A Complementary Laboratory Exercise: Introducing Molecular

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A Complementary Laboratory Exercise: Introducing Molecular Structure−Function Topics to Undergraduate Nursing Health Professions Students Angela L. Mahaffey* Marcella Niehoff School of Nursing, Loyola University Chicago, 1032 West Sheridan Road, Chicago, Illinois 60660, United States

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S Supporting Information *

ABSTRACT: In both 2016 and 2019, the NCLEX-RN (National Council Licensure Examination − RN computerized exam) test plan outlined 15% of content as “pharmacological and parenteral therapies”. The test plan also includes physiological sciences. The topics of pharmacology encompass the review of drug action in living organisms, such as humans. As such, reviewing correlations of molecular structure and functional groups is a recurrent topic in pharmacological education and prerequisite courses. Many nursing students are required to participate in a specific curriculum, prior to matriculation, which covers pharmacology as it pertains to healthcare. The interdisciplinary topics of healthcare and chemistry, advanced pharmacology, pharmaceuticals, and biochemical pathways in human physiology are apparent in multiple undergraduate nursing program curricula. Here, we have an opportunity for the development of a first year Bachelor of Science in Nursing (BSN) chemistry for health professions course that would introduce molecular structure−function relations concerning pharmacological topics and human physiology chemical pathways. A chemistry computer lab exercise was design to complement undergraduate health professions nursing school chemistry classroom lectures on molecular structure−function relations. Online 2D molecular drawing software was employed as a tool for visualizing a list of molecules to primarily help students understand OTC (over-the-counter) drug “active ingredient” structure pertaining to drug function and biological agents in human physiology. Student responses highlight positive feedback to this useful exercise and further recommendation for use in ongoing undergraduate health professions courses. KEYWORDS: First-Year Undergraduate/General, Testing/Assessment, Molecular Recognition, Nonmajor Courses n a number of educational research articles, the “disparity” between nursing and organic chemistry education have become more apparent. This poses a struggle for the Nursing Educator with regard to undergraduate nursing chemistry courses.1 Some viable techniques to tackle this stigma involve a comprehensive review of physiological and biochemistry topics in “health-related scenarios”, which is laudable but does not abate this observed disparity between organic chemistry and nursing education specifically.2 Previously published workshops to encourage K−12 student awareness of computation drug design software and similar computational lectures (and/or workshops) for chemistry, biochemistry, and biotechnology students or novices on the developments in pharmaceutical chemistry have been published yet are not nursing specific to the depth of undertaking this “disparity”.3−5 Drug action mechanism or pharmaceutical posters and figures in a number of articles, although interesting, make for an irresolute level of remediation for the apparent divide between nursing education and topics of organic chemistry.6−8 The basis of the chemistry computer lab exercise introduced in this article is to mainly provide a simple step toward narrowing the boundaries between

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© XXXX American Chemical Society and Division of Chemical Education, Inc.

undergraduate nursing education student interests and organic chemistry topics. A chemistry for health professions virtual laboratories course developed at a university located in the Midwest region of the United States was done so with the premise of encompassing a spectrum of chemistry topics that underline scientific components utilized in healthcare. This course offers nearly a dozen online chemical VL (virtual laboratory) experiments and learning experiences throughout the semester. The subject of chemistry in a health professions curriculum can be daunting for students, bringing to question why chemistry is important for a health professions education program, but is also a viable prerequisite to BSN courses such as Human Physiology,9 Nutrition, and Pharmacology. To answer this question, it is advantageous to highlight one aspect in which chemistry and health professions converge: molecular structure of pharmaceutical medications and the reactions and metabolic processes Received: April 22, 2019 Revised: July 25, 2019

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DOI: 10.1021/acs.jchemed.9b00388 J. Chem. Educ. XXXX, XXX, XXX−XXX

