Introductory Organic Chemistry Course Research Articles

Examining How Supplemental Instruction Impacts Students’ Motivation in Organic Chemistry

This study investigates the effect of Supplemental Instruction (SI) on students’ motivation and learning outcomes in an introductory Organic Chemistry course for non-majors. SI, conducted by experienced facilitators, offers a range of academic support for students that may include reviewing challenging concepts, working through practice problems, and answering student questions. To assess the impact of SI in this Organic Chemistry course, we measured several parameters: student engagement during SI sessions, exam scores and final course grades, as well as self-reported motivation levels at both the beginning and end of the semester. We performed a linear regression analysis and observed a positive correlation between SI participation and improved performance on certain exams for SI participants. Further analysis showed that student motivation alone could be driving these improvements. These results suggest that while SI may be beneficial for some students, greater emphasis should be placed on ensuring that students are motivated to learn difficult concepts.

Analysis of organic chemistry students’ developing reasoning elicited by a scaffolded case comparison activity

Recent efforts in organic chemistry education research focus on investigating activities and strategies designed to elicit students’ mechanistic reasoning. This study investigates how a scaffolded case comparison activity implemented in an introductory organic chemistry course elicits and supports students’ mechanistic reasoning in an authentic classroom setting. The activity included an adaptation of a previously reported reasoning scaffold to support small-group student discussions comparing organic reactions. We analyzed students’ written responses to the in-class activity using Hammer's resources framework and Toulmin's argumentation model, interwoven to create an anti-deficit approach to exploring students’ developing reasoning. The analysis of students’ written artifacts sought to identify ways in which a scaffolded case comparison implemented in a collaborative class setting may support students’ engagement in complex reasoning and argumentation development. We found that the in-class activity elicited students’ writing about various aspects of mechanistic reasoning, including identifying explicit and implicit properties, dynamic reasoning, and multivariate reasoning. These findings indicate that the activity can engage students in complex mechanistic reasoning aspects in the classroom setting. Furthermore, this study extends the literature by detailing the nuances of students’ developing causal reasoning with energetic and electrostatic accounts as shown in their writing. The results highlight students’ emerging causal reasoning with varying levels of complexity and conceptual integration. This study provides direct implications for instructors seeking to implement similar classroom activities. The findings indicate directions for future research on the development of instructional activities and tools that further support students’ developing causal reasoning, such as adapting existing scaffolding structures to support argumentation development and the integration of challenging concepts such as energetics.

Capturing students' identification of the relevance of organic chemistry in writing

Appealing to students' affect in academic settings, such as demonstrating chemistry's relevance to their life, is one strategy instructors may use to support students’ in learning. This study investigates the types of connections that students make to organic chemistry when responding to an open-ended writing assignment. Students enrolled in an introductory level organic chemistry course were asked to choose and write about an organic molecule they felt was important to their life, in doing so students wrote about the molecule's relevance to their life. Analysis of the writing was supported by semi-structured interviews with a subset of the students in which they discussed their approach to completing the assigment. Conclusions from this study suggest that students successfully made connections between their chosen moleucle and their life. Considered through the lens of relevance, students can both seek and find relevance in organic chemistry topics on a personal, societal, or vocational level; and therefore may reinforce their comprehension and appreciation of chemistry.

Recurrent gestures in organic chemistry in tertiary education: creating emblems through material and embodied actions

ABSTRACT Background Science teaching and learning, as discursive practices, occur through the utilization of various semiotic modes. Gestures play a pivotal role as an embodied mode that acts in conjunction with speech in oral communication settings, such as classrooms. Previous research on gestures in chemistry and science education has illuminated how interactions involving different types of gestures can enhance learning opportunities for students. However, the investigation of recurrent gestures and their potential function as emblems in classroom discourse remains unexplored. Purpose The objective of this article is to illustrate how catchments or recurrent gestures were constructed, used, and, to some extent, evolved into emblems within the interaction between an organic chemistry teacher and her students throughout an entire semester. Sample, design and methods For the duration of an entire semester, we non-intrusively observed and recorded video footage of one class from an introductory organic chemistry course taught by an experienced university teacher. Our analysis to identify recurrent gestures involved a thorough examination of the lesson recordings. In addition, we scrutinized other semiotic modes that coincided with the recurrent gestures and assessed the metafunction of the words spoken during gesturing. Results During our observation, we noted the occurrence of 23 catchments, with four of them recurring more than 100 times throughout the semester. These four recurrent gestures were closely tied to fundamental concepts considered crucial in the realm of organic chemistry. Remarkably, three out of these four catchments were consistently associated with visual representations. Conclusion Recurrent gestures serve as a means to embody and impart materiality to exceedingly abstract content. By employing such gestures, the teacher managed to associate unfamiliar and abstract domains with familiar and concrete domains. This process of materialization and embodiment aids in perceiving these concepts as tangible entities that can be manipulated in accordance with their own rules.

