Organic Chemistry Curriculum Research Articles

Ungrading in organic chemistry: students assessing themselves and reflecting on their learning

The focus on grades has diminished the focus on learning. One strategy that aims to return students’ attention to what they are actually learning (and not just earning) is ungrading. Ungrading is thought of as any strategy in which instructors do not assign a number or letter grade to students’ assignments and assessments. Instead, faculty may (1) provide thorough feedback and engage in dialogue with students about their work, and perhaps, (2) allow students to assign their own grade. Whichever style of ungrading they choose, the scholars that have been forging the path for ungrading come from a variety of fields and perspectives, including STEM instructors in more recent years. The focus on incorporating ungrading practices into the organic chemistry curriculum provided here is adapted from a variety of practitioners, and especially the foundational work of chemistry professor Clarissa Sorensen-Unruh. In addition to discussing the current ungrading practices in various fields, we will use this perspective article to share our own experience with and lessons learned from beginning to incorporate ungrading in the undergraduate organic chemistry curriculum, both as it relates to the implementation of the practice and our own perceptions of the student experience and learning outcomes. Ultimately, the goal is to allow students to see the significance of the process of learning and to engage in some metacognitive work that they can apply to different assignments, whether in our class or not. If we want students to focus on learning, perhaps they should do the grading themselves.

An Undergraduate Laboratory Module Integrating Organic Chemistry and Polymer Science.

Polymer science is receiving wider acceptance in the organic chemistry community; thus, it is imperative to include it in the undergraduate organic chemistry curriculum. Despite the ever-increasing popularity of the topic of polymer chemistry in undergraduate curricula, a comprehensive laboratory experiment module describing a polypeptide synthesis by ring-opening polymerization of N-carboxyanhydride (NCA ROP) and a homopolymer synthesis by activators-regenerated by electron-transfer for atom transfer radical polymerization (ARGET ATRP) has yet to be proposed. Herein, we report a semester-long, ten week undergraduate laboratory module focusing on the synthesis and analytical characterization of polyalanine and polystyrene for an advanced organic chemistry class. Students received hands-on-experiences in synthesizing polymers followed by their characterization via proton nuclear magnetic resonance (1H NMR) spectroscopy, electrospray ionization-mass spectrometry (ESI-MS), gel permeation chromatography (GPC), thermogravimetry (TGA), differential scanning calorimetry (DSC), and transmission electron microscopy (TEM), which are not well-presented in the typical organic chemistry curricula. These engaging hands-on lessons in the newly designed laboratory module not only increase students' interests in an interdisciplinary environment of organic chemistry and polymer science but also cultivate their research interests and communication skills and promote critical thinking.

A Snapshot of Organic Chemistry Instruction and Curriculum over the Past 100 Years

Organic chemistry has played a rich role in the development of the field of chemistry and in the teaching and learning of chemical science. This prominence presents a challenge to summarize 100 years of innovation in the teaching of organic chemistry as part of the ongoing project in celebration of the 100th volume of the Journal. The term snapshot is apt given the size of the corpus of articles related to teaching organic chemistry. Nonetheless, a wealth of articles in a virtual issue explore the historical development of the organic curriculum, the nature of the laboratory curriculum in organic chemistry over the years, and a glance at some of the most recent innovation in the field.

Priority and Selectivity Rules To Help Students Predict Organic Reaction Mechanisms

Organic reaction mechanisms lie at the heart of developing an understanding of how the molecular world functions. However, many students simply try to memorize mechanisms, or use their knowledge of the reagent and product to create a mechanism that “works”. This is not helped by the content-heavy organic chemistry curriculum which focuses on rapidly progressing through a range of reaction types and functional groups. For some students, especially nonchemistry majors, OrgChem101 becomes a “rite of passage” to be endured, learned and forgotten. This paper presents an alternative way of introducing students to organic reaction mechanisms, in which mechanistic rationale and thinking is explicitly taught to students, in a simple logical way, before they meet any specific reactions. In particular, to facilitate this, a series of “priority rules” have been developed. These priority rules help students find reactive sites and predict curly arrow mechanisms, even when faced with previously unseen reagents. This approach is designed to empower students to think about organic molecules in a different way, focusing on reactivity and structure. This enables students to realize that they can predict reactions of which they have no prior knowledge by proposing plausible mechanisms from first principles. This approach to mechanistic teaching sits alongside contextualized examples and allows students to rapidly see how the principles they are learning can help them solve real-world problems─ensuring that they develop not only a mechanistic view of the molecular world but also a motivation to learn more.

