| Journal Articles: 113 results |
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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
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The Iodochlorination of Styrene: An Experiment That Makes a Difference R. Gary Amiet and Sylvia Urban
This purpose of this laboratory exercise is to determine the various substitution and elimination products generated in the iodochlorination of styrene and their relative proportions through the application of mechanistic principles and a basic knowledge of GCMS and NMR.
Amiet, R. Gary; Urban, Sylvia. J. Chem. Educ. 2008, 85, 962.
Alkenes |
Constitutional Isomers |
Gas Chromatography |
Instrumental Methods |
Mass Spectrometry |
Mechanisms of Reactions |
NMR Spectroscopy |
Synthesis |
Student-Centered Learning
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Evaluating Mechanisms of Dihydroxylation by Thin-Layer Chromatography Benjamin T. Burlingham and Joseph C. Rettig
Presents a microscale experiment in which cyclohexene is dihydroxylated under three sets of conditions and the products determined through thin-layer chromatography. Teams of students evaluate proposed mechanisms for each dihydroxylation in light of the data collected.
Burlingham, Benjamin T.; Rettig, Joseph C. J. Chem. Educ. 2008, 85, 959.
Addition Reactions |
Alkenes |
Diastereomers |
Mechanisms of Reactions |
Microscale Lab |
Stereochemistry |
Synthesis |
Thin Layer Chromatography
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A Simple Method for Drawing Chiral Mononuclear Octahedral Metal Complexes Aminou Mohamadou and Arnaud Haudrechy
This article presents a simple and progressive method to draw all of the octahedral complexes of coordination units with at least two different monodentate ligands and show their chiral properties.
Mohamadou, Aminou; Haudrechy, Arnaud. J. Chem. Educ. 2008, 85, 436.
Asymmetric Synthesis |
Chirality / Optical Activity |
Coordination Compounds |
Diastereomers |
Enantiomers |
Molecular Properties / Structure |
Stereochemistry |
Transition Elements
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Microwave-Assisted Organic Synthesis in the Organic Teaching Lab: A Simple, Greener Wittig Reaction Eric Martin and Cynthia Kellen-Yuen
A microwave-assisted Wittig reaction has been developed for the organic teaching laboratory. Utilizing this technique, a variety of styrene derivatives have been synthesized from aromatic aldehydes in good yields. The mixture of cis and trans alkenes produced also provides instructors with opportunities to emphasize the spectroscopic analysis of product mixtures.
Martin, Eric; Kellen-Yuen, Cynthia. J. Chem. Educ. 2007, 84, 2004.
Aldehydes / Ketones |
Alkenes |
Chromatography |
Green Chemistry |
Mass Spectrometry |
NMR Spectroscopy |
Spectroscopy |
Synthesis
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The Aromaticity of Pericyclic Reaction Transition States Henry S. Rzepa
Presents an approach that combines two fundamental concepts in organic chemistry, chirality and aromaticity, into a simple rule for stating selection rules for pericyclic reactions in terms of achiral Hckel-aromatic and chiral Mbius-aromatic transition states.
Rzepa, Henry S. J. Chem. Educ. 2007, 84, 1535.
Alkanes / Cycloalkanes |
Alkenes |
Aromatic Compounds |
Mechanisms of Reactions |
Stereochemistry
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Quantitative Measurement of Trans-Fats by Infrared Spectroscopy Edward B. Walker, Don R. Davies, and Mike Campbell
FTIR-ATR spectroscopy provides an efficient analytical tool to measure the percentage of trans-fat in several commercially available lipids and the degree of alkene isomerization induced by brominationdebromination chemical reactions.
Walker, Edward B.; Davies, Don R.; Campbell, Mike. J. Chem. Educ. 2007, 84, 1162.
Alkenes |
Calibration |
Food Science |
Instrumental Methods |
IR Spectroscopy |
Lipids |
Quantitative Analysis |
Fatty Acids
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Dynamic Stereochemistry: A Simple Approach To Delineating Relative Configuration Dipak K. Mandal
A simple approach is presented for delineating relative stereochemistry of the product in reactions involving stereogenic center(s).
Mandal, Dipak K. J. Chem. Educ. 2007, 84, 274.
Chirality / Optical Activity |
Diastereomers |
Enantiomers |
Molecular Properties / Structure |
Stereochemistry
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Precision in Stereochemical Terminology LeRoy G. Wade, Jr.
This article recommends that instructors use the precise terms asymmetric carbon atom and chirality center when they apply, and use the broader term stereocenter only when there is a need to include stereogenic atoms that are not chirality centers.
Wade, LeRoy G., Jr. J. Chem. Educ. 2006, 83, 1793.
Chemical Technicians |
Diastereomers |
Enantiomers |
Stereochemistry |
Nomenclature / Units / Symbols |
Chirality / Optical Activity
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Polar Addition to C=C Group: Why Is Anti-Markovnikov Hydroboration–Oxidation of Alkenes Not "Anti-"? Predrag-Peter Ilich, Lucas S. Rickertsen, and Erienne Becker
The authors redefine Markovnikov or anti-Markovnikov regioselectivity and propose that the teaching of organic chemistry should be based on robust and portable concepts such as energy difference and atomic charge rather than historical labels.
Ilich, Predrag-Peter; Rickertsen, Lucas S.; Becker, Erienne. J. Chem. Educ. 2006, 83, 1681.
Addition Reactions |
Alkenes |
Computational Chemistry |
Mechanisms of Reactions |
Molecular Modeling
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Rapid and Stereoselective Conversion of a trans-Cinnamic Acid to a β-Bromostyrene Thomas A. Evans
The stereoselective synthesis of an aryl vinyl bromide is accomplished in a rapid microscale reaction of trans-4-methoxycinnamic acid with N-bromosuccinimide in dichloromethane. This guided-inquiry experiment links reactivity, stereochemistry, and mechanism in electrophilic addition reactions of alkenes and in E1 and E2 elimination reactions that form alkenes.
Evans, Thomas A. J. Chem. Educ. 2006, 83, 1062.
Alkenes |
Carbocations |
Gas Chromatography |
Mechanisms of Reactions |
Microscale Lab |
NMR Spectroscopy |
Stereochemistry
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Regiospecific Epoxidation of Carvone: A Discovery-Oriented Experiment for Understanding the Selectivity and Mechanism of Epoxidation Reactions Kendrew K. W. Mak, Y. M. Lai, and Yuk-Hong Siu
Peroxy acids and alkaline H2O2 are two commonly used reagents for alkene epoxidation. The former react preferentially with electron-rich alkenes while the latter works better with a,-unsaturated carbonyl compounds. The selectivity of these two reagents on carvone, a naturally occurring compound that contains both types of C=C bonds, is investigated.
