| Journal Articles: 226 results |
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Identification of Secondary Metabolites in Citrus Fruit Using Gas Chromatography and Mass Spectroscopy Jean-Michel Lavoie, Esteban Chornet, and André Pelletier
Using a simple extraction and a gas chromatograph coupled with a mass spectrometer, this protocol allows students in analytical or organic chemistry to quantify and qualify monoterpenes from the peels of limes, grapefruits, and oranges.
Lavoie, Jean-Michel; Chornet, Esteban; Pelletier, André. J. Chem. Educ. 2008, 85, 1555.
Alkenes |
Food Science |
Gas Chromatography |
Mass Spectrometry |
Natural Products |
Plant Chemistry |
Qualitative Analysis |
Quantitative Analysis
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The Synthesis of N-Benzyl-2-azanorbornene via Aqueous Hetero Diels–Alder Reaction Xavier Sauvage and Lionel Delaude
Characterization of the product of this organic synthesis through IR and NMR data analysis provides valuable material to familiarize students with different types of protonproton coupling patterns and their typical ranges, serves to illustrate the concepts of green chemistry and atom efficiency, and can be used to exemplify structural analysis and computational studies.
Sauvage, Xavier; Delaude, Lionel. J. Chem. Educ. 2008, 85, 1538.
Alkenes |
Aqueous Solution Chemistry |
Conformational Analysis |
Green Chemistry |
IR Spectroscopy |
Molecular Modeling |
NMR Spectroscopy |
Stereochemistry |
Synthesis
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Construction of a Polyaniline Nanofiber Gas Sensor Shabnam Virji, Bruce H. Weiller, Jiaxing Huang, Richard Blair, Heather Shepherd, Tanya Faltens, Philip C. Haussmann, Richard B. Kaner, and Sarah H. Tolbert
The objectives of this lab are to synthesize different diameter polyaniline nanofibers and compare them as sensor materials. Its advantages include simplicity and low cost, making it suitable for both high school and college students, particularly in departments with modest means.
Virji, Shabnam; Weiller, Bruce H.; Huang, Jiaxing; Blair, Richard; Shepherd, Heather; Faltens, Tanya; Haussmann, Philip C.; Kaner, Richard B.; Tolbert, Sarah H. J. Chem. Educ. 2008, 85, 1102.
Acids / Bases |
Aromatic Compounds |
Conductivity |
Hydrogen Bonding |
Oxidation / Reduction |
Oxidation State |
pH |
Polymerization |
Synthesis
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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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Pyrolysis of Aryl Sulfonate Esters in the Absence of Solvent: E1 or E2? A Puzzle for the Organic Laboratory John J. Nash, Marnie A. Leininger, and Kurt Keyes
An aryl sulfonate ester is synthesized and then pyrolyzed at reduced pressure. The volatile products are analyzed using gas chromatography to determine whether the thermal decomposition occurs via an E1 or E2 mechanism.
Nash, John J.; Leininger, Marnie A.; Keyes, Kurt . J. Chem. Educ. 2008, 85, 552.
Alkenes |
Carbocations |
Elimination Reactions |
Gas Chromatography |
Mechanisms of Reactions |
Synthesis
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Ring-Opening Polymerization of Lactide To Form a Biodegradable Polymer Jennifer L. Robert and Katherine B. Aubrecht
In this laboratory, students carry out the tin(II) bis(2-ethylhexanoate)/benzyl alcohol mediated ring-opening polymerization of lactide to form the biodegradable polymer polylactide. As the mechanism of the polymerization is analogous to that of a transesterification reaction, the experiment can be used to demonstrate reactions of carboxylic acid derivatives.
Robert, Jennifer L.; Aubrecht, Katherine B. J. Chem. Educ. 2008, 85, 258.
Esters |
Green Chemistry |
NMR Spectroscopy |
Polymerization |
Stereochemistry
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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
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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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Computational Analysis of Stereospecificity in the Cope Rearrangement Laura Glish and Timothy W. Hanks
Experimental product distributions from the Cope rearrangement of disubstituted 1,5-hexadienes can be readily understood by computer modeling of the various possible transitions states. Visual analysis of these geometries allow students to interpret the computational results by analogy to the familiar chair and boat conformations of substituted cyclohexanes.
Glish, Laura; Hanks, Timothy W. J. Chem. Educ. 2007, 84, 2001.
Alkenes |
Computational Chemistry |
Conformational Analysis |
Medicinal Chemistry |
MO Theory |
Molecular Modeling |
Mechanisms of Reactions
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Catalytic Hydrogenation of Maleic Acid at Moderate Pressures Kwesi Amoa
This article demonstrates the reduction of maleic acid in about 90 minutes using moderate-pressure catalytic hydrogenation.
Amoa, Kwesi. J. Chem. Educ. 2007, 84, 1948.
Alkenes |
Catalysis |
Chromatography |
IR Spectroscopy |
Laboratory Equipment / Apparatus |
Spectroscopy |
Thin Layer Chromatography
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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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Electronic Structure Principles and Aromaticity P. K. Chattaraj, U. Sarkar, and D. R. Roy
Electronic structure principles dictate that aromatic molecules are associated with low energy, polarizability, and electrophilicity but high hardness values, while antiaromatic molecules possess the opposite characteristics. These relationships are demonstrated through B3LYP/6-311G** calculations on benzene and cyclobutadiene.
Chattaraj, P. K.; Sarkar, U.; Roy, D. R. J. Chem. Educ. 2007, 84, 354.
Aromatic Compounds |
Molecular Properties / Structure |
Quantitative Analysis |
Theoretical Chemistry |
Alkenes |
Quantum Chemistry
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Refractive Index Determination of Transparent Polymers: Experimental Setup for Multi-Wavelength Determination and Calculation at Specific Frequencies Using Group Contribution Theory Jay Dlutowski, Andres M. Cardenas-Valencia, David Fries, and Larry Langebrake
A simple lab that clearly shows the dependence of light reflection on the angle of incidence for transparent polymers is described. Light transmission measurements are used to determine the reflection magnitude and the refractive index of the material.
Dlutowski, Jay; Cardenas-Valencia, Andres M.; Fries, David; Langebrake, Larry. J. Chem. Educ. 2006, 83, 1867.
Physical Properties |
Polymerization |
UV-Vis Spectroscopy
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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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Photochemical Dimerization of Dibenzylideneacetone. A Convenient Exercise in [2+2] Cycloaddition Using Chemical Ionization Mass Spectrometry G. Nageswara Rao, Chelli Janardhana, V. Ramanathan, T. Rajesh, and P. Harish Kumar
Presents a laboratory procedure for the photochemical dimerization of dibenzylideneacetone, a dienone. The dimerization is confirmed by chemical ionization mass spectrometry, and other spectroscopic techniques are used to establish the structure of the product.
Rao, G. Nageswara; Janardhana, Chelli; Ramanathan, V.; Rajesh, T.; Kumar, P. Harish. J. Chem. Educ. 2006, 83, 1667.
Aldehydes / Ketones |
Alkenes |
Chromatography |
IR Spectroscopy |
Mass Spectrometry |
NMR Spectroscopy |
Photochemistry |
Thin Layer Chromatography
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3,5-Diarylisoxazoles: Individualized Three-Step Synthesis and Isomer Determination Using 13C NMR or Mass Spectroscopy Chad E. Stephens and Reem K. Arafa
Describes the three-step synthesis and definitive characterization of a 3,5-diarylisoxazole via the chalcone and chalcone dibromide. The project is individualized with regard to compound purification, characterization, and literature searches as each student prepares a differently substituted chalcone.
Stephens, Chad E.; Arafa, Reem K. J. Chem. Educ. 2006, 83, 1336.
Alkenes |
Heterocycles |
IR Spectroscopy |
Mass Spectrometry |
NMR Spectroscopy |
Synthesis |
Spectroscopy
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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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Stereospecific Synthesis of the Geometrical Isomers of a Natural Product T. Grove, D. DiLella, and E. Volker
Presents an experiment for the synthesis of (Z) and (E) isomers that is presented to students as a puzzle in which they must determine the identity of the major component in anise oil. A necessary part of the analysis is the preparation the (E) and (Z) isomers of anethole. Molecular modeling is used to explore the conformation of and energy difference between isomers.
Grove, T.; DiLella, D.; Volker, E. J. Chem. Educ. 2006, 83, 1055.
Alkenes |
Computational Chemistry |
Gas Chromatography |
IR Spectroscopy |
NMR Spectroscopy |
Stereochemistry |
Synthesis
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Molecular Handshake: Recognition through Weak Noncovalent Interactions Parvathi S. Murthy
This article traces the development of our thinking about molecular recognition through noncovalent interactions, highlights their salient features, and suggests ways for comprehensive education on this important concept.
Murthy, Parvathi S. J. Chem. Educ. 2006, 83, 1010.
Applications of Chemistry |
Biosignaling |
Membranes |
Molecular Recognition |
Noncovalent Interactions |
Chromatography |
Molecular Properties / Structure |
Polymerization |
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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Iodolactonization of 4-Pentenoic Acid R. David Crouch, Alexander Tucker-Schwartz, and Kathryn Barker
Describes an experiment in which 4-pentenoic acid is converted into a lactone via iodolactonization.
Crouch, R. David; Tucker-Schwartz, Alexander; Barker, Kathryn. J. Chem. Educ. 2006, 83, 921.