The Automated Synthesis of Aspirin: An Undergraduate Practical Activity

Recent advances in laboratory automation and digitization require a teaching strategy for undergraduate students that is inclusive of skills in these areas so that students can be prepared to work within the modern laboratory. Future scientists will need training in coding, microcontrollers, on-demand manufacturing, and robotics. With this in mind, we aim to present a simple automated setup for use in undergraduate teaching, exposing and introducing these additional and integrative skillsets that the new generation of students, researchers, and teaching staff will need within the chemistry field. This automated setup performed the well-known synthesis of aspirin, which is often part of the traditional organic chemistry curriculum. Exposing students to simple laboratory automation is an important first step in preparing them to engage with the technology used in modern laboratories. This activity encourages students to think critically about applying automation within the laboratory and showed them the possibilities that a robotic-orientated workflow combined with programming, coding, and synthesis holds─a new world of exploration, collaboration, and expansion.

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.

Investigating student perceptions of transformational intent and classroom culture in organic chemistry courses

Within chemistry education, there are various curricular and pedagogical approaches that aim to improve teaching and learning in chemistry. Efforts to characterize these transformations have primarily focused on student reasoning and performance, and little work has been done to explore student perceptions of curricular and pedagogical transformations and whether these perceptions align with the transformational intent. To complement our previous work on the Organic Chemistry, Life, the Universe, and Everything (OCLUE) curriculum, we developed this exploratory study to determine if students had perceived the goals of the transformation. As in our previous research on OCLUE, we compared perceptions between OCLUE and a more traditional organic chemistry course. Using inductive and deductive qualitative methodologies, we analyzed student responses to three open-eneded questions focused on how students perceived they were expected to think, what they found most difficult, and how they perceived they were assessed. The findings were classified into three superodinate themes: one where students perceived they were expected to learn things as rote knowledge, such as memorization (“Rote Knowledge”), another where students perceived they were expected to use their knowledge (“Use of Knowledge”), and responses that used vague, generalized language, were uninformative, or did not address the questions asked (“Other”). Students in these two courses responded very differently to the open-ended questions with students in OCLUE being more likely to perceive they were expected to use their knowledge, while students in the traditional course reported rote learning or memorization more frequently. As the findings evolved, our interpretations and discussions were influenced by sociocultural perspectives and other cultural frameworks. We believe this approach can provide meaningful insights into transformational intent and certain features of classroom cultures.

Microwave‐assisted Groebke‐Blackburn‐Bienaymé multicomponent reaction to synthesize imidazo fused heterocycles via in‐situ generated isocyanides from N‐formylamines: An undergraduate organic laboratory experiment

AbstractA one‐pot methodology is developed for the direct conversion of N‐formylamine, 2‐amino pyridine, and aldehyde into 2,3‐substituted imidazo[1,2‐a]pyridine heterocycles using I2‐PPh3‐Et3N reagent system under microwave irradiation. During the reaction, I2‐PPh3‐Et3N converts N‐formylamine into isocyanide, which in the presence of in‐situ generated hydrogen iodide (HI) undergoes Groebke‐Balckburn‐Bienaymé (GBB) multicomponent reaction with aldehyde and 2‐aminopyridine. The in‐situ generated HI eliminates the need for an external catalyst for the GBB reaction. The developed process incorporates the use of readily accessible and cheap reagents and also avoid a separate step for the synthesis of isocyanides having disagreeable odor. Fourteen different GBB based heterocycles have been synthesized to demonstrate the feasibility of the optimized protocol. The preparation of N‐formylamines utilized in the synthesis is also elaborated and the overall process was optimized to be suitable for a typical undergraduate organic laboratory experiment. One of the final products was characterized using FT‐IR, 1H NMR, 13C NMR, DEPT, COSY, HSQC, HRMS, and single‐crystal X‐ray diffraction. Overall, the experiment will be useful in the organic chemistry curriculum to teach about multicomponent reactions, the importance of isocyanides in organic synthesis, formylation of amines, application of microwave irradiation in organic synthesis, and structural elucidation of small organic molecules.

