Undergraduate Organic Chemistry Course Research Articles

Teaching abductive reasoning for use as a problem-solving tool in organic chemistry and beyond

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).

Facilitated Study Groups for Undergraduate Organic Chemistry: Experience from a Large Public Canadian University

Undergraduate organic chemistry courses have a reputation for being difficult among students in biological and physical sciences programs. Due to the extensive problem-solving, visualization, and depiction of chemical structures/reactions required, students may perceive learning such content as similar to learning a new language. Several interventions such as course-integrated tutorials or discussion sessions have aimed to assist students. Another effective approach that chemistry educators might consider is Supplemental Instruction (SI), a well-established program that emphasizes student-driven learning whereby student SI leaders facilitate discussions to help students arrive at solutions while also developing effective communication and study skills. A type of SI, Facilitated Study Groups (FSG), established by the Centre for Teaching and Learning at the University of Toronto Scarborough (UTSC) in 2009, were introduced regularly into organic chemistry courses in 2012. This program provides semester-long optional small-group peer learning sessions, each of which corresponds to a course lecture. The aim of this paper is to provide comprehensive coverage detailing the structure of the organic chemistry FSG program, peer facilitation strategies employed, quantitative/qualitative synthesis of student outcomes indicating program uptake. We consistently find significantly higher grades and significantly lower attrition rates for students who regularly attend FSG sessions in comparison to those who do not (n=16 semesters). Given the growing diversity of undergraduate classes in terms of approaches to learning, language, and cultural barriers (international students, English second-language learners, learning and psychosocial disabilities), our FSG sessions seek to foster inclusion amongst our heterogeneous pool of attendees. Here, we describe strategies that tailored FSG sessions to a diverse group of undergraduate students as suggested by a sizable percentage of the class availing themselves of this resource and by a narrative synthesis of end-of-term surveys. Together, we demonstrate successful adoption of an SI-based model for organic chemistry and present a practical framework that includes pedagogically informed session strategies and cost estimates to guide design of similar programs for post-secondary students at other institutions.

Characterizing and identifying influences on undergraduates’ attitudes towards organic chemistry

Despite the important role organic chemistry plays in a wide range of industries, the undergraduate organic chemistry course sequence is considered to be difficult for and feared by students. Although work has been done to identify and address student difficulties within the cognitive and psychomotor domains, little work has focused on investigating student affect towards organic chemistry. Identifying student emotions towards the course and how these emotions impact students’ learning experiences is a key component in addressing student success in organic chemistry. In general chemistry studies, attitudes have been linked to persistence and performance in the class, but little work has been done to determine what role attitude plays in organic chemistry students’ experiences. In this qualitative study, student attitudes towards organic chemistry and the influences that shape those attitudes were explored. Students displayed a wide range of attitudes towards organic chemistry, including positive, negative, neutral, and blended attitudes. Five major influences were shown to have shaped these attitudes including the reputation of the course, students’ educators, experiences with organic chemistry, experiences with introductory chemistry, and individual experiences. Findings also indicated that many student attitudes towards organic chemistry are in place before they have begun the course, but that students’ attitudes may change after interacting with the course material. Limitations of this investigation, as well as implications for research and practitioners, are discussed.

Helen Tran

For the longest time, Helen Tran didn’t feel a strong pull toward chemistry. Art was her passion. She even remembers how in middle school, she was a teaching assistant for a chemistry class, but she always tried to finish her grading early so she could go work in the art studio next door. The turning point was her first undergraduate organic chemistry course. The material spoke to Tran’s instinct for visualization. Then a polymer chemistry class appealed to her love for building things. Those courses solidified her path in chemistry. Now she calls herself a molecular architect: she designs and makes stretchable, biodegradable electronic materials with her group at the University of Toronto. “She really wants to work at this interface of disciplines between chemistry, polymer science, biology, and materials,” says polymer chemist Ron Zuckermann of Lawrence Berkeley National Laboratory, where Tran worked before starting her PhD. Tran’s group in

Exploring curriculum adoption of green and sustainable chemistry in undergraduate organic chemistry courses: results from a national survey in the United States

This study investigated the integration of sustainable chemistry as well as the United Nations Sustainable Development Goals and planetary boundaries into the organic chemistry curriculum through a national survey of organic chemistry instructors within the United States.

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.

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.