Chem’Sc@pe: an Organic Chemistry Learning Digital Escape Game

This article reports the development of Chem’Sc@pe, an escape game activity for first- and second-year undergraduate students, covering various topics from an introductory organic chemistry course. The objective was to encourage them to review notions learned in class in a fun and collaborative environment. The set comprises a game board representing 6 rooms of a chemistry laboratory, 30 thematic cards with puzzles to solve (multiple-choice questions, exercise, calculation, and model handling), various tools such as molecular models, and an android-based application. Students in teams of three to four had 60 min to solve enigmas related to functional groups, organic nomenclature, hybridization, stereochemistry, as well as lab-based activities. Each correct answer provides players with a 4-digit code, which gives access through the application to further levels and eventually to the conclusion of the game. History cards offering a short biography of famous chemists were also included in the game to promote scientific culture. Chem’Sc@pe was tested in 2021 with 70 first year chemistry students at the University of Montpellier (France). Assessment of the gamification activity by the students returned excellent reviews, showing that they enjoyed playing the game, found it easy to play, and described it as a useful learning experience.

Arrow-Rotation-Method “ARM”, a Simple and Fast Method for Interconverting Fischer Projections and Zigzag Structures

Different molecular representations are usually used to depict the three-dimensional (3D) structure of organic compounds. Mastering the skill of interconverting one form into another is essential for students to ensure success in organic chemistry. The traditional and recently developed methods for completing such interconversions that rely on 3D visualization of 2D paper (screen) structures, absolute configuration assignments, or multistep drawings that require 3D visualization are often time-consuming and difficult, especially for students with 3D visualization difficulties or a certain level of aphantasia, thus turning organic chemistry into a hurdle in their academic pathway. Given the importance of this topic and its impact on students’ understanding of organic chemistry, the Arrow-Rotation-Method (ARM) has been developed to interconvert zigzag structures and Fischer projections in a few simple steps that require only 2D visualization. A quantitative approach was used on a group of students enrolled in an introductory organic chemistry course to evaluate the time efficiency and usefulness of the new method. The results indicated that ARM significantly improved students’ performance in completing the various interconversions compared to the traditional methods and proved to be more student-friendly, time-efficient, and accurate, especially for compounds with multiple chiral centers. ARM was also successfully used to sketch the structure of complex compounds with multiple chiral centers upon conformational change.

Supplementary Discourse - Forming an Online Learning Community with Asynchronous Discussions

The use of social media platforms to promote social interaction in a digital classroom is a common approach used by many educators. However, implementing such a platform is met with many challenges, the biggest being student shyness and reluctance in participating publicly. In this paper, we introduce the Supplementary Discourse (SD) model, inspired by the Supplementary Instruction (SI) model, where the goal is to promote student–student interactions in an online space. The SD model is also applied in an introductory organic chemistry course using Discord, a channel-based social media platform. By engaging students with tutors and discussion questions, we successfully catalyzed the formation of a student learning community, with the Discord server accumulating an average of 86 messages per week in a 13-week period, with students commenting that they felt less intimidated to ask questions in the server.

Blending Online Homework and Large Class Tutorials to Provide Learning Support for Introductory Organic Chemistry

The logistics and cost of running large class tutorials to improve learning for students in high enrolment courses raise questions about whether the associated effort and cost are worthwhile. The option to replace these class activities with online homework with its promise of built-in feedback is attractive. Using an activity theory lens and an experimental design, we compared the impact of class tutorials with online homework to support learning offered in face-to-face lectures on student performance. We found that there were no topics in the introductory organic chemistry syllabus in which students who had completed online homework instead of large class tutorials performed better. In contrast, for all topics except ‘Curved arrows in mechanisms’, the mean performance of students who had attended a large class tutorial was statistically significantly better than for those who completed online homework instead. This large quantitative study with a sample of 667 students demonstrated the advantage conferred by face-to-face tutorials with peer learning and personal feedback even in a large class setting with only three sessions per student. Our recommendation is that an online homework system in blended courses should not replace face-to-face tutorials for topics reliant on personalised instruction and feedback. We advocate for investing resources and effort to provide face-to-face problem-solving sessions in high-enrolment introductory organic chemistry courses to improve performance.

