Stereoselective reduction of ketones to alcohols using baker's yeast is a classic experiment in the undergraduate laboratory. Here we illustrate the reduction of racemic ethyl 2-fluoro-3-oxobutanoate to the corresponding alcohol using a set of four commercially available ketoreductases (KREDs). The reaction sets two stereocenters with four…

In this two-session experiment for an organic chemistry lab, students prepare a macrocyclic host compound--namely, a pillar[5]arene--by means of a templated 1,4-dimethoxybenzene/formaldehyde cyclo-oligomerization (session 1), and then, they explore its molecular recognition properties toward the 1,8-diaminooctane guest with the aid of [superscript…

High-resolution mass spectrometry (HRMS) is an analytical technique that is typically used by mass spectrometry experts. However, with recent advancements, it is becoming more accessible to students in organic chemistry laboratories. Still, a significant knowledge gap exists between these experts and students. A straightforward laboratory…

Benzoin, an [alpha]-hydroxy ketone, is stereoselectively reduced by sodium borohydride to yield hydrobenzoin, the stereochemistry of which is determined by acetalization and analysis of the derivative by NMR spectroscopy. This classical experiment has been enhanced by modern spectroscopic and computational analysis to enable students to…

Lakes are artists' pigments made from colorants bound to an inert substrate, usually hydrated aluminum oxide. Before the late 19th century, lakes were made from natural pigments extracted from plants and insects, extracted either directly from the dyestuff or indirectly from waste materials generated in the manufacture of dyed textiles. The first…

Electrophilic aromatic substitution reactions are common in the organic chemistry laboratory. These reactions, while ubiquitous, use corrosive reagents and halogenated or hydrophobic solvents that produce expensive and hazardous waste streams. The carboxylation of phenols (Kolbe-Schmitt reaction), although aqueous, typically involves conditions…

We describe a three-day advanced organic laboratory experience that includes the solid-phase synthesis of an unknown three amino acid polypeptide for junior/senior undergraduate chemistry majors. Students conduct a series of 1D and 2D NMR experiments (HSQC, HMBC, TOCSY) and analyze the data to identify the side chain residues of the peptide and…

As an alternative to the traditional metallocene laboratory targets, students synthesize Cp[subscript 2]TiCl[subscript 2], bis([eta][superscript 5]-cyclopentadienyl)dichloridotitanium(IV), from the mildly moisture-sensitive cis-TiCl[subscript 4](thf)[subscript 2]. Air-free handling techniques are emphasized, but the (mostly) air-stable,…

An integrated laboratory experience using metal--organic frameworks (MOFs), a nanoporous and crystalline extended solid material composed of metal cations and organic linkers, was developed and adopted for upper-division, major-level chemistry and biochemistry students. In this laboratory, students were guided through the facile solvothermal…

This undergraduate laboratory experiment is designed for first-year general chemistry students with the goal of introducing the brilliant colors and magnetic properties of transition metal complexes within a bioinorganic/cell biology context. In the first laboratory period, a coordination complex formed from ferric chloride and maltol is…

A straightforward procedure for the synthesis of (Ph[subscript 3]P)[subscript 3]CuCF[subscript 3], a robust, air-stable trifluoromethylating agent, is reported herein. This preparation can be completed in a single 3 h laboratory session and typically provides ample yields (~79--86%) and high purity (>90%). The target complex is characterized by…

Nuclear magnetic resonance (NMR) spectroscopy is a very powerful analytical method that has found many applications in physics, chemistry, biology, and medicine. It is an indispensable tool particularly for synthetic chemists because it can be used for a rapid elucidation of the structures of organic compounds. For this reason, NMR spectral…

Nowadays, technologies involving nanoparticles, colloids, sensors, and artificial intelligence are widespread in society, media, and industry. It is thus mandatory to integrate them into the curricula of students enrolled in chemistry and materials science. To this purpose, we designed a simple assay for the detection of glutathione (GSH) using…

Students in a typical instrumental analysis course may learn more than 30 analytical techniques. There are more than 150 components associated with the instrumentation that they learn. To help students organize this large amount of information, we classified these components into four categories: sources, samples, discriminators, and detectors. In…

How do cultural heritage scientists and art conservators identify pigments and other painting media in a decorated object or painting, preferably without taking samples that could potentially damage the artwork? A major emphasis in the characterization, authentication, and conservation of works of art and cultural heritage objects is the use of…