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%.…

An understanding of basic organic chemical reactivity is key for many biosciences students. The reactivities of different carbonyl groups affect their function in many biomolecules. A practical class, the two-step synthesis of paracetamol, has been devised to illustrate the electrophilic reactivities of carbonyls, which was covered in the…

Ultrafast laser pump-probe spectroscopy is an important and growing field of physical chemistry that allows the measurement of chemical dynamics on their natural time scales, but undergraduate laboratory courses lack examples of such spectroscopy and the interpretation of the dynamics that occur. Here we develop and implement an ultrafast…

Elemental analysis is performed in a variety of ways in food and environmental sciences; thus, we have designed an activity in which students gain experience with research-level lab techniques in a real-world context through the quantification of key elements in breakfast cereals using microwave plasma optical emission spectroscopy (MP-OES). The…

An absorption line at 900 nm has been observed in Perspex. Samples of 1 and 2 cm thickness were used and the integrated absorption (line width times peak absorption) of the line was proportionate to the thickness. Facilities for lowering the sample temperature were not available and therefore both measurements were carried out at room temperature.…

As electrochemistry continues to gain broader acceptance and use within the organic chemistry community, it is important that advanced undergraduate students are exposed to fundamental and practical knowledge of electrochemical applications for chemical synthesis. Herein, we describe the development of an undergraduate laboratory experience that…

We present an experiment designed to hone the decision-making skills of (undergraduate) chemistry students by using aqueous crossed aldol reactions. Here, we present two simple crossed aldol reactions based on inexpensive and readily available materials: The condensation of vanillin and cinnamaldehyde with acetone. The procedure uses the variation…

In order to introduce the concept of covalent organic frameworks (COFs), an important class of predictable crystalline porous polymers, an integrated laboratory experiment for advanced organic chemistry students is reported. The importance of these kind of polymers and their multiple applications are presented as a part of key concepts in polymer…

An experiment for the undergraduate organic chemistry laboratory involving a method for the isolation of eugenol from cloves has been developed. The experiment employs microwave-assisted extraction (MAE) of the essential oil from whole cloves using aqueous ethanol and the subsequent isolation of eugenol by acid-base extraction. The MAE allows for…

Synthesis and characterization of nanomaterials yields opportunities for instruction of related topics in solution chemistry and materials science, as well as spectroscopy connecting to band theory, the "particle in a box" quantum mechanical model, and thermodynamics. In collaboration with an undergraduate research assistant, we have…

Student-built photometers are recognized as being useful tools in teaching laboratories that help students understand the concepts behind experimental measurements, and several devices have been reported that employ photoresistors as the detector of choice. We demonstrate here an improvement over these instruments and the analyses thereof,…

Substitution reactions of alcohols are some of the simplest experiments performed in undergraduate organic chemistry laboratory settings. However, the use of gas chromatography (GC) as an analytical tool for these reactions can be at times laborious and time-consuming. In this work, 1-pentanol, 2-pentanol, 3-pentanol, and 2-methyl-2-butanol were…

Optimization of experimental conditions in chromatography is recognized as a wear-and-tear process involving hundreds of experiments in order to maximize the number of separated compounds for each sample. The critical thinking skills and practices entailed cannot be achieved with students in a conventional lecture class. This report provides a…

An operationally simple, reliable synthesis of ethynylated acenes suitable for an upper-division undergraduate organic chemistry laboratory course has been developed. This experiment requires students to synthesize two acene derivatives and can be completed in 6-8 laboratory sessions (3 h each); a shorter experiment could be realized in the…

Friedel-Crafts alkylation reactions using a curated set of alcohols provide students with the opportunity to combine the study of electrophilic aromatic substitution with carbocation rearrangements. In this experiment students may be presented with up to nine alcohols that yield six products, all synthesized under identical reaction conditions.…