Organic Chemistry Course Research Articles

Make or Take: An Active Learning Game of Organic Synthesis

The educational game Make or Take is designed to approach the notoriously challenging topic of organic synthesis in an entertaining and engaging way. In this unique, two-part game, teams of students are given identical lists of several synthetic transformations, each requiring multiple steps to complete. During the first part of the game, teams race to devise and post a sound synthetic sequence for one of the transformations. In the second part of the game, rival teams peer review the posted syntheses. This game is designed to test knowledge of organic reactions, promote the use of retrosynthetic analysis, and improve critical evaluation skills. Student response is exceptionally positive, and improved performance on synthesis questions on subsequent assessments was observed after playing the game. Make or Take is best implemented in second-year undergraduate organic chemistry courses with small-to-medium class sizes. This game is highly versatile and can be altered to include more challenging material for advanced classes.

Teach What You Know Day: An Assignment to Bring Peer Learning into Upper Division Chemistry Courses

Peer learning has become a central feature in many postsecondary classrooms. Many peer learning activities feature near-peer instructors who had previously completed the course and who later serve as peer leaders. There are relatively few examples of activities in which students in a course act as true peer instructors for their classmates. One such activity is described herein. This activity, “Teach What You Know Day” (TWYKD), was implemented in an advanced organic chemistry course. Students in this course had varied background preparation and previous knowledge. Students capitalized on this knowledge to present course topics to their peers. During this activity, the peer leaders gave a lecture and helped their classmates work through practice problems. Assessment of this activity was conducted via a student perception survey and by comparing exam scores on TWYKD and non-TWYKD-related questions. The survey results indicate that the students generally had a positive reaction to this assignment. The exam assessment shows that students were able to learn from their peers. This assignment provides many benefits to students enrolled in upper division chemistry courses. With some personalization of the lecture topics, TWYKD would be a valuable addition to other upper division chemistry courses.

Biginelli Reaction and β-Secretase Inhibition: A Multicomponent Reaction as a Friendly Educational Approach to Bioactive Compounds

Multicomponent reactions (MCRs) represent very interesting tools to reach eco-friendly and sustainable transformations in organic chemistry. In particular, the Biginelli reaction furnishes a very easy approach to the synthesis of a library of biological active compounds in an academic course. Here we describe the realization of several experiments involving the synthesis of potential inhibitors of β-secretase by the Biginelli reaction. All of the obtained compounds were tested with a FRET fluorimetric assay. The experiments were proposed to students either at entry level or during advanced laboratory courses of organic and bioorganic chemistry. The learning objectives at the advanced level were to introduce the students to the practice of combinatorial synthesis and to the evaluation of biological activity of combinatorial libraries by enzyme inhibition assays. The meeting of the learning objectives was probed first by analyzing their daily performance in the laboratory and their increasing proactive attitude, and the contents of their final presentations. The resulting marks obtained by the students were compared with the average evaluation of their career. Second, the students were asked to evaluate the course and their own experience, and the outcome of their evaluation was compared with that of the teachers.

Sample Plan for Easy, Inexpensive, Safe, and Relevant Hands-On, At-Home Wet Organic Chemistry Laboratory Activities

An emergent theme from the past spring during COVID-19 remote learning was the difficulty of providing meaningful, relevant, hands-on, wet chemistry experiences at home and the potential impact of their absence upon student learning and engagement. This article shares the process and results of developing an appropriate, easy, inexpensive, safe, and relevant hands-on, at-home DIY kit of wet laboratory activities for a first-semester high school organic chemistry course. Troubleshooting, tips, handouts, and evidence of learning and engagement are provided to supplement the already-published procedures for many of the activities. Whether instructors have already started teaching or are preparing for an upcoming course, this article should enable the rapid incorporation of an at-home laboratory curriculum to supplement student learning and promote engagement with appropriate alternatives to traditional experiments.

Getting Students Back on Track: Persistent Effects of Flipping Accelerated Organic Chemistry on Student Achievement, Study Strategies, and Perceptions of Instruction

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.

Upper-Year Materials Chemistry Computational Modeling Module for Organic Display Technologies

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.

