First-semester Organic Chemistry Research Articles

Motivation Differences in First-Semester Organic Chemistry: A Comparison between First-Time-in-College Students and Transfer Students

Motivation Differences in First-Semester Organic Chemistry: A Comparison between First-Time-in-College Students and Transfer Students

Cognitive discourse during a group quiz activity in a blended learning organic chemistry course

Abstract Student-centered approaches are critical to improving outcomes in STEM courses. Collaborative learning, in particular, allows students to co-construct understanding of concepts and refine their skills in analyzing and applying information. For collaborative learning to be effective, groups must engage in productive dialogue. The work reported here characterizes the quality of dialogue during group quizzes in a first-semester organic chemistry course. The group quiz sessions were video and audio recorded. The recordings were transcribed and coded using the Interactive, Constructive, Active, Passive (ICAP) framework. The quiz prompts were analyzed using Marzano’s taxonomy. In this study, students within the group demonstrated varying degrees of interactional quality as defined by the ICAP framework. Our data also indicate that the level of constructive and interactive dialogue is highest and most consistent when prompts are at Marzano Level 3 or higher. Marzano Level 3 prompts required students to compare and contrast concepts or extend their understanding of concepts by developing an analogy. Any benefit derived from collaborative learning depends on the quality of dialogue during the group discussion. Implications of these results for research and teaching are offered.

Reduction of Vanillin Isobutyrate: An Infrared Spectroscopy Structure Determination Experiment

In this laboratory experiment, first-semester organic chemistry students use mechanistic reasoning to propose possible outcomes for the reaction of vanillin isobutyrate with a hydride source. The students subsequently run the reaction, isolate the product, and acquire its infrared spectrum. The experiment provides students with the opportunity to hone their skills at proposing mechanisms and interpreting IR spectra. It also serves as an introduction to the chemistry of carbonyl-containing functional groups.

Predictions of success in organic chemistry based on a mathematics skills test and academic achievement

Organic Chemistry I presents challenges to many students pursuing diverse fields of study, oftentimes curtailing further progress in those fields. The ability to identify students at risk of unsuccessful course outcomes may lead to improved success rates by offering tailored resources to those students. Previously identified predictors include college entrance exam scores, grade point averages (GPA), General Chemistry II course grades, first exam scores, and results from a logical thinking assessment. This work explores the use of the 20-item Math-Up Skills Test (MUST) in a first-semester organic chemistry course over two years at a small private university. Analysis of scores on the MUST, which is taken during the first week of the semester, indicates a statistically significant difference between successful and unsuccessful first-time students (n = 74 and 49, respectively) as the MUST has good internal consistency (Cronbach's alpha = 0.861) and a large effect size (Cohen's d = 1.29). Taken alone, the MUST predicts students at risk of not passing the course with 64% accuracy; addition of start-of-term science GPA data improves predictions to 82% accuracy. Predictions are further improved with incorporation of scores from the first exam of the semester. Observations to date indicate that the MUST is an easily administered assessment that can be utilized alone or as part of a trio of measures to predict success in first-semester Organic Chemistry. Implications of a mathematics assessment as a predictor for Organic Chemistry are addressed.

Development and psychometric analysis of an inventory of fundamental concepts for understanding organic reaction mechanisms

Abstract The fundamental concepts for organic reaction mechanisms inventory (FC-ORMI) is a multiple-choice instrument designed to assess students’ conception of fundamental concepts for understanding organic reaction mechanisms. The concepts were identified from open-ended interviews and a national survey of organic chemistry instructors reported in a previous study. This manuscript describes the development of the inventory items related to these identified concepts and the psychometric analysis of the instrument. In the developmental stage, open-ended questions were administered to first-semester organic chemistry students (N = 138), and open-ended interviews were conducted with students (N = 22) from the same pool to gain insight into their thought processes. The answers revealed alternate conceptions which were used to formulate distractors for the inventory. A pilot version and a beta version of the inventory were administered to 105 and 359 first-semester organic chemistry students, respectively. From these administrations, the 26-item alpha version was developed and administered to first-semester undergraduate organic chemistry students (N = 753). Psychometric analysis was conducted at the item and test level using Classical Test Theory and Rasch analysis. The results indicate that the items on the FC-ORMI function well to reveal students’ alternate conceptions. The instrument meets the acceptable standards of validity and reliability for concept inventories.

