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…

A straightforward protocol for the preparation of the colorful and air-stable diphenyl ditelluride is described. In one laboratory session, students isolate their product and characterize it via melting point determination, mass spectrometry, and NMR spectroscopy ([superscript 1]H, [superscript 13]C­{[superscript 1]H}, and [superscript…

An experiment for the synthesis of N-acyl derivatives of natural amino acids has been developed as part of the Distributed Drug Discovery (D3) program. Students use solid-phase synthesis techniques to complete a three-step, combinatorial synthesis of six products, which are analyzed using LC-MS and NMR spectroscopy. This protocol is suitable for…

A laboratory experiment is described that extracts the tetrapyrrolic teal-colored biliverdin IXa, as its dimethyl ester, from commercially available emu eggshells. The extraction of ~10 mg samples of biliverdin is simple and requires two 3 h lab periods: A two-step acid digestion and liquid-liquid extraction, followed by short silica gel flash…

Saccharin (1,2-benzisothiazole-3-one 1,1-dioxide) is an artificial sweetener used in the food industry. It is a cheap and easily available organic compound that may be used in organic chemistry laboratory classes for the synthesis of related heterocyclic compounds and as a derivatizing agent. In this work, saccharin is used as a starting material…

This paper discusses laboratory activities that can improve the meaningfulness of natural product chemistry course. These laboratory activities can be useful for students from many different disciplines including chemistry, pharmacy, and medicine. Students at the third-year undergraduate level of chemistry education undertake the project to…

This inquiry-based experiment is designed for organic or biochemistry undergraduate students to deduce the identity of phospholipids extracted from chicken eggs and dietary supplements. This is achieved using thin-layer chromatography (TLC) data, a series of guided questions of increasing complexity, and provided relative retention factor (Rf)…

In this laboratory experiment, students learn how to use ESI to accelerate chemical synthesis and to couple it with on-line mass spectrometry for structural analysis. The Hantzsch synthesis of symmetric 1,4-dihydropyridines is a classic example of a one-pot reaction in which multiple intermediates can serve to indicate the progress of the reaction…

Benzoyl peroxide is used as a bleaching agent for flour and whey processing, a polymerization initiator in the synthesis of plastics, and the active component of acne medication. Because of its simplicity and wide application, benzoyl peroxide is a target molecule of interest. It can be affordably synthesized in three steps from bromobenzene using…

Students are introduced to spectrophotometry in comparing the antioxidant activity of pure eugenol and oil of cloves from a commercial source using a modified ferric reducing antioxidant power (FRAP) assay. The extraction of the essential oil from dried cloves is demonstrated to facilitate discussions on green chemistry. The anesthetic properties…

A drug discovery project has been successfully implemented in a first-year general, organic, and biochemistry (GOB) health science course and second-year organic undergraduate chemistry course. This project allows students to apply the fundamental principles of chemistry and biology to a problem of medical significance, practice basic laboratory…

When new concepts, models, or theories are introduced in a course, their presentation should be accurate, even if depth is not the goal. In a recent publication in this Journal, the Woodward-Hoffmann rules were invoked in the context of a new laboratory experiment, but the associated description was inaccurate. Here we aim to clarify the…

This laboratory experiment provides undergraduate students enrolled in organic chemistry the opportunity to design and synthesize their own peptide, which is then tested for antimicrobial activity. After reading a primary scientific paper on antimicrobial peptides, students design and synthesize their own hexapeptide that they hypothesize will…

A new solvent-free microwave experiment to synthesize the ionic liquid 1-hexadecyl-3-methylimidazolium bromide (HDMIm-Br) in high yield is presented. The structure is confirmed by IR and [superscript 1]H NMR spectra. HDMIm-Br is then used to prepare an organic-inorganic mesoporous material MCM-41. The microscopic arrangements of mesoporous…

Students in the undergraduate organic laboratory synthesize tetrahydro-2-(4-nitrophenyl)-4-phenyl-2"H"-pyran via the Montmorillonite K10 clay-catalyzed reaction of p-nitrobenzaldehye with methanol, 3-buten-1-ol, and benzene. The synthesis comprises an environmentally friendly tandem Prins-Friedel-Crafts-type multicomponent reaction (MCR) and sets…