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(including those of pharmaceutical compounds) in the human body. A number of chemistry for health professions students (n = 136), completing the exercise noted here, answered the aforementioned questions regarding the presupposed benefit of 2D molecular drawing education and various professions (see Discussion). Pharmacological nursing education also reviews topics encompassing medication and medicinal chemistry knowledge.10 The content of such courses is correlated in an effort to prepare nursing students for the NCLEX-RN (National Council Licensure Examination − RN exam) Test. As of 2019, preparation guides consist of a structured plan outlining 15% of content as “pharmacological and parenteral therapies”.11 As an attempt to promote student interest and cognitive investment in chemical education topics for health professions, a virtual lab course was designed to include a chemistry lab exercise in which students would primarily review the structure of active ingredients in OTC (over-the-counter) medications from a 2D molecular drawing perspective, in order to engage them in pharmacological topics.12 The secondary goal for this exercise was to introduce biochemical agents of human physiology (topics incorporated in the 4 year BSN curriculum plan). In the corresponding molecular functional groups (and structure− function) topical lecture, students learned to classify organic molecules by their function groups, as outlined in the assigned textbook.13 Comparatively, during a pre-lab lecture (see Methods, Student Engagement: Class Discussions; Figure 1A), students were shown a PowerPoint presentation of the molecular structures of active ingredients in OTC medications and antimicrobial productsalongside an image of the labeled OTC medication container. Following, students were asked to identify the functional groups of the structure of the active ingredient molecules in these samplesand any similarities in molecular structures (or groups) for the OTC drug purposes (i.e., functional groups and structures common to OTC analgesics; painkillers). As a complement to this process, a straightforward chemistry exercise is designed in which students are instructed to use 2D molecular drawing software14 to draw a series of molecular visual aids and assess the functional groups from pharmacology and physiology perspectives (Figure 2). This exercise will help bridge chemical education with imminent courses in the nursing baccalaureate programs. It is sensible to note that there are additional numbers of free or affordable 2D chemical molecular drawing software available via a myriad of Web sitesfor student ease of access. For this exercise, the software (ACD/ChemSketch) utilized in the 2D molecular drawing exercise is free and readily available to students at the university.

Figure 1. Designing a molecular drawing virtual lab and lecture construct. (A) This is an illustration of Pre-Lab lecture given to students. (B) In the presence of the Laboratory Instructor, students completed the molecular drawing exercise and following completion of the Drawing Assignment, students completed an online Post Lab assessment as a lab report in which they could transcribe correlations between the 2D molecular drawings, organic function groups, OTC drug synthesis for healthcare, and interdisciplinary uses for 2D molecular drawing software. (C) Post-Lab follow-up lectures.

ture−function topics to be further explored. As such, the following learning goals were set: 1 Explore molecular structure−function of organic compounds commonly seen in OTC drug active ingredients, biological agents, and healthcare (Figure 2). 2 Label molecular structures using chemical nomenclature. 3 Identify patterns in functional groups of OTC drug active ingredients (e.g., “What are some common functional groups observed in the molecular structures of active ingredients of painkillers or analgesics?”). 4 Engage in pre-pharmacology topics (to stimulate preparation for pharmacology courses and NCLEX Licensing Exam). 5 Learn to use chemical drawing software (a skill set not often introduced in an undergraduate nursing chemistry course). 6 Develop important interdisciplinary skill sets by observing chemistry from a pharmacy student education or pharmaceutical professional perspective (Figure 3).15,16

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LEARNING GOALS A complementary chemistry computer lab exercise to organic chemistry structure−function GOB (general organic and biological) chemistry textbook and course lecture topics, in a chemistry for health professions course, was designed with the major purpose of engaging students in introductory pharmacology concepts (as pharmacology is within their 4 year BSN curriculum plan). This exercise also helped to introduce structures of biochemical agents in human physiology chemical pathways (also, within the 4 year BSN curriculum plan). The overall principal focus was to get nursing students thinking about the roles of organic chemistry in healthcare using a concept most familiar to them at the time of the undergraduate course (OTC drug use in healthcare). This exercise served as an easy-to-use hands-on visualization platform for organic chemistry strucB

DOI: 10.1021/acs.jchemed.9b00388 J. Chem. Educ. XXXX, XXX, XXX−XXX

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Figure 2. This is a schematic illustrating the process of the complement lab exercise and its utilization in making molecular structure−function and healthcare connections. These are the two perspectives from which students were encouraged to identify the molecular structures and function and their roles in healthcare.

