Discussions of the primary literature are an important part of undergraduate education, and much work has been done to develop methods of integrating the literature into the curriculum. Examples include individual single-article discussion activities, literature-based courses, and regular journal club events. While many published examples focus on…

A [beta]-lactam, the core structure unit of clinically important antibiotics such as penicillin and cephalosporin, is one of the most commonly encountered four-membered heterocycles in organic chemistry and is widely used in medicine and biochemistry. The Kinugasa reaction, a copper­(I)-catalyzed cycloaddition of a terminal alkyne with a nitrone,…

NMR spectroscopy is a powerful spectroscopic tool that not only allows the determination of structures after synthesis, as usually explained to students of Organic Chemistry, but also is useful in many other fields such as medicine imaging, real-time industrial processes, material sciences, or metabolomics. In this experiment, students performed a…

Organic chemistry reaction mechanisms are central to the discipline of organic chemistry but challenging for students to learn and for instructors to teach. Due to the unique challenges surrounding the topic, reaction mechanisms have been the focal point of many studies within organic chemistry education research. This article provides a scoping…

Green chemistry is finding its place as one of the most essential study topics in the curriculum of future chemists and chemical engineers. Experiments that meet green chemistry principles contribute to make the laboratory a safer working place, generate less waste, and allow students to increase their knowledge in new environmentally friendly…

A series of distinctive gap-fill activities were designed to provide practice and test students' knowledge in retrosynthetic analysis. Developed and tested during the COVID-19 pandemic, the activities allow students to work through authentic multistep syntheses of various organic target molecules. Students were asked to identify appropriate RSA…

In organic chemistry textbooks (S)-(-)-limonene, (-)-limonene or l-limonene, is often given credit for the smell of lemons, while the R-analogue, (+)-limonene or d-limonene, is credited with that of oranges. Results from two odor tests revealed that few persons in the test associated (R)-(+)-limonene with oranges and (S)-(-)-limonene with lemons,…

Interconverting different molecular representations can be problematic for many organic chemistry students. This is certainly the case when converting Fischer projections into bond-line structures. When performing the conversion from a Fischer projection into an all-staggered bond-line structure, students are sometimes taught to draw the fully…

Students need a strong understanding of how to represent chemical compounds in order to succeed in organic chemistry. This project set out to gain a better understanding of students' difficulties with symbolic representations, by identifying the specific errors associated with drawing wedge-dash structures. The focus was on how students…

As a model study for improving undergraduate organic chemistry laboratories with contemporary research concepts and practices, we evaluated a project module aiming at the synthesis of two porphyrin compounds. The module was implemented in a format that differed in several ways from that of a traditional course. It was designed for small student…

As the COVID-19 pandemic transformed higher education, St. John's University (New York), among other academic institutions, worked to incorporate methodologies that would allow for social distancing and the attainment of hands-on experience that is expected of a science laboratory course. To account for the constraints that the pandemic posed, St.…

This article describes a novel method for quantifying fixation disparity and evaluates its role in visuospatial cognition during an authentic learning task, specifically, the determination of molecule chirality in organic chemistry involving mental rotation and pattern comparison. The first study examined the influence of molecular model…

Transfer students are a growing population at four-year higher education institutions, especially in STEM degree programs. Though much work has explored the broad transfer student experience, the experience of these students within specific courses is understudied. Furthermore, knowledge of how transfer students approach STEM courses and their…

We describe a three-day advanced organic laboratory experience that includes the solid-phase synthesis of an unknown three amino acid polypeptide for junior/senior undergraduate chemistry majors. Students conduct a series of 1D and 2D NMR experiments (HSQC, HMBC, TOCSY) and analyze the data to identify the side chain residues of the peptide and…

In this in-class activity, organic chemistry undergraduates try to place an assortment of molecules in chronological order from oldest to most recently synthesized. In the students' first attempt, they use their knowledge of reactions and synthesis to analyze the organic compounds for their structural complexity. Before a second attempt, the names…