Organic Chemistry Course Research Articles

Organic Chemistry, Life, the Universe and Everything (OCLUE): A Transformed Organic Chemistry Curriculum

The fundamental structure of a typical mainstream two-semester organic chemistry course, populated mostly by life science majors and taught at universities throughout the United States, has changed...

You’ve Got Mail (and Homework): Simple Strategies for Promoting Student Engagement with Prelecture Videos

The use of video productions in chemistry courses, though pedagogically beneficial, is not sufficient in and of itself. Students must also be willing to engage with these productions, especially when the videos are meant to be viewed prior to a class. Accordingly, we describe herein the implementation of two simple but effective strategies to promote student engagement with prelecture videos in a sophomore organic chemistry course. These two strategies, e-mail reminders and online homework assignments, represent easy-to-implement tools that have allowed us to achieve consistently high levels of student engagement with assigned videos.

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.

Gold-Catalyzed Rearrangement of Propargyl Alcohols Using Coupling Constants To Determine Isomeric Ratios

Gold is an increasingly prominent transition metal in organic synthesis. The air-stable, water-insensitive cationic gold(I) catalysts enable varieties of synthetic transformations with a simple reaction setup. However, this increased importance has not coincided with an increase in the application of gold in second-year organic chemistry courses. An experiment is described that includes a gold-catalyzed rearrangement of propargyl alcohols targeted at second-year organic chemistry students. The reaction produces a mixture of E and Z isomers of an enone product that students analyze by 1H NMR spectroscopy to determine the major product.

Integrating Biochemistry Into a Program Serving Multiple Tracks in Medical Laboratory Science

<h3>ABSTRACT</h3> This education case study addresses 2 issues: the program-identified need for more biochemistry content in the prerequisite course, Organic Chemistry I, and its availability to the Medical Laboratory Science Online Career Ladder track students. The underlying principles for resolving the issues are the constraints of the program curriculum and the unavailability of an online organic chemistry course at Georgia Southern University. The first step in addressing the issues involved collaboration between the Medical Laboratory Science and Chemistry faculty members to identify the specific biochemistry topics on which program courses build. Because the Biochemistry I course has the prerequisites of 2 semesters of Organic Chemistry and the medical laboratory program of study only had room for 1 course in this area, a new course was designed to address the program-identified content need. The new course was offered in a face-to-face format, but one of the program tracks utilizes entirely online instruction. To allow those students access to the new course, the course instructor obtained e-Faculty status and undertook designing an online version. The process included the expertise of an instructional designer, and the resulting online course was rich in content and teaching strategies to provide the social presence necessary for student engagement in that venue. The online course immediately earned Quality Matters Certification and has been offered 3 times to date. Forty-one students have taken the new course. Of those eligible to apply, 71% entered the Medical Laboratory Science program, and 78% of the entrants have graduated or are on track to do so. The average course grade point average data for the 5 cohorts reveal that the strong level of student success in the face-to-face course has not been observed in the online course (3.55 and 2.53, respectively), requiring continued efforts to deliver content, engage students, and assess learning in alternative ways.

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...

Stereochemistry of Dichlorocarbene Addition to Alkenes: A Collaborative, Discovery-Based Experiment for the Organic Chemistry Laboratory

A multifaceted experiment, accessible to students either in an introductory organic chemistry course or in a more advanced laboratory setting, is described for investigating the addition of dichlorocarbene to E- and Z-β-methylstyrenes. The innovative exercise, which integrates elements of synthesis, mechanisms, instrumental analysis, computational chemistry, and collaboration, provides students with an opportunity to learn important laboratory skills while highlighting key concepts covered in class. In particular, the coupling constants from 1H NMR spectroscopy are used to diagnose the stereochemistry of addition, and integral ratios are evaluated to determine percent conversion of the starting alkenes into dichlorocyclopropanes. The experimental observations are correlated with results from calculations of the singlet–triplet energy gap in the carbene.