Mak, Kendrew K. W.; Lai, Y. M.; Siu, Yuk-Hong. J. Chem. Educ. 2006, 83, 1058.
Alkenes |
Chromatography |
Epoxides |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Mechanisms of Reactions
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A Sequence of Linked Experiments, Suitable for Practical Courses of Inorganic, Organic, Computational Chemistry, and NMR Spectroscopy Grigoriy A. Sereda
A sequence of investigations associated with the iodochlorination of styrene and 1-hexene is described. The sequence is flexible enough to be used in inorganic, organic, computational, and instrumental courses.
Sereda, Grigoriy A. J. Chem. Educ. 2006, 83, 931.
Alkenes |
Computational Chemistry |
Constitutional Isomers |
MO Theory |
NMR Spectroscopy |
Synthesis
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Grubbs's Cross Metathesis of Eugenol with cis-2-Butene-1,4-diol To Make a Natural Product. An Organometallic Experiment for the Undergraduate Lab Douglass F. Taber and Kevin J. Frankowski
Describes the ruthenium catalyzed cross metathesis of eugenol with cis-1,4-butenediol. The experiment is an excellent example of the powerful selectivity possible with the Grubbs' catalyst, demonstrating the preference for trans over cis alkene formation and for cross metathesis over homodimerization.
Taber, Douglass F.; Frankowski, Kevin J. J. Chem. Educ. 2006, 83, 283.
Alkenes |
Catalysis |
IR Spectroscopy |
Mass Spectrometry |
Mechanisms of Reactions |
Microscale Lab |
Natural Products |
NMR Spectroscopy |
Organometallics |
Stereochemistry |
Synthesis |
Thin Layer Chromatography |
Transition Elements
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A Template-Controlled Solid-State Reaction for the Organic Chemistry Laboratory Tomislav Friscic, Tamara D. Hamilton, Giannis S. Papaefstathiou, and Leonard R. MacGillivray
Describes a laboratory experiment that employs linear hydrogen-bond templates to direct [2 + 2] photodimerization in the solid state. The experiment introduces undergraduates to supramolecular and solid-state chemistry, as well as aspects of green chemistry.
Friscic, Tomislav; Hamilton, Tamara D.; Papaefstathiou, Giannis S.; MacGillivray, Leonard R. J. Chem. Educ. 2005, 82, 1679.
Green Chemistry |
Solid State Chemistry |
Crystals / Crystallography |
Alkenes |
Alkanes / Cycloalkanes |
Hydrogen Bonding |
Materials Science |
NMR Spectroscopy
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Diels–Alder Synthesis of endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide Marsha R. Baar and Kristin Wustholz
endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide was synthesized by a DielsAlder cycloaddition of 1,3-cyclohexadiene and N-phenylmaleimide in ethyl acetate. 1,3-Cyclohexadiene and N-phenylmaleimide were selected to illustrate the Alder rule, which reflects a preference for endo products and to overcome the difficulties associated with the traditional combination of 1,3-cyclopentadiene and maleic anhydride.
Baar, Marsha R.; Wustholz, Kristin. J. Chem. Educ. 2005, 82, 1393.
Asymmetric Synthesis |
Microscale Lab |
Stereochemistry |
Addition Reactions |
Alkenes |
IR Spectroscopy |
NMR Spectroscopy
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Cis and Trans Isomers of Cycloalkenes Susan E. Barrows and Thomas H. Eberlein
The purpose of this article is to provide that analysis. In order for a cycloalkene to accommodate a trans double bond one or more of the following nonideal geometries must occur: a twisted p bond; pyramidal sp2-carbon atoms; nonideal sp3 bond angles; or longer than normal CC single and double bonds. This article provides a list of experimentally determined relative energies of the cis and trans isomers within the series cycloheptenecycloundecene, along with computationally derived energies at several levels of theory. It also examines the geometric distortions through which cycloalkenes relieve the strain introduced by a trans double bond.
Barrows, Susan E.; Eberlein, Thomas H. J. Chem. Educ. 2005, 82, 1334.
Computational Chemistry |
Molecular Modeling |
Alkenes |
Diastereomers
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Understanding Rotation about a C=C Double Bond Susan E. Barrows and Thomas H. Eberlein
We present a simple method of introducing the concept of a flexible C=C pi bond into beginning organic chemistry courses. We report the energetic demands of partial twisting about the C=C bond in 2-butene as calculated using DFT, LMP2, and MCSCF methods. Finally, using the results of these calculations, we assessed the degree of strain introduced by the twisted nature of the C=C bond in trans cycloalkenes.
Barrows, Susan E.; Eberlein, Thomas H. J. Chem. Educ. 2005, 82, 1329.
Computational Chemistry |
Molecular Mechanics / Dynamics |
Molecular Modeling |
Alkenes
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The Addition of Bromine to 1,2-Diphenylethene Judith C. Amburgey-Peters and LeRoy W. Haynes
We investigated the reaction of (Z)-1,2-diphenylethene (cis-stilbene) with various brominating reagents and solvents following directions in standard organic chemistry manuals. We were particularly interested in learning which combination of brominating reagent and solvent gave the best yield of (d,l)-1,2-dibromo-1,2-diphenylethane without the formation of significant amounts of meso-1,2-dibromo-1,2-diphenylethane, which is essentially the sole product from the reaction of bromine with (E)-1,2-diphenylethene (trans-stilbene). Based on the results from the standard preparatory methods, some permutations of solvent and brominating reagent were tried.
Amburgey-Peters, Judith C.; Haynes, LeRoy W. J. Chem. Educ. 2005, 82, 1051.
Addition Reactions |
Alkenes |
Carbocations |
Diastereomers |
Enantiomers |
Mechanisms of Reactions |
Stereochemistry
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An Engaging Illustration of the Physical Differences among Menthol Stereoisomers Edward M. Treadwell and T. Howard Black
The differences and similarities in the physical behavior of enantiomers and diastereomers can easily be demonstrated using the commercial stereoisomers (-)-menthol, (+)-menthol, (+)-isomenthol, and (+)-neomenthol. Thin-layer chromatography and melting point determinations clearly show that diastereomers have different physical properties from enantiomers and each other, but that enantiomers have identical physical properties in achiral environments. By obtaining a mixed melting point and optical rotations the difference in enantiomers can be observed.
Treadwell, Edward M.; Black, T. Howard. J. Chem. Educ. 2005, 82, 1046.