A Practical Oxidation Experiment for Undergraduate Students: Bobbitt’s Salt as a “Green” Alternative

Oxidation reactions are critical components of the synthetic toolbox taught to undergraduate students during introductory organic chemistry courses. However, the oxidation reactions discussed in the undergraduate curriculum are often outdated as many organic chemistry textbooks emphasize chromium-based oxidants that are no longer in regular use by practitioners, which may limit an instructor’s time to allocate to discussion of other oxidants. Further, laboratory courses have since either removed oxidation experiments or replaced them with oxidative processes not discussed in lectures, thus leading to a disconnect between the two learning settings. As part of an effort to bridge this divide and modernize the oxidation reactions discussed in our curricula, we have developed a new laboratory experiment that uses a commercially available oxoammonium salt (Bobbitt’s salt) to cleanly oxidize cinnamyl alcohol to cinnamaldehyde. In addition to being a safe, convenient, colorimetric, and “green oxidant” suitable for use in the undergraduate teaching laboratory, the hydride-transfer mechanism allows for overlap with key course concepts presented in both introductory and advanced lecture courses. The procedure is well-suited for small and large organic I, II, or advanced laboratory sections alike and can be completed within a standard 3–4 h laboratory period. Aside from exposing students to a modern green oxidation protocol, the experiment contains expanded opportunities for interpretation of 1H NMR, 13C NMR, and IR spectra. An optional addendum for advanced students involving Hammett correlations was also developed.

Gamification of an Entire Introductory Organic Chemistry Course: A Strategy to Enhance the Students’ Engagement

Gamification of an Entire Introductory Organic Chemistry Course: A Strategy to Enhance the Students’ Engagement

Molecular Model and Its Simplification in Teaching Stereoisomerism at Undergraduate Level

The role of molecular models in teaching chemistry is well-known. It is widely used in explaining the shape of molecules. Several authors have reported the difficulty in teaching stereochemistry/chirality. Some researchers have pleaded that the students face difficulty in solving stereochemistry problems because of poor visualization of three-dimensional structure of molecules. The present paper describes herewith the use of simple and inexpensive ball-stick molecular models in teaching stereoisomerism (conformation, configuration, and chirality in allenes) of organic molecules at undergraduate introductory organic chemistry course. It specially describes the use of simplified molecular models in determining the configuration (R or S) of the molecule.

Students’ Learning Experience with a Flipped Introductory Organic Chemistry Course: A Course Designed for Non-Chemistry Majors

The use of flipped classrooms has been gaining popularity across various disciplines as student-centered active learning pedagogy. In this study, an introductory organic chemistry course was delivered through flipped classroom methodologies, incorporating blended learning to deliver content and group work in the classroom. The learning experiences of non-chemistry majors students enrolled in the course are discussed. The majority of the students adjusted to the pedagogy and felt autonomy in their learning. These students also believed that most of the flipped classroom design components were a good use of their time in learning organic chemistry.

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.

Turning Information Dissipation into Dissemination: Instagram as a Communication Enhancing Tool during the COVID-19 Pandemic and Beyond

In the wake of the coronavirus disease 2019 (COVID-19) pandemic, staff and students at universities worldwide were forced to swiftly adapt to distance learning in order to continue with tertiary education. One of the main challenges we encountered during this period was a marked disconnect between staff and students, leading to lower motivation and engagement by both parties. To address this issue, we explored the social media platform Instagram as an interactive communication channel to engage first-year pharmacy students during an introductory organic chemistry course. This led to the development of @kemipilot, an open Instagram account where student questions were fielded and answered by creating educational images and videos. Despite being a small-scale study, the overwhelmingly positive student response, as well as comparisons between Instagram and the university student forum, suggest that Instagram may be a useful pedagogical tool to complement existing distance learning platforms, even beyond the COVID-19 pandemic.

Strategies Employed in Transitioning Multi-instructor, Multisection Introductory General and Organic Chemistry Courses from Face-to-Face to Online Learning

Herein, we describe our experience transitioning two multi-instructor, multisection courses in both general and organic chemistry online during the COVID-19 pandemic from face-to-face instruction methods to an online content delivery format. Beyond the challenges of common assessments, we also had to coordinate discussion sections hosted by teaching assistants and workshops hosted by undergraduate peer facilitators. We discuss the difference in attendance and assessments before and after the transition to online learning. Additionally, we discuss the different uses of technology to host office hours, deliver synchronous and asynchronous teaching, and facilitate efficient communication between instructors and students. The evolution and adaptation of our assessment and communication strategies as online teaching progressed are also discussed.

