An integrated laboratory experience in X-ray photoelectron spectroscopy (XPS) is designed for undergraduate and graduate students in chemistry, materials science, and other related fields. Focusing on ubiquitous Si, Cu, and their common oxides, students are guided to characterize a series of standard materials by XPS to understand the fundamentals…

Student engagement in evidence-based argumentation plays a central role in science education. These skills can be developed when identifying organic molecules from the spectroscopic data. Molecular structural analysis fosters deep procedural knowledge, as it involves (i) flexibly applying a set of procedures to extract information from spectra,…

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…

A method to synthesize biaryls through the Suzuki-Miyaura cross-coupling reaction using a recyclable fluorous precatalyst is described. This laboratory experiment, which demonstrates the safety benefits of green chemistry, is integrated into an upper-division course. Besides simply using the catalyst for a reaction, students can reuse the catalyst…

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…

The particle-in-a-box experiment is a well-known method used to teach quantum mechanics concepts in physical chemistry laboratories for undergraduates. The investigation involves measuring the wavelength at maximum absorbance ([lambda subscript max]) of electronic transitions in the UV-vis spectrum and linking it to the box length. As the…

The ability to elucidate the structure of organic compounds from their nuclear magnetic resonance (NMR), infrared (IR), and mass spectrometry (MS) spectra is an essential skill, particularly for those engaged in the fields of synthetic and analytical organic chemistry. Spectral analysis constitutes a fundamental component of the curriculum for all…

NMR prediction using ChemDoodle, NMR calculation with Gaussian, and hands-on data collection using a benchtop NMR spectrometer were explored to assess their synergistic capacity in teaching NMR to organic chemistry students. Nine molecules representing functional groups commonly encountered in undergraduate organic chemistry were selected. Spectra…

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,…

As an introduction to quadrupolar effects in NMR spectroscopy, students use low field ([superscript 1]H, 60 MHz), benchtop [superscript 13]C NMR spectroscopy to contrast the spin-spin coupling behavior of [superscript 13]C to the dipolar [superscript 1]H and quadrupolar [superscript 2]D in familiar solvents C(H/D)Cl[subscript 3], C(H/D)[subscript…

NMR spectroscopy is a powerful spectroscopic tool that not only allows the determination of structures after synthesis, as usually explained to students of Organic Chemistry, but also is useful in many other fields such as medicine imaging, real-time industrial processes, material sciences, or metabolomics. In this experiment, students performed a…

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…

A major obstacle that teachers face when they begin their spectroscopy lessons is the lack of a spectrophotometer, mostly due to its relatively high cost. In the present study, the construction of a low-cost do-it-yourself type of instrument is reported. Its construction, as a part of a problem-based scenario, would also help students to enhance…

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),…

Keto-enol tautomerism is a special example of structural isomerism. In this experiment, 6-chlorofulvene is predominantly yielded during the chlorination reaction of 6'-hydroxyfulvene with POCl[subscript 3] in the presence of DMF. The high regioselectivity of this reaction is dominated by intramolecular hydrogen-bonding and steric hindrance,…