This experiment presents a guided-inquiry approach to the demonstration of diastereoselectivity in an undergraduate organic chemistry laboratory. Chiral hindered ketones such as estrone, undergo facile reduction with sodium borohydride in a highly diastereoselective manner. The diastereomeric estradiols produced in the reaction can be analyzed and…

Separation techniques are usually presented in the undergraduate organic laboratory to teach students how to purify and isolate compounds. Often the concept of liquid chromatography is introduced by having students create "silica gel columns" to separate components of a reaction mixture. Although useful, column chromatography can be a laborious…

A microscale experiment is presented in which cyclohexene is dihydroxylated under three sets of conditions: epoxidation-hydrolysis, permanganate oxidation, and the Woodward dihydroxylation. The products of the reactions are determined by the use of thin-layer chromatography. Teams of students are presented with proposed mechanisms for each…

Thin-layer chromatography (TLC) is a very simple and effective technique that is used by chemists by different purposes, including the monitoring of the progress of a reaction. TLC can also be easily used for the analysis and identification of various acid-base indicator dyes.

The discovery that galantamine penetrates the blood-brain barrier has led to its clinical use in the treatment of choline-deficiency conditions in the brain, such as Alzheimer's disease. This experiment involves the isolation and structure elucidation of galantamine from "Leucojum aestivum". Isolation of the alkaloid constituents in "L. aestivum"…

A simple method for the quantitative determination of photosynthetic pigments extracted from green beans using thin-layer chromatography is proposed. Various extraction methods are compared, and it is shown how a simple flatbed scanner and free software for image processing can give a quantitative determination of pigments. (Contains 5 figures.)

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…

This laboratory experiment provides a safe and effective way to instruct undergraduate organic chemistry students about natural-product extraction, purification, and NMR spectroscopic characterization. On the first day, students extract dried habanero peppers with toluene, perform a pipet silica gel column to separate carotenoids from…

In this inquiry-based activity, the usefulness of thin-layer chromatography (TLC) to visualize the difference between spearmint and peppermint is explored. The experiment may be used in any class where TLC is discussed from high school to college. We have used this activity with science majors in an organic chemistry laboratory, with non-science…

A study conducted shows that if digital photography is combined with regular thin-layer chromatography (TLC), it could perform highly improved qualitative analysis as well as make accurate quantitative analysis possible for a much lower cost than commercial equipment. The findings suggest that digitally enhanced TLC (DE-TLC) is low-cost and easy…

Waste newspaper is pulped with acid and its cellulose is hydrolyzed. The resulting glucose syrup is fermented with yeast and distilled to give ethanol. The experiment highlights the potential of applied chemistry to confront problems of economic importance, that is, the effective utilization of biomass to reduce dependence on non-renewable…

Some of the important modern developments of thin-layer chromatography are introduced. Discussed are the theory and instrumentation of thin-layer chromatography including multidimensional and multimodal techniques. Lists 53 references. (CW)

A thin layer chromatography experiment of medical importance is described. The experiment involves extraction of lipids from simulated amniotic fluid samples followed by separation, detection, and scanning of the lecithin and sphingomyelin bands on TLC plates. The lecithin-to-sphingomyelin ratio is calculated. The clinical significance of this…

Presents activities that can be used to introduce thin-layer chromatography at the undergraduate level in relatively less developed countries and that can be performed with very simple and commonly available apparati in high schools and colleges. Activities include thin-layer chromatography with a test-tube, capillary feeder, burette, and rotating…

A novel experiment for the extraction of lycopene from tomato paste without the use of an organic solvent is described. The experiment employs polymer, green, and analytical chemistry. This environmentally friendly extraction is more efficient and requires less time than the traditional approach using an organic solvent. The extraction is…