The free radical chlorination of an alkane experiment is often used in the undergraduate laboratory curriculum to introduce students to the free radical mechanism, substituent effects, intermediate stability, and the relative reactivity of radicals. In this experiment, students monochlorinate multiple alkanes and analyze the reaction mixture using…

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,…

The American Chemical Society advocates a shift from rule-based to risk-based safety education for chemistry graduates, emphasizing meaningful student engagement in the risk assessment process for laboratory work. To implement this paradigm shift, we introduced RAMP (Recognize Hazards, Assess Risk, Minimize Risk, and Prevent Emergencies)-based…

The thermal equilibration of himic anhydride [IUPAC (2-"endo,"3-"endo")-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride] to (2-"exo,"3-"exo")-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride and subsequent recrystallization of the "exo"-product can be performed as a standard…

A straightforward protocol for the preparation of the colorful and air-stable diphenyl ditelluride is described. In one laboratory session, students isolate their product and characterize it via melting point determination, mass spectrometry, and NMR spectroscopy ([superscript 1]H, [superscript 13]C­{[superscript 1]H}, and [superscript…

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…

In this study, students' understanding of some important features of competitive elimination and substitution reactions of alcohols was examined based on their participation in a guided inquiry activity of two organic laboratory experiments: the dehydration of cyclohexanol and the conversion of tert-butyl alcohol into tert-butyl chloride. Students…

A computational experiment investigating common organic chemistry mechanisms has been developed and implemented in a junior/senior-level physical chemistry laboratory course at two institutions. Students investigated various reactions that proceed via S[subscript N]1, S[subscript N]2, E1, and E2 mechanisms using hybrid Density Functional Theory…

A two-week summer camp was designed, implemented, and then updated for high school students focusing on organic chemistry, solar energy, and green chemistry principles. Students learn about laboratory safety, perform organic reactions, go on field trips, and take part in interactive lessons that focus on both fundamental chemistry topics as well…

A safe, convenient, and environmentally benign laboratory experiment for the synthesis of biodiesel from six kinds of vegetable oils has been developed for the introductory organic chemistry laboratory. The experiment uses ultrasonic irradiation in the presence of a base catalyst at room temperature and atmospheric pressure. Because of safer and…

A laboratory experiment is detailed that entails the separation and derivatization of the artificial sweetener sucralose from a commercially available sweetener mixture. The experiment utilizes 1 g packets of a sucralose-based artificial sweetener and involves the separation of the synthetic sweetener from the more polar bulk additives by…

A laboratory experiment introducing the concept of chemical bioconjugation of proteins to undergraduate students in a therapeutically relevant context was developed. Initially, students installed an aldehyde functionality into a protein via the oxidation of the N-terminal threonine residue of the cholera toxin subunit B (CTB) protein, which was…

The development of an enzyme-mediated reaction for the first-year general, organic, and biological chemistry (GOB) teaching laboratory is of significant importance so that the factors that affect enzyme-mediated reactions can be adequately demonstrated, reinforcing the lecture portion of the GOB course. Some of the factors that affect these types…

Experiments written for students who were quarantined during the COVID-19 pandemic are described. These were developed to provide hands-on lab experiences that students would not get due to the online nature of course offerings during the crisis. The laboratories described include an extraction and oxidation of aldehydes from food items, a study…

Given student familiarity with electronic cigarettes (e-cigs), this lab uses a student-built smoke collection apparatus to collect e-cig vapors to teach students about gas chromatography-mass spectrometry (GC-MS). Students in a second semester, introductory organic chemistry course spent 1 week collecting e-cig vapors and 1 week qualitatively…