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Journal Articles: 309 results
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
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 protonproton 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
Teaching Chemistry Students How To Use Patent Databases and Glean Patent Information  Margy MacMillan and Lawton Shaw
This paper describes an effort to teach chemistry students how to use patent databases to search for information on applied chemical technology related to the manufacture of industrial and specialty chemicals.
MacMillan, Margy; Shaw, Lawton. J. Chem. Educ. 2008, 85, 997.
Drugs / Pharmaceuticals |
Industrial Chemistry
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 GCMS 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
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
Annatto Polymeric Microparticles: Natural Product Encapsulation by the Emulsion–Solvent Evaporation Method  Zaine Teixeira, Nelson Durán, and Silvia S. Guterres
In this experiment, extract from annatto seeds is microencapsulated in poly(3-hydroxybutyrate-co-3-hydroxyvalerate) by the emulsionsolvent evaporation method. Encapsulation delays degradation and promotes the sustained release of bixin, an extract useful in the cosmetic and food industries.
Teixeira, Zaine; Durán, Nelson; Guterres, Silvia S. J. Chem. Educ. 2008, 85, 946.
Applications of Chemistry |
Colloids |
Food Science |
Natural Products |
UV-Vis Spectroscopy |
Industrial Chemistry
The Preparation and Enzymatic Hydrolysis of a Library of Esters  Elizabeth M. Sanford and Traci L. Smith
In this investigative case study, students work collaboratively to prepare and characterize a library of esters using Fischer esterification and alcoholysis of acid chlorides and their subsequent enzymatic hydrolysis by pig liver and orange peel esterases.
Sanford, Elizabeth M.; Smith, Traci L. J. Chem. Educ. 2008, 85, 944.
Drugs / Pharmaceuticals |
Enzymes |
Esters |
Industrial Chemistry |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography
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
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
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
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
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
Hydration of Acetylene: A 125th Anniversary  Dmitry A. Ponomarev and Sergey M. Shevchenko
The discovery the hydration of alkynes catalyzed by mercury ions by Mikhail Kucherov made possible industrial production of acetaldehyde from acetylene and had a profound effect on the development of industrial chemistry in the 1920th centuries.
Ponomarev, Dmitry A.; Shevchenko, Sergey M. J. Chem. Educ. 2007, 84, 1725.
Addition Reactions |
Aldehydes / Ketones |
Alkynes |
Catalysis |
Industrial Chemistry |
Reactions
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 Hckel-aromatic and chiral Mbius-aromatic transition states.
Rzepa, Henry S. J. Chem. Educ. 2007, 84, 1535.
Alkanes / Cycloalkanes |
Alkenes |
Aromatic Compounds |
Mechanisms of Reactions |
Stereochemistry
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 brominationdebromination 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
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
Biodiesel Synthesis and Evaluation: An Organic Chemistry Experiment  Ehren C. Bucholtz
In this two week lab sequence students synthesize fatty acid methyl esters from simulated waste vegetable oil and determine whether the glycerol concentration of the resulting product is low enough to meet the specifications for marketable biodiesel.
Bucholtz, Ehren C. J. Chem. Educ. 2007, 84, 296.
Equilibrium |
Esters |
Industrial Chemistry |
Lipids |
Quantitative Analysis
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
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
Using a Simulated Industrial Setting for the Development of an Improved Solvent System for the Recrystallization of Benzoic Acid: A Student-Centered Project  Timothy R. Hightower and Jay D. Heeren
Presents a peer-led, problem-solving organic laboratory exercise that provide students with an opportunity to produce a more efficient recrystallization solvent in an industrial environment.
Hightower, Timothy R.; Heeren, Jay D. J. Chem. Educ. 2006, 83, 1663.
Carboxylic Acids |
Industrial Chemistry |
Separation Science |
Solutions / Solvents
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
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
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
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
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
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
Analysis of the Thickening Agents in Automotive Greases by GC–MS  David Mayotte, Craig J. Donahue, and Cheryl A. Snyder
Describes a laboratory procedure for the identification of the thickening agents in lubricating greases by GCMS.
Mayotte, David; Donahue, Craig J.; Snyder, Cheryl A. J. Chem. Educ. 2006, 83, 902.
Applications of Chemistry |
Consumer Chemistry |
Gas Chromatography |
Industrial Chemistry |
Mass Spectrometry |
Separation Science |
Fatty Acids
Lubricating Grease: A Chemical Primer  Craig J. Donahue
This article provides an overview of the function, properties, composition, and preparation of lubricating grease
Donahue, Craig J. J. Chem. Educ. 2006, 83, 862.
Applications of Chemistry |
Industrial Chemistry |
Fatty Acids
Chemistry of Electronic Gases  James R. Clark
The chemistry of electronic gases can be used in the classroom to provide many interesting examples of molecular structures, chemical reactions, periodic trends, and environmental chemistry.
Clark, James R. J. Chem. Educ. 2006, 83, 857.
Applications of Chemistry |
Gases |
Industrial Chemistry |
Semiconductors |
Solid State Chemistry
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
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
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
Incorporating Chemical Information Instruction and Environmental Science into the First-Year Organic Chemistry Laboratory  R. G. Landolt
Through a cooperative learning strategy, students are challenged to relate concepts learned in organic chemistry to published research, in order to attack a "real-world" environmental problem.
Landolt, R. G. J. Chem. Educ. 2006, 83, 334.
Applications of Chemistry |
Enrichment / Review Materials |
Industrial Chemistry |
Student-Centered Learning
Synthesis of Methyl Diantilis, a Commercially Important Fragrance  William H. Miles and Katelyn B. Connell
Describes the synthesis of a family of fragrances, including the commercially important Methyl Diantilis, and provides an excellent introduction to intellectual property laws.
Miles, William H.; Connell, Katelyn B. J. Chem. Educ. 2006, 83, 285.