Chirality / Optical Activity |
Stereochemistry |
Thin Layer Chromatography |
Diastereomers |
Enantiomers |
Physical Properties
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The Evolution of a Green Chemistry Laboratory Experiment: Greener Brominations of Stilbene Lallie C. McKenzie, Lauren M. Huffman, and James E. Hutchison
We describe two new greener alkene bromination reactions that offer enhanced laboratory safety and convey important green chemistry concepts, in addition to illustrating the chemistry of alkenes. The two alternative reactions, one involving pyridinium tribromide and a second using hydrogen peroxide and hydrobromic acid, are compared to the traditional bromination of stilbene through the application of green metrics, including atom economy, percent experimental atom economy, E factor, and effective mass yield.
McKenzie, Lallie C.; Huffman, Lauren M.; Hutchison, James E. J. Chem. Educ. 2005, 82, 306.
Synthesis |
Green Chemistry |
Aromatic Compounds |
Addition Reactions |
Alkenes
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The Sharpless Asymmetric Dihydroxylation in the Organic Chemistry Majors Laboratory Christopher J. Nichols and Melissa R. Taylor
A six-period laboratory exercise has been developed that uses the convenient Sharpless asymmetric dihydroxylation (AD) to illustrate the principles of a chiral synthesis. Using one particular alkene, students perform a racemic dihydroxylation, an AD using a commercially available AD-mix, and then an AD using an ester derivative of dihydroquinidine that they synthesized themselves. The structures of the products are confirmed with 1H NMR spectroscopy and the enantiomeric excesses of the diols are determined using a chiral GC column.
Nichols, Christopher J.; Taylor, Melissa R. J. Chem. Educ. 2005, 82, 105.
Chirality / Optical Activity |
Chromatography |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Alkenes |
Addition Reactions
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Cis and Trans Isomerization in Cyclic Alkenes: A Topic for Discovery Using the Results of Molecular Modeling Susan E. Barrows and Thomas H. Eberlein
This article describes an activity in which students are led to discover the fundamental reasons behind the unusual instability of the trans isomers in medium-sized cycloalkenes by using the results of molecular modeling. Notably, students will make the unexpected discovery that twisting about p bonds is perhaps more facile than they had been led to believe.
Barrows, Susan E.; Eberlein, Thomas H. J. Chem. Educ. 2004, 81, 1529.
Covalent Bonding |
Computational Chemistry |
Molecular Modeling |
Alkenes |
Molecular Properties / Structure
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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
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Fractional Distillation and GC Analysis of Hydrocarbon Mixtures Craig J. Donahue
Separating and identifying the components of a three-hydrocarbon mixture through fractional distillation and gas chromatography.
Donahue, Craig J. J. Chem. Educ. 2002, 79, 721.
Chromatography |
Gas Chromatography |
Separation Science |
Alkanes / Cycloalkanes |
Alkenes |
Aromatic Compounds |
IR Spectroscopy |
NMR Spectroscopy |
Qualitative Analysis
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Effect of Anisotropy on the Chemical Shift of Vinyl Protons in trans- and cis-1,2-Dibenzoylethylenes. A Small-Group or Recitation Activity Roosevelt Shaw, David Roane, and Sean Nedd
Procedure to help students explain chemical shift differences for vinyl protons in alkene diastereomers.
Shaw, Roosevelt; Roane, David; Nedd, Sean. J. Chem. Educ. 2002, 79, 67.
Magnetic Properties |
NMR Spectroscopy |
Undergraduate Research |
Diastereomers |
Aromatic Compounds |
Alkenes |
Photochemistry |
Molecular Properties / Structure
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Synthesis and Analysis of a Solvatochromic Dye, 1-(p-Dimethylaminophenyl)-2-nitroethylene. An Advanced Undergraduate Laboratory Experiment Dana L. Richter-Egger, Aaron Tesfai, Spencer J. Flamm, and Sheryl A. Tucker
Synthesis and analysis of 1-(p-dimethylaminophenyl)-2-nitroethylene.
Richter-Egger, Dana L.; Tesfai, Aaron; Flamm, Spencer J.; Tucker, Sheryl A. J. Chem. Educ. 2001, 78, 1375.
Fluorescence Spectroscopy |
Synthesis |
Undergraduate Research |
UV-Vis Spectroscopy |
Dyes / Pigments |
Amines / Ammonium Compounds |
Aromatic Compounds |
Alkenes
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Looking beyond the endo Rule in a Diels-Alder Discovery Lab Ronald M. Jarret, Jamie New, Rebecca Hurley, and Laura Gillooly
Procedure to introduce preference for generation of the endo product and the stereochemistry of alkene addition of the Diels-Alder reaction.
Jarret, Ronald M.; New, Jamie; Hurley, Rebecca; Gillooly, Laura. J. Chem. Educ. 2001, 78, 1262.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Alkenes
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The Discovery-Oriented Approach to Organic Chemistry. 5. Stereochemistry of E2 Elimination: Elimination of cis- and trans-2-Methylcyclohexyl Tosylate Marcus E. Cabay, Brad J. Ettlie, Adam J. Tuite, Kurt A. Welday, and Ram S. Mohan
A discovery-oriented lab that illustrates the stereochemistry of the E2 elimination reaction and is a good exercise in 1H NMR spectroscopy. The added element of discovery insures that student interest and enthusiasm are retained.
Cabay, Marcus E.; Ettlie, Brad J.; Tuite, Adam J.; Welday, Kurt A.; Mohan, Ram S. J. Chem. Educ. 2001, 78, 79.
IR Spectroscopy |
Mechanisms of Reactions |
NMR Spectroscopy |
Stereochemistry |
Elimination Reactions |
Reactions |
Alkenes
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The Discovery-Oriented Approach to Organic Chemistry. 4. Epoxidation of p-Methoxy-trans-b-methylstyrene: An Exercise in NMR and IR Spectroscopy for Sophomore Organic Laboratories Rebecca S. Centko and Ram S. Mohan
Illustrates epoxidation of alkenes as well as the reactivity of epoxides toward acids. The experiment involves reaction of p-methoxy-trans-beta-methylstyrene (trans-anethole) with m-chloroperoxybenzoic acid (MCPBA), in both the absence and presence of a buffer, followed by product identification using 1H NMR, 13C NMR, and IR spectroscopy
Centko, Rebecca S.; Mohan, Ram S. J. Chem. Educ. 2001, 78, 77.
IR Spectroscopy |
NMR Spectroscopy |
Epoxides |
Alkenes
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Stereowordimers-Minding Your P's and Q's Edward G. Neeland
The use of words having different colored sides is a excellent way to introduce stereochemical concepts that might not be easily grasped when using molecular examples. We have found that concepts such as enantiomers, diastereomers, identical molecules, chirality, achirality, mirror planes of symmetry, and internal planes of symmetry are readily understood by students when using stereowordimer examples.