Figure 4. Schematic of how students can make connections from 2D molecular structures to human physiology and healthcare. This is a diagram of stepwise reasoning process for students to examine the structure and function of one of ten 2D molecular structures drawn in the exercise and to identify the role of this molecule in biological agents of human physiology pathways and applications in healthcare.

lecture, students reviewed functional groups of chemical compounds in the lecture via an integrated chemistry textbook.13 Additionally, students were instructed to complete a reading requirement of the ACD/ChemSketch freeware (for academic and personal use) manual,14 as an effort to prepare students for the 2D molecular drawing VL session (Figure 1B). Student Engagement: Class Discussions

The class lecture was based on textbook molecular functional groups and structure−function topics (Figure 1A). Here, students were provided with background details of OTC drugs with active ingredients such as Naproxen (C14H14O3) and the inhibition of cyclooxygenase enzyme (making it a prime candidate and active ingredient for treating symptoms of inflammatory issues observed in patients with rheumatic pathologies, menstrual cramps, and gout).18 Another engaging healthcare−organic chemistry discussion is the historical journey of the willow tree and aspirinhere students can anecdotally follow the history of acetylsalicylic acid from 3000 BC (willow extract) to present day. This organic chemical structure−function topic is fortified in an undergraduate health sciences class setting, as it reviews the “anti-inflammatory, analgesic, and antipyretic” mechanisms for aspirin (COX-1 and COX-2 enzymes inhibition) and the discoveries of the 1982 Nobel prize winner in physiology or medicine J. R. Vane are elucidated.19−22

Figure 3. Schematic of how students can make connections from 2D molecular structures to pharmacology and healthcare. This is a diagram of stepwise reasoning process for students to examine the structure and function of one of ten 2D molecular structures drawn in the exercise and to identify the role of this molecule in OTC medicine and applications in healthcare.

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7 Recognize the preliminary roles of molecular structure− function relations in biological agents as a foundation for future human physiology curricular courses (Figure 4). 8 Learn empirical report writing skills in the format of a chemical laboratory report. (This will help nursing students prepare for medical reporting vital to patient care.)

Outcomes/Objectives: 2D Molecular Drawing Laboratories

Organic chemistry education provides the foundation for pharmacological knowledge10,12a curriculum standard for baccalaureate education in nursing programs and NCLEX-RN “Test Plan” (which includes human physiology and pathophysiology courses).11,23 As such (in addition to the Learning Goals) the outcomes (or objectives) for the 2D molecular drawing lab exercise were designed with both pharmacology and human physiology education as a foundation. The immediate outcomes include the following: • Understand functional groups of organic compounds. • Learn nomenclature of chemical compounds using 2D molecular drawing software.

METHOD

Student Pre-Lab Assignment

Prior to the 2D molecular drawing exercise, students were assigned a preparatory laboratory skills assessment on Sakai a learning management system (LMS) based on virtual learning environment (or VLE) software.17 A number of molecular structures were illustrated, in the pre-lab assignments, in which students had to identify the functional groups (Table 1). As this computer lab exercise was designed to be complementary to the C

DOI: 10.1021/acs.jchemed.9b00388 J. Chem. Educ. XXXX, XXX, XXX−XXX

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Table 1. 2D Molecular Drawing Exercise Sample Structures and OTC Drug Active Ingredient Examplesa

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Students participating in this virtual lab activity are provided with a list of OTC drugs in lecture presentation illustrating the role of organic chemistry in healthcare and pharmaceuticals (over-the-counter or OTC drugs), and in the subsequent lab students are given a list of molecules to generate using ACD Chem/Sketch online software. The sample lab activity illustrates possible correlations between the basic structure of organic molecular groups and OTC drug active ingredients.