Alcohols |
Food Science |
Catalysis |
Ethers |
Industrial Chemistry |
IR Spectroscopy |
Lewis Acids / Bases |
NMR Spectroscopy |
Oxidation / Reduction |
Synthesis
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
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
The Entrance and Exit Effects in Small Electrochemical Filter-Press Reactors Used in the Laboratory  Angel Frías-Ferrer, José González-García, Verónica Sáez, Eduardo Expósito, Carlos M. ánchez-Sánchez, Vicente Montiel, Antonio Aldaz, and Frank C. Walsh
An experiment has been designed to aid chemical engineering students in understanding the importance of size in small reactors in order to get suitable data for subsequent extrapolations to larger reactors and, therefore, for the scaleup of small systems. The experimental arrangement and procedures are described, and the theory needed to interpret the experimental results is discussed. Reactor geometry and size and experimental procedure are highlighted as key parameters in the study.
Frías-Ferrer, Angel; González-García, José; Sáez, Verónica; Expósito, Eduardo; ánchez-Sánchez, Carlos M.; Montiel, Vicente; Aldaz, Antonio; Walsh, Frank C. J. Chem. Educ. 2005, 82, 1395.
Electrochemistry |
Industrial Chemistry |
Oxidation / Reduction |
Transport Properties
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 DielsAlder 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
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
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 CC single and double bonds. This article provides a list of experimentally determined relative energies of the cis and trans isomers within the series cycloheptenecycloundecene, 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
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
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
Are We Serious about Preparing Chemists for the 21st Century Workplace or Are We Just Teaching Chemistry?  Sylvia Kerr and Olaf Runquist
What characteristics of employees do you value in the workplace? Sixteen leaders from world-class chemistry-based industries responded: "We want competent scientists who have high-level communication skills, cultural competencies, knowledge of how for-profit organizations function, excellent team problem-solving skills, broad backgrounds, strong work ethics, the ability to move effortlessly from science to business to humanitarian issues, and data-analysis skills." A wish list of 16 valued characteristics was generated.
Kerr, Sylvia; Runquist, Olaf. J. Chem. Educ. 2005, 82, 231.
Professional Development |
Industrial Chemistry |
Student / Career Counseling
Nitrogen: It Always Needs a Fix  Kathryn R. Williams
The fixation of nitrogen was a popular topic in early issues of the Journal of Chemical Education. This column, From Past Issues, briefly summarizes articles on the nonbiological methods for nitrogen fixation.
Williams, Kathryn R. J. Chem. Educ. 2005, 82, 194.
Industrial Chemistry |
Agricultural Chemistry
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
Analysis of Gold Ores by Fire Assay  Kristy M. Blyth, David N. Phillips, and Wilhelm van Bronswijk
This article describes a laboratory exercise for the analysis of gold using the fire-assay technique. This method of analysis not only provides students with an introduction to the technique of fire assay, but also covers some very interesting acidbase and redox chemistry. The gold is collected in a lead button while the remainder of the constituents find their way into a slag. The gold is recovered from the lead by absorption in a boneash cupel.
Blyth, Kristy M.; Phillips, David N.; van Bronswijk, Wilhelm. J. Chem. Educ. 2004, 81, 1780.
Acids / Bases |
Industrial Chemistry |
Metals |
Quantitative Analysis |
Oxidation / Reduction
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
Scaling Up Effects in the Organic Laboratory  Anna Persson and Ulf M. Lindström
A simple, yet safe and effective set of experiments to expose chemistry students to some of the effects that may be encountered when scaling up an organic reaction is described. The exothermic DielsAlder reaction between maleic anhydride and cyclopentadiene was found to be ideal for our purposes and was performed in small, medium, and large scale for comparison. The observed differences of heat evolution between the three scales were significant. Also, to demonstrate how excess heat evolution can be controlled by simple means, two additional experiments in which the reaction was run either with small glass helices or water present were performed.
Persson, Anna; Lindström, Ulf M. J. Chem. Educ. 2004, 81, 1353.
Industrial Chemistry |
Synthesis |
Laboratory Management
The History of Ion Chromatography: The Engineering Perspective  Barton Evans
This article traces the history of the engineering development related to the several generations of ion chromatography instruments, columns, suppressers, and software. In so doing, several representative engineering challenges and their outcomes are discussed including: early directions (traveling without a road map, or "going where the applications are"), dealing with an extremely corrosive mobile phase (aka: the "eluent"), resolving the inherent incompatibilities of nonmetallic flow paths with the benefits of high-pressure, elevated temperature operation, managing the ever-evolving nature of the suppressor, coping with requirements for ultra high-end online systems, and providing extremely simple-to-use dedicated analyzer systems.
Evans, Barton. J. Chem. Educ. 2004, 81, 1285.
Chromatography |
Industrial Chemistry |
Instrumental Methods |
Ion Exchange |
Laboratory Equipment / Apparatus |
Separation Science |
Water / Water Chemistry
Ion Chromatography: An Account of Its Conception and Early Development  Hamish Small
In the late 1950s, a small group of chemists at the Dow Chemical Company envisioned replacing these classical methods of inorganic analysis with but a single, universal chromatographic technique. They called their project "Inorganic Chromatography". This article describes how they developed this concept into a new technique, ready for commercial development into what we know today as "Ion Chromatography". In particular, the account will describe: how the Dow scientists adapted electrical conductance monitoring to chromatography, the introduction of the suppressor to chromatography, the invention of special stationary phases, and the evolution of strategies and principles that would shape and guide the practice of ion chromatography for many years to come.
Small, Hamish. J. Chem. Educ. 2004, 81, 1277.
Chromatography |
Industrial Chemistry |
Instrumental Methods |
Ion Exchange |
Laboratory Equipment / Apparatus |
Separation Science |
Water / Water Chemistry
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 Dambaski
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; Dambaski, Zdravko. J. Chem. Educ. 2004, 81, 1026.
Heterocycles |
Alkenes |
Stereochemistry |
Synthesis |
NMR Spectroscopy
Chlor–Alkali Industry: A Laboratory Scale Approach  C. M. Sánchez-Sánchez, E. Expósito, A. Frías-Ferrer, J. González-García, V. Montiel, and A. Aldaz
An experiment is described that approximates the industrial chloralkali process using a membrane cell.
Sánchez-Sánchez, C. M.; Expósito, E.; Frías-Ferrer, A.; González-García, J.; Montiel, V.; Aldaz, A. J. Chem. Educ. 2004, 81, 698.