Neeland, Edward G. J. Chem. Educ. 1998, 75, 1573.
Stereochemistry |
Diastereomers |
Enantiomers |
Molecular Properties / Structure
|
Photodimerization of Maleic Anhydride Zhang, Zhijun
Why the photodimerization of maleic anhydride produces the cis, tans, cis product.
Zhang, Zhijun J. Chem. Educ. 1998, 75, 1515.
Photochemistry |
Stereochemistry |
Molecular Properties / Structure |
Alkenes
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Models and Molecules - A Workshop on Stereoisomers Robert W. Baker, Adrian V. George, and Margaret M. Harding
A molecular model workshop aimed at first year university undergraduates has been devised to illustrate the concepts of organic stereochemistry. The students build models to teach the relationship within, and between, conformational isomers, enantiomers, and diastereomers.
Baker, Robert W.; George, Adrian V.; Harding, Margaret M. J. Chem. Educ. 1998, 75, 853.
Molecular Properties / Structure |
Stereochemistry |
Molecular Modeling |
Enantiomers |
Diastereomers
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S. M. Tanatar and His Contribution to the Field of Thermal Rearrangements Ludmila Birladeanu
Thermal rearrangements constitute an important chapter in organic chemistry. Surprisingly, the name of its discoverer remains unknown. The present article is meant to remedy this situation by describing some of the work of the 19th century Russian chemist S. M. Tanatar (1849 - 1917) who, based on the thermochemical data provided by Berthelot, envisaged the possibility of transforming cyclopropane into propene under the influence of heat alone.
Birladeanu, Ludmila. J. Chem. Educ. 1998, 75, 603.
Gases |
Thermodynamics |
Synthesis |
Alkanes / Cycloalkanes |
Alkenes
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A History of the Double-Bond Rule Bernard E. Hoogenboom
From his experience as an industrial chemist, Otto Schmidt recognized the bond weakening in hydrocarbons and in 1932 postulated the "Double-Bond Rule," stating that the presence of a double bond in a hydrocarbon has an alternating strengthening and weakening effect on single bonds throughout the molecule, diminishing with distance from the double bond.
Hoogenboom, Bernard E. J. Chem. Educ. 1998, 75, 596.
Learning Theories |
Mechanisms of Reactions |
Alkenes
|
A -78°C Sequential Michael Addition for the Organic Lab Michael W. Tanis
This paper introduces a cold-temperature enolate alkylation reaction that can be performed safely and inexpensively by undergraduate students in approximately two 3-hour lab sessions.
Tanis, Michael W. J. Chem. Educ. 1997, 74, 112.
Addition Reactions |
Alkenes |
Aldehydes / Ketones |
Synthesis
|
Playing with the Soccer Ball-an Experimental Introduction to Fullerene Chemistry Achim Hildebrand, Uwe Hilgers, Rudiger Blume, Dagmar Wiechoczek,
For the first time a selection of simple experiments with C60 on high-school and university level are presented: the bromination with Winkler's solution, hydroxylation with an alkaline permanganate solution, cycloadditions of dichlorcarbene and cyclopentadiene and the formation of a molecular complex with o-dimethoxybenzene.
Hildebrand, Achim; Hilgers, Uwe; Blume, Rudiger; Wiechoczek, Dagmar. J. Chem. Educ. 1996, 73, 1066.
Alkenes
|
Diastereospecific Synthesis of an Epoxide: An Introductory Experiment in Organic Synthetic and Mechanistic Chemistry James A. Ciaccio
A two-step epoxide synthesis that can be presented to students in the form of two mechanistic "puzzles" that probe the stereoselectivity of two important reactions: halohydrin formation from alkenes and epoxide formation via intramolecular Williamson ether synthesis.
Ciaccio, James A. J. Chem. Educ. 1995, 72, 1037.
Stereochemistry |
Molecular Properties / Structure |
Mechanisms of Reactions |
Synthesis |
Epoxides |
Alkenes
|
Hydrochlorination of (R)-Carvone Miles, William H.; Nutaitis, Charles F.; Berreth, Christina L.
This paper describes the hydrochlorination of (R)-carvone that illustrates the concepts of regioselectivity and chemoselectivity.
Miles, William H.; Nutaitis, Charles F.; Berreth, Christina L. J. Chem. Educ. 1994, 71, 1097.
Laboratory Management |
Alkenes |
Alkanes / Cycloalkanes
|
An Advanced Inorganic Laboratory Experiment Using Synthesis and Reactivity of a Cycloheptatriene Molybdenum Complex Timmers, Francis J.; Wacholtz, William F.
The reactions in the laboratory experiment described herein involve the synthesis, reactivity, and characterization of cycloheptatriene molybdenum.
Timmers, Francis J.; Wacholtz, William F. J. Chem. Educ. 1994, 71, 987.
Synthesis |
Organometallics |
Alkenes
|
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
|
An Experiment in trans-cis Isomerization: Synthesis and Kinetics of trans-Dichlorotetraamminecobalt(III) Chloride Borer, Londa L.; Erdman, Howard W.
Synthesis and kinetics investigation of trans-dichlorotetraamminecobalt(III) chloride.
Borer, Londa L.; Erdman, Howard W. J. Chem. Educ. 1994, 71, 332.
Diastereomers |
Synthesis |
Kinetics |
Coordination Compounds |
UV-Vis Spectroscopy |
IR Spectroscopy |
Conductivity
|
The stereochemistry of commercial 2,6-dimethylcyclohexanone: An application of capillary gas chromatography Garner, Charles M.
One example of how capillary gas chromatography can be employed in undergraduate organic laboratories.
Garner, Charles M. J. Chem. Educ. 1993, 70, A310.
Gas Chromatography |
Microscale Lab |
Laboratory Equipment / Apparatus |
Aldehydes / Ketones |
Diastereomers |
Stereochemistry
|
Organometallic benzene complexes Maslowsky, Edward, Jr.
A look at benzene's flexibility and subsequent interactions with metal atoms.
Maslowsky, Edward, Jr. J. Chem. Educ. 1993, 70, 980.
Organometallics |
Diastereomers |
Aromatic Compounds
|
Benzene isomers? (the author replies) Potgieter, J. H.
Additional isomers of benzene.
Potgieter, J. H. J. Chem. Educ. 1992, 69, 859.
Aromatic Compounds |
Alkenes |
Diastereomers
|
Benzene isomers? Reinecke, Manfred G.
Additional isomers of benzene.
Reinecke, Manfred G. J. Chem. Educ. 1992, 69, 859.
Aromatic Compounds |
Diastereomers |
Alkenes
|
An introduction to fullerene structures: Geometry and symmetry. Boo, W. O. J.
