The ability to elucidate the structure of organic compounds from their nuclear magnetic resonance (NMR), infrared (IR), and mass spectrometry (MS) spectra is an essential skill, particularly for those engaged in the fields of synthetic and analytical organic chemistry. Spectral analysis constitutes a fundamental component of the curriculum for all…

To prepare students to use science knowledge in their later personal or professional lives, we must attend to what they believe it means to know and learn science (i.e., epistemology). Unfortunately, we have little understanding of how students' epistemologies shift and are stabilized as they navigate their science courses. Researchers have made…

The acid-catalyzed dehydration of regioisomeric methylcyclohexanols is a classic organic chemistry experiment featured in a variety of laboratory textbooks and literature. The mechanistic details of this reaction have received an inconsistent and occasionally inaccurate treatment, wherein the reaction has been described as a mix of E1, E2-like,…

Resonance is a fundamental chemistry concept first introduced to students in General Chemistry I, reintroduced in Organic Chemistry I, and then utilized throughout other higher-level chemistry courses. A molecule or ion can be said to exhibit resonance when it can be represented by two or more chemical structures (i.e., Lewis structures) that…

An undergraduate laboratory experiment has been developed for the synthesis of a reactive cross-linker that is useful in various highly visual demonstrations of organic reactivity, click chemistry, and biobased polymer synthesis. A triazolinedione-based cross-linker, which is known as a useful reagent for click chemistry, can be obtained from…

The work presented in the following chapters was undertaken with the goal of understanding and improving education in organic chemistry. Initial work, described in Chapters 1 and 2, focuses on students' ability to explain and rationalize the outcomes of organic chemistry reactions. Chapter 1 explores the relationship between assessment emphasis…

As detection and subsequent remediation of misconceptions developed within high-school organic chemistry courses in regard to various classes of organic compounds are a prerequisite for meaningful learning of more advanced organic chemistry content, this study sought to identify high-school students' misconceptions about alcohols and carbonyl…

Here we showcase an undergraduate teaching laboratory in which students synthesize and characterize colloidal nanoparticles of organic semiconductors and assess their suitability for applications in printed electronics such as solar cells and bioelectronics. Scanning electron microscopy, UV-visible spectroscopy, and photoluminescence spectroscopy…

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…

Offering an advanced organic chemistry course at a primarily undergraduate institution poses a challenge of condensing graduate organic synthesis into one course. This course was designed so students choose and read recent total synthesis papers from the literature in lieu of relying on a textbook or other pre-existing course materials. Following…

S[subscript N]2 reactions are of fundamental importance in introductory organic chemistry courses, and a number of experiments suitable for the first-semester undergraduate organic lab have been previously reported. Most of these experiments have used alkyl halides as electrophiles, but alkyl halides are often less than ideal for reasons of…