An efficient synthesis of the exorbitantly priced Lambert-Eaton myasthenic syndrome drug amifampridine was developed and applied in the second-semester undergraduate organic chemistry laboratory. The two-step synthesis entails a nucleophilic aromatic substitution reaction of commercial 4-chloro-3-nitropyridine with methanolic ammonia to afford…

A multioutcome, discovery-based column (CC) and thin layer chromatography (TLC) experiment has been designed for introductory organic chemistry. Multiple outcomes were established using commercially available two- and three-component analgesic medications based on acetaminophen, acetylsalicylic acid (aspirin), and ibuprofen. A series of 11…

The pharmacologically active lignans sesamin and sesamolin are minor components of sesame oil and ingredients in OTC dietary supplement capsules. We report an introductory undergraduate organic laboratory experiment combining natural product isolation and spectral analysis in which students isolate a mixture of sesamin and sesamolin by either (1)…

Hydrogels are soft water-rich materials with physical properties that can be easily tuned by modifying their network structure. For instance, increasing or decreasing the cross-linking density has a profound effect on their water absorption capabilities and mechanical strength. These physical changes are showcased in a new experiment for organic…

A one-pot multicomponent synthesis of unsymmetrical indole-substituted methane derivative based on two consecutive reactions of p-methylbenzaldehyde with N-methylindole and 5,5-dimethyl-1,3-cyclohexanedione is described as an experiment that was carried out by second-year undergraduate chemistry students individually in a laboratory classroom. The…

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…

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…

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…

A deep understanding of organic chemistry requires a learner to understand many concepts and have fluency with multiple skills. This understanding is particularly necessary for constructing and using mechanisms to explain chemical reactions. Electrophilicity and nucleophilicity are two fundamental concepts to learning and understanding reaction…