Module II presents seven case studies that highlight the successful replacement of petroleum-based industrial chemicals with renewable soybean oil or meal, demonstrating the application of green principles and sustainable innovation. Each case study is supported by references that allow educators to expand the material or assign readings for students. While each study could be further enriched with additional chemistry topics, the authors have intentionally designed them to be easily integrated into existing curricula, with the goal of sparking deeper exploration based on instructor interests and expertise. Six of the case studies focus on specific applications--such as transformer oils or wood adhesives--that connect fundamental chemistry concepts with real-world uses. These examples emphasize both the performance benefits and sustainability attributes of soy-based technologies while posing discussion questions to engage students in critical thinking. One case study features polyols derived from soybean oil and is complemented by a video series by Professor Mojgan Nejad of Michigan State University. These polyols play a vital role in more sustainable polyurethane production and provide an accessible entry point into polymer chemistry. Each of the six case studies includes a detailed Word document along with a PowerPoint presentation that summarizes the content for effective use in the classroom. The module was reviewed by Andrew Aebly (Ph.D.), Jessica Tischler (Ph.D.), Robert Bice (Ed.D), Rachel Jones Lipinski (Ph.D.), Nikita Burrows (Ph.D.), Anita Nehra (Ph.D.), and Vaso Lykirounou (Ph.D).

Module III presents two laboratory experiments drawn from recent primary literature publications and incorporates novel green chemistry syntheses. The first experiment involves the epoxidation of soybean oil using Oxone® and acetone (to generate dimethyl dioxirane) as the oxidizing agent. This chemistry was introduced in the “Exploring Techno-Economic Assessments” case study and can be paired with that curriculum for an integrated learning experience. In the second experiment, the epoxidized soybean oil is crossed linked with malic acid and tannic acid to produce an adhesive derived entirely from natural feedstocks. Reported in Nature in 2023, this innovative chemistry provides an excellent example of bio-inspired design of new sustainable materials. Additionally, a laboratory activity was designed to be performed as a ‘dry-lab’ after the second experiment. In the case where the laboratory experiment is not performed to generate data for the activity, the sample data in the instructor’s guide may be given to students.

An interactive and free-of-charge online platform, The Biorefinery Experience, was created using Xerte, a flexible template for creating interactive learning objects. Through this accessible site containing videos with transcripts and a range of questions to engage users, a systems thinking approach has been adopted to outline holistic and interconnected considerations in the design of a first-generation sugar cane biorefinery. Systems oriented concept map extension diagrams have been used extensively to assist learners in visualizing links between biorefineries to social, economic, and environmental interfaces. Users also design their own biorefinery using real data and then redesign a biorefinery as a function of time, demonstrating holistic system understanding, retrospection, and prediction. The Biorefinery Experience was implemented with 35 undergraduate students. Survey feedback demonstrated an enjoyable way to learn about biorefining while utilizing a whole systems approach, allowing students to consider real problems relating holistically and temporally to grand challenges (such as the United Nations Sustainable Development Goals).

The second-year undergraduate Organic Chemistry course sequence is often cited as one of the most, if not the most, challenging for students in the US. Thus, a persistent question remains: What is it about Organic Chemistry that makes the course so difficult for students? Herein, we put forward the hypothesis that a new mode of thinking and problem solving is expected of the students; these skills have not yet been developed in their prior scientific coursework and are often not deliberately taught in Organic Chemistry. This form of reasoning and problem solving, known as abductive reasoning, is highlighted for its connection to medical diagnosis and scientific thinking. We provide examples to showcase how instructors could explicitly foreground the reasoning process in their classroom. Ultimately, we argue that teaching how to reason using abduction may benefit students in both the short term (in the course) and the long term (in their careers as scientists and medical practitioners).

Natural products and their analogs have been explored to stop the progression of cancer cells without unwanted side effects. Chalcones, compounds synthesized naturally in plants, have demonstrated potential as anti-cancer treatments. A library of bis-chalcones that are similar in structure to EF-24, a bis-chalcone molecule known to have anti-cancer properties, has been synthesized in order to examine their medicinal properties. This report highlights the synthesis of ten novel analogs, their anti-cancer activities, and conformational analysis via cryo-NMR and corroboration by density functional theory calculations of the lead compound 1b, tert-butyl 3,5-bis((E)-4-methylbenzylidene)-4-oxopiperidine-1-carboxylate.

