Regioselectivity in hetero Diels-Alder reactions can be observed in a simple reaction between a nonsymmetrical heterodiene and an unsymmetrical heterodienophile. A 9 h and easy to implement laboratory experiment is described, in which students can observe the regioselectivity of inverse "electron-demand" hetero Diels-Alder reactions of…

Typical laboratory exercises for undergraduate organic chemistry students involve bulk phase reactions with work up of product. In this study, students performed accelerated versions of the Katritzky reaction of para-substituted anilines with pyrylium salts in three ways: (i) by dropcasting reagents onto a paper surface and allowing solvent to…

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…

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…

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…

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…

Multicomponent reactions (MCRs) represent very interesting tools to reach eco-friendly and sustainable transformations in organic chemistry. In particular, the Biginelli reaction furnishes a very easy approach to the synthesis of a library of biological active compounds in an academic course. Here we describe the realization of several experiments…

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.…

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…

This communication describes an updated experiment of peptide synthesis, involving determination of the loading capacity of a Fmoc-protected amino functionalized resin using UV-vis spectroscopy and a subsequent synthesis of a dipeptide in order to exemplify the experimental solid-phase synthesis procedure as an alternative technique in organic…

University of Michigan--Dearborn offers a one semester, two credit, stand-alone Organic Chemistry Laboratory course aimed at students with an interest in health-related careers. The COVID-19 pandemic led to a campus closure and a subsequent transition to a partially remote laboratory curriculum developed on-the-fly for the Winter 2020 semester…