TIGER

Journal Articles: 25 results
Percy Julian, Robert Robinson, and the Identity of Eserethole  Addison Ault
The Nova production Percy JulianForgotten Genius, which included the very public disagreement over the identity of "eserethole," the key intermediate for the synthesis of the alkaloid physostigmine, left three important chemical questions unanswered.
Ault, Addison. J. Chem. Educ. 2008, 85, 1524.
Constitutional Isomers |
Enantiomers |
Natural Products |
Stereochemistry |
Synthesis
Regioselectivity in Organic Synthesis: Preparation of the Bromohydrin of α-Methylstyrene  Brad Andersh, Kathryn N. Kilby, Meghan E. Turnis, and Drew L. Murphy
In the described experiment, the regiochemical outcome of the addition of "HOBr" to a-methylstyrene is investigated. Although both "classic" qualitative analysis and instrumental techniques are described, the emphasis of this experiment is on the utilization 13C and DEPT-135 NMR spectroscopy to determine the regiochemical outcome of the addition.
Andersh, Brad; Kilby, Kathryn N.; Turnis, Meghan E.; Murphy, Drew L. J. Chem. Educ. 2008, 85, 102.
Addition Reactions |
Alcohols |
Alkenes |
Constitutional Isomers |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Synthesis
Determination of the Rotational Barrier for Kinetically Stable Conformational Isomers via NMR and 2D TLC  Gregory T. Rushton, William G. Burns, Judi M. Lavin, Yong S. Chong, Perry Pellechia, and Ken D. Shimizu
After the synthesis of a N,N'-diaryl naphthalene diimide, students estimate the rotational barrier about a CarylNimidesingle bond by studying the reequilibration of the two resulting isomers using two-dimensional thin-layer chromatography, followed by a more accurate determination through a 1H NMR time study.
Rushton, Gregory T.; Burns, William G.; Lavin, Judi M.; Chong, Yong S.; Pellechia, Perry; Shimizu, Ken D. J. Chem. Educ. 2007, 84, 1499.
Alcohols |
Chromatography |
Conformational Analysis |
Equilibrium |
Kinetics |
NMR Spectroscopy |
Physical Properties |
Rate Law |
Thin Layer Chromatography
Developing Critical Thinking Skills: The "Sabotaged" Synthesis of Methyl p-Bromobenzoate  Eric J. Mahan and Mary Alice Nading
Before beginning an experiment, students are told that someone might have sabotaged their experiment to produce other-than-expected results. The objective is to perform the experiment, determine if any sabotage has occurred, and, if so, identify the changes that were made to the reagents as well as the person responsible.
Mahan, Eric J.; Nading, Mary Alice. J. Chem. Educ. 2006, 83, 1652.
Alcohols |
Carboxylic Acids |
Esters |
IR Spectroscopy |
NMR Spectroscopy |
Mass Spectrometry |
Synthesis
Diastereoselectivity in the Reduction of α-Hydroxyketones. An Experiment for the Chemistry Major Organic Laboratory  David B. Ball
Describes a research type, inquiry-based project where students synthesize racemic ahydroxyketones using umpolung, a polarity-reversal approach; investigate chelating versus non-chelating reducing agents; and determine the diastereoselectivity of these reducing processes by NMR spectroscopy.
Ball, David B. J. Chem. Educ. 2006, 83, 101.
Addition Reactions |
Aldehydes / Ketones |
Chirality / Optical Activity |
Chromatography |
Conferences |
Constitutional Isomers |
Enantiomers |
NMR Spectroscopy |
Stereochemistry |
Synthesis |
Conformational Analysis
1H NMR Measurement of the Trans–Cis Photoisomerization of Cinnamic Acid Derivatives  Basil Danylec and Magdy N. Iskander
Procedure that illustrates trans-cis photoisomerization.
Danylec, Basil; Iskander, Magdy N. J. Chem. Educ. 2002, 79, 1000.