The formidable task of organizing the fullerenes can be simplified greatly by categorizing them by their symmetries.
Boo, W. O. J. J. Chem. Educ. 1992, 69, 605.
Alkenes |
Molecular Properties / Structure |
Group Theory / Symmetry |
Stereochemistry |
Diastereomers
|
The synthesis of E-beta-bromostyrene: An experiment illustrating the use of IR bending modes to distinguish E and Z isomers and the concept of kinetic and thermodynamic controlled reactions. Strom, Laura A.; Anderson, James R.; Gandler, Joseph R.
An experiment illustrating the concept of thermodynamic and kinetically controlled reactions to produce E and Z isomers (respectively); the use of IR to distinguish E and Z isomers; and the different properties of E and Z isomers (only the E isomer has a pleasant odor).
Strom, Laura A.; Anderson, James R.; Gandler, Joseph R. J. Chem. Educ. 1992, 69, 588.
Synthesis |
IR Spectroscopy |
Stereochemistry |
Kinetics |
Thermodynamics |
Alkenes |
Diastereomers |
Mechanisms of Reactions |
Molecular Properties / Structure
|
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
|
The Wittig synthesis of alkenes by phase-transfer catalysis: The syntheses of 4,4'-dichlorostilbenes and of E, E-1,4 -diphenylbutadiene Breuer, Stephen W.
The syntheses of 4,4'-dichlorostilbenes and of E, E-1,4 -diphenylbutadiene.
Breuer, Stephen W. J. Chem. Educ. 1991, 68, A58.
Synthesis |
Microscale Lab |
Alkenes |
Aromatic Compounds
|
Isomerization of dimethyl maleate to dimethyl fumarate: An undergraduate experiment illustrating amine-catalyzed alkene isomerization, stereochemical principles, sublimation, and product identification by spectroscopic methods Fryhle, Craig B.; Rybak, Carol M.; Pulley, Kenneth E.
An undergraduate experiment illustrating amine-catalyzed alkene isomerization, stereochemical principles, sublimation, and product identification by spectroscopic methods.
Fryhle, Craig B.; Rybak, Carol M.; Pulley, Kenneth E. J. Chem. Educ. 1991, 68, 1050.
Amines / Ammonium Compounds |
Diastereomers |
Gas Chromatography |
NMR Spectroscopy |
Fourier Transform Techniques |
Catalysis
|
A projection for bond location in chair cyclohexane and related structures Woolf, A. A.
Benefits and drawbacks of 2D representations for chair cyclohexane and related structures.
Woolf, A. A. J. Chem. Educ. 1991, 68, 646.
Alkanes / Cycloalkanes |
Diastereomers |
Enantiomers |
Constitutional Isomers
|
Decarboxylative elimination of 2,3-dibromo-3-phenylpropanoic acid to E or Z 1-bromo-2-phenylethylene (Beta-Bromostyrene): An experiment illustrating solvent effect on the stereochemical course of a reaction Mestdagh, Helene; Puechberty, Anne
An experiment illustrating solvent effect on the stereochemical course of a reaction.
Mestdagh, Helene; Puechberty, Anne J. Chem. Educ. 1991, 68, 515.
Elimination Reactions |
Alkenes |
Stereochemistry |
Solutions / Solvents
|
A convenient synthesis of 3,4-pentadien-1-ol from 3-butyn-1-ol: Spectral analysis and unusual durability of the allene moiety Price, William A.; Patten, Timothy E.
Description of a convenient synthesis of 3,4-pentadien-1-ol from 3-butyn-1-ol: Spectral analysis and unusual durability of the allene moiety.
Price, William A.; Patten, Timothy E. J. Chem. Educ. 1991, 68, 256.
Synthesis |
Alcohols |
Alkenes |
NMR Spectroscopy
|
Representing isomeric structures Thall, Edwin
"Representing isomeric structures" is the name of a technique this author has developed to help students learn to draw molecular structures of isomers in their first organic chemistry class.
Thall, Edwin J. Chem. Educ. 1991, 68, 190.
Constitutional Isomers |
Diastereomers
|
The synthesis of 2'-bromostyrene Corvari, Linda; McKee, James R.; Zanger, Murray
Organic chemistry laboratories need not be the repositories of foul smells. This synthesis produces an aroma akin to hyacinth.
Corvari, Linda; McKee, James R.; Zanger, Murray J. Chem. Educ. 1991, 68, 161.
Synthesis |
NMR Spectroscopy |
IR Spectroscopy |
Stereochemistry |
Alkenes
|
Microscale synthesis of cis-diamminedihaloplatinum(II) and a corresponding trans isomer: A rapid and convenient method of preparing cisplatin - An anticancer drug. A laboratory experiment for inorganic and bioinorganic chemistry Singh, Mono M.; Szafran, Zvi; Pike, Ronald M.
Involves drug synthesis, application of the trans effect, and preparation and characterization of isomers under different reaction conditions.
Singh, Mono M.; Szafran, Zvi; Pike, Ronald M. J. Chem. Educ. 1990, 67, A261.
Microscale Lab |
Synthesis |
Drugs / Pharmaceuticals |
Bioinorganic Chemistry |
Diastereomers
|
The stereochemistry of additions to trans-anethole McGahey, Lawrence
Trans-anethole is brominated with pyridinium bromide perbromide in dichloromethane.
McGahey, Lawrence J. Chem. Educ. 1990, 67, 554.
Addition Reactions |
Stereochemistry |
Mechanisms of Reactions |
Alkenes |
Diastereomers |
Enantiomers
|
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 derivation of the Masamune rule of multiplicativity in double asymmetric induction Nakayama, Kensaku
The ability to prepare one diastereomeric or enantiomeric isomer in excess in a given chemical transformation where a stereoisomeric distribution of products is possible is currently one of the most highly sought goals in the field of synthetic organic chemistry.
Nakayama, Kensaku J. Chem. Educ. 1990, 67, 20.
Synthesis |
Diastereomers |
Enantiomers
|
The resolution of a completely inorganic coordination compound: A modified classic experiment for the inorganic laboratory Yasui, Takaji; Ama, Tomoharu; Kauffman, George B.
Reproducing Alfred Werner's experiment demonstrating the Co(III) possesses an octahedral configuration.
Yasui, Takaji; Ama, Tomoharu; Kauffman, George B. J. Chem. Educ. 1989, 66, 1045.
Coordination Compounds |
Synthesis |
Diastereomers
|
Photochemical and thermal isomerization of trans- and cis-1,2-dibenzoylethylene: A microscale approach Klemm, Dennis V; Tuncay, Atilla
Both conversions are analyzed through thin layer chromatography.