Measuring Changes in Undergraduate Chemistry Students’ Reasoning with Reaction Coordinate Diagrams: A Longitudinal, Multi-institution Study

The Reaction Coordinate Diagram Inventory (RCDI) was developed to measure chemistry students’ thinking and confidence when interpreting the kinetic and thermodynamic information encoded within reaction coordinate diagrams (RCDs). The RCDI was designed based upon analyses of qualitative data collected in semi-structured interviews with general chemistry students or organic chemistry students to ensure all items and distractors were grounded in students’ ideas and reasoning. A longitudinal, multi-institution research study was conducted using the RCDI to measure changes in undergraduate chemistry students’ reasoning with RCDs, and their confidence in doing so, at three points in time: (1) end of second-semester general chemistry, (2) beginning of first-semester organic chemistry, and (3) end of first-semester organic chemistry. The three institutions participating in this longitudinal study taught organic chemistry using either a traditional functional group curriculum or a mechanisms approach. Findings include evidence that individual students performed significantly better with significantly higher confidence as they progressed through courses, but that some RCD misconceptions, such as incorrectly assuming reaction progress indicates a time unit, are persistent throughout. Although two of the institutions taught organic chemistry using a mechanisms curriculum and one institution used the traditional functional group approach, no evidence exists of significant differences among students’ RCDI total score and average confidence across institutions.

First-Semester Organic Chemistry during COVID-19: Prioritizing Group Work, Flexibility, and Student Engagement

Our first-semester organic chemistry class focused on structured group work to enable active learning in class. When Smith College switched to online learning after spring break, the class was adapted to fit into an online learning model while retaining active learning. Using feedback from students, we implemented two tracks, one focused on independent work and one focused on group work. Using Zoom’s breakout rooms, we were able to simulate the full-class and small-group experiences of our in-person class with the help of student learning assistants to facilitate group learning. Slack was introduced for class questions and communications. Student feedback was positive overall and indicated that their perceptions about group work improved over the semester. In the case of in-person classes in the fall, this method might be preferable to a class in which social distancing hampers student-to-student discussion.

Microwave-Assisted Isolation of Eugenol from Cloves

An experiment for the undergraduate organic chemistry laboratory involving a method for the isolation of eugenol from cloves has been developed. The experiment employs microwave-assisted extraction (MAE) of the essential oil from whole cloves using aqueous ethanol and the subsequent isolation of eugenol by acid–base extraction. The MAE allows for extraction of the essential oil in a fraction of the time of steam-distillation, which is commonly part of a second-year undergraduate laboratory experience. The experiment combines multiple lab techniques and reinforces the introduction of spectroscopy in first-semester organic chemistry.

Development and evaluation of a Lewis acid–base tutorial for use in postsecondary organic chemistry courses

A well-developed understanding of the Lewis acid–base model is highly important for the understanding of organic chemistry. As such, students should receive instruction and be assessed on use of the model. Online tutorials and constructed-response items provide a means for confirming that students have a well-developed conceptualization of the Lewis acid–base model. In a prior study, a predictive logistic regression model was presented that can be used with constructed-response assessment items to determine use of a Lewis acid–base model in written responses. In this study, we use that predictive model to evaluate the effectiveness of a tutorial designed to promote meaningful understanding of the Lewis acid–base model in three different instructional contexts: first-semester organic chemistry students before summative assessment, first-semester organic chemistry students after summative assessment, and second-semester organic chemistry students. Additionally, we evaluated the learning gains of one set of first-semester students after a 3-week time delay. McNemar’s test results suggest that the tutorial had a net positive impact in all three instructional contexts, with the most significant impact observed with the second-semester students. This work has implications for further development of literature-based tutorials to promote meaningful understanding of organic chemistry reaction mechanisms assessed by constructed-response items.