Getting Past the Rules and to the WHY: Causal Mechanistic Arguments When Judging the Plausibility of Organic Reaction Mechanisms

Citizens in all roles need to be able to construct causal explanations of scientific phenomena and engage in coherent argumentation, supported by evidence and sound reasoning. These skills are needed in many contexts, from making everyday decisions to addressing complex global issues. One goal of instruction in this area is to get past assessment questions that can be answered using only memorized rules (e.g., SN1 reactions are favored with tertiary halide substrates), toward answers that require reasoning with evidence (why is an SN1 pathway favored under certain conditions?). Previous work has suggested that these reasoning skills may not be effectively taught, practiced, or learned in organic chemistry courses or directly assessed on exams. In this study, we explored students’ ability to construct scientific arguments using evidence in the context of organic reaction mechanisms, specifically when comparing two proposed reaction mechanisms, making a claim as to which was most plausible, and providing reasoning. We used a qualitative coding scheme to analyze (1) the features and concepts students discussed in their arguments on exams, including the concept of granularity, (2) the connections (links) made between features and concepts, (3) the modes of reasoning revealed in the arguments, and (4) how the ideas and claims were explicitly compared. We found that ∼60% of arguments with correct claims established causal relationships between the relative stability of the carbocation intermediates and the relative activation energy barriers to the formation of these intermediates. However, the vast majority of students did not go to sufficient granularity to meet the expectations in the course, which they could have done by invoking Hammond’s postulate and hyperconjugation in their arguments. Incorrect claims were often supported by causal arguments but these arguments were incorrectly based on drawing a causal relationship between the relative steric hindrance of the starting materials and activation energy. Over 60% of students provided a linear causal mechanistic argument to justify their claim, independent of whether their claims were correct. Over 90% of arguments at least partially compared key concepts explicitly, with over 20% doing so completely. The findings suggest that the majority of students in this study understood the need to provide cause-and-effect relationships to justify their answer, beyond identifying reaction features and their effects; however, students may have struggled to identify which features of those molecules were relevant.

Career Ladder: Vy Dong

1976 Lone Star to Golden State Vy Dong’s mother and father were pen pals living in Vietnam around the end of the Vietnam War. Dong’s father had joined South Vietnam’s navy, but the two reunited by chance at a refugee camp in Guam. Her parents married and immigrated to Texas, where Dong was born. They worked odd jobs while their children were young. “They didn’t really have a chance to go to college,” Dong says. Dong’s father eventually became a machinist, and her mother became a manicurist. When Dong was in first grade, her family moved to Southern California. 1994 California chemistry Dong earned a merit-based scholarship from the University of California, Irvine, where she initially pursued an ecology major. She was attracted to the idea of teaching from a young age. But she fell in love with chemistry after taking an organic chemistry course with Larry E. Overman. “I

Online Education to Develop Complex Reasoning Skills in Organic Chemistry

Chemistry 331 is an upper level organic chemistry course for students interested in health-related careers with an enrollment of approximately 150 students per semester. It assumes that students have a basic knowledge of organic chemistry principles and concepts and it builds on this base with advanced concepts in organic synthesis, mechanism of reactions, and spectroscopy with a biological perspective. Three years ago we moved to an online format to better serve the needs of students with disparate backgrounds and to help them master the concepts and applications of organic chemistry at an advanced level. The course includes online lectures with embedded problems, computer-graded quizzes, and online discussion sections. he exams are in the standard format and are proctored on campus or in off-campus testing centers. The format of the course increases flexibility for the students, increases interaction among students and between students and faculty, and improves student performance on examinations that require complex reasoning skills.

