A multi-session research-like module has been developed for use in the undergraduate organic teaching laboratory curriculum. Students are tasked with planning and executing the synthesis of a novel fluorous dye molecule and using it to explore a fluorous affinity chromatography separation technique, which is the first implementation of this technique in a teaching laboratory. Key elements of the project include gradually introducing students to the use of the chemical literature to facilitate their searching, as well as deliberate constraints designed to force them to think critically about reaction design and optimization in organic chemistry. The project also introduces students to some advanced laboratory practices such as Schlenk techniques, degassing of reaction mixtures, affinity chromatography, and microwave-assisted chemistry. This provides students a teaching laboratory experience that closely mirrors authentic synthetic organic chemistry practice in laboratories throughout the world.

A Research Module for the Organic Chemistry Laboratory: Multistep Synthesis of a Fluorous Dye Molecule

Organic syntheses : collective volumes I, II, III, IV, V cumulative indices

This article describes a wide range of commercially available UV–vis spectrometers, with particular emphasis on educational models, and how this technique can be included in all aspects of the chemistry curriculum. Portable instrumentation and new software technologies are also highlighted.

UV–Visible Spectrometers: Versatile Instruments across the Chemistry Curriculum

R,S-Ibuprofen dissolved in chiral and achiral solvents recrystallizes at varied pressure and temperature in the same racemic form I of monoclinic space group P21/c. At 4.0 GPa the crystal is compressed to 78% of its ambient-pressure volume. The main structural transformation is the compression of intermolecular van der Waals contacts, increasing the effects of intermolecular interactions in the crystal environment, which results in the more skew position of OH···O bonded carboxyl groups and more stabile H-atoms in the bistable H-bonds. Consequently, the H-atoms remain ordered in all pressure ranges investigated, despite the compression of the H-bonds by over 0.1 A at 4 GPa. The crystal compression and thermal expansion obey the reverse relationship rule of temperature and pressure effects; however, the compression is considerably nonlinear due to the strong reduction of void volume up to about 0.8 GPa.

High-Pressure Crystallization and Structural Transformations in Compressed R,S-Ibuprofen

Acetate, acetone, achiot (Spanish-–Colombia), achiote (Spanish–-Peru), achiote seeds, achiotillo, achiotin, annotta, annatto extract, annatto tree, aploppas, apocarotenoids, arnotta, arnotto (Nativ...

An Evidence-Based Systematic Review of Annatto (Bixa orellana L.) by the Natural Standard Research Collaboration

The synthesis of dyes has long been a popular topic in organic chemistry laboratory experiments because it allows students to see first hand that reactions learned in class can be used to make compounds with useful applications In this experiment electrophilic aromatic substitution reactions are used to synthesize several triarylmethane and xanthene dyes (fluorescein, erythrosin B, thymolphthalein, and rhodamine B) These dyes can be readily synthesized using equipment found in most common second-year organic labs Hydroscopic Lewis acids, which are often troublesome to use in a typical lab setup, are avoided The dyes synthesized in this experiment can each be completed in one four-hour laboratory session Approximately 30 minutes in a subsequent period will be required for UV�vis analysis, and the student samples give UV�vis spectra that match commercially available dye samples

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Synthesis of Triarylmethane and Xanthene Dyes Using Electrophilic Aromatic Substitution Reactions

In this experiment the over-the-counter pain reliever ibuprofen is resolved using (S)-(-)-α-phenethylamine as the resolving agent. This procedure has several key advantages over previous resolution experiments. First, it involves the resolution of a well-known medicinal compound of commercial importance. Second, the resolution process is simpler and more foolproof than previous experiments. Third, the product obtained at the end of the resolution process is chemically stable. Finally, the reagents used in this resolution are relatively inexpensive and easily obtained.

The Resolution of Ibuprofen, 2-(4'-Isobutylphenyl)propionic Acid

In this experiment the carotenoid bixin is isolated from annatto (Bixa orellana) seeds using column chromatography. The experiment has several key advantages over previous pigment separation experiments. First, unlike other experiments significant quantities of the carotenoid (typically 20 to 25 mg) can be isolated from small quantities of plant material. Second, in this experiment students learn how to choose the appropriate solvent for a chromatographic separation by analyzing several potential solvents using thin-layer chromatography. After isolation, the purified bixin is analyzed by UV�vis and IR spectroscopy.

Separation of the Carotenoid Bixin from Annatto Seeds Using Thin-Layer and Column Chromatography.

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 e-caprolactone is described. The first step involves an acid-catalyzed transesterification of the lactone to form ethyl 6-hydroxyhexanoate. Ethyl 6-hydroxyhexanoate is converted to the desired compound via acetylation under mildly basic conditions to give ethyl 6-acetoxyhexanoate in good yield. The product is characterized using 1H NMR spectroscopy, IR spectroscopy, gas chromatography, thin layer chromatography, and by comparison to commercial samples.

James V. McCullagh

Papers

Synthesis of Triarylmethane and Xanthene Dyes Using Electrophilic Aromatic Substitution Reactions

The Resolution of Ibuprofen, 2-(4'-Isobutylphenyl)propionic Acid

Separation of the Carotenoid Bixin from Annatto Seeds Using Thin-Layer and Column Chromatography.

Synthesis of the Commercial Fragrance Compound Ethyl 6-Acetoxyhexanoate: A Multistep Ester Experiment for the Second-Year Organic Laboratory