Simple experiments with immobilized enzymes as a contribution to green and sustainable chemistry education in the high school laboratory

Abstract Green chemistry became an eminent trend in chemical research and industry since the 1990s, and thus green chemistry is also increasingly suggested to become an issue in chemistry education. One of the principles of green chemistry is to use effective catalysis in general, and enzymatic catalysis under mild conditions in particular. This article presents a set of experiments under catalysis by immobilized lipase that were developed and tested in an action research project for developing a green organic chemistry curriculum for the senior secondary schooling level in Germany.

Social justice meets STEM education

Education It is critical that STEM students learn how science has been implicated in creating social inequities over time. Ali et al. describe a method for incorporating social justice themes into an organic chemistry curriculum. Instructors deliberately infused social justice themes into a standard curriculum by including key compounds that have had important social, cultural, and environmental impacts. Students then predicted products and identified functional groups of compounds now placed in a historical and social context. Although most of the students agreed that this method made the material more relevant, only 4% reported social justice discussions in other STEM courses, highlighting a plethora of missed opportunities. STEM instructors across disciplines are encouraged to emulate this approach and infuse social justice into their courses. J. Chem. Educ. 97 , 3984 (2020).

T1 Measurement by NMR Inversion Recovery: An Upper-Division Undergraduate Experiment in Advanced NMR Techniques Demonstrating the Concept of Contrast-Enhanced MRI

Nuclear magnetic resonance (NMR) spectroscopy is the tool of choice for organic chemists to determine the molecular structure of organic molecules and, as a result, is a fundamental topic in the organic chemistry curriculum. A novel laboratory module has been developed to expand the scope of NMR spectroscopy beyond structure validation at the undergraduate level to include how organic chemistry and FT-NMR spectroscopy are directly related to contrast-assisted magnetic resonance imaging (MRI). This laboratory module allows students to synthesize commercially available MRI contrast agents and exposes students to the important concepts of longitudinal relaxation time (T1) and relaxation rate (r1), and how both properties can be enhanced by paramagnetic contrast agents. By using an NMR spectrometer for inversion recovery experiments, students will be able to bridge the concepts of NMR and MRI, while understanding how organic chemistry plays a vital role in a technology that revolutionized diagnostic and therapeutic medicine.

The Shrewd Guess: Can a Software System Assist Students in Hypothesis-Driven Learning for Organic Chemistry?

The mechanism maps that guide student instruction in organic chemistry curricula are structural representations of bond-breaking and bond-making events that transform a reactant into a product. For students, these pathways represented by electron pushing formalism (EPF) can be challenging to navigate. For instructors, providing formative feedback to students to support their learning of the EPF arrow system is difficult to provide in a timely manner. The Mechanisms App (“the App”) was developed as a method for students to explore the electron movement of organic chemistry through a touch screen interface of a smart phone or tablet with real-time feedback of these moves. In this paper, the pedagogical content of the App and its backend system is described. This system produces a graphical record of a user’s move within the App and is called a decision tree. A study of students’ use of the App in two different modes was devised to understand whether the in-app experience can facilitate a hypothesis-driven approach to learning EPF. Examples of classroom implementation for the App in a variety of institutions and future research are also described.

Beyond Green Chemistry: Teaching Social Justice in Organic Chemistry

A strategy for incorporating social justice themes into an introductory organic chemistry curriculum is described. We have deliberately infused social justice themes into the standard organic chemistry curriculum by discussing the history and social impact of key compounds. Using these key compounds that have had significant social, cultural, and environmental impacts, students practiced arrow-pushing mechanisms, predicted products, and identified pKa values and functional groups. We believe this approach helps make the material more relevant to students, keep students engaged, and emphasize the real-world applications of the concepts and compounds that they are learning about. Details on the implementation and the evaluation of this work are discussed.