Hydrogels are soft water-rich materials with physical properties that can be easily tuned by modifying their network structure. For instance, increasing or decreasing the cross-linking density has a profound effect on their water absorption capabilities and mechanical strength. These physical changes are showcased in a new experiment for organic chemistry and polymer science teaching laboratories based on the practical green synthesis and characterization of lactose methacrylate derived hydrogels. Lactose, a disaccharide derived from dairy waste byproducts, is functionalized with photoreactive methacrylate groups using methacrylic anhydride. The resulting mixture is subsequently photoirradiated to generate a cross-linked hydrogel. Structure-property relationships are assessed through comparative studies of three hydrogels of varying compositions. Compression tests and swelling studies in different aqueous environments offer a guided-inquiry experience. Students determine a relationship between cross-linking density and the physical properties of the hydrogels. This experiment highlights the valorization of biomass and multiple green chemistry principles including use of renewable feedstocks, atom economy, energy efficiency, waste prevention, and water as a benign solvent. Learning outcomes for an organic chemistry laboratory course include introduction to disaccharide and cross-linked polymer structures, observable physical change dependency with cross-linking density, and laboratory methods for evaluating water absorption capacities. Objectives aligned with a polymer course are incorporating mechanical compression instrumentation, mechanistic understanding of light-induced free radical polymerizations, and an appreciation for the application of hydrogels to commercial products. Overall, the translation of a current literature publication to an inexpensive and versatile experiment engages students in a modern example of sustainable polymer chemistry.

We present measurements of the effect of first-generation secondary organic aerosol (SOA) material on the growth of ∼10 nanometer diameter seed particles composed of sulfuric acid and water. Experiments were performed in an atmospheric pressure, vertically aligned flow reactor where OH was produced from HONO photolysis in the presence of either SO2 or a monoterpene. For typical conditions, organic compounds at ∼300 ppbv are exposed to photooxidation for a time of ∼80 s at a [OH] of about 6 × 106 cm-3: thus, oxidation products have minimal OH exposure. The measured size changes of the sulfuric acid seed particles can then be attributed to the uptake of first-generation products. Along with descriptions of the apparatus and the procedure, the analysis to obtain SOA yields by comparing them to growth with H2SO4(g) is detailed. Results from photooxidation experiments of αpinene, limonene, and myrcene give SOA yields of 0.040, 0.084, and 0.16, respectively. These SOA yields roughly double with each addition of a double bond to the compound. The αpinene and limonene results are in accord with the results of many previous SOA experiments, while the myrcene SOA yield stands alone. Photooxidation of myrcene also led to significant nucleation, and the species responsible is comparable to H2SO4 at a 35% relative humidity in its nucleation capability.

Nucleation rates involving sulfuric acid and water measured in a photolytic flow reactor have decreased considerably over a time period of several years. Results show that the system – flow reactor, gas supplies and lines, flow meters, valves, H2SO4 photo-oxidant sources – has reached a baseline stability that yields nucleation information such as cluster free energies. The baseline nucleation rate is punctuated by temporary bursts that in many instances are linked to cylinder changes, delineating this source of potential contaminants. Diagnostics were performed to better understand the system, including growth studies to assess H2SO4 levels, chemiluminescent NO and NOx detection to assess the HONO source, and deployment of a second particle detector to assess the nanoparticle detection system. The growth of seed particles shows trends consistent with the sizes of nucleated particles and provides an anchor for calculated H2SO4 concentrations. The chemiluminescent detector revealed that small amounts of NO are present in the HONO source, ∼ 10 % of HONO. The second condensation-type particle counter indicates that the nanoparticle mobility sizing system has a bias at low sulfuric acid levels. The measured and modeled nucleation rates represent upper limits to nucleation in the binary homogeneous system, H2SO4-H2O, as contaminants might act to enhance nucleation rates and ion-mediated nucleation may contribute. Nonetheless, the experimental nucleation rates, which have decreased by an order of magnitude or larger since our first publication, extrapolate to some of the lowest rates reported in experiments with photolytic H2SO4. Results from experiments with varying water content and with ammonia addition are also presented and have also decreased by an order of magnitude from our previous work; revised energetics of clusters in this three-component system are derived which differ from our previous energetics mainly in the five-acid and larger clusters.

Green Tycoon is a free-of-charge game-based mobile application that embraces a systems thinking approach to introducing students to a biorefining process model within green chemistry. Players adopt the role of a manager in a chemical factory, synthesizing the fictional compound, Yorkanone. Through upgrading the system and engaging with the integrated quiz, players can learn fundamental green chemistry principles while appreciating some of the considerations in biorefining. Green Tycoon was implemented with 33 undergraduate students where survey feedback demonstrated that the game was engaging and innovative and was a helpful tool to appreciate the importance of green chemistry when designing chemical processes. On the basis of pretest and post-test questions to evaluate learning gain, Green Tycoon proved to be a useful resource to introduce students to green chemistry and its role in moving toward a bioeconomy. Design of the mobile application serves as a useful example of what an upper-division undergraduate student with no coding knowledge can achieve through a chemistry education research project.

