Alexey Leontyev

This study examined two assessment approaches—a case comparison prompt and a reasoning chain construction task to elicit students’ knowledge and application of green chemistry within the context of SN1 and SN2 reactions. The case comparison prompt presented students with a context-specific evaluation of two reactions, whereas the reasoning chain construction task required a general comparison of SN1 and SN2 reactions. Following each open-ended assessment, students were asked to select a conclusion regarding the overall greener reaction. The assessments were administered as an online survey, and student responses were analyzed using the twelve principles of green chemistry. Analysis of student responses showed that students consistently selected the same reaction type across assessments despite differences in task format. Across both assessments, students most frequently prioritized the use of safer solvents over considerations related to stereochemical outcomes, leading them to identify the SN1 reaction as the greener option. Overall, this study reveals how students apply green chemistry considerations to organic reactions across two open-ended assessment formats and demonstrates consistent patterns in their conclusions despite differences in the assessment formats. Importantly, the findings also revealed alternative lines of reasoning and misconceptions that are not readily captured by closed-ended assessments alone.

Creative exercises (CEs) consist of open-ended prompts to which students provide a series of relevant, distinct, and accurate statements, thus requiring that students make connections between concepts. In this study, CEs were incorporated into a one-semester Survey of Organic Chemistry course to identify what connections between chemistry concepts students made and what incorrect conceptions or misconceptions about chemistry students held. Students (N = 79) enrolled in the course first completed a practice CE as an in-class group activity followed by individually responding to a CE bonus problem on each of their four course exams. The number of different concepts students addressed for each CE increased over the semester, indicating that students made increasing content connections about course material; however, misconceptions about early concepts, such as nomenclature and assigning configurations, remained consistent throughout the semester. Furthermore, the CEs were found to be instrumental in shedding light on misconceptions and knowledge structures of students across varying performance levels. Overall, students reported that they viewed the CEs favorably and would like to see CEs incorporated in future courses.

One key limitation for assessing student knowledge of green chemistry is the lack of readily available assessments capable of eliciting reliable and valid data. Therefore, in this study we sought to evaluate the ability of a previously reported open-ended prompt [] to probe student conceptions about the greenness of chemical reactions. Responses to this prompt, which we titled the Green Chemistry Generic Comparison (GC)(2) prompt, were collected from students enrolled in organic chemistry I and II lecture and laboratory courses (N = 642) and from students enrolled in general chemistry II lecture courses (N = 272). This prompt was found to be sensitive for detecting gains in green chemistry knowledge in pre- and post- conditions. Furthermore, psychometric analysis revealed that, while addressing certain green chemistry principles was well within the students' ability range, other principles exceeded that range. These findings indicate that this prompt provides a rapid and effective method for both measuring student knowledge and eliciting student conceptions of the green chemistry principles.

This paper addresses the development and evaluation of a case study designed to introduce both the core chemistry concepts of oxidation and reduction reactions as well as green chemistry within the undergraduate organic chemistry curriculum. The developed case study consisted of two parts that can be used in tandem or independently. Part 1 focused on calculating oxidation states and determining whether the provided bioderived reactions represented oxidation or reduction reactions, and Part 2 focused on evaluating the greenness of oxidation reactions. Students reported positive learning gains for both the core chemistry concepts of oxidation and reduction reactions and green chemistry and reported that they viewed the case study favorably. It is our hope that other educators use this case study module to incorporate green chemistry into their organic courses and use its development as inspiration to create further case studies that integrate green chemistry into the curriculum. GRAPHICAL ABSTRACT

This study sought to explore the integration of green and sustainable chemistry into the organic chemistry curriculum through a national survey of organic chemistry instructors (n = 160) within the United States. It was found that faculty were most familiar with the green chemistry topics of reaction efficiency and catalysis and least familiar with the topics of efficiency metrics and life cycle impacts of chemicals. This unfamiliarity with efficiency metrics and life cycle impacts of chemicals was echoed in a low perceived importance for chemistry and related science students to know these concepts and subsequently the incorporation of green chemistry topics was amongst the lowest of the topics evaluated. Similarly, it was found that most faculty were unaware of the United Nations Sustainable Development Goals and planetary boundaries, and thus the integration of these topics into the curriculum was also low. To identify which factors affected the integration of green chemistry, the survey items were developed using the Teacher-Centered Systemic Reform model. Stepwise linear regression was used to identify which factors significantly affected its integration into the teaching curriculum and assessments. Overall, it was found that that teacher thinking factors held the greatest impact. In addition, departmental requirement or encouragement of green chemistry integration was found to significantly impact its incorporation for both the curriculum and assessments. These results suggest that there is a need both to provide training opportunities for faculty to become more familiar with these topics and their relevance to the organic curriculum and to work with people in leadership roles at the universities to encourage departmental integration.

As implementation of green chemistry into university-level courses increases, it is vital that educators have a tool to rapidly measure student knowledge of green chemistry principles. We report the development of the Assessment of Student Knowledge of Green Chemistry Principles (ASK-GCP) and evaluation of its sensitivity and effectiveness for measuring student knowledge of green chemistry. The 24-item true–false instrument was given to a total of 448 students to gather data on the reliability, validity, and sensitivity. The instrument proved to be sensitive for distinguishing known groups with various levels of green chemistry knowledge and instructional exposure. The instrument was able to detect gains in green chemistry knowledge in pre- and post- conditions. Psychometric analysis revealed that the item difficulty range matches the sample ability range. The findings verified that the ASK-GCP is an efficient and accurate instrument to measure student knowledge of green chemistry principles.

We provide a case-study for thermal grafting of benzenediazonium bromide onto a hydrogenated Si(111) surface using ab initio molecular dynamics (AIMD) calculations. A sequence of reaction steps is identified in the AIMD trajectory, including the loss of N₂ from the diazonium salt, proton transfer from the surface to the bromide ion that eliminates HBr, and deposition of the phenyl group onto the surface. We next assess the influence of the phenyl groups on photophysics of hydrogen-terminated Si(111) slabs. The nonadiabatic couplings necessary for a description of the excited-state dynamics are calculated by combining ab initio electronic structures and reduced density matrix formalism with Redfield theory. The phenyl-terminated slab shows reduced nonradiative relaxation and recombination rates of hot charge carriers in comparison with the hydrogen-terminated slab. Altogether, our results provide atomistic insights revealing that (i) the diazonium salt thermally decomposes at the surface allowing the formation of covalently bonded phenyl group, and (ii) the coverage of phenyl groups on the surface slows down charge carrier cooling driven by electron–phonon interactions, which increases photoluminescence efficiency at the near-infrared spectral region.