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 Effects of Concept Map Teaching Strategy in Undergraduate Organic Chemistry Course

The Effects of Concept Map Teaching Strategy in Undergraduate Organic Chemistry Course

Teaching Organic Chemistry at the American University of Beirut Through the COVID-19 Pandemic

The COVID-19 pandemic has single-handedly overturned a traditional lecture-based educational system at universities on a global scale. The required abrupt move to an online platform for education has caused tremendous challenges for educational systems in general and specifically also in the chemical sciences. In Lebanon particularly, the COVID-19 pandemic raked havoc on a country entrenched in popular uprising and riddled by an economic collapse observing unprecedented devaluation of the national currency. In this situation, the move to online education had caused tremendous stress and burden for faculty and students raising the need to develop mitigation strategies by embracing reduction in material and a careful consideration of students’ mental health. This commentary presents the author’s experience of delivering undergraduate Organic Chemistry courses at the American University of Beirut (AUB) through the COVID-19 pandemic, during the spring and summer 2020 semesters. While the author’s pre-recorded lectures of Organic Chemistry I were vital to the online delivery of course material, this commentary particularly highlights the inclusion of supplementary online assignments that include: videos to illustrate a covered organic chemistry concept, instructional videos to explain a multiple choice question (MCQ) of their creation, a cartoon to exemplify an organic chemistry concept, a cartoon to reflect on studying organic chemistry during the COVID-19 pandemic and a group assignment that allowed students to assume social responsibility.

Investigating perceptions of the structure and development of scientific knowledge in the context of a transformed organic chemistry lecture course

Organic Chemistry, Life, the Universe and Everything (OCLUE) is an undergraduate lecture-based organic chemistry course that has been transformed in line with the vision for science education set out by the ‘Framework for K-12 Science Education: Practices, Crosscutting Concepts and Core Ideas’ (National Research Council, 2012). OCLUE is designed to progress students understanding of core ideas in organic chemistry through the use of scientific practices such as constructing explanations, predictions and models. The purpose of this study is to generate theory on how OCLUE students conceptualise the structure and development of scientific knowledge. Eleven students with diverse experiences and exam performances were interviewed. The data was collected and analysed in accordance with the tenants of constructivist grounded theory (Charmaz, 2000). OCLUE students conceptualised a hierarchical structure of scientific knowledge whereby behind claims and answers in science is important information that determines the validity of the claim or answer. Being adept in utilising this information was important to students in OCLUE as it provided them with the opportunity to account for why phenomena occur in organic chemistry. Students explained that the process of developing scientific knowledge is rarely straight-forward or pre-determined. Instead it was believed that scientists needed to piece together what they know in seemingly random ways in order to solve science puzzles. In the context of OCLUE, students explained that memorising information ahead of OCLUE exams was insufficient. Instead they had to synthesise and interrogate their prior understanding to figure out new problems encountered in OCLUE exams. Students attributed the efficacy of OCLUE's pedagogy to helping them engage in constructivist thinking processes that involved interrogating and applying their prior knowledge. This contributes to the understanding that OCLUE has set out a precedent organic chemistry course that can foster a more scientific way of learning science that contrasts students’ engagement in considerably arduous memorisation techniques.

Using Retrosynthetic Graphic Organizers and Molecule of the Week Activities in Organic Chemistry Tutorials

The tutorials of a second-year undergraduate organic chemistry course have been modified to include a retrosynthetic exercise in conjunction with a Molecule of the Week (MoW) challenge. In contrast...

TMI (Too much information)! Effects of given information on organic chemistry students’ approaches to solving mechanism tasks

We report our qualitative study of twenty-four students enrolled in the second-semester of a second-year undergraduate (sophomore-level) organic chemistry course, Organic Two. We asked the research participants to propose the product and electron-pushing mechanism of elementary mechanistic steps in the absence and presence of the corresponding overall transformation. We also asked the students about their preferences of representational systems when working on tasks common to Organic Two to ascertain the extent to which an external representation, rather than a task, might evoke a problem-solving strategy. In addition to familiarity to instructional materials, the main reason for which the students preferred line-angle formulas for nearly all of the task types is that the representational system allowed them most readily extract relevant, or otherwise useful, information without distracting them. However, line-angle formulas did not seem to cue students to the three-dimensional attributes of molecules; only dash-and-wedge structures and Newman and chair conformers did so. For the electron-pushing tasks, the research participants’ reasoning processes included at least some chemical characteristics of the species involved in the transformation when they were not given the product of reaction. When provided with the overall transformation, however, the students changed their focus to getting to the product. Consequently, they replaced correct answers with incorrect ones when given the reaction products. These results raise the possibility that traditional mechanism tasks may mask students’ mechanistic reasoning ability.

