Asking students to explain why phenomena occur at a molecular level is vital to increasing their understanding of chemistry concepts. One way to elicit students' mechanistic reasoning and guide construction of knowledge is through Writing-to-Learn (WTL), which is a promising approach for students in organic chemistry courses. In the design of WTL…

An experiment for the undergraduate organic chemistry laboratory involving a method for the isolation of eugenol from cloves has been developed. The experiment employs microwave-assisted extraction (MAE) of the essential oil from whole cloves using aqueous ethanol and the subsequent isolation of eugenol by acid-base extraction. The MAE allows for…

The complete structural analysis and resynthesis of an unknown compound, selected from a library of dipeptides, provided a framework for a course that built from expository experiments toward a guided-inquiry approach. We used this semester-long lab as a replacement for conventional second semester organic chemistry laboratory and successfully…

Educators at Mississippi State University developed an at-home, kitchen chemistry style laboratory to accompany the Survey of Organic Chemistry lecture course. The course featured 12 lab activities; eight hands-on experiences that focused primarily on important organic concepts including acid strength, extraction techniques, chromatographic…

In this experiment for an introductory undergraduate organic chemistry lab, students tetraalkylate tertbutylcalix[4]arene, a bowl-shaped macrocyclic oligophenol, and examine the supramolecular chemistry of the tetraether product by proton nuclear magnetic resonance (NMR) spectroscopy. Complexation with a sodium ion reduces the conformational…

A multistep synthesis of quinolone antibiotic analogues was developed as a laboratory experiment for intermediate/advanced undergraduate students. Students can synthesize a range of "des"fluoroenoxacin analogues via a five-step sequence. The experiment includes a range of key practical laboratory techniques including thin-layer…

Imines are important in biological chemistry and as intermediates in organic synthesis. An experiment for introductory undergraduate organic chemistry is presented in which benzaldehyde was condensed with "p"-methoxyaniline in toluene to give 4-methoxy-"N"-(phenylmethylene)benzenamine. Water was removed by azeotropic…

A reliable method for bleach-based alcohol oxidation has been developed. Use of sodium bisulfate as the acid additive in the reaction mixture eliminates the various problems associated with acetic acid, which has commonly been used for this type of oxidation. By conducting the reaction in an ethyl acetate/water two-phase reaction mixture,…

A new two-step experiment has been designed and developed for the curriculum of the Organic Chemistry Laboratory 2 (CHEM2240L) sophomore course at Xavier University of Louisiana, in New Orleans. Initially, cyclohexanol was converted to cyclohexanone using bleach as the oxidizing agent followed by the formation of the cyclohexanone oxime. However,…

Fluency in both the construction and interpretation of molecular structures is a critical learning objective in the second-year organic chemistry curriculum. With the introduction of PerkinElmer's ChemDraw structure drawing tool into undergraduate laboratory courses, students are challenged to develop fundamental molecular drawing skills using…

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…

Amides are usually prepared using amines and acyl halides, which often implies a two-step procedure. Alternatively, coupling reagents can be used in a single-step reaction with good yields, which seems to be suitable for organic chemistry laboratory classes. This work was designed to synthesize "N"-hexylcinnamamide through a one-step…

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…

A simple, microscale experiment was developed with the aim of demonstrating the concept of umpolung in synthetic organic chemistry. Starting from a common alkyl sulfinate, students perform a polarity inversion by performing a Grignard-based sulfoxide synthesis and a Mannich-type formamide synthesis. The products are purified without chromatography…

An integrated laboratory experiment applying concepts and techniques developed in organic chemistry, inorganic chemistry, and instrumental analysis is presented for use by students interested in undergraduate research. The experiment incorporates some advanced laboratory practices such as multistep organic synthesis and purification, detailed…