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…

This experiment combines analytical techniques of solid-phase extraction (SPE) and gas chromatography quadrupole time-of-flight mass spectrometry (GC-QTOF-MS) to determine organochlorine pesticides (OCPs) in river water as a means to develop and improve student understanding of the use of GC-QTOF-MS for qualitative and quantitative analysis. In…

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…

A set of inexpensive and pedagogically rich experiments focusing on S[subscript N]1, E1, and E2 reactions have been updated to include modern computational and spectroscopic analyses. The S[subscript N]1 experiment involves treatment of "tert"-amyl alcohol with hydrochloric acid to generate the corresponding alkyl chloride, which is used…

Biodiesel is an important biomass, largely employed in the transport sector and produced from vegetable oils. Additionally, waste cooking oils may be reused to produce biodiesel fuel, minimizing environmental pollution. A laboratory experiment that affords a widespread way to discuss degradation concepts and tools for used vegetable oil…

Carbohydrates are an essential group of molecules to the organic chemistry classroom providing molecular relevance to a common ingredient in chemical biology. While the meticulous elucidation of the carbohydrate structures by Fischer and others is an engaging topic in the lecture, there are few laboratory experiments that can emulate carbohydrate…

A continuous flow photopinacol coupling of benzophenone has been developed and implemented in the undergraduate laboratory. This photoreduction was accomplished using 2-propanol as an H atom donor and cosolvent in the reaction. The simple and inexpensive UV light source and flow reactor design (less than $350/photochemical flow system) provide an…

Williamson ether experiments are commonly performed by students in undergraduate organic chemistry instructional laboratory courses. In this multioutcome experiment, students were provided 4-bromophenol and one of three alkyl halides: 1-bromopentane, 1-bromobutane, or 1-bromo-3-methylbutane. The alkyl halides served as the unknown component of the…

In this communication, we describe five at-home laboratory experiments and demonstrations that complement a semester-long analytical chemistry curriculum. The experiments were successfully carried out by remote undergraduate students enrolled in a hybrid analytical chemistry course during the COVID-19 pandemic. Students used their personal…

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…

[superscript 1]H NMR spectroscopy is a molecular characterization technique that is ubiquitously used in research and teaching laboratories alike. Strategic deuteration of molecules is a commonly employed technique in the deconvolution of [superscript 1]H NMR signals. Here this approach is applied in a second-year chemistry course in which…

A fluorometer is a device that measures the spectroscopic properties of fluorescent materials, and fluorometry is used widely in chemistry research settings to characterize fluorescent samples. One of the obstacles faced by undergraduate programs looking to implement fluorometer-based experiments into their laboratory curriculum is the high cost…

In this guided-inquiry lesson, students were tasked with determining the efficacy of an at-home drinking water filter at removing lead (Pb) from tap water using graphite furnace atomic absorption spectroscopy by determining the concentration of lead before and after filtration. The lesson was structured to allow students to choose and perform…

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…

Preprocessing is a critical step in the analysis pipeline of spectroscopic data. However, students are rarely introduced to preprocessing when learning spectral techniques in laboratory courses which in turn may affect and delay their progress in the field. Despite its undoubtable importance, students will be mainly performing spectroscopic…