Integrating 360° Videos in an Undergraduate Chemistry Laboratory Course

With 360° cameras becoming increasingly available at affordable costs, 360° videos have been gaining momentum online as an exciting visual medium that engages viewers in an immersive 360° panoramic view. In this report, we share insights of our experience in using 360° cameras to capture several laboratory techniques in an undergraduate organic chemistry course and raise pertinent issues regarding the 360° videos. In summary, we found that 360° videos add value in terms of its large field of view, but pose some potential problems in terms of disorientation and lack of focus.

Simple and Effective Integration of Green Chemistry and Sustainability Education into an Existing Organic Chemistry Course

Green chemistry and sustainable development have become increasingly important topics for the education of future chemists. The cross-disciplinary nature of green chemistry and sustainable development often means these subjects are taught in conjunction with other subjects, such as organic chemistry and chemical engineering. Herein, a straightforward and efficient approach for vertical integration of green chemistry concepts within existing undergraduate organic chemistry courses is shown. The gradual self-evaluation, “greenification”, and reassessment of an organic chemistry course at KTH Royal Institute of Technology from 2013 to 2017 is described, with particular focus on the laboratory course and a novel green chemistry project designed to promote sustainability thinking and reasoning. The laboratory project, which can also be conducted as an independent organic chemistry laboratory exercise, required students to critically evaluate variations of the same Pechmann condensation experiment according to ...

Using Undergraduate Facilitators for Active Learning in Organic Chemistry: A Preparation Course and Outcomes of the Experience

In this study, we describe a course to educate and prepare undergraduate “facilitators” for small group problem solving sessions in a large, first semester, introductory undergraduate organic chemistry course. We then explore the outcomes of the facilitator experience for one cohort of facilitators through qualitative analysis of written reflections, surveys, and field notes. Our findings suggest that the course achieved its goals of providing facilitators with effective teaching techniques and reinforcing content knowledge, and it created a forum for the facilitators to provide feedback to each other and to the course instructor. Furthermore, the course catalyzed the development of professional skills, enhanced metacognitive abilities, reinforced the benefits of active learning, and exposed facilitators to educational literature. These findings are noteworthy because they demonstrate the various potential benefits for undergraduates that facilitate active learning in large chemistry courses.

Strategies of Successful Synthesis Solutions: Mapping, Mechanisms, and More

Organic synthesis problems require the solver to integrate knowledge and skills from many parts of their courses. Without a well-defined, systematic method for approaching them, even the strongest students can experience difficulties. Our research goal was to identify the most successful problem-solving strategies and develop associated teaching models and learning activities. Specifically we asked: (1) What problem-solving strategies do undergraduate students use when solving synthesis-type problems? Are these strategies used correctly/as intended? (2) What strategies have the highest association with successful answers? (3) What relationships exist between these strategies? We analyzed more than 700 responses to synthesis problems from the final exams of undergraduate organic chemistry courses at a large, research-intensive institution. We analyzed the data using an open-coding system and a theoretical framework based on meaningful learning and representational systems in problem-solving. Our analysis f...

A Simple Card Game To Teach Synthesis in Organic Chemistry Courses

The sheer number of reactions covered in an undergraduate organic chemistry course can be overwhelming. Students are expected to demonstrate a thorough knowledge of these reactions in order to understand the logic of organic synthesis. A method that allows students to systematically solve organic synthesis problems without memorizing dozens of reactions would be beneficial. Two new card games, Synthesis and Synthetic Dominos, have been developed using a variation of traditional flash cards. Both of these games allow players to develop the logical skills needed to solve organic synthesis problems, review organic functional groups, and review reaction reagents. The first game, Synthesis, is a solitaire game that uses reaction cards to link up a starting material and target by connecting functional group conversions. The game play mimics the process used to solve synthesis problems. The second game, Synthetic Dominos, is a single-player or multiplayer game that has a gameplay similar to that of Dominos. An i...

ChemKarta: A Card Game for Teaching Functional Groups in Undergraduate Organic Chemistry

Students in undergraduate organic chemistry courses are frequently overwhelmed by the volume and complexity of information they are expected to learn. To aid in students’ learning of organic functional groups, a novel card game “ChemKarta” is reported that can serve as a useful alternative to flashcards. This pedagogy is a simple matching game, in which students identify functional groups on molecules. ChemKarta has a large card set to immerse students in course material and to allow teachers to mine the game for class and exam questions. It is easily customized by the addition or removal of cards to adjust content to fit an individual course. Students found the game easy to learn and responded favorably to its use as an educational tool.