Alkenes |
Carboxylic Acids |
IR Spectroscopy |
Mechanisms of Reactions |
NMR Spectroscopy |
Reactions |
Synthesis
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The Amazingly Versatile Titanocene Derivatives Donald C. Bowman
Derivatives of titanocene are remarkably versatile in their chemical applications. This article presents a brief review of the derivatives' uses in the fields of polymers, medical oncology, and organic synthesis.
Bowman, Donald C. J. Chem. Educ. 2006, 83, 735.
Applications of Chemistry |
Catalysis |
Drugs / Pharmaceuticals |
Organometallics |
Polymerization |
Synthesis
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Ozonolysis Problems That Promote Student Reasoning Ray A. Gross Jr.
The structural features inherent in acyclic monoterpenes that follow the isoprene rule often lead to unique sets of ozonolysis products from which their structures, excluding stereochemistry, can be determined from molecular formulas only. This article shows how students may elucidate the structures of these compounds by analysis of the oxidative and reductive workup products.
Gross, Ray A., Jr. J. Chem. Educ. 2006, 83, 604.
Aldehydes / Ketones |
Alkenes |
Alkynes |
Carboxylic Acids |
Oxidation / Reduction |
Student-Centered Learning
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Electrophilic Additions to Alkenes Thomas M. Bertolini and Phuc D. Tran
A worksheet of 18 reactions is presented as a learning aid to comprehend the regiochemistry and stereochemistry of alkene electrophilic addition.
Bertolini, Thomas M.; Tran, Phuc D. J. Chem. Educ. 2006, 83, 590.
Addition Reactions |
Alkenes |
Reactions
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Teaching Chemistry Laboratory Skills in Industrial Contexts Julianne M. Braun and Carol White
A recently completed project has produced a compilation of 40 laboratory experiments presented within the contexts of five major industries. This article provides a summary of these experiments, along with a discussion of ancillary materials.
Braun, Julianne M.; White, Carol. J. Chem. Educ. 2006, 83, 353.
Applications of Chemistry |
Industrial Chemistry |
Metals |
Polymerization |
Water / Water Chemistry
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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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A Green Polymerization of Aspartic Acid for the Undergraduate Organic Laboratory George D. Bennett
Based on a technology that won a Presidential Green Chemistry Challenge Award, this experiment involves the thermal polymerization of aspartic acid and subsequent hydrolysis to give sodium poly(aspartate). The procedure is suitable for introducing students to the important topic of polymers and for illustrating several of the principles of green chemistry.
Bennett, George D. J. Chem. Educ. 2005, 82, 1380.
Green Chemistry |
Synthesis |
Industrial Chemistry |
Natural Products |
Polymerization |
Proteins / Peptides
|
Thermal Degradation and Identification of Heat-Sensitive Polymers. Applications of Pyrolysis and Distillation and Instrumental Methods of Analysis Stuart C. Clough and Emma W. Goldman
An experiment for undergraduate teaching laboratories is described that involves the identification of samples of polystyrene and poly(methyl methacrylate). This involves the thermal degradation of the polymers (a destructive distillation) into their respective monomers. The monomers are then identified using infrared spectroscopy, proton nuclear magnetic resonance spectroscopy, and gas chromatographymass spectrometry.
Clough, Stuart C.; Goldman, Emma W. J. Chem. Educ. 2005, 82, 1378.
Nonmajor Courses |
IR Spectroscopy |
Mass Spectrometry |
NMR Spectroscopy |
Polymerization
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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
|
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
|
Polymers (Oxford Chemistry Primers No. 85) (David Walton and J. Phillip Lorimer) John H. Shibata
Although the title suggests a broad, general coverage of polymers, in reality this book focuses primarily on synthesis and the macroscopic properties of polymers. A significant portion of the book emphasizes practical considerations of polymerscommercial aspects determined by the properties of polymers and the industrial processes for polymer synthesis and three-dimensional network formation. In many cases, specific polymer types and materials are described in detail. The concreteness of explicit examples to illustrate the principles of polymerization and the properties of networks and functional polymers are appropriate for readers seeking a practical introduction to polymers.
Shibata, John H. J. Chem. Educ. 2005, 82, 533.
Polymerization |
Synthesis
|
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
|
A Substitute for “Bromine in Carbon Tetrachloride” Joshua M. Daley and Robert G. Landolt
Benzotrifluoride (BTF) is a suitable solvent substitute for carbon tetrachloride in experiments requiring application of bromine (Br2) in free radical or addition reactions with organic substrates. A 1 M solution of Br2 in BTF may be used to distinguish hydrocarbons based on the ease of abstraction of hydrogen atoms in thermally or light-induced free radical substitutions. Efficacy of minimization of solvent use, by aliquot addition to neat samples, has been established.
Daley, Joshua M.; Landolt, Robert G. J. Chem. Educ. 2005, 82, 120.
Alkenes |
Free Radicals |
Green Chemistry |
Qualitative Analysis |
Reactions
|
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
|
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
|
Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory Experiment Sam H. Leung and Stephen A. Angel
In this experiment (E)- and (Z)-1-(4-bromophenyl)-2-phenylethene are synthesized by a solvent-free Wittig reaction. The reaction is effected by grinding the reactants in a mortar with a pestle. Both the E and Z isomers of the product are produced as evidenced by thin-layer chromatography and 1H NMR analysis. The E isomer is isolated by crystallization with ethanol in this experiment. In addition to learning about the Wittig reaction, students are also introduced to the ideas of mechanochemistry and green chemistry.
Leung, Sam H.; Angel, Stephen A. J. Chem. Educ. 2004, 81, 1492.
Chromatography |
Green Chemistry |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Reactions |
Aldehydes / Ketones |
Alkenes
|
Regioselective Synthesis of a Stereodefined Heterocyclic Push–Pull Alkene. 1H NMR Studies and Two-Dimensional TLC Illustrating Z/E Isomerization Rade Markovi, Marija Baranac, Vesna Jovanovi, and Zdravko Dambaski
Facile and direct regioselective synthesis of the 4-oxothiazolidine derivative from inexpensive chemicals as an example of kinetic versus thermodynamic control is described.
Markovi, Rade; Baranac, Marija; Jovanovi, Vesna; Dambaski, Zdravko. J. Chem. Educ. 2004, 81, 1026.
Heterocycles |
Alkenes |
Stereochemistry |
Synthesis |
NMR Spectroscopy
|
The Study of Elimination Reactions Using Gas Chromatography: An Experiment for the Undergraduate Organic Laboratory Devin Latimer
This article describes an investigation of elimination reactions of alkyl halides. 1-Bromopentane or 2-bromopentane are reacted with either sodium ethoxide or potassium tert-butoxide. Gas chromatography is used to monitor the relative amounts of 1-pentene, (E)-2-pentene, and (Z)-2-pentene produced.
Latimer, Devin. J. Chem. Educ. 2003, 80, 1183.
Chromatography |
Instrumental Methods |
Synthesis |
Gas Chromatography |
Elimination Reactions |
Mechanisms of Reactions |
Alkenes |
Stereochemistry
|
Organic Functional Group Playing Card Deck Michael J. Welsh
Organic functional group playing card deck used for review of the name and structure of organic functional groups that can be used to play any game that a normal deck of cards is used for.
Welsh, Michael J. J. Chem. Educ. 2003, 80, 426.
Nomenclature / Units / Symbols |
Nonmajor Courses |
Enrichment / Review Materials |
Alcohols |
Aldehydes / Ketones |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes |
Amides |
Amines / Ammonium Compounds |
Aromatic Compounds |
Carboxylic Acids |
Esters |
Ethers |
Mechanisms of Reactions |
Synthesis
|
Chemical Recycling of Pop Bottles: The Synthesis of Dibenzyl Terephthalate from the Plastic Polyethylene Terephthalate Craig J. Donahue, Jennifer A. Exline, and Cynthia Warner
Procedure in which students depolymerize a common plastic (PET from 2-L pop bottles) under mild conditions using nontoxic chemicals to produce monomer building blocks.
Donahue, Craig J.; Exline, Jennifer A.; Warner, Cynthia. J. Chem. Educ. 2003, 80, 79.
Industrial Chemistry |
Synthesis |
Aromatic Compounds |
Polymerization
|
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
|
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
|
Colorful Azulene and Its Equally Colorful Derivatives Robert S. H. Liu
Analysis of azulene and related compounds for an explanation of their respective colors.
Liu, Robert S. H. J. Chem. Educ. 2002, 79, 183.
Atomic Properties / Structure |
MO Theory |
UV-Vis Spectroscopy |
Aromatic Compounds |
Alkenes
|
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
|
Preparation of a D-Glucose-Derived Alkene. An E2 Reaction for the Undergraduate Organic Chemistry Laboratory Peter Norris and Andrew Fluxe
Synthesis of four carbohydrate derivatives that highlight techniques such as inert atmosphere work, rotary evaporators, and flash column chromatography.
Norris, Peter; Fluxe, Andrew. J. Chem. Educ. 2001, 78, 1676.
Carbohydrates |
NMR Spectroscopy |
Synthesis |
Alkenes |
Elimination Reactions |
Chromatography
|
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
|
An Introduction to the Scientific Process: Preparation of Poly(vinyl acetate) Glue Robert G. Gilbert, Christopher M. Fellows, James McDonald, and Stuart W. Prescott
Exercise to give students experience in scientific processes while introducing them to synthetic polymer colloids.