Exploring Student Thinking about Addition Reactions

Organic chemistry is a required course sequence for many STEM students. However, research indicates that organic chemistry reaction mechanisms are especially challenging for students due to a mixture of underlying conceptual difficulties, the process-oriented thinking inherent to the discipline, and the representations commonly used to depict mechanisms. While student reasoning about many of the reaction types covered in the organic chemistry curriculum has been studied previously, there is minimal research focused specifically on how students think about the mechanisms of addition reactions. Understanding students’ conceptions about addition reactions is valuable for both instructors and researchers, as these reactions are among the first for which students must consider different chemical properties to make a decision about alternate reaction pathways. This study provides insight into how students think about these reactions by probing first semester organic chemistry students’ thinking using think-aloud interviews as they worked through two addition reactions. To elicit a range of thinking, students worked through the mechanisms using either paper and pencil or an app that dynamically represents the molecules. Generally, students were able to identify the steps of the two addition reactions but did not always successfully apply chemical thinking during the mechanistic steps. Most prominently, both groups of students struggled with the concepts related to carbocation stability, frequently misapplying stabilization via substitution and demonstrating difficulty in identifying the potential for resonance stabilization. Our results suggest that instructors should emphasize the conceptual grounding that directs mechanistic steps, in particular when determining carbocation stability. More generally, our findings suggest that instructors must emphasize the skill of considering and weighing different chemical properties when making decisions about alternative reaction pathways.

PKa values in the undergraduate curriculum: introducing pKa values measured in DMSO to illustrate solvent effects

The concepts of acidity and pKa values often occupy a privileged place in the undergraduate organic chemistry curriculum. However, by neglecting the relationship between solvent and acidity, many students come to understand acidity as a fixed property of a molecule, invariant regardless of reaction conditions. Moreover, the sole use of pKa values measured in water leads to serious analytical faults in several important areas of the introductory organic curriculum. In this paper, we consider the (mis)uses of aqueous pKa values in the organic curriculum and their pedagogical effects, argue for the adoption of pKa values measured in an organic solvent (DMSO) in organic textbooks and reference materials, and explore the thermodynamic origin of the effect of solvent on acidity. Suggestions for class discussions and activities are provided.

Reorganization of the Organic Chemistry Curriculum to Improve Student Outcomes

The material of a standard second-year undergraduate organic chemistry class has been reorganized and reframed to emphasize the mechanistic connections between reactions and to clarify the language...

A Safe and Green Benzylic Radical Bromination Experiment

Radical chemistry is an essential part of the organic chemistry curriculum. Free radical halogenation experiments provide an excellent opportunity to introduce important topics related to the outcome and mechanism of organic reactions. In this communication, a green photochemically activated benzylic bromination of p-toluic acid is described. In contrast with previous versions of this reaction, visible light provides the energy necessary to homolytically cleave the Br—Br bond and initiate the radical cascade. Thus, photochemical activation allows a safer, faster, and cheaper alternative to chemical free radical initiators. Furthermore, the reaction is conveniently performed in environmentally friendly acetonitrile, as a replacement for toxic and ozone-depleting chlorinated solvents, such as the usual carbon tetrachloride.

Reformation and Practice of Organic Chemistry Curriculum for Simultaneous Cultivation of Ability and Morality

Reformation and Practice of Organic Chemistry Curriculum for Simultaneous Cultivation of Ability and Morality

New, Milder Hypervalent Iodine Oxidizing Agent: Using μ-Oxodi(phenyliodanyl) Diacetate, a (Diacetoxyiodo)benzene Derivative, in the Synthesis of Quinones

The synthesis of substituted 1,4-benzoquinones, a biologically important class of compounds, was developed using μ-oxodi(phenyliodanyl) diacetate, a (diacetoxyiodo)benzene-based oxidizing reagent, in order to introduce second-year undergraduate organic laboratory students in their second semester or advanced organic students to increasingly popular and environmentally friendly hypervalent iodine chemistry. This experiment develops on concepts found in the undergraduate organic chemistry curriculum; conveniently fits into approximately two 3 h lab modules; and utilizes regularly found equipment and inexpensive, commercially available chemicals.

Incorporating Chemical Structure Drawing Software throughout the Organic Laboratory Curriculum

Fluency in both the construction and interpretation of molecular structures is a critical learning objective in the second-year organic chemistry curriculum. With the introduction of PerkinElmer’s ...