Spectroscopic characterization of molecules is typically reinforced in the organic chemistry teaching laboratory via the analysis of reaction products by NMR and IR, and initial coverage of these topics can include experiments involving the identification of unknown compounds. To combine the unknown identification component with common laboratory…

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…

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…

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…

Chemistry undergraduate curricula typically place Nuclear Magnetic Resonance (NMR) lectures under either Organic Chemistry or Spectroscopy courses, aiming for students to acquire basic knowledge for the determination of the structure of simple organic compounds. On the other hand, regarding laboratory practice, NMR is frequently disregarded by…

The synthesis of a [2]rotaxane through three- or five-component coupling reactions has been adapted to an organic chemistry experiment for upper-division students. The experimental procedure addresses the search for the most favorable reaction conditions for the synthesis of the interlocked compound, which is obtained in a yield of up to 71%.…

The chlorination reaction of aromatic compounds is highly important for the synthesis of pharmaceutical products. As the most common chlorination reagent, chlorine is restricted from undergraduate laboratory experiment training due to its toxicity. In this work, we reported the chlorination of aromatic compounds with chlorine generated from the…

A multistep synthesis of quinolone antibiotic analogues was developed as a laboratory experiment for intermediate/advanced undergraduate students. Students can synthesize a range of "des"fluoroenoxacin analogues via a five-step sequence. The experiment includes a range of key practical laboratory techniques including thin-layer…

An undergraduate laboratory experiment for the synthesis of biologically significant bis-4-hydroxycoumarins using a new catalyst is described here. An experimental setup plan, monitoring the reaction by TLC, isolation of the product, safe laboratory handling procedures, and significance of data reproducibility of the result are the main learning…

Recently, topical products advertising cannabinoid ingredients have gained popularity. Consumers are seeing an increase of commercial products containing ingredients from hemp oil to cannabidiol (CBD) due to health benefit claims. Cosmetic products containing cannabinoids are currently not regulated at the federal level. A laboratory experiment…

The benzoin condensation of benzaldehyde is a staple of the undergraduate organic chemistry laboratory, introducing the current topic of nucleophilic carbene organocatalysis. Our procedure makes notable improvements to current practice, including the elimination of solvent waste and an "18-fold reduction of reaction time." We have…

Asking students to explain why phenomena occur at a molecular level is vital to increasing their understanding of chemistry concepts. One way to elicit students' mechanistic reasoning and guide construction of knowledge is through Writing-to-Learn (WTL), which is a promising approach for students in organic chemistry courses. In the design of WTL…

This paper describes the design, implementation, and evaluation of an inquiry-based laboratory for sophomore-level organic chemistry into a mostly cookbook, existing laboratory curriculum. For the laboratory, students were required to generate their own procedures and use their own recorded data from prior laboratory assignments to identify an…

Amides are usually prepared using amines and acyl halides, which often implies a two-step procedure. Alternatively, coupling reagents can be used in a single-step reaction with good yields, which seems to be suitable for organic chemistry laboratory classes. This work was designed to synthesize "N"-hexylcinnamamide through a one-step…

The complete structural analysis and resynthesis of an unknown compound, selected from a library of dipeptides, provided a framework for a course that built from expository experiments toward a guided-inquiry approach. We used this semester-long lab as a replacement for conventional second semester organic chemistry laboratory and successfully…