Gilbert, Robert G.; Fellows, Christopher M.; McDonald, James; Prescott, Stuart W. J. Chem. Educ. 2001, 78, 1370.
Industrial Chemistry |
Noncovalent Interactions |
Surface Science |
Polymerization |
Applications of Chemistry |
Colloids
|
Moving Past Markovnikov's Rule E. Eugene Gooch
Extension of the Markovnikov Rule for addition reactions across a carbon-carbon double bond.
Gooch, E. Eugene. J. Chem. Educ. 2001, 78, 1358.
Synthesis |
Reactions |
Alkenes |
Addition Reactions |
Mechanisms of Reactions
|
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
|
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
|
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
|
Bromination, Elimination, and Polymerization: A 3-Step Sequence for the Preparation of Polystyrene from Ethylbenzene Elizabeth M. Sanford and Heather L. Hermann
An organic chemistry lab that introduces students to polymer chemistry is presented. Students complete a radical bromination of ethylbenzene, which is followed by elimination to give styrene. A radical polymerization is then completed to produce polystyrene.
Sanford, Elizabeth M.; Hermann, Heather L. J. Chem. Educ. 2000, 77, 1343.
Free Radicals |
Synthesis |
Polymerization
|
A Puzzling Alcohol Dehydration Reaction Solved by GC–MS Analysis Michael W. Pelter and Rebecca M. Macudzinski
The reaction of 2-methyl-2-propanol with ~50% sulfuric acid at 100 C yields isobutylene, which reacts further by a "puzzling" reaction. By coupling the GC/MS analysis of the product mixture with their knowledge of the mechanism of alcohol dehydration and alkene reactivity, students are able to identify the major products of this reaction.
Pelter, Michael W.; Macudzinski, Rebecca M. J. Chem. Educ. 1999, 76, 826.
Synthesis |
Microscale Lab |
Mass Spectrometry |
Gas Chromatography |
Alcohols |
Alkenes
|
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
|
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
|
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
|
On the Disproportionations of Cyclohexene and Related Compounds Alex Bunjes, Ingo Eilks, Manfred Pahlke, and Bernd Ralle*
The catalytic hydrogenation of liquid hydrocarbons is easy to realize in a simple laboratory experiment using a palladium catalyst. In the case of hydrogenation cyclohexen or cyclohexadiene in addition to the expected finding of cyclohexane among the hydrogenation products, the formation of benzene can be observed. In absence of hydrogen, the disproportionation of both starting materials to cyclohexane and benzene takes place.
Bunjes, Alex; Eilks, Ingo; Pahlke, Manfred; Ralle, Bernd. J. Chem. Educ. 1997, 74, 1323.
Alkanes / Cycloalkanes |
Aromatic Compounds |
Alkenes |
Synthesis
|
Old MacDonald Named a Compound: Branched Enynenynols Dennis Ryan
An imaginary teacher of organic chemistry thinks up some whimsical compounds for his students to name using IUPAC nomenclature rules.
Ryan, Dennis. J. Chem. Educ. 1997, 74, 782.
Learning Theories |
Nomenclature / Units / Symbols |
Alcohols |
Alkenes |
Alkynes |
Molecular Properties / Structure
|
Rayon from Dryer Lint: A Demonstration Michael A. Knopp
Threads of rayon several cm in length formed from ordinary household dryer lint stirred into the traditional Schweizer reagent mixture.
Knopp, Michael A. J. Chem. Educ. 1997, 74, 401.
Polymerization
|
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
|
Preparation and Solution Polymerization of Diacetylenes Bruce A. Hathaway and Angela M. Scates
Most published student laboratory syntheses of symmetrical diacetylenes follow Hay's procedure, with some modifications for using air as a source of oxygen. We report a simpler procedure, which has been useful in preparing a variety of diacetylenes. In addition, we have developed conditions suitable for solution polymerization of these diacetylenes to PDA's, using short-wave UV light.
Hathaway, Bruce A.; Scates, Angela M. J. Chem. Educ. 1997, 74, 111.
Synthesis |
Alkenes
|
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
|
The Neglected Element in Sophomore Organic Chemistry Kelly L. Bieda and Suzzane T. Purrington
There are many aspects of organic chemistry that would benefit from the inclusion of organofluorine chemistry. The properties of fluorine help in the clarification of many topics such as bond strength, leaving groups, substitution reactions, radical reactions, polymers, pharmaceuticals, and enzymes.
Bieda, Kelly L.; Purrington, Suzanne T. J. Chem. Educ. 1996, 73, 754.
Drugs / Pharmaceuticals |
Enzymes |
Polymerization |
Nucleophilic Substitution
|
Testing the Electrical Resistivity of Wax and Copper Composites: An Experiment for Simulating the Electrical Behavior of Metal-Filled Plastics Gabriel Pinto
Testing the Electrical Resistivity of Wax and Copper Composites: An Experiment for Simulating the Electrical Behavior of Metal-Filled Plastics
Gabriel Pinto. J. Chem. Educ. 1996, 73, 683.
Materials Science |
Polymerization |
Solids |
Physical Properties
|
Polymer Science Pilot Program Mary L. Maier
The Polymer Science Pilot Program consists of a sequence of experiences with polymers, designed to focus upon the ways in which these materials resemble and/or compare with nonpolymers in physical properties, versatility, and function.
Mary L. Maier. J. Chem. Educ. 1996, 73, 643.
Polymerization |
Physical Properties |
Materials Science
|
Relative Stabilities and Reactivities of Isolated Versus Conjugated Alkenes: Reconciliation Via a Molecular Orbital Approach Chariklia Sotiriou-Leventis, Samir B. Hanna, and Nicholas Leventis
The well-accepted practice of generating a pair of molecular orbitals, one of lower energy and another of higher energy than the original pair of overlapping atomic orbitals, and the concept of a particle in a one-dimensional box are implemented in a simplified, nonmathematical method that explains the relative stabilities and reactivities of alkenes with conjugated versus isolated double bonds.
Sotiriou-Leventis, Chariklia; Hanna, Samir B.; Leventis, Nicholas. J. Chem. Educ. 1996, 73, 295.
Alkenes |
MO Theory
|
Olefin Metathesis Polymerization: The Unexpected Role of Carbenoid Species in Formation of Macromolecules Donald M. Snyder
One particularly interesting topic still rarely seen outside of the research literature is the subject of metathesis polymerization. This article is intended to present the interested reader with a brief introduction to the mechanism of this unique process, its historical background, and some recent developments in the field.
Snyder, Donald M. J. Chem. Educ. 1996, 73, 155.
Polymerization |
Alkenes |
Mechanisms of Reactions
|
Nitroalkenes: Conjugate Nitro Compounds (Perekalin, V. V.; Lipina, E. S.; Berestovitskaya, V. M.; Efremov, D. A.)
Monograph.
J. Chem. Educ. 1995, 72, A93.
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
|
Using High Performance Liquid Chromatography to Determine the C60:C70 Ratio in Fullerene Soot: An Undergraduate Chemistry Lab Michael C. Zumwalt and M. Bonner Denton
Apparatus for producing fullerene soot and procedure for determining its C60-C70 ratio.
Zumwalt, Michael C.; Denton, M. Bonner. J. Chem. Educ. 1995, 72, 939.
Chromatography |
Separation Science |
Main-Group Elements |
Laboratory Equipment / Apparatus |
Alkenes |
HPLC |
Quantitative Analysis
|
Paper Models for Fullerenes C60-C84 John M. Beaton
Photocopyable patterns to construct C60-C84.
J. Chem. Educ. 1995, 72, 863.
Main-Group Elements |
Molecular Modeling |
Molecular Properties / Structure |
Alkenes
|
The Addition of Hydrogen Bromide to Simple Alkenes Hilton M. Weiss
Synthesis of 1-bromohexane.
Weiss, Hilton M. . J. Chem. Educ. 1995, 72, 848.
Synthesis |
Mechanisms of Reactions |
Addition Reactions |
Alkenes
|
Thermosetting Resins W. Peng and B. Riedl
A general description of the different chemical systems used as thermosetting resins, their applications, and some physicochemical aspects of their polymerization.
Peng, W.; Riedl, B. J. Chem. Educ. 1995, 72, 587.
Polymerization |
Industrial Chemistry |
Applications of Chemistry
|
A New Investigative Laboratory for Introductory Organic Chemistry Involving Polymer Synthesis and Characterization Kharas, Gregory B.
Project to develop a model organic laboratory curriculum that gives students the opportunity to be imaginative and creative by pursuing research projects in organic and polymer synthesis using a guided-discovery model.
Kharas, Gregory B. J. Chem. Educ. 1995, 72, 534.
Polymerization |
Synthesis
|
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
|
A Simple and Safe Catalytic Hydrogenation of 4-Vinylbenzoic Acid De, Shantanu; Gambhir, Geetu; Krishnamurty, H. G.
An alternative procedure to catalytic hydrogenation is catalytic transfer hydrogenation. In this technique, the reduction of an organic compound is achieved with the aid of a donor substance in the presence of a catalyst.
De, Shantanu; Gambhir, Geetu; Krishnamurty, H. G. J. Chem. Educ. 1994, 71, 992.
