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…

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…

Starting with a double replacement reaction in alcohol between Ni(H[subscript 2]O)[subscript 6](NO[subscript 3])[subscript 2] and NaX, students exploit solubility differences to produce a solution of NiX[subscript 2] and a NaNO[subscript 3] precipitate. They then synthesize a bis(N,N-diethylethylenediamine) Ni(II) complex with chloride, bromide,…

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…

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 the last decades spectroscopy began to play an essential role in physics education research with the recognition that atomic spectra constitute a good occasion to study the concepts of quantum mechanics. Moreover, activities in which atomic spectra are studied in order to understand star structure and evolution have proved particularly engaging…

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…

Quantum dots are colloidal semiconductor nanocrystals that display size-dependent electronic and optical properties. These materials are a visual demonstration of a quantum-mechanical effect. Here we present a laboratory exercise for undergraduate/Bachelor students as an introduction to colloidal nanocrystals and quantum dots. The students…

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…

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…

Ultraviolet (UV)-visible (Vis) spectroscopy is widely used in all modern laboratories as a routine method of analysis. The monitoring of chemical reactions in an aqueous solution involving a gas product is a demanding task but particularly for oscillatory reactions which are obtainable in a narrow concentration range. In this work, the…

Low-dimensional materials especially graphene-based are of high interest to a broad community. One of the most fundamental aspects in the biomedical field is material characterization, which helps understand their property and tune for application. Though the existing teaching curricula are well standardized to include basic principles and…