Development of a machine learning-based tool to evaluate correct Lewis acid–base model use in written responses to open-ended formative assessment items

Acid–base chemistry is a key reaction motif taught in postsecondary organic chemistry courses. More specifically, concepts from the Lewis acid–base model are broadly applicable to understanding mechanistic ideas such as electron density, nucleophilicity, and electrophilicity; thus, the Lewis model is fundamental to explaining an array of reaction mechanisms taught in organic chemistry. Herein, we report the development of a generalized predictive model using machine learning techniques to assess students’ written responses for the correct use of the Lewis acid–base model for a variety (N = 26) of open-ended formative assessment items. These items follow a general framework of prompts that ask: why a compound can act as (i) an acid, (ii) a base, or (iii) both an acid and a base (i.e., amphoteric)? Or, what is happening and why for aqueous proton-transfer reactions and reactions that can only be explained using the Lewis model. Our predictive scoring model was constructed from a large collection of responses (N = 8520) using a machine learning technique, i.e., support vector machine, and subsequently evaluated using a variety of validation procedures resulting in overall 84.5–88.9% accuracies. The predictive model underwent further scrutiny with a set of responses (N = 2162) from different prompts not used in model construction along with a new prompt type: non-aqueous proton-transfer reactions. Model validation with these data achieved 92.7% accuracy. Our results suggest that machine learning techniques can be used to construct generalized predictive models for the evaluation of acid–base reaction mechanisms and their properties. Links to open-access files are provided that allow instructors to conduct their own analyses on written, open-ended formative assessment items to evaluate correct Lewis model use.

Implementing Peer-Led Team Learning and Cyber Peer-Led Team Learning in an Organic Chemistry Course

Implementing Peer-Led Team Learning and Cyber Peer-Led Team Learning in an Organic Chemistry Course

Drawing Methods for Lowest Energy Boat and Pentane Conformations

Pentane and boat conformations help predict and understand the stereochemical outcome of several chemical reactions. This report presents two methods that teach the processes of drawing the lowest energy boat conformations and pentane conformations. Both techniques use cyclohexane drawings that students learn in undergraduate organic chemistry courses. We provide step-by-step instructions for both techniques and show that implementing these methods results in improved student performance in questions related to boat and pentane conformations.

DIFICULDADES NO ENSINO E NA APRENDIZAGEM DE QUÍMICA ORGÂNICA DO ENSINO SUPERIOR - ESTUDO DE CASO EM DUAS UNIVERSIDADES FEDERAIS

DIFFICULTIES IN TEACHING AND LEARNING ORGANIC CHEMISTRY IN HIGHER EDUCATION - A CASE STUDY IN TWO FEDERAL UNIVERSITIES. This research investigates difficulties associated to the curricular component Organic Chemistry I based on a study case of Chemistry undergraduate courses (Bachelor and Teachers education) in two Federal Universities in the Brazilian South region. The analytical process integrated official documents of the courses (pedagogic projects, students’ grades), questionnaires, interviews, and researcher’s logbook of classes. Results show that the students’ success in Organic Chemistry I is lower than the sum of failure, unattendance, and temporary cancellation rates altogether in the curricular component offered by the different teachers and institutions studied. A complex scenario is highlighted in relation to factors that affect learning and teaching processes in undergraduate Organic Chemistry courses. The subjects’ responses highlight difficulties related to specific contents, such as conformation and spatial visualization of molecules, stereochemistry, and reaction mechanisms; lack of concepts from High School; and individual habits and characteristics of teachers, students, or both, such as didactics, concentration, and engagement. The results report on the importance of rethinking strategies and methodologies in the context of Organic Chemistry I in Higher Education

The Impact of Supplemental Instruction on the Learning Achievements and Attitudes of Organic Chemistry Students

Supplemental Instruction (SI) has been a successful implementation into Colleges and Universities across the globe. SI has been found to reduce attrition and improve learning and success rate among participating students. At the City College of New York, we recently implemented SI into Organic Chemistry I courses to further support struggling students with the content and concept learning of Organic Chemistry, which is considered a difficult course with a high attrition rate. Our motivation for this research was to examine the impact of SI integration in a large lecture format Organic Chemistry course while assisting students learn and succeed in this challenging course. The objective of this research is to examine whether supplemental instruction (SI) impacts participants’ learning achievement, attitudes, and learning competencies. The experimental design was based on a quasi-experimental approach which included a questionnaire of open-ended and Likert-scaled questions that was distributed to SI participants, and SI participants’ grades were compared to the grades of non-SI participants. Data suggest that integrating Supplemental Instruction (SI) into Organic Chemistry courses positively impacts students’ attitudes towards the content and experience in the course, helps them better understand concepts and materials, improves students’ problem-solving skills, and is effective in improving students’ achievement, success, and the learning. SI participants had an overall passing average of 81%, compared to about 50% for non-SI participants. SI participation provided the participants with a unique and individualized learning experience that resulted in an enhanced conceptual understanding.