Electrochemistry |
Industrial Chemistry |
Oxidation / Reduction
Analysis of an Air Conditioning Coolant Solution for Metal Contamination Using Atomic Absorption Spectroscopy. An Undergraduate Instrumental Analysis Exercise Simulating an Industrial Assignment  Michael J. Baird
The analysis of eight metals in an ethylene glycolywater solution by atomic absorption spectroscopy provided a real-life assignment for students in an instrumental analysis course.
Baird, Michael J. J. Chem. Educ. 2004, 81, 259.
Atomic Properties / Structure |
Green Chemistry |
Industrial Chemistry |
Metals |
Atomic Spectroscopy
Steam Hydrocarbon Cracking and Reforming  Michael Golombok
We examine steam hydrocarbon reforming and steam hydrocarbon cracking as an example of two processes that operate under different chemical reactivity regimes: equilibrium determined and kinetically determined, respectively. The feed streams and reaction conditions are similar, but the products are different. The role of catalysis for the two processes is compared and the effects on the kinetics are discussed.
Golombok, Michael. J. Chem. Educ. 2004, 81, 228.
Aromatic Compounds |
Equilibrium |
Gases |
Industrial Chemistry |
Kinetics
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
ChemTechLinks: Alliances for Chemical Technician Education  Tamara Nameroff
ChemTechLinks (CTL) is a project of the American Chemical Society (ACS) Educational and International Activities Division and funded by the National Science Foundation to support and advance chemistry-based technician education. The project aims to help improve technician education programs, foster academic-industry alliances, provide professional development opportunities for faculty, and increase student recruitment into chemical technology.
Nameroff, Tamara. J. Chem. Educ. 2003, 80, 993.
Chemical Technicians |
Industrial Chemistry |
Professional Development |
Administrative Issues
Tensile Strength Measurements on Biopolymer Films  Eugene S. Stevens and Mark D. Poliks
Measuring the tensile strength of biopolymer films using a simple student apparatus; results are compared with data obtained from industry-standard equipment.
Stevens, Eugene S.; Poliks, Mark D. J. Chem. Educ. 2003, 80, 810.
Biotechnology |
Carbohydrates |
Industrial Chemistry |
Laboratory Equipment / Apparatus |
Materials Science |
Proteins / Peptides
The Chemistry of Fragrances: A Group Exercise for Chemistry Students  Roger Duprey, Charles S. Sell, and Nigel D. Lowe
Description of the Fragrance structured learning package (SLP), developed by the Department of Chemistry at the University of York to illustrate the roles of professional chemists in industrial organizations.
Duprey, Roger; Sell, Charles S.; Lowe, Nigel D. J. Chem. Educ. 2003, 80, 513.
Consumer Chemistry |
Industrial Chemistry |
Synthesis |
Student / Career Counseling |
Applications of Chemistry
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
Process Development as a Curriculum Component in Organic Chemistry Courses: Points of View from Academia and Industry  Marek Konieczny and Atsuhiko Zanka
Suggestions for introducing process development into the organic chemistry curriculum - solving real-life, practical problems by applying theoretical knowledge.
Konieczny, Marck; Zanka, Atsuhiko. J. Chem. Educ. 2003, 80, 248.
Industrial Chemistry |
Medicinal Chemistry |
Administrative Issues
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
Analytical Chemistry in a GMP Environment: A Practical Guide (edited by James M. Miller and Jonathan B. Crowther)  David T. Harvey
Emphasizes issues faced by analytical chemists working in the pharmaceutical industry subject to federal regulations, such as the FDA's Good Manufacturing Practice (GMP) rules.
Harvey, David T. J. Chem. Educ. 2002, 79, 1419.
Industrial Chemistry |
Drugs / Pharmaceuticals
Preparation and Characterization of Bayerite Samples: Use of Diffuse Reflectance Infrared Spectroscopy to Monitor Purification  Nsoki Phambu, Bernard Humbert, and Andre Burneau
Experiment that gives students an opportunity to prepare an inorganic compound that is neither commercially available not found in catalogs.
Phambu, Nsoki; Humbert, Bernard; Burneau, Andre. J. Chem. Educ. 2002, 79, 1117.
Industrial Chemistry |
IR Spectroscopy |
Quantum Chemistry |
Raman Spectroscopy |
Synthesis |
Fourier Transform Techniques
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
The Avtex Saga: National Security versus Environmental Protection  Susan Groves and Frank A. Settle Jr.
History of the controversy surrounding the production of rayon at Fron Royal, Virginia, the state's largest Superfund site and, at one time, the nation's second largest source of air pollution; includes discussion of the use of this case study with classes.
Groves, Susan; Settle, Frank A., Jr. J. Chem. Educ. 2002, 79, 685.
Industrial Chemistry
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
Determination of Free Lime in Clinker and Cement by Iodometry. An Undergraduate Experiment in Redox Titrimetry  Oi-Wah Lau, Shiu-Fai Luk, Nina L. N. Cheng, and Hoi-Yin Woo
Experiment to determine the free lime in cement and clinker through iodometry.
Lau, Oi-Wah; Luk, Shiu-Fai; Cheng, Nina L. N.; Woo, Hoi-Yin. J. Chem. Educ. 2001, 78, 1671.
Acids / Bases |
Industrial Chemistry |
Quantitative Analysis |
Oxidation / Reduction |
Titration / Volumetric Analysis |
Separation Science
Workplace Skills Taught in a Simulated Analytical Department  Susan Sonchik Marine
2-year Chemical Technology Program that progressively builds lab and workplace skills, with a focus on a course that simulates an industrial analytical department.
Marine, Susan Sonchik. J. Chem. Educ. 2001, 78, 1448.
Chemical Technicians |
Industrial Chemistry
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
Determining the Percent Water in Organic Solvents Using the Zwitterionic Dimroth-Reichardt Betaine ET-30 Dye. An Industrially Relevant Application of a Previously Published Laboratory Experiment  Mark F. Vitha
ET-30 is used to determine the percent water in an organic solvent. This experiment, combined with a case study from Procter & Gamble's workshop "Professional Analytical Chemists in Industry", teaches students about the importance of dry organic solvents, the differences in diode array and scanning UV-vis spectrophotometers, the use of a wide variety of instrumental and wet-chemical analyses in answering analytical questions, and the application of the scientific approach to the solution of industrial chemical problems.
Vitha, Mark F. J. Chem. Educ. 2001, 78, 370.