Klemm, Dennis V; Tuncay, Atilla J. Chem. Educ. 1989, 66, 519.
Photochemistry |
Stereochemistry |
Microscale Lab |
Thin Layer Chromatography |
Diastereomers
|
The interconversion of cis and trans isomers McGinn, Clifford J.; Wheatley, William B.
Trans-alkene oxides are converted to cis-alkenes on treatment with tributylphosphine, yet this reaction does not appear in most organic textbooks.
McGinn, Clifford J.; Wheatley, William B. J. Chem. Educ. 1989, 66, 486.
Stereochemistry |
Diastereomers |
Alkenes |
Mechanisms of Reactions
|
Stereochemistry of cyclic hydrocarbons Perkins, Robert R.
The topic of stereochemistry always poses great difficulties for many students in introductory organic chemistry. The following problems can be used as a tutorial question after having introduced the various terms associated with stereochemistry. The question requires skills at the applications level in the Bloom taxonomy.
Perkins, Robert R. J. Chem. Educ. 1988, 65, 860.
Alkanes / Cycloalkanes |
Chirality / Optical Activity |
Stereochemistry |
Diastereomers |
Constitutional Isomers
|
cis and trans-Stilbenes: Chromatographic separation and photochemical isomerization Levine, Samuel G.; Barhoriak, Kathleen Doubek; Cho, Ho S.
An organic chemistry laboratory that has historic significance.
Levine, Samuel G.; Barhoriak, Kathleen Doubek; Cho, Ho S. J. Chem. Educ. 1988, 65, 79.
Separation Science |
Photochemistry |
Diastereomers |
Chromatography
|
Mnemonic for Z and E nomenclature Thomas, C. W.
A visual reminder that makes it unnecessary to memorize the German terms.
Thomas, C. W. J. Chem. Educ. 1988, 65, 44.
Diastereomers |
Alkenes |
Nomenclature / Units / Symbols
|
A synthesis of chrysanthemic ester: An undergraduate experiment Kelly, Lawrence F.
Procedure for producing a mixture of cis- and trans-ethyl chrysanthemates.
Kelly, Lawrence F. J. Chem. Educ. 1987, 64, 1061.
Esters |
Synthesis |
Catalysis |
Diastereomers |
Stereochemistry
|
A very brief, rapid, simple, and unified method for estimating carbon-13 NMR chemical shifts: The BS method Shoulders, Hen; Welch, Steven C.
The "BS" method is so brief and simple that students can memorize and use it to interpret 13C NMR spectra with ease.
Shoulders, Hen; Welch, Steven C. J. Chem. Educ. 1987, 64, 915.
NMR Spectroscopy |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes |
Instrumental Methods
|
Addition of iodine to alkenes: A pseudo-first-, second-, or third-order kinetics experiment Field, Kurt W.; Wilder, Deborah; Utz, Arthur; Kolb, Kenneth E.
A simple, inexpensive, class-tested experiment for determining the kinetics of iodine addition to various alkenes in several solvents.
Field, Kurt W.; Wilder, Deborah; Utz, Arthur; Kolb, Kenneth E. J. Chem. Educ. 1987, 64, 269.
Alkenes |
Kinetics
|
A Wittig reaction that gives only one stereoisomer Silversmith, Ernest F.
This popular experiment can be extended to illustrate the use of spectroscopy to elucidate stereochemistry.
Silversmith, Ernest F. J. Chem. Educ. 1986, 63, 645.
Stereochemistry |
Diastereomers |
Separation Science
|
Stress the twofold axis of the threo isomer Tavernier, D.
The author weighs in on the the controversy of the threo and erythro nomenclature.
Tavernier, D. J. Chem. Educ. 1986, 63, 511.
Nomenclature / Units / Symbols |
Molecular Properties / Structure |
Stereochemistry |
Enantiomers |
Diastereomers
|
The Wittig reaction in the undergraduate organic laboratory Warner, John C.; Anastas, Paul T.; Anselme, Jean-Pierre
Using phase-transfer catalysis to prepare cis- and trans-stilbenes from the Wittig condensation of benzaldehyde.
Warner, John C.; Anastas, Paul T.; Anselme, Jean-Pierre J. Chem. Educ. 1985, 62, 346.
Mechanisms of Reactions |
Synthesis |
Catalysis |
Diastereomers |
Stereochemistry
|
A short set of 13C-NMR correlation tables Brown, D. W.
The object of these tables is to enable a student to calculate rapidly approximate d values for 13C nuclei in as wide a variety of compounds as possible.
Brown, D. W. J. Chem. Educ. 1985, 62, 209.
NMR Spectroscopy |
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes |
Aromatic Compounds |
Amides |
Carboxylic Acids |
Esters
|
Models for illustrating chirality at two centers Feldman, Martin R.
This note suggests common objects that can be used as models to illustrate chirality at two centers, and to introduce the concepts of diastereomers and the meso configuration.
Feldman, Martin R. J. Chem. Educ. 1984, 61, 1050.
Molecular Properties / Structure |
Molecular Modeling |
Chirality / Optical Activity |
Diastereomers |
Stereochemistry |
Enantiomers
|
The evaluation of strain and stabilization in molecules using isodesmic reactions Fuchs, Richard
The stabilities of cyclic hydrocarbons are analyzed using isodesmic and metathetical isodesmic reactions.
Fuchs, Richard J. Chem. Educ. 1984, 61, 133.
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Alkenes |
Aromatic Compounds
|
Aromatic substitution reactions: when you've said ortho, meta, and para you haven't said it all Traynham, James G.
The author presents a range of examples for nucleophilic, electrophilic, and free-radical reactions where the ipso is an important, predominant, or even exclusive site of reaction.
Traynham, James G. J. Chem. Educ. 1983, 60, 937.
Nucleophilic Substitution |
Electrophilic Substitution |
Free Radicals |
Diastereomers |
Stereochemistry |
Reactions
|
An experiment on isomerism in metal-amino acid complexes: Preparation and characterization of cobalt(III) complexes containing N-bonded monodentate, O-bonded monodentate and N,O-chelated glycine ligands Harrison, R. Graeme; Nolan, Kevin B.
Synthesis of three cobalt(III) complexes that illustrate three possible modes of bonding of glycine to a metal ion, as well as methods for distinguishing among the products.
Harrison, R. Graeme; Nolan, Kevin B. J. Chem. Educ. 1982, 59, 1054.
Stereochemistry |
Amino Acids |
Coordination Compounds |
Synthesis |
Diastereomers |
IR Spectroscopy |
Crystal Field / Ligand Field Theory
|
The preparation and characterization of the geometric isomers of a coordination complex: cis- and trans-bis-glycinato copper(II) monohydrates O'Brien, Paul
The preparation of the cis and trans isomers of the kinetically labile bis glycinato copper(II) has a number of advantages including its facility, economy, ready theoretical interpretation, and biological relevance.