Tired of Failing Students? Improving Student Learning Using Detailed and Automated Individualized Feedback in a Large Introductory Science Course

Providing students with timely, targeted, and useful feedback regarding their understanding of course topics is generally accepted as a good educational practice. However, when classes are very large there are challenges that prevent many instructors from accomplishing this goal. This study explores the perceived helpfulness to students and the instructor of implementing a relatively new method of automated scoring and feedback in a large section of an organic chemistry course. Prior research has shown this method to be helpful in other STEM classes. In the current study, students in two different offerings of a stand-alone organic chemistry course completed an anonymous survey in which they were asked to provide feedback about their perceptions of the new methodology. The faculty member who taught the course was also asked to respond to a series of questions regarding the feedback system. Both students and the instructor provided favorable comments about the helpfulness of the methodology and the feedback provided by it. The instructor found it helpful for providing individual feedback to students, which had previously not been possible due to the number of students enrolled in the course. Students reported that the feedback helped them to identify course topic strengths and challenge areas and that they planned to study the material differently going forward. The results indicate that this intervention can help improve student understanding of course topics and necessary actions for improving future performance in the course.

Student Perceptions Using Augmented Reality and 3D Visualization Technologies in Chemistry Education

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.

Techniques adopted in teaching students organic chemistry course for several years

Organic chemistry is a compulsory course for both science and science education students. Therefore a proper course design is needed to ease the understanding of the concepts considered difficult in terms of learning activities, application of technology, and innovation in the curriculum structure. Various studies have been carried out to solve problems in organic chemistry courses, with the majority focused on concept mastery due to students' difficulty. Furthermore, their thinking skills need to be improved after graduating from the university in accordance with the 21st century, which is associated with the application of technology and curriculum modification. The results showed that most studies in organic chemistry courses focused on improving students' concept, understanding, and thinking abilities. Therefore, little application of technology and curriculum modification is still needed in the innovation of organic chemistry courses, especially in applying technology. In conclusion, courses related to organic chemistry still need innovation, especially in the application of technology. This research can serve as a reference for developing organic chemistry learning in the future.

Practical Applications of Organic Chemistry: Improving Student Knowledge of GC–MS through Qualitative Analysis of Nicotine in Electronic Cigarette Vapors

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.

Results of a Peer Review Activity in an Organic Chemistry Laboratory Course for Undergraduates

This paper presents preliminary results of the incorporation of the peer review process into the laboratory component of an organic chemistry course for second year undergraduate students in the biological sciences in Italy. The study was conducted on a class of 64 students and incorporated a training session, a double-blind peer revision of laboratory reports, and a final debriefing phase with evaluation of the activity both by the instructor and by the students. Improvement of students’ writing skills was monitored together with their ability to provide a feedback review and to critically analyze the feedback comments received. The results indicate that the participants made moderate improvements in their ability to write a laboratory report and were able to evaluate the quality of their peers’ writing but also struggled with various aspects of the peer review process.

Transmutation of Scent: An Evaluation of the Synthesis of Methyl Cinnamate, a Commercial Fragrance, via a Fischer Esterification for the Second-Year Organic Laboratory

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...

Using the Research Literature to Develop an Adaptive Intervention to Improve Student Explanations of an SN1 Reaction Mechanism

Two key topics of many second-year organic chemistry courses are substitution and elimination reactions. Predicting and explaining substitution and elimination reactions tends to be a challenging t...

NAIR DA FRANÇA E ARAÚJO: PRIMEIRA MULHER A SE GRADUAR, NA BAHIA, EM BACHARELADO EM QUÍMICA

Professor Nair de França e Araujo was born in 1931 in the city of Maragogipe, inland Bahia. Daughter of housewife Victorina da França e Araújo, and joiner Elpidio Cyrilo de Araújo, she was the first woman to graduate, in Bahia, with a bachelor's degree in Chemistry in 1954, when the Course still worked at the College of Philosophy of the University of Bahia, today UFBA. In 1959, she attended a Specialization Course in Organic Chemistry at the University of São Paulo (USP) and, in 1976, defended her master's dissertation in Organic Chemistry by developing a research on the synthesis of nitriles starting from aldehydes in organic compounds, in partnership with the Local Petrochemical Pole.

Converting an Organic Chemistry Course to an Online Format in Two Weeks: Design, Implementation, and Reflection

As the SARS-CoV-2 pandemic spread throughout the world, universities were faced with extraordinary challenges. Shelter-in-place orders were given, in-person classes were canceled, and at the Univer...