Dyes / Pigments |
Instrumental Methods |
UV-Vis Spectroscopy |
Water / Water Chemistry |
Industrial Chemistry
Demonstration of Surface Tension  Andrew J. Rosenthal
Even though surface tension is a tensor with a relatively small magnitude, when it acts on particles with a small radius, the overall force produced is substantial. Surface tension is responsible for the destabilization of many colloidal systems. This short paper describes a simple demonstration that illustrates the phenomenon.
Rosenthal, Andrew J. J. Chem. Educ. 2001, 78, 332.
Colloids |
Food Science |
Industrial Chemistry |
Surface Science
Chemistry: An Industry-Based Laboratory Manual (by John Kenkel)  Sue K. Ballard
Laboratory manual for training potential chemistry-based laboratory technicians.
Ballard, Sue K. J. Chem. Educ. 2001, 78, 167.
Industrial Chemistry |
Chemical Technicians
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
A Short, One-Pot Synthesis of Bupropion (Zyban®, Wellbutrin®)  Daniel M. Perrine, Jason T. Ross, Stephen J. Nervi, and Richard H. Zimmerman
A one-pot synthesis of ()-2-(t-butylamino)-3'-chloropropiophenone (bupropion) as its hydrochloride salt (Zyban, Wellbutrin), an important antidepressant drug used in the treatment of nicotine addiction, is described. The procedure is suitable for students in their first year of organic chemistry.
Perrine, Daniel M.; Ross, Jason T.; Nervi, Stephen J.; Zimmerman, Richard H. J. Chem. Educ. 2000, 77, 1479.
Drugs / Pharmaceuticals |
Industrial Chemistry |
Medicinal Chemistry |
Synthesis |
Applications of Chemistry
Chromatographic Separations Using Solid-Phase Extraction Cartridges: Separation of Wine Phenolics  Charles A. Brenneman and Susan E. Ebeler
We describe a simple laboratory experiment that demonstrates the principles of chromatographic separation using solid-phase extraction columns and red wine. By adjusting pH and mobile phase composition, the wine is separated into three fractions of differing polarity. The content of each fraction can be monitored by UV-vis spectroscopy.
Brenneman, Charles A.; Ebeler, Susan E. J. Chem. Educ. 1999, 76, 1710.
Chromatography |
Natural Products |
Separation Science |
Industrial Chemistry
Innovations for an Industry-Based Curriculum: The I.O.N.S. Concept  John Kenkel, Bradette Hemmerling, and Paul Kelter
This paper describes an innovative concept, I.O.N.S. (Innovative Options and New Solutions), the name of a fictitious consulting corporation for which an introductory student is a chemistry technician; the activities and content are designed to build an understanding of chemistry in industry and society.
Kenkel, John; Hemmerling, Bradette; Kelter, Paul B. J. Chem. Educ. 1999, 76, 889.
Industrial Chemistry |
Learning Theories |
Applications of Chemistry |
Chemical Technicians
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
Properties of Zeolite A Obtained from Powdered Laundry Detergent (the author replies)  Lindquist, David
The thermal instability of zeolite NH4-A and the inability to form zeolite H-A.
Lindquist, David J. Chem. Educ. 1999, 76, 470.
Industrial Chemistry |
Catalysis
Properties of Zeolite A Obtained from Powdered Laundry Detergent  Davis, Pamela J.; Bekkum, Herman van; Coker, Eric N.
The thermal instability of zeolite NH4-A and the inability to form zeolite H-A.
Davis, Pamela J.; Bekkum, Herman van; Coker, Eric N. J. Chem. Educ. 1999, 76, 469.
Industrial Chemistry |
Catalysis
An Undergraduate Experiment in Polyester (PET) Synthesis  Andrew N. Cammidge
The most important polyester manufactured industrially is PET (polyethyleneterephthalate). We describe an experiment that conveniently mimics the industrial synthesis in the undergraduate laboratory.
Cammidge, Andrew N. J. Chem. Educ. 1999, 76, 236.
Synthesis |
Equilibrium |
Stoichiometry |
Industrial Chemistry
Fifty-Year Trends in the Chemical Industry: What Do They Mean for Chemical Education?  Chadwick A. Tolman and George W. Parshall
This article describes some of these changes from the perspectives of the authors, whose careers span most of the preceding half-century. We describe five illustrative technological developments in the industry and changes we have seen in the industrial research laboratory, and offer viewpoints on how these changes affect the educational needs of students going into industrial careers.
Tolman, Chadwick A.; Parshall, George W. J. Chem. Educ. 1999, 76, 177.
Industrial Chemistry |
Student / Career Counseling
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
Developing Professional Skills in a Third-Year Undergraduate Chemistry Course Offered in Western Australia  Jeffrey G. Dunn, Robert I. Kagi, and David N. Phillips
There is a growing need for a teaching that links students to situations they will encounter upon gaining employment. The Chemistry and Technology unit has been developed over a 12-year period and is presented in the final semester of the course. It comprises six modules and is taught by lecturers from industry and the staff of the School. The Professional Practice, Consumer Chemistry, and Environmental modules are ones that most teachers could consider in their course.
Dunn, Jeffrey G.; Kagi, Robert I.; Phillips, David N. J. Chem. Educ. 1998, 75, 1313.
Consumer Chemistry |
Industrial Chemistry |
Electrochemistry |
Green Chemistry |
Geochemistry
Synthesis of NMP, a Fluoxetine (Prozac) Precursor, in the Introductory Organic Laboratory  Daniel M. Perrine, Nathan R. Sabanayagam, and Kristy J. Reynolds
A synthesis of the immediate precursor of the widely used antidepressant fluoxetine (Prozac) is described. The procedure is short, safe, and simple enough to serve as a laboratory exercise for undergraduate students in the second semester of introductory organic chemistry and is one which will be particularly interesting to those planning a career in the health sciences.
Perrine, Daniel M.; Sabanayagam, Nathan R.; Reynolds, Kristy J. J. Chem. Educ. 1998, 75, 1266.
Drugs / Pharmaceuticals |
Industrial Chemistry |
Medicinal Chemistry |
Synthesis |
Aromatic Compounds
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
To Teach Chemists Engineering  Raphael Semiat and Baruch Grinbaum
Based on our experience in R&D programs in the industry, working with chemists, engineers of all disciplines and technicians, we have encountered a problem with the ability of fresh chemists and biologists to cooperate with other professional workers on mutual problems: the lack of common language, professional limitations and ways of cooperation with coworkers.
