focus on the collection of nicotine in the e-cig vapor. Students compared the retention time of nicotine with an injection standard, quinoline, whose structural similarities provided strong discussions about the role of polarity and boiling points in chromatography. This injection standard ensured that all students would minimally be able to compare the retention time of two structurally similar compounds. Each lab group analyzed different e-cig liquids. Students improved upon their ability to interpret mass spectrometry data by predicting fragmentation patterns for both nicotine and quinoline. This lab experiment serves as a connection between lecture and lab material, while promoting student engagement and learning. The students who performed this experiment increased their knowledge of GC-MS and built foundational chemistry skills that can be applied to solve other real-world questions.

Three-dimensional visualization of molecular simulations in virtual reality (VR) is an emerging teaching tool in chemical education. This work describes a VR application which can generate a 3D molecular dynamics (MD) simulation from arbitrary molecular structures and renders that MD simulation trajectory on a VR headset in real-time. This system uses the ZeroMQ (ZMQ) message passing framework for multisimulation to multiclient VR visualization of MD simulation. All MD simulations are done in the HOOMD-blue simulation engine, and the graphics for the VR are rendered in Unity3D. The key feature that sets this software apart from previous 3D viewer programs is the real-time simulation and thus the ability to manipulate thermodynamic variables like temperature on the fly. This allows viewers to build an intuitive understanding of the effects of thermodynamics state variables in a hands-on way. This application was used as a pedagogical tool with high school students, and the curriculum used, along with outcomes of the activity, has been presented here. This application can provide an interactive tool for teaching thermodynamics and statistical mechanics, and even as a diagnostic tool for MD simulations for research purposes.

A new two-step experiment has been designed and developed for the curriculum of the Organic Chemistry Laboratory 2 (CHEM2240L) sophomore course at Xavier University of Louisiana, in New Orleans. Initially, cyclohexanol was converted to cyclohexanone using bleach as the oxidizing agent followed by the formation of the cyclohexanone oxime. However, there were several problems such as reaction monitoring and product analysis associated with this chemical procedure. To improve upon and resolve those problems, we developed these new procedures by changing the substrates from cyclohexanol to 9-fluorenol, a few reaction conditions, and the method of analysis. The experiments were implemented as part of the curriculum in Fall 2019 and Spring 2020, and while performing this new two-step experiment, students were able to see the reaction progress successfully. The procedure and the execution of these experiments will be discussed here.

A strategy for incorporating social justice themes into an introductory organic chemistry curriculum is described. We have deliberately infused social justice themes into the standard organic chemistry curriculum by discussing the history and social impact of key compounds. Using these key compounds that have had significant social, cultural, and environmental impacts, students practiced arrow-pushing mechanisms, predicted products, and identified pK[subscript a] values and functional groups. We believe this approach helps make the material more relevant to students, keep students engaged, and emphasize the real-world applications of the concepts and compounds that they are learning about. Details on the implementation and the evaluation of this work are discussed.

Secondary metabolite compounds contained in each plant genus have certain characteristics, which is true also of the flavonoid in the genus "Artocarpus." In the experiment described here, third-year undergraduate students performed the isolation and characterization of cycloartocarpin from the roots of "Artocarpus altilis" (commonly known as breadfruit), giving them experience in skills such as extraction, fractionation, purification, and the structural elucidation of cycloartocarpin. Manipulation of the liquor by thin-layer and gravitation column chromatographic techniques proved to be a simple method to isolate cycloartocarpin. The flavonoid structure, cycloartocarpin, was treated with structure elucidation 1- and 2-dimensional NMR and infrared spectrometry. Students then compared the structure of the cycloartocarpin obtained with that of other flavonoids from the genus "Artocarpus" and other plant genera. From these comparisons, they were able to formulate structural characteristics of the flavonoid compounds of the genus "Artocarpus." The laboratory method, accomplished in four, 3 h laboratory sessions, allowed students to readily understand the process of isolating flavonoids and their peculiarities.