Synthesis of a Crosslinked Epoxy Resin Medallion in the Organic Chemistry Laboratory

Polymer synthesis has a limited inclusion in most organic chemistry lecture curricula, so emphasizing the concepts of polymer chemistry in a laboratory setting gives students hands-on experience in new content and broadens the scope of the class. The details and outcomes of a robust and well-developed laboratory procedure for the synthesis of a crosslinked epoxy network polymer are described. This experiment has been a part of a first-semester, introductory undergraduate organic chemistry laboratory curriculum for more than two decades and has positively impacted over eight hundred students. The experiment had the unique aspect that students cured the resin in a round, seven-centimeter mold, forming a hardened epoxy disk. This disk, or medallion, was decorated in two different ways: first, a design was etched into the mold before curing to form a permanent imprint; second, the final epoxy medallion was decorated, post-cure, with colored permanent markers and glitter glue. After this laboratory experiment, students took home a durable ornament as a memento of their first-semester organic chemistry laboratory course.

Characterization of First-Semester Organic Chemistry Peer-Led Team Learning and Cyber Peer-Led Team Learning Students’ Use and Explanation of Electron-Pushing Formalism

The purpose of this parallel convergent mixed methods study was to characterize organic chemistry students’ expression of electron-pushing formalism skills who had participated in peer-led team learning (PLTL) and cyber peer-led team learning (cPLTL), a synchronous online version of peer-led team learning (PLTL) workshops. A new electron-pushing formalism analytic framework was developed from a review of the literature in addition to analysis of students’ interview artifacts, using a constant-comparison process. Utilization of this new electron-pushing formalism analytic framework for coding student interview artifacts revealed that cPLTL students were significantly less likely to successfully draw the product suggested by the curved arrows than their PLTL classmates. Implications for instructors are suggested, including encouraging students to verbally explain their rationale while drawing mechanisms as well as optimizing graphical collaborative learning activities for online learners.

ConfChem Conference on Select 2016 BCCE Presentations: Specifications Grading in the Flipped Organic Classroom

Specifications Grading is a system of course-long student assessment based on the division of learning objectives into clearly defined skill tests or assignments. Each skill is evaluated at a mastery level, with opportunities for students to learn from their mistakes and then be re-evaluated for skill tests, or resubmit assignments. Specifications Grading was adapted into a previously flipped, first-semester organic chemistry course, with generally positive feedback from both the professor and the students. This Communication summarizes one of the invited papers to the Select 2016 BCCE Presentations ACS CHED Committee on Computers in Chemical Education online ConfChem held from October 30 to November 22, 2016.

Chiral Analysis by Tandem Mass Spectrometry Using the Kinetic Method, by Polarimetry, and by 1H NMR Spectroscopy

The goal of this laboratory exercise was for students to understand the concept of chirality and how enantiomeric excess (ee) is experimentally determined using the analysis of ibuprofen as an example. Students determined the enantiomeric excess of the analyte by three different instrumental methods: mass spectrometry, nuclear magnetic resonance spectroscopy, and optical polarimetry. This laboratory exercise introduced mass spectrometry into the first-semester organic chemistry curriculum. Further, it allowed the students to compare and contrast the analytical figures of merit for each technique, a topic usually discussed later in chemistry courses. The ee resolution, sensitivity, limits of detection, and required sample preparation were considered. Furthermore, this laboratory experiment taught students how to use the kinetic method for chiral analysis by mass spectrometry, a new technique in a student laboratory exercise. Students’ knowledge of how to select the appropriate technique for enantiomeric ex...

Students’ interpretations of mechanistic language in organic chemistry before learning reactions

Research on mechanistic thinking in organic chemistry has shown that students attribute little meaning to the electron-pushing (i.e., curved arrow) formalism. At the University of Ottawa, a new curriculum has been developed in which students are taught the electron-pushing formalism prior to instruction on specific reactions—this formalism is part of organic chemistry's language. Students then learn reactions according to the pattern of their governing mechanism and in order of increasing complexity. If students are fluent in organic chemistry's language, they should have lower cognitive load demands when learning new reactions, and be better positioned to connect the three levels of chemistry's triplet (i.e., Johnstone's triangle). We developed a qualitative research protocol to explore how students use and interpret the mechanistic language. Twenty-nine first-semester organic chemistry students were interviewed, in which they were asked to (1) explain a mechanism, given all the starting materials, intermediates, products, and electron-pushing arrows, (2) draw in arrows for a reaction mechanism, given the starting materials and products of each step, and (3) predict the product of a reaction step, given the starting materials and electron-pushing arrows for that step. To investigate the students’ ideas about mechanistic language rather than their knowledge of specific reactions, we selected reactions for the interview guide that had not yet been taught. Following transcription, we analyzed the interviews using constant comparative analysis to explore how students used and interpreted the mechanistic language. Four categories of student thinking emerged with electron movement underlying students’ thinking throughout the interviews. Herein, we discuss these categories, students’ interpretation of the symbolism, connections to learning theory, and implications for teaching, learning, and research.

