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…

A laboratory exercise for the synthesis of a sulfonated styrene-"co"-maleic anhydride polymer and its application as a stain blocker on nylon-6,10, is described. The effectiveness of the sulfonated polymer to prevent the conjugate base of an acid dye from staining the polyamide is demonstrated. This experiment is designed for…

"N"-Formamides are important intermediates in the synthesis of many pharmacologically active compounds and are used as protecting groups for amines or as catalysts in different reactions. The current "N"-formylation experiment is designed as a part of an introductory organic chemistry course for undergraduate students. The…

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,…

Regioselectivity in hetero Diels-Alder reactions can be observed in a simple reaction between a nonsymmetrical heterodiene and an unsymmetrical heterodienophile. A 9 h and easy to implement laboratory experiment is described, in which students can observe the regioselectivity of inverse "electron-demand" hetero Diels-Alder reactions of…

We present an experiment designed to hone the decision-making skills of (undergraduate) chemistry students by using aqueous crossed aldol reactions. Here, we present two simple crossed aldol reactions based on inexpensive and readily available materials: The condensation of vanillin and cinnamaldehyde with acetone. The procedure uses the variation…

An undergraduate laboratory experiment for the synthesis of biologically significant bis-4-hydroxycoumarins using a new catalyst is described here. An experimental setup plan, monitoring the reaction by TLC, isolation of the product, safe laboratory handling procedures, and significance of data reproducibility of the result are the main learning…

A pedagogically useful undergraduate organic-chemistry-laboratory experiment has been developed that involves the synthesis of two structurally simple, achiral "O,O"- and "N,N"-acetal substrates with no stereocenters. The experiment introduces students to a "new" and more effective variant of classical acetal…

A simple, inexpensive, discovery-based experiment for undergraduate organic laboratories has been developed that demonstrates the Lewis acid and shape-selective properties of zeolites. Calcined zeolite Na-Y promotes the electrophilic aromatic bromination of toluene with a significantly higher para/ortho ratio than observed under conventional…

An experimental protocol that provides an excellent way to discuss concepts at the crossroads of organic chemistry and biochemistry employing biocatalysis is presented. By evaluating several reaction parameters (enzyme source, organic solvent, and acyl donor), it was possible to conduct an enzymatic kinetic resolution experiment using…

This synthesis of ethyl 6-acetoxyhexanoate (Berryflor) is designed as an experiment for use in a second-year organic chemistry course focusing on the synthesis and reaction of esters. The compound is described as having a raspberry-like odor with jasmine and anise aspects. A two-step procedure for its synthesis beginning with inexpensive…

The Clemmensen reduction is a common example of a reaction demonstrating the deoxygenation of carbonyl groups, which is a topic that has been widely studied in the field of organic chemistry. The use of trimethylchlorosilane, as a substitute for concentrated hydrochloric acid, allows for the reduction of carbonyl groups. The Clemmensen reduction…

A multistep experiment for a synthesis laboratory course that incorporates topics in organic synthesis, chemical analysis, and instrumental analysis was developed. Students prepared a tertiaryamine-functionalized polyacrylonitrile fiber (PAN[subscript T]F), and it was subsequently utilized as an immobilized catalyst in a three-component…

A one-day laboratory epoxidation experiment, requiring no purification, is described, wherein the students are given an "unknown" stereoisomer of 3-hexen-1-ol, and use [superscript 1]H NMR coupling constants to determine the stereochemistry of their product. From this they work backward to determine the stereochemistry of their starting…