Lessons Learned from the COVID-19 Crisis: Adjusting Assessment Approaches within Introductory Organic Courses

This communication describes a variety of virtual student assessment strategies employed at the University of Toronto during the academic disruption caused by the 2020 COVID-19 global pandemic. Instructors focused their efforts toward maintaining a positive learning environment and offering meaningful evaluation methods for students in each of three introductory organic chemistry courses. Assessment schemes were initially modified in response to moving courses to a virtual platform, and a variety of support measures were used while students completed the course material and prepared for online “final assignments”, which in two courses included a virtual rehearsal test. The readiness for and delivery of online final assignments is outlined (including methods to effectively maintain academic integrity), and the important roles of graduate student teaching assistants in successfully completing each course are highlighted. Specific outcomes and reflections are discussed, including approaches which, with hindsight, were considered unnecessary, and others that proved to be valuable virtual teaching and assessment tools.

A Visual Organic Chemistry Reaction: The Synthesis of 4-Amino-3-nitrobenzoic Acid Methyl Ester via Fischer Esterification

The synthesis of 4-amino-3-nitrobenzoic acid methyl ester is a simple Fischer esterification reaction designed as an experiment for use in an introductory organic chemistry course. The compound was synthesized as a one-pot reaction within 30 min to 16 h, with 1 h producing a workable yield. The bright-yellow solid was purified using liquid–liquid extraction, and the extraction process was monitored by a marked color change. The product was then characterized by 1H and 13C NMR spectroscopy and thin-layer chromatography.

Optimizing Pre-service Chemistry Teachers Understanding in Reaction Related Concepts of Alipahtic Hydrocarbons

The prime purpose of this investigation was to improve Pre-service Chemistry Teachers (PCTs) understanding of reaction related concepts of Aliphatic Hydrocarbons (AHCs). Participants were 12 PCTs selected from a pool of 87 second year PCTs taking Introductory Organic Chemistry course in Arbaminch college of Teachers Education, Southern Nations, Nationalities and Peoples Regional State (SNNPRS), Ethiopia. The study was carried out in 2017 G.C. The selection of partakers was made on random basis. Case study method was employed in this in-depth investigation. The study was conducted in 7 weeks duration covering all concepts of AHCs. Conventional Instructional Approach (CIA) was employed in the Comparison Group (CG) and Conceptual Change Instructional Approach (CCIA) through the use Conceptual Change Texts (CCTs) was used in the Intervention Group (IG). A semi-structured interview was used for evaluating understanding of PCTs in relation to reactions of AHCs. To analyze the interview data, a framework analysis approach was followed. Analyses showed that the PCTs in IG had improved gaining of reaction related concepts of AHCs than those in CG. Participants in the IG reflected reduced Alternative Conceptions (ACs) and more Correct Conceptions (CoCs) than those in the CG. Reduced ACs and more CoCs from analyses of detailed recordings of PCTs responses confirmed enhanced understanding of reactions of AHCs in the IG.

Organic Chemistry for Biology-Oriented Students

Restructuring the syllabus of an introductory organic chemistry course to better suit the need of biology-oriented students and provide fundamental understanding of chemical principles of biochemical transformations is proposed. It is recommended that certain organic reactions less relevant to natural biological systems are replaced with biochemical reactions as illustrations.

Introducing Diversity through an Organic Approach

An introductory organic chemistry course is a gate keeper to the science pipeline. Instructors can improve student learning by making deliberate efforts to understand and accommodate the various levels of classroom diversity. The changes in the demographics of the United States and the national push to cultivate women and minorities in the sciences also necessitate the need for inclusive classrooms that enrich all types of student learning. Such an inclusive learning environment was promoted in an organic chemistry classroom at a four year college in rural Arkansas for the first time in Fall 2016 and was continued in the subsequent years; it took a unique approach involving comparing the diversity of carbon-based molecules to social diversity. Student responses were overwhelmingly positive and creative. They compared molecular and social diversity in outstanding ways. Also, the diversity assignment was very instrumental as an educational tool that accentuated the value of the versatility of carbon and its bonding in creating the basis of life, according to the results of the pre- and postsurveys incorporated to the assignment in Fall 2018. The assignment provides a stimulating platform to celebrate diversity and foster inclusion in the organic chemistry classrooms, while reinforcing teaching on the versatility of carbon and its bonding.