Catalysis |
Oxidation / Reduction |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes
|
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
|
Not So Late Night Chemistry with USD Koppang, Miles D.; Webb, Karl M.; Srinivasan, Rekha R.
Through the program, college students enhance their knowledge and expertise on a chemical topic and gain experience in scientific presentations. They also serve as role models to the high school students who can relate to college students more easily than the chemistry faculty members and their high school students.
Koppang, Miles D.; Webb, Karl M.; Srinivasan, Rekha R. J. Chem. Educ. 1994, 71, 929.
Forensic Chemistry |
Polymerization |
Electrochemistry |
Isotopes |
Acids / Bases
|
Using Formal Charges in Teaching Descriptive Inorganic Chemistry DeWit, David G.
Using the concept of formal charges to predict bond properties, determine molecular structure, and explain reactivities and the tendency to polymerize.
DeWit, David G. J. Chem. Educ. 1994, 71, 750.
Descriptive Chemistry |
Molecular Properties / Structure |
Lewis Structures |
Polymerization
|
Chemical Magic: Polymers from a Nonexistent Monomer Seymour, Raymond B.; Kauffman, George B.
Synthesis, properties, and applications of polyvinyl alcohol and related polymers.
Seymour, Raymond B.; Kauffman, George B. J. Chem. Educ. 1994, 71, 582.
Polymerization |
Alcohols
|
The Hydration of 1-Hexene and 1-Hexyne Touchette, Kim M.; Weiss, Hilton M.; Rozenberg, Daniel
The sulfuric acid-catalyzed hydration of 1-hexene and 1-hexyne.
Touchette, Kim M.; Weiss, Hilton M.; Rozenberg, Daniel J. Chem. Educ. 1994, 71, 534.
Alkynes |
Alkenes |
Alcohols |
Catalysis |
Synthesis
|
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
|
GC/MS experiments for the organic chemistry laboratory: I. E2 elimination of 2-bromo-2-methyloctane Novak, Michael; Heinrich, Julie; Martin, Kristy A.; Green, John; Lytle, Scott
Two capillary GC/MS experiments that were designed for and tested in a sophomore organic laboratory course.
Novak, Michael; Heinrich, Julie; Martin, Kristy A.; Green, John; Lytle, Scott J. Chem. Educ. 1993, 70, A103.
Gas Chromatography |
Alkenes |
Alkanes / Cycloalkanes |
Alcohols |
Elimination Reactions |
Synthesis
|
A fast, easy-to-run and safe ene reaction between benzyne and [beta]-pinene Drouin, Jacques; Jacq, Philippe
A fast, easy-to-run and safe ene reaction between benzyne and [beta]-pinene.
Drouin, Jacques; Jacq, Philippe J. Chem. Educ. 1993, 70, 863.
Alkenes |
Aromatic Compounds |
Alkynes |
Reactions
|
Polymer additives: III. Surface property and processing modifiers Stevens, Malcolm P.
The final installment of a three-part paper on the subject of polymer additives. Some of the properties these additives bring to polymers are: anti-blocking agents, anti-fogging agents, antistatic agents, coupling and releasing agents, blowing and crosslinking agents, defoaming agents, emulsifiers, and heat stabilizers.
Stevens, Malcolm P. J. Chem. Educ. 1993, 70, 713.
Polymerization |
Materials Science |
Applications of Chemistry |
Consumer Chemistry
|
Hydrochlorination of 1-propynylbenzene on alumina: A demonstration of kinetic and thermodynamic control using HCl produced in situ and molecular modeling Pienta, Norbert J.; Crawford, Scott D.; Kropp, Paul J.
A hydrochlorination experiment that provides sufficient latitude in choice of conditions.
Pienta, Norbert J.; Crawford, Scott D.; Kropp, Paul J. J. Chem. Educ. 1993, 70, 682.
Molecular Modeling |
Alkynes |
Alkenes |
Gas Chromatography |
NMR Spectroscopy |
Microscale Lab
|
Polymer spherulites: II. Crystallization kinetics Marentette, J. M.; Brown, G. R.
A commonplace polarized light microscope equipped with a hot stage permits examination of crystallization kinetics in addition to morphology and birefringence.
Marentette, J. M.; Brown, G. R. J. Chem. Educ. 1993, 70, 539.
Kinetics |
Crystals / Crystallography |
Polymerization
|
Polymer additives: II. Chemical and aesthetic property modifiers Stevens, Malcolm P.
Part two of a series that picks up on a discussion of additives that alter chemical and aesthetic properties of polymers.
Stevens, Malcolm P. J. Chem. Educ. 1993, 70, 535.
Materials Science |
Polymerization |
Dyes / Pigments |
Applications of Chemistry |
Consumer Chemistry
|
Differential scanning calorimetry study of the cross-linking of styrene and an unsaturated polyester: The chemistry of canoe manufacture. Vebrel, Joel; Grohens, Yves; Kadmiri, Abderazak; Gowling, Eric W.
An activity geared toward a course where experiments are designed to investigate the preparation of materials, the properties essential to understanding their formation, and the optimization of their application.
Vebrel, Joel; Grohens, Yves; Kadmiri, Abderazak; Gowling, Eric W. J. Chem. Educ. 1993, 70, 501.
Materials Science |
Polymerization |
Reactions |
Calorimetry / Thermochemistry
|
Identifying polymers through combustion and density Blumberg, Avrom A.
Using analytical chemistry class experiences as a way to not only quantitatively and qualitatively analyze substances, but also to gain practical experience with characteristic chemical reactions of those substances.
Blumberg, Avrom A. J. Chem. Educ. 1993, 70, 399.
Physical Properties |
Qualitative Analysis |
Polymerization |
Quantitative Analysis
|
Example of the Wolff-Kishner reduction procedure suitable for an undergraduate organic lab experiment: Preparation of oxindole Soriano, David S.
Example of the Wolff-Kishner reduction procedure suitable for an undergraduate organic lab experiment.
Soriano, David S. J. Chem. Educ. 1993, 70, 332.
Alkenes
|
The Aqueous Ring-Opening Metathesis Polymerization of Furan-Maleic Anhydride Adduct: Increased Catalytic Activity Using a Recyclable Transition Metal Catalyst Viswanathan, Tito; Jethmalani, Jagdish
ROMP offers an opportunity for an experiment that should fit well within the context of a laboratory in organic or polymer chemistry because the experimental yield can be characterized at the molecular level.
Viswanathan, Tito; Jethmalani, Jagdish J. Chem. Educ. 1993, 70, 165.
Polymerization |
NMR Spectroscopy
|
Microscale elimination reactions: Experiments for organic chemistry using the small scale approach Gilow, Helmuth M.
Procedure illustrating E1 and E2 reactions.
Gilow, Helmuth M. J. Chem. Educ. 1992, 69, A265.
Microscale Lab |
Reactions |
Elimination Reactions |
Alcohols |
Alkenes |
Catalysis
|
Quantitative analysis by FTIR: Thin films of copolymers of ethylene and vinyl acetate. Mathias, Lon J.; Hankins, Marie G.; Bertolucci, Craig M.; Grubb, Tina L.; Muthiah, Jeno.
Quantitation of coploymers of ethylene and vinyl acetate using FTIR.
Mathias, Lon J.; Hankins, Marie G.; Bertolucci, Craig M.; Grubb, Tina L.; Muthiah, Jeno. J. Chem. Educ. 1992, 69, A217.
IR Spectroscopy |
Fourier Transform Techniques |
Quantitative Analysis |
Alkenes |
Carboxylic Acids
|
Interfacial polymerizations: Microscale polymer laboratory experiments for undergraduate students. Lewis, Ronald G.; Choquette, Michael; Darden, Edward H.; Gilbert, Mark P.; Martinez, Douglas; Myhaver, Cindy; Schlichter, Karen; Woudenberg, Richard; Zawistowski, Keith.
Experimental procedure for vinyl polymerizations modified to fit a microscale format.
Lewis, Ronald G.; Choquette, Michael; Darden, Edward H.; Gilbert, Mark P.; Martinez, Douglas; Myhaver, Cindy; Schlichter, Karen; Woudenberg, Richard; Zawistowski, Keith. J. Chem. Educ. 1992, 69, A215.
Polymerization |
Microscale Lab |
Surface Science
|
New recrystallization solvent for synthesis of a bicyclo[2.2.1]heptene Harrison, Ernest A., Jr.
Toluene/hexane shown to be superior to EtOAc/MeOH as recrystallization solvent.
Harrison, Ernest A., Jr. J. Chem. Educ. 1992, 69, 860.
Synthesis |
Alkenes |
Solutions / Solvents |
Laboratory Management
|
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
|
Free-radical polymerization of acrylamide Silversmith, Ernest F.
A rapid and foolproof thermal polymerization.
Silversmith, Ernest F. J. Chem. Educ. 1992, 69, 763.
Free Radicals |
Polymerization |
Reactions
|
C60 and C70 made simply. Craig, Norman C.; Gee, Gilbert C.; Johnson, Adam R.
Procedure and apparatus for synthesizing C60 and C70.
Craig, Norman C.; Gee, Gilbert C.; Johnson, Adam R. J. Chem. Educ. 1992, 69, 664.