• Draw 2D molecular structures using software. • Identify and describe molecular structure−function relationships of selected molecular drawings, pertaining to active ingredient compounds OTC drugs and implications in healthcare (Figure 3). • Identify and describe molecular structure−function relationships of selected molecular drawings, pertaining to biological agents in human physiological reactions and implications in healthcare (Figure 4). With these set outcomes, the assignment was intended to predominantly help students recognize functional groups of chemical compounds and the roles of those functional groups in the molecular design of OTC drugs and further student understanding of the intrinsic structures of biological agents of human physiological pathways. The novelty in this approach is that drawing the 2D molecular structures is the first step of this exercise, to both help students visual the molecular structure− function relationship as they make connections to OTC drug compounds, biological agents, and healthcare and introduce undergraduate nursing students to chemical software they would otherwise most likely not employ. Figures 3 and 4 are explicative diagrams students were ideally expected to illustrate or discuss in their lab reports.

molecular drawing software, the Instructor encouraged students to view organic chemistry topics from a different perspective (from the hypothetical viewpoint of a pharmaceutical R&D chemist or medicinal or organic chemical analyst) of OTC drugs (Figure 3). This was done to further promote student engagement and highlight the important role of organic chemistry education in pharmacology (Figure 1, Table 1)12,14and interprofessional perspectives of a nursing student as a pharmaceutical specialist. Nurses often garner a relative perspective of other health science professionals to better collaborative efforts with colleagues, a skill set allowing allied health professionals to coordinate their efforts so they align for effective patient care. This lab provided a safe environment for an organic synthesis laboratory projectwith marginal ease of use. An anonymous and completely voluntary student poll was administered via the Sakai LMS,17 asking students of the ACD/ ChemSketch software or similar software ease of useless than 7% (of n = 136) noted that the software was difficult to use (n = 9, of 136) (Figure 5).

Designing a 2D Molecular Drawing Lab Exercise for Nursing Students

A supplemental ACD/ChemSketch tutorial and manual was available to students with further instructions on using the ACD/ChemSketch freeware.14 Students were provided with a list of compounds with varying functional classes (see the Supporting Information): amine, alcohol, ketone, thiol, alkane, aromatic (benzene derivatives), and aldehyde. Following receipt of the chemical compounds list, students were instructed to generate drawings of the compounds using the ACD/ ChemSketch freeware, save as a pdf, and upload into SAKAI LMS (Figure 1B). Lastly, students were instructed to submit a formal lab report, which included the following discussion topic: “Now that you have completed the “ChemSketch Molecular Drawing” Lab assignment, please consider the following discussion topic: List the advantages of employing Molecular Drawing in Pharmacology and Medicinal Chemistry”. As students used the 2D

Figure 5. Poll results of ease of use of ACD/ChemSketch software or similar software, for students in the chemistry health professions course. This anonymous voluntary student poll was administered using the Sakai LMS.17 D

DOI: 10.1021/acs.jchemed.9b00388 J. Chem. Educ. XXXX, XXX, XXX−XXX

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RESULTS Using the Sakai LMS17 students were able to complete and submit the Pre-Lab assignments relating to molecular group functionalities. For the eight (8) undergraduate health professions (mostly nursing students) sections (ntotal = 167), an average Pre-Lab assignment score of over 90.00% was indicative of students grasping the corresponding pre-lab and lecture materials for the lab exercise and exhibiting sufficient lab preparation skills. Upon completing the molecular drawing lab exercise, students were responsible for uploading the digital assignment file for submission into the Sakai LMS. For the eight (8) sections (ntotal = 167), an average score of over 99.00% was apparent, following preliminary lectures. These results highlight the health professions students’ (in this program) ability to successfully use the molecular drawing lab and identify structures (including functional groups) of organic compounds on the list provided during the molecular drawing lab exercise. The limitations of this study are that the results were recorded following preliminary lectures. Additionally, prior to the preliminary lecture and assignment approximately 20% of students were sufficient in organic structure−function topics (Figure 6). Lastly, this exercise was introduced in the initial

following fields of study/research would MOST benefit f rom the Molecular Drawing?”, to which nearly 57% (ntotal = 136) noted that organic chemistry, pharmacology, and healthcare students and practitioners would find this exercises useful” (Figure 7). As

