An organic chemistry experiment designed for senior undergraduates focuses on bifunctional catalysis, a critical yet often omitted topic at the undergraduate level, but essential for advanced studies in chemistry. By utilization of a tertiary amine-thiourea catalyst in the asymmetric Michael addition reaction, the experiment showcases the…

Synthesis of (Z)-alkenes is challenging because the (E) stereoisomers are usually more stable. Energy transfer photocatalysis has emerged as an efficient strategy for (E) [right arrow] (Z) alkene isomerization. We report the development of an advanced undergraduate laboratory experiment that introduces students to contemporary organic…

Quinacridone red and violet are visually different colors, an observation confirmed by their visible reflectance spectra and CIE L*a*b* coordinates. However, their IR spectra are extremely similar. Though chemically identical, the two quinacridones are polymorphs. In this experiment, designed for and tested by nonscience majors, the pigments are…

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…

Spectroscopic methods of molecular structure identification and analysis constitute part of inorganic, organic, analytical, and physical chemistry in both undergraduate and postgraduate chemistry curricula. Despite the importance and complexity of the relevant concepts, it is only recently that studies on spectroscopy have started to appear in the…

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…

In this second-semester organic chemistry lab experiment, students work collaboratively using a combination of chemical synthesis and NMR spectroscopy to investigate the diastereoselectivity associated with the Meerwein-Ponndorf-Verley (MPV) reduction of two ketone substrates having carbonyl groups flanked by an [alpha]-chiral carbon with…

Space telescopes are some of the most precise and complicated machines ever built. Not only must they survive the harshness of space travel, but they also need to be incredibly accurate: misalignments by fractions of a millimetre can have huge effects on the quality of the images they capture. In 1990, the Hubble Space Telescope became the first…

Infrared (IR) spectra of biologically derived materials display distinct absorption bands correlating to individual macromolecules: protein, polysaccharide, lipid, and nucleic acids. A series of experiments aimed at teaching qualitative bioorganic spectroscopy using attenuated total reflectance (ATR) Fourier transform infrared (IR) with biological…

The NMR spectrometer is a commonly used spectroscopic instrument that records resonance frequencies of nuclei present in molecular systems. While the NMR frequencies fall within the radio frequency regime for a given molecular system, they are presented in terms of chemical shifts in the audio frequency regime, thereby having the versatility to be…

Purpurogallin (PPG), an orange-red crystalline compound from nutgalls and oak bark, is an exemplar of numerous, ubiquitous natural colorants, biosynthesized through oxidative dimerization-decarboxylation of phenolic compounds. It possesses antioxidant, anticancer, and anti-inflammatory effects. Herein, a robust method is presented to allow…

One of the most important aspects associated with the modern production of chemicals is sustainability. To teach students and young scientists to design their research in the spirit of "sustainable development," students should be made accustomed to seeking solutions that are not only efficient and cost-effective but also safe and…

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…

The imine condensation reaction is commonly addressed in second semester organic chemistry classrooms as imines and their derivatives are found in many pharmaceutical scaffolds and biological and catalytic processes. Despite this, imine condensations are still absent from many organic chemistry laboratory curriculums. The work discussed here…

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…