NMR Spectroscopy |
Photochemistry |
Stereochemistry |
Aromatic Compounds |
Alcohols |
Esters |
Alkenes |
Molecular Properties / Structure
Organic-Solvent-Free Phase-Transfer Oxidation of Alcohols Using Hydrogen Peroxide  Martin Hulce and David W. Marks
Six representative alcohols are oxidized to the corresponding aldehyde or ketone, integrating the various techniques of extraction, drying, filtration, column chromatography, gas chromatography, NMR and IR spectroscopy, and reaction kinetics.
Hulce, Martin; Marks, David W. J. Chem. Educ. 2001, 78, 66.
Catalysis |
Oxidation / Reduction |
Reactions |
Kinetics |
Chromatography |
Gas Chromatography |
Separation Science |
NMR Spectroscopy |
IR Spectroscopy |
Alcohols |
Phenols
Reduction of 2,6-Dimethylcyclohexanone with Sodium Borohydride Revisited: A Correction on the Structural Assignments of the Products, and the Discovery of a Solvent Effect  Bruce A. Hathaway
Changing the solvent from methanol to ethanol produced a different ratio of cis-cis to trans-trans than was reported in the original work. Therefore, a short series of solvents was investigated to determine if there was a solvent effect. The results indicate that as the size and bulk of the solvent increase, the proportion of the trans alcohol product increases.
Hathaway, Bruce A. J. Chem. Educ. 1998, 75, 1623.
Stereochemistry |
NMR Spectroscopy |
Aldehydes / Ketones |
Alcohols
The Dehydration of 2-Methylcyclohexanol Revisited: The Evelyn Effect  Todd, David
Modification to an earlier procedure that allows students to observe the results of a hydride shift mechanism.
Todd, David J. Chem. Educ. 1994, 71, 440.
Alcohols |
Mechanisms of Reactions |
Gas Chromatography |
Alkenes |
Elimination Reactions
Microscale yeast mediated enantiospecific reduction of vanillin, and the absolute configuration of (-)-(R)-[alpha]-deuteriovanillyl alcohol: A bioorganic chemistry experiment   Lee, Moses
An experiment is introduced to a sophomore chemistry course that demonstrates the effeciency and enantiospecificity of microbial/enzyme-mediated reactions and the use of NMR methods in determining the optical activity and absolute configuration of chiral alcohols.
Lee, Moses J. Chem. Educ. 1993, 70, A155.
Enantiomers |
Alcohols |
Bioorganic Chemistry |
Chirality / Optical Activity |
NMR Spectroscopy |
Microscale Lab
A kinetic study of the isomerization of eugenol: The quantitative use of NMR, GC, and HPLC in a single organic laboratory experiment that demonstrates alternative approaches to solving a problem   Peterson, Thomas H.; Bryan, James H.; Keevil, Thomas A.
Description of an experiment that allows students to be aware that there is often more than one approach to designing an experiment,and that the quality of the experimental results often depend on the proper choice of instrument(s).
Peterson, Thomas H.; Bryan, James H.; Keevil, Thomas A. J. Chem. Educ. 1993, 70, A96.
Aromatic Compounds |
NMR Spectroscopy |
Alcohols |
Kinetics
A source of isomer-drawing assignments  Kjonaas, Richard A.
A comprehensive source from which instructors can choose a wide variety of good isomer drawing examples to use as homework assignments and exam questions.
Kjonaas, Richard A. J. Chem. Educ. 1992, 69, 452.
Stereochemistry |
Alcohols |
Alkanes / Cycloalkanes |
Alkenes |
Aldehydes / Ketones |
Ethers |
Esters |
Alkynes
Hydroboration for the large organic laboratory  Pickering, Miles
This paper reports an experiment in hydroboration without large hood space requirements, without special glassware requirements, and without inert atmospheric precautions.
Pickering, Miles J. Chem. Educ. 1990, 67, 436.
Oxidation / Reduction |
Alkenes |
Alcohols |
Qualitative Analysis
A series of synthetic organic experiments demonstrating physical organic principles  Sayed, Yousry; Ahlmark, Chris A.; Martin, Ned H.
The sequence of reactions described here incorporates several common synthetic organic transformations involving alkenes, alcohols, alkyl halides, and ketones that demonstrate some important principles of physical organic chemistry.