Figure 7. Graphic of the student response poll to the usefulness of molecular drawing software in chemical and healthcare research and practices. This anonymous voluntary student poll was administered using the Sakai LMS.17

a point of discussion, it appears that in this pool of 136 (mostly undergraduate nursing) students that the exercise would present a welcomed addition to chemical, pharmacology, nursing, and health professions education curriculum. It is prudent to note one limitation for this exercise is that it is framed for non-majors; as such, chemistry majors may require additional conceptualized methods in this exercise to be congruent with the overall undergraduate chemistry major curriculum. Student polling was 100% anonymous and voluntary (through Sakai LMS) with no personal identifiers or required factors for IRB consent.

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Figure 6. Student poll on recognizing the important role of chemical structure−function in OTC (over the counter) drugs. This anonymous voluntary student poll was administered using the Sakai LMS.17

CONCLUSION Designing an easy-to-use minimal virtual chemistry lab exercise for non-majors, which utilizes molecular drawing software, such as the ACD/ChemSketch freeware (for academic and personal use) manual14 is a beneficial tool for teaching nursing (and health professions) students the building blocks of organic compound structures. The evaluations for this chemistry computer lab exercise illustrates how students have met this exercise with positive feedback introduced in an undergraduate chemistry for health professions (non-chemistry majors) virtual lab course (Figures 5−7). Additionally, coupling this molecular drawing exercise with lectures on functional groups and geometry of organic compounds allows students to identify connections between organic molecular design, molecular group functionalities, and the role organic compounds as active ingredients in OTC drugs. Developing a lecture presentation illustrating the identification and correlations between functional groups and geometry of organic compounds in pharmaceutical drug categories (i.e. analgesics, including but not limited to acetaminophen or aspirin and antimicrobial agents/ointments, such as bacitracin or neomycin−bacitracin− polymyxin B), highlights the presence of specific functional groups (e.g., amine or alcohols) in the active ingredients of OTC drugs. Using the previous as a “launching pad” to continue

semesters of which this new “chemistry for health professions course” was fully integrated within the school of nursing purview. As a result, there is no tangible calculable “chemistry for health professions course” data that could be gathered (prior to the inception of the new course) which would prove comparable to these results.

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DISCUSSION To measure the (student perceived) usefulness of this simple molecular drawing exercise in an undergraduate chemical for health professions lab course, an additional voluntary anonymous Sakai17 poll was designed. Students were asked whether they were able to “recognize” correlations between the structure and function of an organic molecule of the active ingredient in an OTC drug, over 60% (of n = 136) of participants answered “yes”, attributing this new found knowledge to the molecular drawing exercise. Less than 18% of students noted that they already acquired an awareness of the aforementioned prior to the exercise (Figure 6). Lastly, the following question was presented in an anonymous voluntary student poll regarding the 2D molecular drawing exercise, “In your opinion, which of the E