Laboratory Equipment / Apparatus |
Synthesis |
Alkenes
|
Simple generation of C60 (Buckminsterfullerene). Iacoe, David A.; Potter, William T.; Teeters, Dale.
A simple means for the production of fullerene-enhanced graphitic soot using equipment commonly found in most undergraduate chemistry and physics laboratories.
Iacoe, David A.; Potter, William T.; Teeters, Dale. J. Chem. Educ. 1992, 69, 663.
Synthesis |
Laboratory Equipment / Apparatus |
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
|
Ethylene-An unusual plant hormone Ainscough, Eric W.; Brodie, Andrew M.; Wallace, Anna L.
This article discusses some of the early historical observations about this ethylene, the production and concentration of ethylene in plants, the ethylene biosynthesis pathway, and the possible site of ethylene action.
Ainscough, Eric W.; Brodie, Andrew M.; Wallace, Anna L. J. Chem. Educ. 1992, 69, 315.
Alkenes |
Plant Chemistry |
Biosynthesis
|
The addition of hydrogen bromide to unsymmetrical alkenes Weiss, Hilton M.
The original article was valuable in pointing out the utility of HBr in acetic acid for the addition of HBr to alkenes.
Weiss, Hilton M. J. Chem. Educ. 1992, 69, 172.
Alkenes
|
Higher order cycloaddition reactions of adamantyl isobenzofulvene and isobenzofuran: A microscale synthesis illustrating the involvement of highly reactive intermediates and a simple FMO treatment of their cycloaddition periselectivities Russell, Richard A.; Longmore, Robert W.; Warrener, Ronald N.
The authors have developed an undergraduate laboratory experiment to illustrate a cycloaddition reaction using a simple mathematical approach.
Russell, Richard A.; Longmore, Robert W.; Warrener, Ronald N. J. Chem. Educ. 1992, 69, 164.
Microscale Lab |
Alkenes |
Synthesis |
MO Theory
|
Addition of IBr to fatty acids on the overhead projector Solomon, Sally; Fulep-Poszmik, Annamaria; Kulp, Gary; Yu, Heung
The interhalogen compound IBr dissolved in CCl4 is added to petroleum ether solutions of fatty acids to test for unsaturation.
Solomon, Sally; Fulep-Poszmik, Annamaria; Kulp, Gary; Yu, Heung J. Chem. Educ. 1992, 69, 66.
Alkanes / Cycloalkanes |
Alkenes
|
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
|
A quick and effective demonstration of anti-Markovnikov addition to alkenes Brown, Trevor M.; Dronsfield, Alan T.; Hitchcock, Ian
This reaction can be performed in less then 10 minutes and the product is easily identifiable.
Brown, Trevor M.; Dronsfield, Alan T.; Hitchcock, Ian J. Chem. Educ. 1991, 68, 785.
Alkenes |
Addition Reactions
|
Hydroboration-oxidation of (1R)-(+)-alpha-pinene to isopinocampheol: A microscale experiment that displays regio- and stereochemistry using NMR spectroscopy and molecular mechanics calculations Blankespoor, Ronald L.; Piers, Kenneth
The hydroboration-oxidation of alkenes is an important route to alcohols and therefore receives considerable treatment in standard organic textbooks. These authors present their findings of an example (an alkene that undergoes the hydroboration oxidation process) that displays both regiochemistry and stereochemistry.
Blankespoor, Ronald L.; Piers, Kenneth J. Chem. Educ. 1991, 68, 693.
Alkenes |
Oxidation / Reduction |
NMR Spectroscopy |
Alcohols
|
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
|
An internal comparison of the intermolecular forces of common organic functional groups: A thin-layer chromatography experiment Beauvais, Robert; Holman, R. W.
Due to the latest trends in organic chemistry textbook content sequences, it has become desirable to develop an experiment that is rapid, simple, and general, that would compare and contrast the various functional group classes of organic molecules in terms of their relative polarities, dipole moments, and intermolecular forces of attraction.
Beauvais, Robert; Holman, R. W. J. Chem. Educ. 1991, 68, 428.
Alkanes / Cycloalkanes |
Alkenes |
Alcohols |
Carboxylic Acids |
Aldehydes / Ketones |
Esters |
Qualitative Analysis |
Thin Layer Chromatography |
Noncovalent Interactions |
Molecular Properties / Structure
|
Synthesis of a bicyclo[2.2.1]heptene Diels-Alder adduct: An organic chemistry experiment utilizing NMR spectroscopy to assign endo stereochemistry Harrison, Ernest A., Jr.
An organic chemistry experiment utilizing NMR spectroscopy to assign endo stereochemistry via synthesis of a bicyclo[2.2.1]heptene Diels-Alder adduct.
Harrison, Ernest A., Jr. J. Chem. Educ. 1991, 68, 426.
Alkanes / Cycloalkanes |
Synthesis |
Alkenes |
Aromatic Compounds |
NMR Spectroscopy |
Thin Layer Chromatography
|
The diverse nature of the C6H6 molecule Potgeiter, J. H.
The purpose of this discussion is to show that C6H6 describes more than just one kind of benzene.
Potgeiter, J. H. J. Chem. Educ. 1991, 68, 280.
Aromatic Compounds |
Alkenes |
Reactions |
Constitutional Isomers
|
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
|
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
|
Organic Nomenclature (Lampman, Gary) Damey, Richard F.
An interactive tutorial / drill for naming organic compounds.
Damey, Richard F. J. Chem. Educ. 1990, 67, A220.
Nomenclature / Units / Symbols |
Enrichment / Review Materials |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes |
Ethers |
Alcohols |
Amines / Ammonium Compounds |
Phenols
|
Synthesis of a phenol-formaldehyde thermosetting polymer Bedard, Y.; Riedl, B.
Procedure that allows for the synthesis of a 50% aqueous solution of a prepolymer that, with the proper application of heat and pressure, can be used to bind together wood or other materials.
Bedard, Y.; Riedl, B. J. Chem. Educ. 1990, 67, 977.
Synthesis |
Aldehydes / Ketones |
Phenols |
Polymerization
|
An operationally simple hydroboration-oxidation experiment Kabalka, George W.; Wadgaonkar, Prakash P.; Chatla, Narayana
The reactions involve the use of in situ generated diborane as the hydroborating reagent and sodium perborate as the oxidizing agent to convert cyclopentene to cyclopentanol.
Kabalka, George W.; Wadgaonkar, Prakash P.; Chatla, Narayana J. Chem. Educ. 1990, 67, 975.
Synthesis |
Mechanisms of Reactions |
Alkenes |
Alcohols
|
Keeping track of directions of atomic orbitals: A useful device in organic chemistry Talaty, Erach R.
The usefulness of keeping track of the directions of atomic orbitals.
Talaty, Erach R. J. Chem. Educ. 1990, 67, 655.
Atomic Properties / Structure |
Alkenes |
Alkynes
|
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
|
The addition of hydrogen bromide to unsymmetrical alkenes: Introductory experiments in NMR spectroscopy and mechanistic chemistry Brown, Trevor M.; Dronsfield, Alan T.; Ellis, Robert
As an introduction to NMR the authors center their work around the addition of hydrogen bromide to unsymmetrical alkenes and use the coupling patterns in the proton NMR spectra to establish whether the addition product is consistent with the Markovnikov rule.
Brown, Trevor M.; Dronsfield, Alan T.; Ellis, Robert J. Chem. Educ. 1990, 67, 518.
NMR Spectroscopy |
Alkenes |
Mechanisms of Reactions
|
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
|
The preparation of Indanthrene Scarlet GG: A vat dye experiment for the introductory organic chemistry laboratory Lutz, Wilson B.
The vat dye Indanthrene Scarlet GG can easily be synthesized and applied to cloth within a single two hour laboratory period.
Lutz, Wilson B. J. Chem. Educ. 1990, 67, 71.
Synthesis |
Dyes / Pigments |
Alkenes
|
A Diels-Alder reaction for the overhead projector Kolb, Kenneth E.
Reacting the strong dienophile tetracyanothylene with anthracene as the diene.
Kolb, Kenneth E. J. Chem. Educ. 1989, 66, 955.
Alkenes |
Mechanisms of Reactions
|
A valence isomer trapping procedure for introductory organic laboratory: Synthesis of a homobarrelene derivative Kurtz, David W.; Johnson, Richard P.
Norcaradiene is trapped out of its cycloheptatriene valence isomer in a Diels-Alder reaction with maleic anhydride.
Kurtz, David W.; Johnson, Richard P. J. Chem. Educ. 1989, 66, 873.
Alkenes |
Mechanisms of Reactions
|
Isomerization of dimethyl maleate to dimethyl fumarate: An undergraduate experiment utilizing high performance liquid chromatography Ledlie, David B.; Wenzel, Thomas J.; Hendrickson, Susan M.
Introduces students to liquid chromatography, the stereoisomerization of alkenes, certain aspects of free radical chemistry, and thermodynamics.
Ledlie, David B.; Wenzel, Thomas J.; Hendrickson, Susan M. J. Chem. Educ. 1989, 66, 781.
HPLC |
Mechanisms of Reactions |
Esters |
Stereochemistry |
Free Radicals |
Alkenes |
Thermodynamics
|
The catalytic hydrogenation of methyl oleate by in situ hydrogen generation Plummer, Ben
Modification of the catalytic hydrogenation of methyl oleate into methyl stearate.