Sayed, Yousry; Ahlmark, Chris A.; Martin, Ned H. J. Chem. Educ. 1989, 66, 174.
Synthesis |
Alkenes |
Alcohols |
Aldehydes / Ketones |
Reactions
Chemical applications of graph theory. Part II. Isomer enumeration  Hansen, Peter J.; Jurs, Peter C.
An in-depth look at the study of isomer enumeration.
Hansen, Peter J.; Jurs, Peter C. J. Chem. Educ. 1988, 65, 661.
Chemometrics |
Constitutional Isomers |
Alkanes / Cycloalkanes
Molecular structure: Property relationships  Seybold, Paul G.; May, Michael; Bagal, Ujjvala A.
How molecular structure can be represented mathematically and how this can lead to a better understanding of the connection between molecular structures and properties.
Seybold, Paul G.; May, Michael; Bagal, Ujjvala A. J. Chem. Educ. 1987, 64, 575.
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Alcohols
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
The determination of the stereochemistry of erythro-1,2-diphenyl-1,2-ethanediol: an undergraduate organic experiment  Rowland, Alex T.
The author describes a successful experiment that has been conducted by first-year organic chemistry students which illustrates the power of H NMR spectroscopy in a configuration determination.
Rowland, Alex T. J. Chem. Educ. 1983, 60, 1084.
Phenols |
Alcohols |
NMR Spectroscopy |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
Student preparation of alkanols from alkenes  McKee, J. R.; Kauffman, J. M.
The hydration of 1-hexene to form 2-hexanol demonstrates Markovnikov addition, produces a higher yield of alcohol, and starts with a less expensive alkene than cyclohexene hydrations.
McKee, J. R.; Kauffman, J. M. J. Chem. Educ. 1982, 59, 695.
Alcohols |
Alkenes |
Mechanisms of Reactions |
Addition Reactions
Stereochemical nonequivalence of ligands and faces (heterotopicity)  Eliel, Ernest L.
Reviews the concepts associated with stereochemical non-equivalence (heterotopicity).
Eliel, Ernest L. J. Chem. Educ. 1980, 57, 52.
Stereochemistry |
Enantiomers |
Diastereomers |
Constitutional Isomers |
Group Theory / Symmetry
Syntheses and rearrangements of cage molecules related to cubane  Jefford, Charles W.
This article looks at the synthesis of cubane, basketene, miscellaneous homocubane chemistry, snoutene, triqunacene, hypostrophene, tris-homocubane, and catalysis by transition metals.
Jefford, Charles W. J. Chem. Educ. 1976, 53, 477.
Catalysis |
Transition Elements |
Alkenes |
Synthesis |
Aromatic Compounds |
Heterocycles |
Alcohols
Saving a life with alcohol  Scala, A. A.
Using alcohol as a treatment for ethylene glycol poisoning.
Scala, A. A. J. Chem. Educ. 1973, 50, 365.
Alcohols |
Toxicology |
Metabolism |
Constitutional Isomers
Periodate cleavage of glycols: A quantitative organic analysis experiment  Schenk, George H.
This reaction is much used by organic chemists and uses the familiar standard solutions of iodine and sodium arsenite, common buffers, and stable organic glycols, such as ethylene glycol and pinacol.
Schenk, George H. J. Chem. Educ. 1962, 39, 32.
Quantitative Analysis |
Alcohols |
Reactions
Aspects of isomerism and mesomerism. III. Stereoisomerism  Bent, Richard L.
Examines the tetrahedral nature of carbon, multiple bonds, enantiomorphism, diastereoisomerism, and geometric isomerism.
Bent, Richard L. J. Chem. Educ. 1953, 30, 328.
Molecular Properties / Structure |
Enantiomers |
Diastereomers |
Constitutional Isomers
Aspects of isomerism and mesomerism. II. Structural isomerism  Bent, Richard L.
Examines the relationship between structural, optical, and geometric isomerism.
Bent, Richard L. J. Chem. Educ. 1953, 30, 284.
Molecular Properties / Structure |
Constitutional Isomers |
Enantiomers |
Diastereomers