The combination of organic synthesis and analytical chemistry into a related laboratory experiment is an excellent demonstration of the utility of making a compound to then be used further. Herein we describe an undergraduate laboratory experiment that involves the straightforward synthesis of an internal standard, ethyl 6-acetyloxyhexanoate, for…

The educational game "Make or Take" is designed to approach the notoriously challenging topic of organic synthesis in an entertaining and engaging way. In this unique, two-part game, teams of students are given identical lists of several synthetic transformations, each requiring multiple steps to complete. During the first part of the…

The laboratory experiment regarding esterification of ethylene glycol with acetic acid to ethylene glycol diacetate using resin catalysts in a continuous flow was designed to carry out the reaction in a flow through an inquiry-guided approach. Incorporating the burgeoning field of continuous flow chemistry into the educational infrastructure, the…

The Suzuki-Miyaura cross-coupling reaction, which is one of the most important methods for C-C bond formation in modern organic synthesis, exhibits broad functional group compatibility. A Suzuki-Miyaura cross-coupling protocol is reported that is suitable for demonstrating this compatibility in undergraduate laboratories. In this reaction, two…

Polymerization reaction media can have a profound effect on the physical properties of the resultant polymer. This phenomenon is showcased in a new experiment for the organic chemistry and polymer science teaching laboratories wherein the radical copolymerization of biobased [beta]-myrcene and dibutyl itaconate is performed using a nonhazardous…

We report on a simple, rapid, and room-temperature undergraduate-level experiment for gold nanoparticle synthesis, analysis, and utilization as a catalyst for the sodium-borohydride-assisted reduction of methylene blue and Congo red dyes. Typical procedures toward gold nanoparticle formation require an elaborate, lengthy synthesis (some requiring…

A robust laboratory protocol for the three-step synthesis of "p"-tolyl 2,3,4,6-tetra-"O"-benzoyl-1-thio-[beta]-d-glucopyranoside from commercial glucose pentaacetate is reported. The previously reported procedures have been modified to accommodate laboratories and students without proper training or equipment needed to conduct…

A broadly applicable semester-long course-based undergraduate research experience (CURE)-inspired organic II laboratory course was developed from an engaging story supported by the current literature surrounding paraben use in consumer products. The project involves the synthesis of brominated parabens followed by an investigation into the…

The implementation of environmentally friendly, solvent-free mechanochemical synthesis in an undergraduate chemistry teaching laboratory is described. As a model reaction, the experiment addresses the catalytic mechanochemical synthesis of a small library of sulfonylureas, including a known active pharmaceutical ingredient, tolbutamide. The…

In order to introduce the concepts of biocatalysis and its utility in synthesis to organic chemistry students, a multistep synthesis of endogenous cannabinergic ligand 2-arachidonoylglycerol (2-AG) was tailored for use as a laboratory exercise. Over four weeks, students successfully produced 2-AG, purifying and characterizing products at each…

This paper describes a first-year undergraduate exercise involving the synthesis of an "unknown" polyiodide salt, (NMe[subscript 4])[I[subscript 5]], and the determination of its formula using the classic iodine-thiosulfate (iodometric) titration. The exercise introduces students to simple synthetic and titrimetric techniques, assists…

The effects of kinetic vs thermodynamic control on "endo"/"exo" stereoisomer ratios can be observed in a simple Diels-Alder reaction between "N"-phenylmaleimide and furan. The use of microwave-promoted synthesis affords the cycloadducts in yields ranging from 65-100%, employing reaction times of 1-10 min at…

Describes a laboratory exercise illustrating the use of the Cannizzaro reaction in synthesis, the production of commercial resin, and the importance of natural products in industrial chemistry. (SL)

Presents an account of the life of Otto Diels and explains his research on the constitution of cholesterol, the Diels-Alder reaction, and synthesis of cantharadin. (GS)

An undergraduate experiment combining synthesis, NMR analysis and mechanistic understanding is reported. The students perform an organocatalyzed cyclopropanation reaction of (E)-dec-2-enal and are then required to determine the diastereoselectivity and assign the relative configuration of each product using NMR spectroscopy.