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 noncross-linked polymer whose H-1 NMR spectrum is suitable for student analysis and estimation of polymer number-average molar mass (M-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 H-1 NMR spectroscopy.

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.

The arrows depicting electron movement and the bond-making and breaking events are the maps that guide student instruction in organic chemistry curricula. For students, the pathways represented by electron pushing formalism (EPF) can be tough 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 (“Mechanisms”) 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 and do so within a game-like experience. In this paper the pedagogical content of the Mechanisms app (“Mechanisms”) is described along with studies of students’ use of the app to understand whether the open-ended experience to construct understanding of EPF is valuable as a formative assessment method. Presented in this paper are the results of Mechanisms use by analysis of a multi-institution anonymous student survey, with a usability study of organic chemistry students, and with three case studies detailing the use of the app in college classrooms.

As the role of polymers in undergraduate chemistry curricula continues to expand, opportunities will emerge for adopting experiments involving smart materials (i.e., materials that change properties in response to external stimuli). Slime demonstrations are routinely carried out with poly(vinyl alcohol) (i.e., PVA) hydrogels because the polymer is inexpensive and nontoxic, and the resulting material has interesting physical properties. This report describes an activity where PVA is processed into an autonomous self-healing smart material. Specifically, students prepare rigid PVA hydrogels using a simple freeze/thaw protocol. The resulting material is cut, and the severed edges are pressed together to initiate autonomous self-healing. Healing is observed by measuring sufficiently high (i.e., >40 kPa) uniaxial tensile strengths at the repaired surface. Preparing the hydrogel does not require chemical additives beyond commercially available PVA (i.e., M-w similar to 145,000 g mol(-1)) and water. Additionally, the tensile strength can be determined using a spring force gauge and a ruler. The simplicity of the procedure, use of low-cost materials, and ties to green chemistry make the activity suitable for use in high school or introductory college chemistry settings. Furthermore, procedural variation and more rigorous analysis make the activity versatile by allowing the protocol to be used in second- or third-year chemistry courses (e.g., organic and physical chemistry). Overall, the activity provides a straightforward approach to introducing students to modern topics in polymer chemistry and materials science.

The use of online collaborative assignments between three organic chemistry classrooms, two in the United States and one in Canada, was examined for impact on learners' communication abilities and confidence. Students were assigned a partner from another university and challenged to communicate over video chat to collaboratively solve problems for six weekly assignments in organic chemistry. One focus of the intervention was to aid in increasing student ability to communicate chemical concepts using verbal, written, and symbolic modes. In this chapter, we will discuss the focus of each assignment, identifying communication modes and how the assignments build in communication complexity. Postassignment reflections will also be described along with exemplary outcomes of student metacognition displayed through these reflections.

Green Machine is a competitive strategy card game facilitating a systems thinking approach to learning recycling processes and green chemistry in accordance with the United Nations Sustainable Development Goals. Players compete to be the first to be able to launch their recycling plant by collecting a series of playing cards. Players must use interpersonal skills to consider the interconnected systems while showing an appreciation for commercial awareness and versatility, as dynamic problem solving (reflecting real-world scenarios) is required to play the game successfully. The card game was implemented with 19 U.K. graduate students and 29 U.S. second-year undergraduate students. Survey feedback showed that Green Machine was an innovative resource that was enjoyable to play and engaged students in learning recycling processes through systems thinking. On the basis of pre- and post-test questions to evaluate learning gain, Green Machine is a helpful resource to introduce students not only to green chemistry and sustainability but also to taking a systems thinking approach to learning.

The International Network for Chemistry Language Development is a community of faculty and students that employ video conferencing technologies in collaborative learning experiences. Learners partner with an international peer at another university to complete online collaborative assignments (OCAs). OCAs focus on shared learning and professional experience rather than assessment of knowledge to practice chemistry communication in the oral, written, and symbolic domains. We present OCAs as an example of the Third Space, where control over interactions and learning is negotiated between unfamiliar remote students, empowering students as emerging experts. This digital Third Space results in the formation of trust (a) between student partners to prepare for—and contribute during—the OCAs, and (b) between students and faculty as partners in teaching and learning. Additionally, we report how revisions to the OCA design are achieved with current students as consultants and partners, and former students as co-researchers and co-designers.