O'Brien, Paul J. Chem. Educ. 1982, 59, 1052.
Synthesis |
Stereochemistry |
Diastereomers |
IR Spectroscopy |
Coordination Compounds |
Crystal Field / Ligand Field Theory
|
An easily conducted free radical substitution for organic chemistry courses Pavlis, Robert R.
The photobromination of 1,2-diphenylethane into its dibromo derivative, (2R) (3S) 1,2-dibromo-1,2-diphenylethane.
Pavlis, Robert R. J. Chem. Educ. 1982, 59, 658.
Free Radicals |
Reactions |
Molecular Properties / Structure |
Stereochemistry |
Diastereomers |
Photochemistry |
Alkanes / Cycloalkanes |
Aromatic Compounds
|
Diastereomers, geometric isomers, and rotation about bonds McCullough, John J.
A simple and consistent introduction to the stereochemistry of carbon, diastereomers, and geometric isomers.
McCullough, John J. J. Chem. Educ. 1982, 59, 37.
Stereochemistry |
Diastereomers |
Molecular Properties / Structure
|
An undergraduate laboratory program project involving photocyclizations in independent syntheses of novel chrysenes and phenanthrenes Letcher, R. M.
This experiment attempts to fulfill such objectives as providing meaningful and viable preparative reactions, providing an opportunity for independent laboratory work within a project framework and under conditions of nearly equal opportunity and experience.
Letcher, R. M. J. Chem. Educ. 1981, 58, 1020.
Undergraduate Research |
Synthesis |
Aromatic Compounds |
Photochemistry |
Diastereomers |
NMR Spectroscopy |
Alcohols |
Thin Layer Chromatography
|
A helpful stereochemical instructional tool England, Don
The figure found in this note has been helpful in aiding student understanding of stereochemistry.
England, Don J. Chem. Educ. 1981, 58, 31.
Stereochemistry |
Molecular Modeling |
Molecular Properties / Structure |
Chirality / Optical Activity |
Diastereomers |
Enantiomers
|
Bent bonds and multiple bonds Robinson, Edward A.; Gillespie, Ronald J.
Considers carbon-carbon multiple bonds in terms of the bent bond model first proposed by Pauling in 1931.
Robinson, Edward A.; Gillespie, Ronald J. J. Chem. Educ. 1980, 57, 329.
Covalent Bonding |
Molecular Properties / Structure |
Molecular Modeling |
Alkenes |
Alkynes
|
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
|
Optical illusions in drawings of cyclohexane derivatives Feldman, Martin R.
An optical illusion in the representation of chair cyclohexanes.
Feldman, Martin R. J. Chem. Educ. 1979, 56, 659.
Molecular Properties / Structure |
Stereochemistry |
Enantiomers |
Diastereomers |
Alkanes / Cycloalkanes
|
Conformations of substituted ethanes Kingsbury, Charles A.
Provides a state-of-the-art view of conformational analysis, with an emphasis on sp3 hybridized acyclic molecules.
Kingsbury, Charles A. J. Chem. Educ. 1979, 56, 431.
Molecular Properties / Structure |
Conformational Analysis |
Alkanes / Cycloalkanes |
Diastereomers
|
Identification of geometrical isomers of the cobalt(III)-iminodiacetate system: An inorganic experiment Lawrance, Geoffrey A.; Rix, Colin J.
Procedure for the preparation and isolation of two differently colored geometric isomers of Co(IDA)2- and their characterization using pmr and visible spectroscopy.
Lawrance, Geoffrey A.; Rix, Colin J. J. Chem. Educ. 1979, 56, 211.
Stereochemistry |
Diastereomers |
Coordination Compounds |
Spectroscopy |
UV-Vis Spectroscopy
|
Amine-catalyzed isomerization of diethylmaleate to diethylfumarate Glover, Irving T.; Cushing, Gary W.; Windsor, Chris M.
The authors have used the reaction in this paper in their introductory organic chemistry course to illustrate principles of GLC , geometric isomerism, homogeneous catalysis, and activation energy determinations.
Glover, Irving T.; Cushing, Gary W.; Windsor, Chris M. J. Chem. Educ. 1978, 55, 812.
Diastereomers |
Enantiomers |
Catalysis |
Gas Chromatography
|
Stoichiometric study in the gas phase: Bromination of unsaturated hydrocarbons Charlson, A. J.; Shapiro, J. S.; Ware, G. W.; Watton, E. C.
Many college and high school manuals describe an experiment involving bromine addition to carbon-carbon double bonds. This experiment leaves many questions unanswered and may lead to confusion with the photo-bromination of hydrocarbons where decoloration of bromine occurs. This experiment leads students to many misconceptions regarding this reaction.
Charlson, A. J.; Shapiro, J. S.; Ware, G. W.; Watton, E. C. J. Chem. Educ. 1978, 55, 338.
Stoichiometry |
Alkenes
|
Project for problem-oriented undergraduate organic or integrated undergraduate laboratory Silveira, Augustine, Jr.
This paper reports on an open-ended project which allows a great degree of flexibility in the laboratory. The project provided about a 6-week study for groups of 24 students each.
Silveira, Augustine, Jr. J. Chem. Educ. 1978, 55, 57.
Synthesis |
Undergraduate Research |
Spectroscopy |
Diastereomers |
Addition Reactions |
MO Theory |
Elimination Reactions |
Thermodynamics |
Kinetics
|
Isomerism about a double bond: Use of cis and trans Fernelius, W. Conard; Loening, Kurt; Adams, Roy M.
Limitations of the cis and trans nomenclature.
Fernelius, W. Conard; Loening, Kurt; Adams, Roy M. J. Chem. Educ. 1976, 53, 727.
Diastereomers |
Nomenclature / Units / Symbols
|
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
|
Calculation of the number of cis-trans isomers in a "symmetric" polyene Har-zvi, Ron; Wittes, Janet Turk
A problem in which students are to derive a general expression for the number of cis-trans isomers in a "symmetric" straight chain polyene when there are n double bonds.
Har-zvi, Ron; Wittes, Janet Turk J. Chem. Educ. 1975, 52, 545.
Stereochemistry |
Molecular Properties / Structure |
Diastereomers |
Alkenes
|
Determining homotopic, enantiotopic, and diastereotopic faces in organic molecules Ayral Kaloustian, Semiramis; Kaloustian, Moses K.
Presents a simple set of rules, based on considerations of symmetry, that allows a succinct classification of the five types of molecular faces of interest to the organic chemist and the biochemist.
