TIGER

Journal Articles: 12 results
Borohydride Reduction of Estrone  Animesh Aditya, David E. Nichols, and G. Marc Loudon
This experiment presents a guided-inquiry approach to the demonstration of diastereoselectivity using chiral hindered ketones that undergo facile reduction with sodium borohydride. The resulting diastereomeric estradiols can be analyzed and differentiated by thin-layer chromatography and melting point.
Aditya, Animesh; Nichols, David E.; Loudon, G. Marc. J. Chem. Educ. 2008, 85, 1535.
Aldehydes / Ketones |
Diastereomers |
IR Spectroscopy |
Microscale Lab |
Stereochemistry |
Steroids |
Thin Layer Chromatography
Chemical Aspects of General Anesthesia: Part II. Current Practices  Robert Brunsvold and Daryl L. Ostercamp
With the basic elements of balanced general anesthesia in place by the 1950s, the focus turned to developing safer and more effective agents and to improving procedures. During the last half-century a new generation of intravenous induction anesthetics, inhalational anesthetics, and muscle relaxants has emerged.
Brunsvold, Robert; Ostercamp, Daryl L. J. Chem. Educ. 2006, 83, 1826.
Bioorganic Chemistry |
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Synthesis
The Step-by-Step Robinson Annulation of Chalcone and Ethyl Acetoacetate. An Advanced Undergraduate Project in Organic Synthesis and Structural Analysis  Lionel Delaude, Jean Grandjean, and Alfred F. Noels
The Robinson annulation is a three-step process involving a Michael addition followed by an internal aldol condensation and a dehydration. It is possible to stop the reaction after every step and to isolate the three products, allowing students to confirm the validity of the stepwise mechanism and develop a more thorough understanding of the whole process.
Delaude, Lionel; Grandjean, Jean; Noels, Alfred F. J. Chem. Educ. 2006, 83, 1225.
Catalysis |
Chirality / Optical Activity |
Conformational Analysis |
Diastereomers |
IR Spectroscopy |
Synthesis |
NMR Spectroscopy |
Stereochemistry
Acetal Protecting Groups in the Organic Laboratory: Synthesis of Methyl 4,6-O-Benzylidene-α-D-Glucopyranoside  Alexei V. Demchenko, Papapida Pornsuriyasak, and Cristina De Meo
The synthesis of methyl 4,6-O-benzylidene-a-D-glucopyranoside provides an opportunity to synthesize a cyclic acetal; stereoselectively introduce a chirality center; and learn extraction, evaporation, precipitation, optical rotation, melting point measurement, thin-layer chromatography, IR-spectroscopy, mass spectrometry, and various NMR techniques.
Demchenko, Alexei V.; Pornsuriyasak, Papapida; De Meo, Cristina. J. Chem. Educ. 2006, 83, 782.
Carbohydrates |
IR Spectroscopy |
Medicinal Chemistry |
NMR Spectroscopy |
Thin Layer Chromatography |
Synthesis
Cholesterol and Plants  E. J. Behrman and Venkat Gopalan
Current textbooks give an inaccurate picture of the occurrence of cholesterol in plants and the role of plant sterols in the mammalian uptake of cholesterol.
Behrman, E. J.; Gopalan, Venkat. J. Chem. Educ. 2005, 82, 1791.
Metabolism |
Plant Chemistry |
Steroids
Microscale Synthesis and Spectroscopic Analysis of Flutamide, an Antiandrogen Prostate Cancer Drug  Ryan G. Stabile and Andrew P. Dicks
The synthesis involves N-acylation of a trisubstituted aromatic compound, 3-trifluoromethyl-4-nitroaniline. The procedure is easily adapted to generate structural analogues of flutamide. A significant feature is the curricular flexibility afforded by this experiment.
Stabile, Ryan G.; Dicks, Andrew P. J. Chem. Educ. 2003, 80, 1439.
Drugs / Pharmaceuticals |
IR Spectroscopy |
Mechanisms of Reactions |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Aromatic Compounds
The Michael Reaction  Thomas Poon, Bradford P. Mundy, and Thomas W. Shattuck
Biography, overview, computational analysis, and examples of the Michael reaction in organic syntheses and natural systems.
Poon, Thomas; Mundy, Bradford P.; Shattuck, Thomas W. J. Chem. Educ. 2002, 79, 264.
Computational Chemistry |
Synthesis |
Mechanisms of Reactions
The Sassafras Tree and Designer Drugs: From Herbal Tea to Ecstasy  French, Larry G.
Using historical development of material from the sassafras tree and elicit synthesis of the drug ecstasy (MDMA) as a venue for presenting methodology for amine synthesis in organic chemistry.
French, Larry G. J. Chem. Educ. 1995, 72, 484.
Drugs / Pharmaceuticals |
Synthesis |
Enrichment / Review Materials |
Molecular Properties / Structure
Preparation of (S)-(+)-5,8a-Dimethyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione: An Undergraduate Experiment in Asymmetric Synthesis  Markgraf, J. Hodge; Fei, John F.; Ruckman, Robert E.
An asymmetric Robinson annelation suitable for the undergraduate organic laboratory.
Markgraf, J. Hodge; Fei, John F.; Ruckman, Robert E. J. Chem. Educ. 1995, 72, 270.
Synthesis |
Chirality / Optical Activity |
Aldehydes / Ketones
Carbon-11: Where familiar chemistry still holds new challenges  Feliu, Anthony L.
Organic synthesis for biomedical applications with carbon-11 is made feasible by the high activities which can be cyclotron produced compared to the quantity required for a patient study.
Feliu, Anthony L. J. Chem. Educ. 1990, 67, 364.
Isotopes |
Synthesis
Microscale organic laboratory: IV: A simple and rapid procedure for carrying out Wittig reactions  Pike, R. M.; Mayo, D. W.; Butcher, D. W.; Butcher, S. S.; Hinkle, R. J.
This paper offers two examples that illustrate a new synthetic method. This synthesis is the first feasible preparation of a particular group available for the introductory organic laboratory.
Pike, R. M.; Mayo, D. W.; Butcher, D. W.; Butcher, S. S.; Hinkle, R. J. J. Chem. Educ. 1986, 63, 917.
Synthesis |
Aromatic Compounds |
Heterocycles |
Alkenes |
Alcohols
Alicyclic chemistry: The playground for organic chemists  Ferguson, Lloyd N.
This article reviews a number of general topics that have been of special interest in alicyclic chemistry, including conformational analysis, the nonclassical versus classical norbornyl cation, Woodward-Hoffmann electrolytic rules, the aromaticity of nonbenzoid rings, strained ring systems, bridgehead activity, and photochemical syntheses and rearrangements.
Ferguson, Lloyd N. J. Chem. Educ. 1969, 46, 404.
Conformational Analysis |
Synthesis |
Photochemistry