Plummer, Ben J. Chem. Educ. 1989, 66, 518.
Catalysis |
Alkenes |
Laboratory Equipment / Apparatus
|
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
|
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
|
Markownikoff's rule: What did he say and when did he say it? Tierney, John
The author traces the origin of this important rule.
Tierney, John J. Chem. Educ. 1988, 65, 1053.
Alkenes |
Synthesis
|
The SHOP process: An example of industrial creativity Reuben, Bryan; Wittcoff, Harold
The Shell Higher Olefins Process is probably the most remarkable industrial chemical process to have been developed in the past decade; this article highlights the process.
Reuben, Bryan; Wittcoff, Harold J. Chem. Educ. 1988, 65, 605.
Industrial Chemistry |
Surface Science |
Alcohols |
Polymerization |
Applications of Chemistry |
Fatty Acids
|
Organic lecture demonstrations Silversmith, Ernest F.
Organic chemistry may not be known for its spectacular, attention getting chemical reactions. Nevertheless, this author describes a few organic chemistry reactions that put points across and generate interest. This article provides a convenient sources of demonstrations and urges others to add to the collection. Demonstrations concerning: carbohydrates, spectroscopy, proteins, amines, carbohydrates, carboxylic acids, and much more.
Silversmith, Ernest F. J. Chem. Educ. 1988, 65, 70.
Molecular Properties / Structure |
Nucleophilic Substitution |
Acids / Bases |
Physical Properties |
Alkenes |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity |
Aldehydes / Ketones |
Alcohols
|
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 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
|
Preparation of cyclopentadiene from its dimer Dickson, Ronald S.; Dobney, Bruce J.; Eastwood, Frank W.
Procedure for preparing cyclopentadiene from its dimer.
Dickson, Ronald S.; Dobney, Bruce J.; Eastwood, Frank W. J. Chem. Educ. 1987, 64, 898.
Alkenes |
Synthesis
|
Classroom demonstrations of polymer principles. Part II. Polymer formation Rodriguez, F.; Mathias, L. J.; Kroschwitz, J.; Carraher, C. E., Jr.
Photopolymerization of acrylamide, bulk polymerization of methyl methacrylate, phenolic resins, and household adhesives and sealants.
Rodriguez, F.; Mathias, L. J.; Kroschwitz, J.; Carraher, C. E., Jr. J. Chem. Educ. 1987, 64, 886.
Polymerization
|
Expanded polystyrene: An experiment for undergraduate students Feigenbaum, Alexandre; Scholler, Denise
Two very simple procedures to produce expanded polystyrene.
Feigenbaum, Alexandre; Scholler, Denise J. Chem. Educ. 1987, 64, 810.
Polymerization
|
Generation of cyclopentadiene Ruekberg, Benjamin P.
Procedure and apparatus for generating cyclopentadiene.
Ruekberg, Benjamin P. J. Chem. Educ. 1987, 64, 726.
Alkenes |
Synthesis
|
A safe, convenient method of generating bromine for qualitative analysis Slayden, Suzauee W.; Do, Thuy H.; Smiley, Kimberly Y.; Nelson, Donna J.
A safe, convenient method of generating bromine used as a qualitative test for unsaturation, active methylene groups, phenols, and amines.
Slayden, Suzauee W.; Do, Thuy H.; Smiley, Kimberly Y.; Nelson, Donna J. J. Chem. Educ. 1987, 64, 368.
Qualitative Analysis |
Alkenes |
Phenols |
Amines / Ammonium Compounds |
Laboratory Management
|
Concerning dehydration of 2-methycyclohexanol Feigenbaum, A.
One half of class dehydrates 2-methycyclohexanol, the other half dehydrates 1-methycyclohexanol; gas chromatography retention times are then compared for the two product mixtures.
Feigenbaum, A. J. Chem. Educ. 1987, 64, 273.
Alcohols |
Alkenes |
Stereochemistry |
Constitutional Isomers |
Gas Chromatography
|
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
|
Voltammetric monitoring of Br- and Br3- concentrations during the bromination of styrene by Br3-: A laboratory experiment Desbene Monvernay, Annie; Berthelot, Jacques; Desbene, Paul-Louis
Electrochemical titration of Br- and Br3- and voltammetric monitoring of styrene bromination by TBEBr3.
Desbene Monvernay, Annie; Berthelot, Jacques; Desbene, Paul-Louis J. Chem. Educ. 1987, 64, 86.
Electrochemistry |
Titration / Volumetric Analysis |
Alkenes |
Reactions
|
Comparison of chemical oxidation of alkanes, alkenes, and alcohols on the overhead projector Kolb, Kenneth E.
This overhead projector demonstration utilizes two classical oxidants, permanganates and dichromate, to distinguish between alkanes, alkenes, and primary, secondary, and tertiary alcohols.
Kolb, Kenneth E. J. Chem. Educ. 1986, 63, 977.
Alcohols |
Alkanes / Cycloalkanes |
Alkenes |
Oxidation / Reduction |
Qualitative Analysis
|
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
|
Number of oxidations relative to methylene: A convenient method of recognizing and quantifying organic oxidation-reduction Kjonaas, Richard A.
This paper describes the use of a type of molecular oxidation number called "Number of oxidations relative to methylene".
Kjonaas, Richard A. J. Chem. Educ. 1986, 63, 311.
Oxidation / Reduction |
Qualitative Analysis |
Alkenes
|
A demonstration of the cuprammonium rayon process Kauffman, George B.; Karbassi, Mohammad
Generating rayon by dissolving cellulose in Schweizer's reagent.
Kauffman, George B.; Karbassi, Mohammad J. Chem. Educ. 1985, 62, 878.
Polymerization
|
Synthesis and a simple molecular weight determination of polystyrene Armstrong, Daniel W.; Marx, John N.; Kyle, Don; Alak, Ala
Procedure for synthesizing styrene and determining its molecular weight using thin layer chromatography.
Armstrong, Daniel W.; Marx, John N.; Kyle, Don; Alak, Ala J. Chem. Educ. 1985, 62, 705.
Synthesis |
Polymerization |
Chromatography
|
The NBS reaction: A simple explanation for the predominance of allylic substitution over olefin addition by bromine at low concentrations Wamser, Carl C.; Scott, Lawrence T.
What factors govern the reaction of Br2 with an alkene to give either allylic substitution or double bond addition?
Wamser, Carl C.; Scott, Lawrence T. J. Chem. Educ. 1985, 62, 650.
Mechanisms of Reactions |
Free Radicals |
Kinetics |
Alkenes
|
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
|
Who is anti-Markovnikov? Tedder, J. M.
What are the factors that control the rate and orientation of free radical addition to alkenes?
Tedder, J. M. J. Chem. Educ. 1984, 61, 237.
Mechanisms of Reactions |
Addition Reactions |
Free Radicals |
Alkenes
|
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
|
Oil shale - Heir to the petroleum kingdom Schachter, Y.
A discussion of oil shale provides students with real-world problems that require chemical literacy.
Schachter, Y. J. Chem. Educ. 1983, 60, 750.
Applications of Chemistry |
Alkenes |
Alkanes / Cycloalkanes |
Green Chemistry
|
Isobutylene revisited: An experiment introducing both qualitative and quantitative application of NMR spectroscopy Tremelling, Michael J.; Hammond, Christina N.
The product distribution is a contradiction to the general rule that the more highly substituted alkene is more stable.
Tremelling, Michael J.; Hammond, Christina N. J. Chem. Educ. 1982, 59, 697.
Alkenes |
NMR Spectroscopy |
Addition Reactions |
Molecular Properties / Structure
|
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
|
On the crosslinked structure of rubber: Classroom demonstration or experiment: A quantitative determination by swelling Sperling, L. H.; Michael, T. C.
Uses a rubber band to examine the crosslinked behavior of rubber.
Sperling, L. H.; Michael, T. C. J. Chem. Educ. 1982, 59, 651.
Applications of Chemistry |
Polymerization |
Molecular Properties / Structure
|
Pi bonding without tears Akeroyd, F. Michael
A non-mathematical treatment of sigma-pi bonding applied to conjugation, hyperconjugation, Markovnikoff addition, aromaticity, and aromatic substitution.
Akeroyd, F. Michael J. Chem. Educ. 1982, 59, 371.
Alkenes |
Mechanisms of Reactions |
Addition Reactions |
Aromatic Compounds
|
The problem of syn- versus anti-addition: An organic chemistry laboratory experiment Silversmith, Ernest F.
An experiment that allows a student to determine whether an addition to a carbon-carbon double bond proceeds in syn- or anti-fashion.
Silversmith, Ernest F. J. Chem. Educ. 1982, 59, 346.
Addition Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure |
Stereochemistry |
Synthesis |
Alkenes
|
Bent-bond models using framework molecular models Sund, Eldon H.; Suggs, Mark W.
Using tubing to represent double and triple bonds.
Sund, Eldon H.; Suggs, Mark W. J. Chem. Educ. 1980, 57, 638.
Molecular Modeling |
Alkenes |
Alkynes |
Covalent Bonding
|
Competency-based modular experiments in polymer science and technology Pearce, Eli M.; Wright, Carl E.; Bordoloi, Binoy K.
15 modular experiments in polymer science are listed; one of these is presented in detail.
Pearce, Eli M.; Wright, Carl E.; Bordoloi, Binoy K. J. Chem. Educ. 1980, 57, 375.