Ayral Kaloustian, Semiramis; Kaloustian, Moses K. J. Chem. Educ. 1975, 52, 56.
Molecular Properties / Structure |
Diastereomers
|
Photochemical and thermal interconversion of cis and trans isomers. An organic laboratory experiment Silversmith, Ernest F.; Dunson, Fay C.
The photoisomerization of trans-1,4-diphenyl-2-butene-1,4-dione to the cis isomer.
Silversmith, Ernest F.; Dunson, Fay C. J. Chem. Educ. 1973, 50, 568.
Photochemistry |
Molecular Properties / Structure |
Diastereomers |
Stereochemistry
|
An integrated nmr and photochemical organic chemistry experiment Glaros, George; Cromwell, Norman H.
The authors describe a photochemical experiment involving a compound that was prepared in the authors' previous paper.
Glaros, George; Cromwell, Norman H. J. Chem. Educ. 1971, 48, 204.
Aromatic Compounds |
Diastereomers
|
A weevil's loss is our gain or sex strikes the pages on the Journal. Brasted, Robert C.
The trans-isomer of the boll weevil sex attractant is a million times more active than the cis-isomer.
Brasted, Robert C. J. Chem. Educ. 1970, 47, 447.
Natural Products |
Diastereomers |
Molecular Properties / Structure |
Agricultural Chemistry |
Applications of Chemistry
|
A modern look at Markovnikov's rule and the peroxide effect Isenberg, Norbert; Grdinic, Marcel
Presents a "carbonium ion" definition of Markovnikov's Rule and examines the peroxide effect.
Isenberg, Norbert; Grdinic, Marcel J. Chem. Educ. 1969, 46, 601.
Mechanisms of Reactions |
Stereochemistry |
Diastereomers |
Free Radicals |
Alkenes |
Addition Reactions
|
Organic chemistry Dolbier, William R., Jr.
Presents an explanation that encompasses all electrophilic additions to alkenes within a single, unifying picture.
Dolbier, William R., Jr. J. Chem. Educ. 1969, 46, 342.
Addition Reactions |
Alkenes |
Mechanisms of Reactions |
Stereochemistry
|
The photoisomerization of azobenzene: A TLC experiment for the undergraduate organic laboratory Janssen, Jerry F.
The photoisomerization of azobenzene provides a rare opportunity to explore molecular photochemistry in undergraduate organic chemistry.
Janssen, Jerry F. J. Chem. Educ. 1969, 46, 117.
Chromatography |
Thin Layer Chromatography |
Photochemistry |
Diastereomers
|
Simple models for polymer stereochemistry Rodriguez, F.
Models made by drawing on folding transparent plastic sheets are proposed as being an alternative for illustrating polymer structures.
Rodriguez, F. J. Chem. Educ. 1968, 45, 507.
Molecular Modeling |
Molecular Properties / Structure |
Diastereomers
|
3-Sulfolene: A butadiene source for a Diels-Alder synthesis: An undergraduate laboratory experiment Sample, Thomas E., Jr.; Hatch, Lewis F.
By selecting a suitable diene cyclic sulfone, the common complication in performing a Diels-Alder experiment can be avoided.
Sample, Thomas E., Jr.; Hatch, Lewis F. J. Chem. Educ. 1968, 45, 55.
Alkenes |
Synthesis |
Mechanisms of Reactions
|
Conformational analysis and chemical reactivity Idoux, John P.
Uses acyclic chemistry to illustrate important concepts regarding conformational analysis and chemical reactivity.
Idoux, John P. J. Chem. Educ. 1967, 44, 495.
Conformational Analysis |
Stereochemistry |
Diastereomers
|
Concepts of species and state in chemistry and molecular physics Goodfriend, P. L.
This article examines the concepts of species and state in chemistry and molecular physics.
Goodfriend, P. L. J. Chem. Educ. 1966, 43, 95.
Quantum Chemistry |
Diastereomers |
Molecular Properties / Structure
|
An aid to visualizing fused ring systems Vogel, George
Presents a method for visualizing fused ring systems without the use of models.
Vogel, George J. Chem. Educ. 1965, 42, 278.
Molecular Modeling |
Molecular Properties / Structure |
Diastereomers
|
Resolving coordination compounds by a second order asymmetric synthesis Kauffman, George B.; Sugisaka, Nobuyuki; Reid, Ian K.
This experiment involves the resolution of an optically active complex cation, the trisoxalatochromate(III) ion and provides the student with an excellent introduction to the phenomenon of second order asymmetric synthesis.
Kauffman, George B.; Sugisaka, Nobuyuki; Reid, Ian K. J. Chem. Educ. 1964, 41, 461.
Diastereomers |
Coordination Compounds |
Chirality / Optical Activity
|
Dipole moments of symmetrical organic molecules Moulton, W. N.
Examines the use of dipole moments to assign cis or trans configurations to olefins.
Moulton, W. N. J. Chem. Educ. 1961, 38, 522.
Molecular Properties / Structure |
Diastereomers
|
The unraveling of geometric isomerism and tautomerism Ihde, Aaron J.
Examines the work of Van't Hoff in unraveling isomerism due to carbon-carbon double bonds using fumaric and maleic acids as exemplars.
Ihde, Aaron J. J. Chem. Educ. 1959, 36, 330.
Molecular Properties / Structure |
Stereochemistry |
Diastereomers
|
Polymerization of ethylene at atmospheric pressure: A demonstration using a "Ziegler" type catalyst Zilkha, Albert; Calderon, Nissim; Rabani, Joseph; Frankel, Max
A simple experiment on the polymerization of ethylene at atmospheric pressure is described using a "Ziegler" type catalyst prepared from amyl lithium and titanium tetrachloride.
Zilkha, Albert; Calderon, Nissim; Rabani, Joseph; Frankel, Max J. Chem. Educ. 1958, 35, 344.
Polymerization |
Reactions |
Catalysis |
Alkenes
|
Student experiments on derivatives of 1,2-diphenylethane Fieser, Louis F.
Johannes Thiele's classical demonstration of 1,4-addition by reductive acetylation of benzil is used to present a number of interesting theoretical points and an opportunity to separate cis- and trans- isomers through chromatography.
Fieser, Louis F. J. Chem. Educ. 1954, 31, 291.
Molecular Properties / Structure |
Diastereomers |
Chromatography
|
Isomers of octahedral complexes with nonbranching ligands Trimble, Russell F., Jr.
The purpose of this paper is to present a tabulation of the various ways in which ligands can be distributed about an octahedral frame.
Trimble, Russell F., Jr. J. Chem. Educ. 1954, 31, 176.
Coordination Compounds |
Molecular Biology |
Diastereomers
|
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
|
|