Exploration of Substituent and Isotope Effects on Reaction Rates by a Computational Modeling Experiment

The effects of substitution on reaction rates are at the heart of both physical chemistry and organic chemistry. In this paper, we present a computational laboratory module to explore the effects of group substitution and isotopic substitution on reaction rates by using a readily accessible graphical interface, a computational engine, and spreadsheet software. The module focuses on simple unimolecular isomerization reactions, often used as a classic example for kinetics in first-year, organic, and physical chemistry courses. In the context of a physical or physical organic chemistry course, the module is used to illustrate substituent and/or isotope effects on reaction rates, as well as chemical reaction rate calculations.

Flipping the class – University chemistry students’ experiences from a new teaching and learning approach

Abstract University chemistry courses have for a long time had a similar conventional approach to teaching, with chemistry professors lecturing in a traditional manner. Today, flipped learning approaches have found their ways into higher education with positive results. In particular, US innovations in this area have made positive impressions on Swedish university chemistry educators, resulting in an interest and curiosity in integrating a flipped model into the course curricula. The rationale behind flipped learning is to incorporate an active learning approach into lecture, thereby increasing both student engagement and learning outcomes. In this paper, an implementation project where an organic chemistry course has changed focus from traditional teaching to flipped learning, will be presented. The focus in this mixed-methods study will be on students’ cognitive and affective responses when meeting a new teaching and learning approach. Through following a project where a conventional approach to an organic chemistry course is changed into a more student-active focus, we elaborate on implications for course development of chemistry curricula.

Using a Multitouch Book to Enhance the Student Experience in Organic Chemistry

In recent years, researchers have worked diligently to identify more effective means of facilitating student learning. Some promising pedagogical techniques that have emerged include the flipped-class model and test-enhanced learning. These pedagogical strategies have been incorporated into a multitouch book. A multitouch book is a dynamic platform that allows instructors to combine text, videos, interactive figures, and quizzes into an electronic book. A multitouch book was created and implemented in an organic-chemistry sequence. The course content in the multitouch book is divided into individual learning units. Each unit contains concise informative text, explanatory videos, and quizzes in a structured manner. The multitouch book contains all of the topics traditionally covered in a sophomore-level organic-chemistry course and was created using a variety of elements to engage students in a manner that best matches their learning preference. The multitouch book was created in iBooks Author, which has widgets that allow for the facile insertion of the videos, figures, images, and quizzes. Student response to the multitouch book was overwhelmingly positive.

Super-Star Learning Assisted Sectionalized Examinations in University Organic Chemistry Course

Super-Star Learning Assisted Sectionalized Examinations in University Organic Chemistry Course

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.

Patterns of reactions: a card sort task to investigate students’ organization of organic chemistry reactions

Research has shown that within a traditional organic chemistry curriculum, organic chemistry students struggle to develop deep conceptual understanding of reactions and attribute little meaning to the electron-pushing formalism. At the University of Ottawa, a new curriculum was developed for organic chemistry in which students are taught the language of the electron-pushing formalism prior to learning about specific reactions. Reactions are then organized by governing pattern of mechanism rather than by functional group and are taught in a gradient of complexity. To investigate how students are making connections across reactions within the new curriculum, a card sort task was developed. The card sort task consisted of 25 cards, each depicting the reactants and solvent for a reaction taught during the two-semester organic chemistry sequence. The first part of the task asked participants to sort 15 of 25 cards into categories. Then, participants were given the 10 remaining cards to incorporate into categories with the previous 15. Participants were asked to explain the characteristics of each category and their sorting process. Students (N= 16) in an organic chemistry course were interviewed while enrolled in the second semester course. We analyzed the students’ sorts based on which cards were sorted frequently together, the underlying characteristics used to form the categories, and the participants’ sorting processes. Participants created categories based on different levels of interpreting the reactions on the cards, with levels ranging from recognizing identical structural features to identifying similar types of mechanisms. Based on this study, if we want students to develop mechanistic thinking, we think students need to be more explicitly directed to the patterns present in organic reaction mechanisms and given opportunities to uncover and identify patterns on their own, during both summative and formative assessments.