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(7) Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. An In-Pharm-ative Educational Poster Anthology Highlighting the Therapeutic Agents That Chronicle Our Medicinal History. J. Chem. Educ. 2013, 90, 1403− 1405. (8) McGrath, N. A.; Brichacek, M.; Njardarson, J. T. A Graphical Journey of Innovative Organic Architectures That Have Improved Our Lives. J. Chem. Educ. 2010, 87, 1348−1349. (9) Mahaffey, A. L. Interfacing virtual and face-to-face teaching methods in an undergraduate human physiology course for health professions students. Adv. Physiol. Educ. 2018, 42, 477−481. (10) Barkhouse-MacKeen, C. D.; Murphy, A. L. Pharmacology in undergraduate nursing education: Innovative strategies for enhancing medication related knowledge, attitudes, skills and behaviours. J. Nurs. Educ. Pract. 2012, 3, 91−101. (11) National Council of State Boards of Nursing. 2019 NCLEX Test Plan, 2019; https://www.ncsbn.org/2019_RN_TestPlan-English.pdf (accessed Jul. 26, 2019). (12) Blakemore, D. C.; Castro, L.; Churcher, I.; Rees, D. C.; Thomas, A. W.; Wilson, D. M.; Wood, A. Organic synthesis provides opportunities to transform drug discovery. Nat. Chem. 2018, 10, 383. (13) Raymond, K. W. General, organic, and biological chemistry: An integrated approach; John Wiley & Sons: Hoboken, NJ, USA, 2014. (14) Advanced Chemistry Development ACD/ChemSketch for Academic and Personal Use; ACD/Labs, Toronto, Canada; https://www.acdlabs. com/resources/freeware/chemsketch/ (accessed Jul. 26, 2019). (15) Cropp, C. D.; Beall, J.; Buckner, E.; Wallis, F.; Barron, A. Interprofessional Pharmacokinetics Simulation: Pharmacy and Nursing Students’ Perceptions. Pharmacy (Basel, Switzerland) 2018, 6, 70. (16) Wilbur, K.; Kelly, I. Interprofessional impressions among nursing and pharmacy students: a qualitative study to inform interprofessional education initiatives. BMC Med. Educ. 2015, 15, 53. (17) Apereo Foundation Sakai. Meeting the Needs of a Global Community; https://www.sakaiproject.org (accessed Jul. 26, 2019). (18) National Center for Biotechnology Information, U.S. National Library of Medicine. Naproxen, PubChem CID = 156391; https:// pubchem.ncbi.nlm.nih.gov/compound/156391 (accessed Jul. 26, 2019). (19) Vane, J. R.; Botting, R. M. The mechanism of action of aspirin. Thromb. Res. 2003, 110, 255−258. (20) NobelPrize.org. John R. Vane − Biographical; Nobel Media AB, Stockholm, 1982; https://www.nobelprize.org/prizes/medicine/ 1982/vane/biographical/ (accessed July 26, 2019). (21) Vane, J. R. Inhibition of Prostaglandin Synthesis as a Mechanism of Action for Aspirin-like Drugs. Nature New Biology 1971, 231, 232. (22) Connelly, D. A History of Aspirin. Clin. Pharm. 2014, 6, 53. (23) National Council of State Boards of Nursing. 2016 NCLEX-RN Test Plan, 2016; https://www.ncsbn.org/RN_Test_Plan_2016_Final. pdf (accessed Jul. 26, 2019).

discussions on the role of molecular structure−function in biochemical pathways and healthcare provides a foundation for the undergraduate nursing students as they prepare for future human physiology courses. As observed in Figures 3 and 4, forming these connections between chemistry topics, with the aid of interactive visual tools such as 2D (or 3D) molecular drawing software, creates a bridge to the subject of organic chemical functional groups of compounds involved in medicinal and biological reactions in the human body, which would be useful in undergraduate health sciences education. This complementary exercise is a tool designed to help undergraduate nursing students recognize the ubiquitous nature of chemistry (and molecular structure−function relations) in healthcare sciences.

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ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available on the ACS Publications website at DOI: 10.1021/acs.jchemed.9b00388. Student lab report format and supplemental molecular drawing instructions (PDF, DOCX) Pre-lab online worksheet for chemical drawing exercise (PDF, DOCX) Pre-lab KEY online worksheet for chemical drawing exercise (PDF, DOCX)

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. ORCID

Angela L. Mahaffey: 0000-0003-3387-7063 Notes

The author declares no competing financial interest.

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ACKNOWLEDGMENTS I thank the ACS|JCE reviewers for their editing suggestions. I also acknowledge Marcella Niehoff School of Nursing mentor Lisa Skemp.

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REFERENCES

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DOI: 10.1021/acs.jchemed.9b00388 J. Chem. Educ. XXXX, XXX, XXX−XXX