Polymerization
|
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
|
Diphenylbutadienes syntheses by means of the Wittig reaction: Experimental introduction to the use of phase transfer catalysis Gillois, J.; Guillerm, G.; Stephen, E.; Vo-Quang, L.
Intended as a project carried out by students at the end of introductory organic chemistry.
Gillois, J.; Guillerm, G.; Stephen, E.; Vo-Quang, L. J. Chem. Educ. 1980, 57, 161.
Synthesis |
Catalysis |
Alkenes |
Aldehydes / Ketones |
Stereochemistry
|
Polymer preparations in the laboratory Lampman, Gary M.; Ford, Doug W.; Hale, Wayne R.; Pinkers, Arthur; Sewell, Christopher G.
Some convenient procedures for preparing polymers that have been used in a course for industrial arts students.
Lampman, Gary M.; Ford, Doug W.; Hale, Wayne R.; Pinkers, Arthur; Sewell, Christopher G. J. Chem. Educ. 1979, 56, 626.
Polymerization |
Nonmajor Courses |
Industrial Chemistry
|
Polymer photophysics: A negative photoresist Bramwell, Fitzgerald B.; Zadjura, Richard E.; Stemp, Leo; Fahrenholtz, Susan R.; Flowers, John M.
A negative photoresist is formulated that consists of a solution of a photosensitive film-forming polymer or resin that is used to create the negative image of an object on a glass slide.
Bramwell, Fitzgerald B.; Zadjura, Richard E.; Stemp, Leo; Fahrenholtz, Susan R.; Flowers, John M. J. Chem. Educ. 1979, 56, 541.
Photochemistry |
Polymerization
|
A topical alkene preparation and oxidation Mitchell, Reginald H.; Hawkins, Blaine F.; West, Paul R.
Thermally depolymerizing polystyrene to styrene followed by an investigation of the properties of the flammable monomer produced.
Mitchell, Reginald H.; Hawkins, Blaine F.; West, Paul R. J. Chem. Educ. 1979, 56, 526.
Alkenes |
Synthesis |
Polymerization
|
Petroleum chemistry Kolb, Doris; Kolb, Kenneth E.
The history of petroleum chemistry.
Kolb, Doris; Kolb, Kenneth E. J. Chem. Educ. 1979, 56, 465.
Natural Products |
Geochemistry |
Applications of Chemistry |
Industrial Chemistry |
Catalysis |
Polymerization
|
Improving the Nylon rope trick Bieber, Theodore I.
Suggestions for improving this classic demonstration and why they do so.
Bieber, Theodore I. J. Chem. Educ. 1979, 56, 409.
Polymerization
|
Ethylene: The organic chemical industry's most important building block Fernelius, Condrad W.; Wittcoff, Harold; Varnerin, Robert E.
The sources, chemistry, and industrial uses of ethylene.
Fernelius, Condrad W.; Wittcoff, Harold; Varnerin, Robert E. J. Chem. Educ. 1979, 56, 385.
Alkenes |
Industrial Chemistry |
Applications of Chemistry |
Polymerization
|
Acne lotion - Great for pimples and making polymers! May, Jeffrey
Benzoyl peroxide can easily be separated from acne lotion.
May, Jeffrey J. Chem. Educ. 1979, 56, 239.
Polymerization |
Consumer Chemistry |
Separation Science
|
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
|
Balloon models for organic molecules Niac, G.
A balloon model can be used to demonstrate properties of small, organic molecules.
Niac, G. J. Chem. Educ. 1978, 55, 303.
Molecular Properties / Structure |
Alcohols |
Alkenes |
VSEPR Theory
|
Synthesis and characterization of vinyl pyridine styrene copolymers Morcellet, M.; Morcellet, J.; Delporte, M.; Estevez, J.
The number of experiments in polymer chemistry are rather limited for undergraduates. This note shares a synthesis and characterization in polymer chemistry.
Morcellet, M.; Morcellet, J.; Delporte, M.; Estevez, J. J. Chem. Educ. 1978, 55, 22.
Synthesis |
Polymerization
|
The Preparation of polyurethane foam: A lecture demonstration Dirreen, Glen E.; Shakhashiri, Bassam Z.
A polyurethane foam is produced by forming a polyurethane polymer concurrently with a gas evolution process.
Dirreen, Glen E.; Shakhashiri, Bassam Z. J. Chem. Educ. 1977, 54, 431.
Reactions |
Polymerization
|
Ethylene by naphtha cracking. Free radicals in action Wiseman, Peter
Ethylene manufacture, the mechanism of ethylene formation, maximizing ethylene yield, the effect of feedstock composition, and secondary reactions.
Wiseman, Peter J. Chem. Educ. 1977, 54, 154.
Free Radicals |
Industrial Chemistry |
Alkenes |
Mechanisms of Reactions |
Reactions |
Applications of Chemistry
|
A demonstration of polymer crosslinking and gel formation without heating Ross, Joseph H.
Produces an elastic gel at room temperature and provides an effective demonstration of gel properties to use in a discussion of lyophilic colloids.
Ross, Joseph H. J. Chem. Educ. 1977, 54, 110.
Polymerization |
Molecular Properties / Structure |
Colloids
|
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
|
Grignard dehydration reactions. An undergraduate organic experiment. Duty, Robert C.; Ryder, Bernard L.
In this laboratory, the authors have incorporated the Grignard reaction in a step-wise synthesis that has been successful in demonstrating several experimental and instrumental techniques.
Duty, Robert C.; Ryder, Bernard L. J. Chem. Educ. 1976, 53, 457.
Grignard Reagents |
Reactions |
Synthesis |
Alkenes
|
The hydroboration-oxidation of alkenes. A convenient anti-Markownikoff hydration experiment Kabalka, George W.; Hedgecock, Herbert C., Jr.
A hydroboration-oxidation sequence that relies on the borane dimethylsulfide complex as the hydroborating agent and trimethylamine-N-oxide dihydrate as the oxidizing agent.
Kabalka, George W.; Hedgecock, Herbert C., Jr. J. Chem. Educ. 1975, 52, 745.
Alkenes |
Oxidation / Reduction |
Addition Reactions
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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
|
Microbial oxidation of alkenes. An integrated organic-biology experiment Kumler, Philip L.; DeJong, Peter J.
The conversion of an appropriate terminal alkene to a 1,2-epoxyalkane by Pseudomonas oleovorans introduces students to the techniques used in carrying out chemical conversions employing microorganisms.
Kumler, Philip L.; DeJong, Peter J. J. Chem. Educ. 1975, 52, 475.
Oxidation / Reduction |
Alkenes |
Bioorganic Chemistry |
Biotechnology |
Natural Products
|
A series of related organic experiments with optional structure determinations Fairless, Billy J.; Ragsdale, Gary; Kerby, Claudia
The authors wish to report three related experiments that have been received with enthusiasm by organic students.
Fairless, Billy J.; Ragsdale, Gary; Kerby, Claudia J. Chem. Educ. 1974, 51, 61.
Phenols |
Alkenes |
NMR Spectroscopy
|
Polymerization as a model chain reaction Morton, Maurice
The building of long chain macromolecules offers the best opportunity for the study of chain reactions and the free radical mechanism.
Morton, Maurice J. Chem. Educ. 1973, 50, 740.
Conferences |
Professional Development |
Polymerization |
Reactions |
Free Radicals |
Kinetics |
Mechanisms of Reactions
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Dihalocarbene addition reaction Goh, S. H.
This experiment illustrates the synthetic utility of carbenes and that of phase transfer catalysis.
Goh, S. H. J. Chem. Educ. 1973, 50, 678.
Alkenes |
Addition Reactions |
Reactions |
Mechanisms of Reactions |
Catalysis |
Synthesis
|
The preparation of "Bouncing Putty." An undergraduate experiment in silicone chemistry Armitage, D. A.; Hughes, M. N.; Sinden, A. W.
Describes a method for preparing bouncing putty.
Armitage, D. A.; Hughes, M. N.; Sinden, A. W. J. Chem. Educ. 1973, 50, 434.
Polymerization
|
Non-conventional photochemical imaging processes Sahyun, M. R. V.
Considers the history and development of non-conventional photochemical imaging processes as well as the mechanisms of the photochemical formation of dyes, photochromism, and photopolymerization.
Sahyun, M. R. V. J. Chem. Educ. 1973, 50, 88.
Photochemistry |
Dyes / Pigments |
Applications of Chemistry |
Polymerization
|
Reactivity ratios from copolymerization kinetics. A quantitative gas-liquid chromatography experiment Mukatis, W. A.; Ohl, Temple
Gas-liquid chromatography is used to follow the rate of disappearance of two monomers as they polymerize.
Mukatis, W. A.; Ohl, Temple J. Chem. Educ. 1972, 49, 367.
Chromatography |
Gas Chromatography |
Polymerization |
Kinetics |
Rate Law
|
Acid hydrolysis of nylon 66 Berkowitz, W. F.
Presents a procedure for the hydrolysis of nylon 66.
Berkowitz, W. F. J. Chem. Educ. 1970, 47, 536.
Polymerization |
Synthesis
|
Indene reactions: An organic chemistry laboratory problem Garrison, James A.
Students are given a problem in which they are to determine which of two published accounts of reaction products involving derivatives of idene is correct.