Using iSpartan To Support a Student-Centered Activity on Alkane Conformations

Strategies employed in the organic chemistry course must have the shared benefit of promoting concept mastery and visual literacy. With this in mind, an iSpartan-enabled visualization and computational activity was developed to complement learning in the first-semester, introductory organic chemistry course. The activity provides students an opportunity to draw molecules, collect structure-based data, and engage in group discussions related to acyclic alkane conformations. Students do not receive a lecture or complete required reading on conformations. Instead, the activity along with group- and instructor-facilitated discussions serves as the method of content delivery for the topic. Pretest and post-test scores suggest improvements in each student’s ability to interpret Newman Projections and determine relative conformation energies and stabilities. A survey was administered to determine the degree to which each student valued the activity and the associated technology, the response to which suggests th...

The Chemistry Connections Challenge: Encouraging Students To Connect Course Concepts with Real-World Applications

A thought-provoking activity called the “Chemistry Connections Challenge” (CCC) has been introduced to an introductory organic chemistry course as a method of highlighting the real-world applications of course content. Identifying how course material can be utilized in the world around them may be difficult for students in introductory organic chemistry courses, particularly those geared toward life science disciplines. This activity was created as a means to improve student attitudes toward organic chemistry by encouraging them to explore how course content is applied to nature, research, and everyday life. In preparation for the activity, students are exposed to several instructor-generated “Chemistry Connections” slides shown in class during the first 4 weeks of the semester. Then, students are invited to create their own slide as part of the “Chemistry Connections Challenge” activity. As students complete the activity they engage with the course material in a meaningful way which can stimulate new way...

Self‐beliefs in organic chemistry: Evaluation of a reciprocal causation, cross‐lagged model

AbstractThis study is designed to test a reciprocal causation, cross‐lagged model of self‐concept, self‐efficacy, and achievement in a postsecondary STEM course. Both self‐efficacy and self‐concept are known to be related to achievement; however, there is a need to untangle the relationship between the two constructs as well as their association to achievement across time to best direct future research efforts. To achieve this research interest, a longitudinal measurement strategy was used to measure chemistry self‐concept and self‐efficacy for learning and performance before and after achievement measures (i.e., two term examinations) in a postsecondary organic chemistry course context. A reciprocal causation, cross‐lagged model best fits the data as a representation of the relationships between these three measures over time as compared to autoregressive, performance effects, and self‐belief effects models. Significant paths in the reciprocal causation, cross‐lagged model include the first self‐concept measure to the first achievement measure as well as from the second self‐concept measure to the third self‐efficacy measure. Relationships from achievement to each subsequent self‐belief measure were also significant. This study demonstrates the ability of longitudinal measurements of multiple constructs in postsecondary STEM educational research to collect nuanced information that is overlooked when pre‐measure designs of single constructs are used. In the classroom, an initial measure of self‐concept can inform instructors of the likelihood of students to succeed on an initial achievement measure, at which point they may choose to implement some of the targeted intervention strategies from literature.

Development and evaluation of the organic chemistry‐specific achievement emotions questionnaire (AEQ‐OCHEM)

AbstractAffect is associated with success and persistence in STEM courses and degree programs. Measurement tools that produce valid and reliable data are essential to capturing the impact of evidenced‐based instructional practices and reformed curricula on learning. We report the development of the Achievement Emotions Questionnaire for use in postsecondary organic chemistry courses (AEQ‐OCHEM). Instrument development was based on the control‐value theory of achievement emotions and included a revision of the seminal Achievement Emotions Questionnaire (AEQ) used to measure institutional‐level learning. A thorough psychometric evaluation of the AEQ‐OCHEM was conducted including alternative measurement models and an extensive investigation of the nomological framework. All AEQ‐OCHEM subscales were determined to be coherent and distinct. Implications for future research using the AEQ‐OCHEM are offered. A call for the development of more discipline‐ and course‐based instruments is made. Finally, tools that measure achievement emotions in the context of instructional laboratories and undergraduate research are needed for more robust considerations of affect in STEM contexts.