One of the greatest challenges in a student's ability to successfully complete reactions in organic chemistry is the ability to differentiate between reactions that have similar structures and proceed through similar reaction mechanisms. Featured in this article is an interleaved reaction review activity called a reaction web. Students are divided…

Functional group analysis is an essential part of the curriculum for identifying unknown organic compounds. However, traditional methods of analyzing functional groups use excess reagents and generate a large amount of waste material that is difficult to dispose of. This work is focused on alternative methods for detecting functional groups such…

Often, eye-tracking researchers define areas of interest (AOIs) to analyze eye-tracking data. Although AOIs can be defined with systematic methods, researchers in organic chemistry education eye-tracking research often define them manually, as the semantic composition of the stimulus must be considered. Still, defining appropriate AOIs during data…

Synthesis of (Z)-alkenes is challenging because the (E) stereoisomers are usually more stable. Energy transfer photocatalysis has emerged as an efficient strategy for (E) [right arrow] (Z) alkene isomerization. We report the development of an advanced undergraduate laboratory experiment that introduces students to contemporary organic…

Paal--Knorr reactions are a classical method for synthesizing pyrroles, using 1,4-dicarbonyl compound and amine as reactants. It has the characteristics of green chemistry, as only two molecules of water are lost. In this teaching and learning experiment, 2,5-hexanedione and 4-"tert"-butylaniline were used to synthesize…

This paper describes a data set of IR, MS, H-1 NMR, C-13 NMR, DEPT, and 2D NMR spectra designed for undergraduate teaching. The data files are provided as MestReNova documents containing all the available spectra for each of the 251 different compounds in the data set. The spectral data in these files can be processed, manipulated, copied, and…

The urea cycle disorder drug glycerol phenylbutyrate (Ravicti) is presently one of the most expensive medications in the United States, with annual costs estimated at $800,000 as of 2023. An expedient synthesis of this orphan drug was successfully adapted for the undergraduate organic chemistry laboratory. Activation of 4-phenylbutyric acid with…

The aim of this study was to elucidate and describe students' thinking about organic chemistry reactions of small versus large drug-like molecules. Thirty-six students enrolled in a Pharmaceutical Organic Chemistry course participated in individual, think-aloud interviews. The interview protocol included questions about five reactions with the…

The ability to extract structural information from a drawing of a molecule is key to being successful in organic chemistry. One source of difficulty for novices in interpreting structures is that hydrogens bound to carbon are represented implicitly in the often-used line-angle structures. Other representations that explicitly show hydrogens, such…

SSurfactants or surface-active agents are interesting groups of compounds with characteristic structures, allowing them to decrease the surface tension. A surfactant consists of a hydrophilic head and a hydrophobic tail. Typically, surfactant molecules aggregate into micelles at the critical micelle concentration. In this work, the concept of…

An organic chemistry experiment designed for senior undergraduates focuses on bifunctional catalysis, a critical yet often omitted topic at the undergraduate level, but essential for advanced studies in chemistry. By utilization of a tertiary amine-thiourea catalyst in the asymmetric Michael addition reaction, the experiment showcases the…

Approximations can help to orient the student in an organic chemistry laboratory. There the student needs to develop the solvent systems for the reaction and isolation of organic reactants and products. The adage "like dissolves like" helps in this regard, but this approach is vague and entirely qualitative. More quantitative approaches…

The helium-plasma (HePI) ionization mass spectrometry method was used to track the formation of reaction products and consumption of reactants by continually monitoring the vapors in the reaction headspace in real time. Two examples of the application procedure are presented here: a nucleophilic acyl substitution reaction and a 1,4-nucleophilic…

The addition of research-focused experiences to undergraduate chemistry laboratory courses has been shown to bolster student learning, enhance student retention in STEM, and improve student self-identity as scientists. In the area of synthetic organic chemistry, the preparation of libraries of compounds with novel optical and electronic properties…

Teaching the three-dimensional structure of saccharides has consistently been a challenging aspect of organic chemistry courses, impeding students' ability to grasp more advanced topics in biochemistry and food chemistry. In this article, we designed and developed a novel d-glucopyranose model using 3D printing technology for the first time. This…