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…

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…

Short chain fatty acids (SCFAs) are produced in the gut as a result of microbial action on ingested dietary fiber and have been associated with several health benefits. Herein an undergraduate student experiment that uses gas chromatography equipped with either a flame ionization detector or mass spectrometer for the analysis and quantitation of…

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…

This study highlights the importance of incorporating modern mass spectrometry techniques into undergraduate education. By focusing on the structure-characterizing capability of MS, students are able to gain hands-on experience with cutting-edge techniques and better understand how MS can be used to solve real-world problems. The three-step lipid…

In this laboratory teaching experiment, commercial cannabis oils were analyzed by undergraduate organic chemistry students using gas chromatography-mass spectrometry (GC-MS) to investigate three isomeric cannabinoids commonly found in cannabis products: cannabidiol (CBD), [delta][superscript 9]-tetrahydrocannabinol ([delta][superscript 9]-THC),…

In this laboratory experiment, first-semester organic chemistry students use mechanistic reasoning to propose possible outcomes for the reaction of vanillin isobutyrate with a hydride source. The students subsequently run the reaction, isolate the product, and acquire its infrared spectrum. The experiment provides students with the opportunity to…

Raman scattering spectroscopies are important analytical tools in modern chemistry. Here, we describe the construction of the unamplified Raman scattering analysis (URSA) instrument: an inexpensive, open-table Raman spectrometer that uses a 532 nm diode-pumped laser as a light source. Upon application of this spectrometer to DNA extracted from…

Nuclear magnetic resonance (NMR) spectroscopy is commonly introduced to students in the classroom, but its hands-on use in undergraduate laboratories is far less common. The significant costs to purchase and maintain a traditional high-field NMR spectrometer means that many institutions cannot offer this service to their students. Benchtop NMR…

Raman spectroscopy has become a popular analytical tool because of its ability to probe nondestructively and provide fingerprint information about materials. The advancements in the field of Raman spectroscopy and the expanding scope of applications warrant the introduction of the topic in the formal education curriculum. The introduction of Raman…

In this paper, we present a concise and technique-heavy route to the synthesis of dimedone for a second-year organic chemistry curriculum. Our preparation of dimedone guides students through a Michael addition followed by a Dieckmann cyclization, basic ester hydrolysis, and thermal decarboxylation, while allowing time for mechanistic discussion…

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…

General chemistry courses serve as foundational curriculum within most STEM undergraduate curricula, and hence, it is essential to assess student knowledge and application of learning outcomes for courses such as Introduction to Chemistry and Organic Chemistry. Within the United States, paper-and-pencil examinations are typical for measuring…

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…