Semiat, Raphael; Grinbaum, Baruch. J. Chem. Educ. 1998, 75, 583.
Industrial Chemistry
The DuPont Conference: Implications for the Chemical Technology Curriculum  John Kenkel, Sue Rutledge, and Paul B. Kelter
Southeast Community College (SCC) hosted the first DuPont Conference for Chemical Technology Education at its Lincoln, Nebraska campus October 4-6, 1997. The conference brought together fourteen practicing chemists and chemistry technicians and five college and university faculty members for the express purpose of suggesting new laboratory activities that would help relate the real world of work to the education of chemical laboratory technicians in community colleges.
Kenkel, John; Rutledge, Sue; Kelter, Paul B. J. Chem. Educ. 1998, 75, 531.
Industrial Chemistry
A Chemical Technology Program Partnership  Gary Hicks
Highlights a small 2-year college and its relations with chemical companies.
Hicks, Gary. J. Chem. Educ. 1998, 75, 18.
Administrative Issues |
Professional Development |
Industrial Chemistry
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
Vanillin: Synthetic Flavoring from Spent Sulfite Liquor  Martin B. Hocking
The isolation and preparation of vanillin, its commercial preparation from lignin, and environmental concerns.
Hocking, Martin B. J. Chem. Educ. 1997, 74, 1055.
Consumer Chemistry |
Industrial Chemistry |
Food Science |
Natural Products |
Applications of Chemistry |
Aromatic Compounds |
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
Education for Industry  Lynn Melton
This column addresses a broader question about the function and performance of both undergraduate (and graduate) education in preparing students for industrial careers.
Melton, Lynn. J. Chem. Educ. 1997, 74, 754.
Industrial Chemistry
An Introduction to Industrial Chemistry, 3rd ed. edited by Alan Heaton  reviewed by Robert H. Paine
This treatise "provides undergraduate students of chemistry and chemical engineering with an appreciation of the major features of the chemical industry."
Paine, Robert H. J. Chem. Educ. 1997, 74, 627.
Industrial Chemistry
Partners in Chemical Education: Proceedings of the International Conference on Industry - Education Initiatives in Chemistry edited by J. N. Lazonby and D. J. Waddington  reviewed by Hal Harris
Considers the question "What is the place of industrial chemistry in the curriculum?"
Harris, Hal. J. Chem. Educ. 1997, 74, 626.
Industrial Chemistry
Properties of Zeolite A Obtained from Powdered Laundry Detergent: An Undergraduate Chemistry Experiment  David A. Lindquist and Alison L. Smoot
A number of laboratory experiments using zeolites filtered from a suspension of powdered laundry detergent are described. The various experiments illustrate the myriad uses of zeolites as desiccants, ion exchange materials, and catalysts.
Lindquist, David A.; Smoot, Alison L. . J. Chem. Educ. 1997, 74, 569.
Catalysis |
Consumer Chemistry |
Industrial Chemistry |
Ion Exchange
The Chemistry of Paper Preservation: Part 4. Alkaline Paper  Henry A. Carter
The use of alkaline paper can minimize the problem of acidity for new papers. This study focuses on the chemistry involved in the sizing of both acid and alkaline papers and the types of fillers used. The advantages and potential problems in alkaline paper making are also discussed.
Carter, Henry A. J. Chem. Educ. 1997, 74, 508.
Acids / Bases |
Industrial Chemistry |
Applications of Chemistry
The PACT Ambassador Outreach Program: More Than Just a Bunch of "Old White-Haired Scientists"  Mark Sabo, Mickey Sarquis, Chris Ennis
The Ambassador Program described in this article provides a mechanism for industrial/academic interaction to take place. The Ambassador Program brings industrial scientists and technicians into high school and two-year college classrooms to expose both students and teachers to issues faced in the industrial workplace and laboratory.
Sabo, Mark; Sarquis, Mickey; Ennis, Chris. J. Chem. Educ. 1997, 74, 450.
Industrial Chemistry
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
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
Patty's Industrial Hygiene and Toxicology. Volume 2E: Toxicology, Fourth Edition (Clayton, George D.; Clayton, Florence E.)  
New title in a continuing series.
J. Chem. Educ. 1995, 72, A109.
Industrial Chemistry |
Toxicology
Patty's Industrial Hygience and Toxicology, Volume 2D: Toxicology, Fourth Edition (Clayton, George D.; Clayton, Florence E.)  
Continuing series.
J. Chem. Educ. 1995, 72, A93.
Toxicology |
Industrial Chemistry
Nitroalkenes: Conjugate Nitro Compounds (Perekalin, V. V.; Lipina, E. S.; Berestovitskaya, V. M.; Efremov, D. A.)  
Monograph.
J. Chem. Educ. 1995, 72, A93.
Alkenes
Bioprocess Production of Flavor, Fragrance, and Color Ingredients (Gabelman, Alan)  
Monograph.
J. Chem. Educ. 1995, 72, A73.
Food Science |
Consumer Chemistry |
Industrial Chemistry
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
A World of Color: Investigating the Chemistry of Vat Dyes  Dianne N. Epp
Background and activities involving natural dyes known as vat dyes.
Epp, Dianne N. J. Chem. Educ. 1995, 72, 726.
Dyes / Pigments |
Consumer Chemistry |
Industrial Chemistry |
Enrichment / Review Materials
Using Models to Understand and Design Sweeteners  D. Eric Walters
Review of the ways in which models have been used to help us understand the relationship between chemical structure and sweet taste.
Walters, D. Eric. J. Chem. Educ. 1995, 72, 680.
Food Science |
Molecular Properties / Structure |
Industrial Chemistry |
Molecular Modeling
Discovery of Highly Sweet Compounds from Natural Sources  A. Douglas Kinghorn and Edward J. Kennelly
Discovery of highly sweet compounds from natural sources (particularly plants); assays for sweetness; and specific examples of recently discovered, naturally-occurrring, sweet compounds.
Kinghorn, A. Douglas; Kennelly, Edward J. J. Chem. Educ. 1995, 72, 676.