Self-efficacy and academic performance in first-semester organic chemistry: testing a model of reciprocal causation

Self-efficacy is an affective learning outcome that has been associated with academic performance and retention in STEM. Self-efficacy has been defined as students' beliefs about their ability to complete a given task, and it can be affected by a student's positive or negative experience in a course. In this study, students' chemistry self-efficacy in an organic chemistry course and its reciprocal causation relationship with performance in the course was examined using structural equation modeling (SEM). Organic chemistry self-efficacy (OCSE) was measured five times during the semester and students' scores in four term exams and a final exam were used as measures of performance. Five different models were proposed and tested to explain the relationship between OCSE and performance. A reciprocal causation model with an exam snowball effect was found to best explain the relationship between OCSE and performance compared to other alternative models including a reciprocal causation model without the snowball effect and an autoregressive model. This model suggests a significant positive relationship between OCSE and performance throughout the semester, providing empirical support for the reciprocal relationship of these two measures. Implications for research and instruction are discussed in terms of the reciprocal relationship between self-efficacy and performance.

Formalizing the First Day in an Organic Chemistry Laboratory Using a Studio-Based Approach

A novel studio-based lab module that incorporates student-centered activities was designed and implemented to introduce second-year undergraduate students to the first-semester organic chemistry laboratory. The “First Day” studio module incorporates learning objectives for the course, lab safety, and keeping a professional lab notebook.

Extraction of Maltol from Fraser Fir: A Comparison of Microwave-Assisted Extraction and Conventional Heating Protocols for the Organic Chemistry Laboratory

Two methods for the extraction of maltol from Fraser fir needles are performed and compared in this two-week experiment. A traditional benchtop extraction using dichloromethane is compared to a microwave-assisted extraction using aqueous ethanol. Students perform both procedures and weigh the merits of each technique. In doing so, students see a trade-off between the ease of working with a highly volatile organic solvent and the selectivity that can be achieved with the greener solvent combination. This experiment combines multiple lab techniques, highlights the connections between chemistry and biology, and provides straightforward 1H NMR spectra to support the introduction of spectroscopy in first-semester organic chemistry.

Factors Contributing to Problem-Solving Performance in First-Semester Organic Chemistry

Problem solving is a highly valued skill in chemistry. Courses within this discipline place a substantial emphasis on problem-solving performance and tend to weigh such performance heavily in assessments of learning. Researchers have dedicated considerable effort investigating individual factors that influence problem-solving performance. The purpose of this study is to inspect the influences of a core set of factors (prior science achievement, knowledge structures, spatial ability, gender, and ethnicity) and their overall contributions to problem solving in organic chemistry using multivariate regression analyses. Results indicate that knowledge structures are a key predictor of problem-solving performance and account for a significant proportion of the variation in students’ problem-solving scores. Implications for research and practice in chemistry are discussed.

Using Whiskey-Flavoring Compounds To Teach Distillation and IR Spectroscopy to First-Semester Organic Chemistry Students

Laboratory techniques, such as boiling point determination, distillation, and infrared spectroscopy, are commonly taught during first-semester undergraduate organic chemistry courses. This integrated experiment teaches the usefulness of combining these different laboratory techniques for structure elucidation purposes. The idea of whiskey distillation is used as a real-world example to engage organic chemistry students and teach the importance of skills such as boiling point determination, simple and fractional distillation, structure elucidation, IR spectroscopy, and critical thinking. Students do not distill real whiskey samples but rather mixtures containing two different whiskey-flavoring compounds.

Development and Implementation of a First-Semester Hybrid Organic Chemistry Course: Yielding Advantages for Educators and Students

A first-semester organic chemistry course was developed as a hybrid course. The students met face-to-face for one class each week (50 minutes) and the lectures were accessible online via Adobe Connect. Quizzes were scheduled for almost every lecture with access online through ANGEL. In addition, the students had three in-class tests and one final exam. There were 29 students total, from three different semesters, enrolled in the hybrid class. A description of and suggestions for hybrid course development are described.