Garrison, James A. J. Chem. Educ. 1970, 47, 300.
Alkenes |
Alcohols
|
The dehydration of 3,3-dimethyl-2-butanol Taber, Richard L.; Grantham, Gary D.; Champion, William C.
Presents an experiment that demonstrates the usefulness of gas chromatography as an analytical technique, emphasizes structural rearrangement, makes use of elementary thermodynamics, and gives the student some experience in the original literature.
Taber, Richard L.; Grantham, Gary D.; Champion, William C. J. Chem. Educ. 1969, 46, 849.
Alcohols |
Alkenes |
Gas Chromatography
|
A unique laboratory-lecture in organic chemistry Nienhouse, Everett J.
The laboratory-lecture considered centers about the products obtained from the dehydration of 4-methyl-2-pentanol.
Nienhouse, Everett J. J. Chem. Educ. 1969, 46, 765.
Alcohols |
Alkenes
|
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
|
Taking the peel out of paint Myers, Raymond R.
Prepolymerization and heating has helped to reduce the peeling of paint.
Myers, Raymond R. J. Chem. Educ. 1969, 46, 173.
Polymerization |
Consumer Chemistry |
Applications of Chemistry
|
Kinetics of condensation polymerization: Preparation of a polyester McCaffery, Edward L.
This experiment involves determining the reaction-rate constant for a condensation polymerization.
McCaffery, Edward L. J. Chem. Educ. 1969, 46, 59.
Kinetics |
Polymerization |
Synthesis |
Esters |
Rate Law
|
Substitution products in the Hofmann elimination Baumgarten, Ronald J.
Textbooks often state or imply that alkenes are the only products formed when tetra- alkylammonium hydroxides are heated.
Baumgarten, Ronald J. J. Chem. Educ. 1968, 45, 122.
Alkenes
|
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
|
Dehydration of 2-methylcyclohexanol Taber, Richard L.; Champion, William C.
This short article describes a simple alcohol dehydration that illustrates the Saytzeff Rule.
Taber, Richard L.; Champion, William C. J. Chem. Educ. 1967, 44, 620.
Alcohols |
Gas Chromatography |
Alkenes
|
Preparation of terephthaloyl chloride: Prelude to ersatz Nylon Rose, Norman C.
Describes the preparation of terephthaloyl chloride, from which nylon may be generated.
Rose, Norman C. J. Chem. Educ. 1967, 44, 283.
Synthesis |
Polymerization
|
Preparation and crosslinking of an unsaturated polyester: An organic chemistry experiment Stevens, M. P.
Unsaturated polyesters are ideally suited for introducing students to polymer chemistry in the laboratory because they are easy to prepare, the use both condensation and addition polymerization, and they serve to demonstrate the techniques involved in preparing the most widely used polymers.
Stevens, M. P. J. Chem. Educ. 1967, 44, 160.
Polymerization |
Esters
|
The chemistry of tetrasulfur tetranitride Allen, Christopher W.
The chemistry of sulfur-nitrogen compounds has several features of interest and importance: stability of the sulfur-nitrogen bond, tendency to form six- and eight-membered rings, ring contraction, polymerization, and negative ion formation.
Allen, Christopher W. J. Chem. Educ. 1967, 44, 38.
Covalent Bonding |
Polymerization
|
Bromination of alkanes: Experiment illustrating relative reactivities and synthetic utility Warkentin, J.
The radical halogenation of alkanes lend themselves well to the teaching of basic material such as bond dissociation energies, potential energy profiles, enthalpy of reaction, activation energy, and reaction rate.
Warkentin, J. J. Chem. Educ. 1966, 43, 331.
Electrochemistry |
Alkanes / Cycloalkanes |
Rate Law |
Kinetics |
Synthesis |
Alkenes |
Mechanisms of Reactions |
Free Radicals
|
The effect of structure on chemical and physical properties of polymers Price, Charles C.
Suggests using polymers to teach the effect of changes in structure on chemical reactivity, the effect of structure on physical properties, the role of catalysts, and the basic principles of a chain reaction mechanism.
Price, Charles C. J. Chem. Educ. 1965, 42, 13.
Physical Properties |
Molecular Properties / Structure |
Polymerization |
Kinetics |
Reactions |
Catalysis |
Mechanisms of Reactions
|
Editor's note: "The nylon rope trick" Morgan, Paul W.
Describes the popularity of the nylon rope trick.
Morgan, Paul W. J. Chem. Educ. 1965, 42, 12.
Polymerization
|
Polymer synthesis in the undergraduate organic laboratory Sorenson, Wayne R.
Presents a series of experiments on polymer synthesis for the undergraduate organic laboratory.
Sorenson, Wayne R. J. Chem. Educ. 1965, 42, 8.
Synthesis |
Polymerization |
Reactions |
Mechanisms of Reactions
|
PolystyreneA multistep synthesis Wilen, S. H.
Suggestions for research to accompany a previously published article.
Wilen, S. H. J. Chem. Educ. 1963, 40, A463.
Undergraduate Research |
Reactions |
Polymerization |
Synthesis
|
PolystyreneA multistep synthesis: For the undergraduate organic chemistry laboratory Wilen, Samuel H.; Kremer, Chester B.; Waltcher, Irving
Describes a multistep synthesis in which polystyrene is synthesized from benzene.
Wilen, Samuel H.; Kremer, Chester B.; Waltcher, Irving J. Chem. Educ. 1961, 38, 304.
Polymerization |
Synthesis
|
Letters to the editor Lambert, Frank L.
The author calls attention to polymer models.
Lambert, Frank L. J. Chem. Educ. 1960, 37, 490.
Molecular Modeling |
Molecular Properties / Structure |
Polymerization
|
Letters to the editor Morgan, Paul W.; Kwolek, Stephanie L.
Offers modifications to "The Nylon Rope Trick."
Morgan, Paul W.; Kwolek, Stephanie L. J. Chem. Educ. 1959, 36, 530.
Polymerization
|
The nylon rope trick: Demonstration of condensation polymerization Morgan, Paul W.; Kwolek, Stephanie L.
Describes the chemistry and variations of the classic polymerization demonstration.
Morgan, Paul W.; Kwolek, Stephanie L. J. Chem. Educ. 1959, 36, 182.
Polymerization
|
Laboratory preparation of cellophane Miller, Meredith
Offers a simplified procedure suitable for the preparation of cellophane for small-scale classroom demonstration purposes.
Miller, Meredith J. Chem. Educ. 1958, 35, 517.
Synthesis |
Polymerization
|
Anionic polymerization of vinyl monomers: A demonstration Zilkha, Albert; Albeck, Michael; Frankel, Max
Describes experiments on the polymerization of styrene using butyl lithium as a catalyst by an anionic mechanism.
Zilkha, Albert; Albeck, Michael; Frankel, Max J. Chem. Educ. 1958, 35, 345.
Polymerization |
Catalysis
|
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
|
Low-temperature polymerization: A laboratory demonstration Jenkins, L. T.
This demonstration illustrates the use of a low-temperature redox system for suspension polymerization of various monomers.
Jenkins, L. T. J. Chem. Educ. 1956, 33, 231.
Polymerization
|
Note on the representation of the electronic structures of acetylene and benzene Noller, Carl R.
The three dimensional nature of molecular orbitals in acetylene and benzene are illustrated.
Noller, Carl R. J. Chem. Educ. 1955, 32, 23.
Alkenes |
Alkynes |
Aromatic Compounds |
Molecular Properties / Structure |
Covalent Bonding |
MO Theory
|
Linear polymerization and synthetic fibers Moncrieff, Robert W.
Examines early research in polymers, the synthesis of polyesters and polyamides, the polymerization of hydrocarbons, and condensation and addition polymerization.
Moncrieff, Robert W. J. Chem. Educ. 1954, 31, 233.
Polymerization
|
Hyperconjugation: An elementary approach Ferreira, Ricardo Carvalho
Presents kinetic, thermochemical, and spectroscopic evidence for hyperconjugation in organic species.
Ferreira, Ricardo Carvalho J. Chem. Educ. 1952, 29, 554.
Alkenes
|
Lecture demonstrations with silicones Spalding, David P.
Offers a series of demonstrations designed to illustrate some of the basic properties of the silicones that make them unusual substances, including their resistance to high and low temperatures, unusual surface properties, and chemical inertness.
Spalding, David P. J. Chem. Educ. 1952, 29, 288.
Polymerization
|
The mechanisms of the reactions of aliphatic hydrocarbons Schmerling, Louis
Examines the formation of carbonium ions and free radicals, the polymerization of olefins, hydrogen-halogen exchange, the condensation of haloalkanes with alkenes, the alkylation of paraffins, the condensation of paraffins with chloroolefins, the cracking of paraffins and olefins, and the isomerization of paraffins.
Schmerling, Louis J. Chem. Educ. 1951, 28, 562.
Mechanisms of Reactions |
Alkanes / Cycloalkanes |
Free Radicals |
Polymerization
|
The preparation of "2-bromo-naphthalene" Wolfe, Winthrop C.; Doukas, Harry M.
Presents a procedure for the preparation of "2-bromo-naphthalene" in large or small amounts.
Wolfe, Winthrop C.; Doukas, Harry M. J. Chem. Educ. 1951, 28, 472.
Synthesis |
Alkenes
|
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