Natural Products |
Plant Chemistry |
Food Science |
Consumer Chemistry |
Industrial Chemistry |
Enrichment / Review Materials
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
An Environmental Chemistry Curriculum Using Case Studies  Cheng, Vincent K. W.
Using case studies to make environmental chemistry more interesting and relevant for students.
Cheng, Vincent K. W. J. Chem. Educ. 1995, 72, 525.
Water / Water Chemistry |
Industrial Chemistry
Mass Transfer and Car Driving  Mukesh, D.
Explaining the concept of mass transfer using an analogy of driving a car.
Mukesh, D. J. Chem. Educ. 1995, 72, 436.
Kinetics |
Industrial Chemistry
Corrosion Inhibitors for Aluminum: Student Experiments  Muller, Bodo
Investigation of the effect different chelating agents have on inhibiting the corrosion of aluminum flakes in paint (metallic basecoats).
Muller, Bodo J. Chem. Educ. 1995, 72, 350.
Electrochemistry |
Metals |
Oxidation / Reduction |
Industrial Chemistry |
Coordination Compounds
Inhibition of Enzymatic Browning Reaction by Sulfite  Kim, Hie-Joon
Laboratory procedure for demonstrating the function of sulfite as an effective food additive.
Kim, Hie-Joon J. Chem. Educ. 1995, 72, 242.
Enzymes |
Food Science |
Consumer Chemistry |
Industrial Chemistry
Emphasizing Mineral Chemistry in an Analytical Chemistry Unit  Dunn, Jeffrey G.; Mullings, Lindsay R.; Phillips, David N.
An analytical chemistry laboratory unit that illustrates principles and procedures used by mineral processing industries.
Dunn, Jeffrey G.; Mullings, Lindsay R.; Phillips, David N. J. Chem. Educ. 1995, 72, 220.
Metallurgy |
Geochemistry |
Industrial Chemistry
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
Improving Creativity, Solving Problems, and Communicating with Peers in Engineering and Science Laboratories  Drake, Bruce D.; Acosta, Gracia M.; Wingard, Donald A.; Smith, Richard L., Jr.
Brining the laboratory experience into closer alignment with necessary industrial skills by emphasizing experimental selection, design, analysis, group problem-solving, and peer communication.
Drake, Bruce D.; Acosta, Gracia M.; Wingard, Donald A.; Smith, Richard L., Jr. J. Chem. Educ. 1994, 71, 592.
Industrial Chemistry
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
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
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
Interactive chemistry teaching units developed with the help of the local chemical industry: Applying classroom principles to the real needs of local companies to help students develop skill in teamwork, communications, and problem solving  Pontin, J. A.; Arico, E.; Pitoscio Filho, J.; Tiedemann, P. W.; Isuyama, R.; Fettis, G. C.
As part of a process of effective curriculum innovation, the authors are developing a project to produce teaching materials for chemistry undergraduate courses with an emphasis on the concerns of the local chemical industry.
Pontin, J. A.; Arico, E.; Pitoscio Filho, J.; Tiedemann, P. W.; Isuyama, R.; Fettis, G. C. J. Chem. Educ. 1993, 70, 223.
Applications of Chemistry |
Green Chemistry |
Industrial Chemistry |
Student-Centered Learning
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
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
A walk through snow  Dills, Charles E.
The importance of teaching students the problems of scaling chemical reactions up and down.
Dills, Charles E. J. Chem. Educ. 1992, 69, 784.
Industrial Chemistry |
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 multiscale approach to organic chemistry laboratory: Introduction of kilo-scale experiments.  Perlmutter, Howard D.; Kapichak, Rudolph K.
Experiments in which reactions are run on volumes ranging from 0.5 mL to 5 L; includes a syllabus, a description of equipment, and other important considerations.
Perlmutter, Howard D.; Kapichak, Rudolph K. J. Chem. Educ. 1992, 69, 506.
Industrial Chemistry
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
Chemistry and popular culture: The 007 bond.  Last, Arthur M.
The purpose of this paper is to show how chemistry references from Bond books and movies can be related to a variety of topics taught in a typical undergraduate chemistry course.
Last, Arthur M. J. Chem. Educ. 1992, 69, 206.
Natural Products |
Industrial Chemistry
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
The Top Fifty Industrial Chemicals (Chang, Raymond; Tikkanen, Wayne)  Pribula, Alan J.
The authors have gathered information together in one place about the 50 chemicals produced in the greatest quantity annually by the U.S. chemical industry.
Pribula, Alan J. J. Chem. Educ. 1990, 67, A114.
Industrial Chemistry
Organic Building Blocks of the Chemical Industry (Szmant, Harry H.)  Kauffman, George B.
Szmant's book provides a comprehensive review of the origin, use, and role in the national and international economy of the entire spectrum of today's most commonly used industrial chemicals.
Kauffman, George B. J. Chem. Educ. 1990, 67, A83.
Industrial Chemistry
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
Industrial chemistry in the organic laboratory: C4 alkylations  Teegarden, David M.; Varco-Shea, Theresa C.; Conklin, Karen T.; Markle, Cynthia A.; Anderson, Scott D.
A set of experiments to illustrate reactions of the tertiary-butyl group; the products are all compounds that occur in consumer products and have received considerable attention in the popular press (BHT, BHA, TBHQ, and MTBE).
Teegarden, David M.; Varco-Shea, Theresa C.; Conklin, Karen T.; Markle, Cynthia A.; Anderson, Scott D. J. Chem. Educ. 1990, 67, 619.
Industrial Chemistry |
Aromatic Compounds |
Phenols |
Synthesis |
Mechanisms of Reactions
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
Industrial chemistry: An intensive short course made possible through the cooperation of area chemical industry  Gumprecht, Donald L.; Thrasher, Joseph S.
It is a widely held belief that chemistry majors going into industry have little knowledge of what they will be confronted with. A course was developed in order to remedy this situation.
Gumprecht, Donald L.; Thrasher, Joseph S. J. Chem. Educ. 1990, 67, 321.
Industrial Chemistry
Measurement of diffusivity of organic liquids through polymer membranes: A simple and inexpensive laboratory experiment  Aithal, U. Shanthamurthy; Aminabhavi, Tejraj M.
Characterization of liquid interaction with polymer membranes by using simple laboratory tests and a small sample of polymer membrane is of great value in understanding the actual behavior of a large industrial rubber sample.
Aithal, U. Shanthamurthy; Aminabhavi, Tejraj M. J. Chem. Educ. 1990, 67, 82.
Industrial Chemistry |
Separation Science
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
The stepwise nitration of toluene: A multistep microscale synthesis based on an industrial process  Russell, Richard A.; Switzer, Robert W.; Longmore, Robert W.
The stepwise synthesis of 2,4,6-trinitrotoluene is a simple but important industrial example of electrophilic aromatic substitution that reflects a decreasing reactivity accompanying the increasing degree of nitration.
Russell, Richard A.; Switzer, Robert W.; Longmore, Robert W. J. Chem. Educ. 1990, 67, 68.
Microscale Lab |
Industrial Chemistry |
Aromatic Compounds |
Synthesis |
HPLC
The diazo copying process: An example and demonstration of applied organic chemistry for the undergraduate student  Osterby, Bruce
Demonstrating the chemistry of the diazo copying process.
Osterby, Bruce J. Chem. Educ. 1989, 66, 1026.
Applications of Chemistry |
Industrial Chemistry |
Aromatic Compounds |
Dyes / Pigments
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
An optimization exercise for organic chemistry  Anderson, Martin M.
It is desirable that students gain some experience in the use of optimization methods in their undergraduate courses in order to prepare them for industry.
Anderson, Martin M. J. Chem. Educ. 1988, 65, 77.
Student / Career Counseling |
Industrial Chemistry
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
An introduction to HAZOP: A hazard and operability technique  Pitts, Martin J.
Purpose, method, and use of HAZOP, a technique developed to find and control unanticipated dangers in the chemical industry.
Pitts, Martin J. J. Chem. Educ. 1987, 64, A44.
Industrial Chemistry
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
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
Laboratory safety guidelines: 40 steps for a safer laboratory  Kaufman, James A.
Revision of a DOW safety brochure including 26 steps requiring minimal expense and 14 steps requiring moderate expense.
Kaufman, James A. J. Chem. Educ. 1987, 64, 161.
Industrial Chemistry |
Laboratory Management
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
Industrial chemistry at Michigan Tech  Bates, D. K.; Ponter, A. B.
List of required and optional courses in the industrial chemistry program at Michigan Tech.
Bates, D. K.; Ponter, A. B. J. Chem. Educ. 1985, 62, 745.
Industrial Chemistry
Industrial chemistry: A series of new courses at the undergraduate level  Jasinski, Jerry P.; Miller, Robert E.
Courses described include "An Introduction to Industrial Chemistry", "Polymers: Synthesis and Separation Techniques", and "Inorganic and Organic Industrial Chemistry".
Jasinski, Jerry P.; Miller, Robert E. J. Chem. Educ. 1985, 62, 742.
Industrial Chemistry
An industrial chemistry course to bridge the academia-industry gap  Szmant, H. Harry
Objectives, content, and suggested assignments for an industrial chemistry course.
Szmant, H. Harry J. Chem. Educ. 1985, 62, 736.
Industrial Chemistry
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
Industrial chemistry bibliography  Marmor, Solomon
A bibliography of industrial chemistry articles published in the Journal from 1968-1983, recent texts, and symposia.
Marmor, Solomon J. Chem. Educ. 1985, 62, 331.
Industrial Chemistry |
Applications of Chemistry
A course on synthetic fuels  Kimmel, Howard S.; Tomkins, Reginald P. T.
Outline, content, and student projects for a course on synthetic fuels.
Kimmel, Howard S.; Tomkins, Reginald P. T. J. Chem. Educ. 1985, 62, 249.
Industrial Chemistry |
Applications of Chemistry
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
Safety and Accident Prevention in Chemical Operations, Second Edition (Fawcett, Howard H.; Wood, William S.)  Houk, Cliff
Information to make work environments safer.
Houk, Cliff J. Chem. Educ. 1984, 61, A139.
Laboratory Management |
Industrial Chemistry
Experiments integrating evaluation of chemical hazards into the chemistry curriculum  Pierce, J. T.; McDonald, S. M.; Scogin, M. S.
One way of making students aware of the need for regular monitoring of laboratories is to offer an introduction to the science of industrial hygiene as part of the chemistry curriculum.
Pierce, J. T.; McDonald, S. M.; Scogin, M. S. J. Chem. Educ. 1984, 61, A83.
Industrial Chemistry |
Laboratory Management
An industrial sabbatical  Myers, W. H.
Experiences of an academic chemist who took a year-long sabbatical in industrial chemistry.
Myers, W. H. J. Chem. Educ. 1984, 61, 1081.
Industrial Chemistry |
Professional Development
Teaching industrial chemistry and business at the baccalaureate level  Chenier, Philip J.
Description of the program requirements and a sample program sequence for the chemistry-business comprehensive major.
Chenier, Philip J. J. Chem. Educ. 1984, 61, 997.
Industrial Chemistry
The extraction of gold and its simulation with copper  Bradley, J. D.; Brand, M.; Louli, J. A. M.
The simulation of the extraction of gold by the use of its analog, copper, makes it possible to capitalize on the glamor of gold without sacrificing any chemical principles.
Bradley, J. D.; Brand, M.; Louli, J. A. M. J. Chem. Educ. 1984, 61, 634.
Separation Science |
Metallurgy |
Industrial Chemistry |
Applications of Chemistry |
Oxidation / Reduction |
Metals
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
A private corporation as part of a chemistry department  Bayer, Richard
Agreement between Carroll College and Bionomics Corporation, examples of problems and projects, and keys to a successful relationship.
Bayer, Richard J. Chem. Educ. 1984, 61, 159.
Industrial Chemistry |
Administrative Issues
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
A touch of reality in the sophomore organic laboratory  Schumm, M. K.
Two organic projects are described which are designed so that they are similar to real industrial problems. From "Using 'Real World' Examples in the Teaching of Chemistry - A Symposium", 7th BCCE, Stillwater OK, 1982.
Schumm, M. K. J. Chem. Educ. 1983, 60, 1040.
Industrial Chemistry |
Applications of Chemistry
Polymer chemistry for introductory general chemistry courses  Polymer Core Course Committee in General Chemistry
There exists a breadth in what is taught today as General or Introductory Chemistry. This breadth is typically limited by topics covered in popular texts and by specifications described by the ACS Committee on Professional Training. A new committee makes an effort to recommend polymer-related topics that can be added within these limits.
Polymer Core Course Committee in General Chemistry J. Chem. Educ. 1983, 60, 973.
Industrial Chemistry
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
Electrochemistry of the Hall-Heroult process for aluminum smelting  Haupin, W. E.
A discussion of aluminum holds great pedagogical value on many fronts: discussion of the Bayer process, electrolysis of alumina, electrolyte chemistry, dissolution of alumina, electrode reactions, current efficiency, cell voltage, and other topics for advanced graduate study. From State-of-the-Art Symposium: Electrochemistry, ACS meeting, Kansas City, 1982.
Haupin, W. E. J. Chem. Educ. 1983, 60, 279.
Electrochemistry |
Electrolytic / Galvanic Cells / Potentials |
Applications of Chemistry |
Industrial Chemistry |
Oxidation / Reduction
The determination of anionic surfactants in natural and waste waters  Crisp, P. T.; Eckert, J. M.; Gibson, N. A.
The experiment described in this paper is suitable for the measurement of subpart per million concentrations of anionic surfactants in natural waters and industrial effluents.
Crisp, P. T.; Eckert, J. M.; Gibson, N. A. J. Chem. Educ. 1983, 60, 236.
Industrial Chemistry |
Water / Water Chemistry |
Surface Science
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
Chemistry in action: How to plan a visit to the chemical industry  Nae, Hemi; Mandler, Vera; Hofstein, Avi; Samuel, David
Important considerations in planning a visit to the chemical industry.
Nae, Hemi; Mandler, Vera; Hofstein, Avi; Samuel, David J. Chem. Educ. 1982, 59, 582.
Industrial Chemistry |
Applications of Chemistry
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
Inorganic chemistry from the perspective of an industrial chemist  Laudise, R. A.
Sold state chemistry is intellectually challenging, economically useful and, in the view of the author, fun.
Laudise, R. A. J. Chem. Educ. 1980, 57, 762.
Industrial Chemistry |
Solid State Chemistry |
Applications of Chemistry
Conversion of (+)-Limonene to (-)-Carvone: An organic laboratory sequence of local interest  Rothenberger, Otis S.; Krasnoff, Stuart B.; Rollins, Ronald B.
Orange oil is converted to one of the components of spearmint oil; the detectable odor difference is due to stereochemical factors.
Rothenberger, Otis S.; Krasnoff, Stuart B.; Rollins, Ronald B. J. Chem. Educ. 1980, 57, 741.
Stereochemistry |
Molecular Properties / Structure |
Synthesis |
Separation Science |
Industrial Chemistry |
Applications of Chemistry |
Enantiomers
The chlor-alkali industry  Leddy, James J.
Details the electrolytic conversion of NaCl brine into chlorine, sodium hydroxide, and hydrogen.
Leddy, James J. J. Chem. Educ. 1980, 57, 640.
Industrial Chemistry |
Solutions / Solvents |
Aqueous Solution Chemistry
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
Apple dunking  O'Connor, Rod
Question regarding the ratio between ions of p-nitrophenylhydrazone in reducing the pH of basic effluent.
O'Connor, Rod J. Chem. Educ. 1980, 57, 598.
Acids / Bases |
Aqueous Solution Chemistry |
Solutions / Solvents |
pH |
Industrial Chemistry
Electroforming: An improvised experiment on electroplating  Gorodetsky, Malka; Singerman, Ammon
The difference between electroplating and electroforming, and an experiment in the latter.
Gorodetsky, Malka; Singerman, Ammon J. Chem. Educ. 1980, 57, 514.
Electrochemistry |
Industrial Chemistry
What industry should do for campus safety  Shreeve, Jean'ne M.; Renfrew, Malcolm M.
Industry can do much by critically examining the safety competencies of chemists and chemical engineers hired from universities.
Shreeve, Jean'ne M.; Renfrew, Malcolm M. J. Chem. Educ. 1980, 57, 435.
Industrial Chemistry |
Student / Career Counseling
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
Allyl alcohol plant stream analysis: Relating industrial chemistry to the undergraduate laboratory  Bard, James R.; Sandoval, Antonio A.
Exercise that seeks to familiarize students with an industrial chemical process using a reaction not normally found in undergraduate textbooks and to broaden appreciation of NMR spectroscopy to include its analytical capabilities and limitations by showing how NMR could be used for analysis of a typical plant stream.
Bard, James R.; Sandoval, Antonio A. J. Chem. Educ. 1980, 57, 218.
Alcohols |
Industrial Chemistry |
Applications of Chemistry |
NMR Spectroscopy
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
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
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
Industrial hygiene training at Quinnipiac College  Van Atta, Floyd A.
Describes the upper and lower divisions of the Bachelor of Science in Industrial Hygiene Program.
Van Atta, Floyd A. J. Chem. Educ. 1979, 56, 28.
Industrial Chemistry
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
Industrial analytical procedure for undergraduate analytical chemistry  Hurtubise, Robert J.
A procedure for determining the amount of BHA in cooking oil.
Hurtubise, Robert J. J. Chem. Educ. 1977, 54, 651.
Industrial Chemistry |
Food Science |
Oxidation / Reduction |
Quantitative Analysis
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
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
Development of an industrially oriented BS program in chemistry and chemical technology  Nelson, David A.; Holt, Smith L.; Archer, Vernon S.; Hurtubise, Robert J.; Barden, Roland E.
A new program was started that is directed toward preparing a student to enter an industrial chemical environment or other area of applied chemistry immediately upon graduation.
Nelson, David A.; Holt, Smith L.; Archer, Vernon S.; Hurtubise, Robert J.; Barden, Roland E. J. Chem. Educ. 1976, 53, 148.
Industrial Chemistry |
Student / Career Counseling
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
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
Odor generation in the kraft process  Karnofski, Michael A.
Considers the kraft process, sources of odors in the process, and the chemistry of the formation of those odors.
Karnofski, Michael A. J. Chem. Educ. 1975, 52, 490.
Industrial Chemistry |
Nonmajor Courses |
Applications of Chemistry
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
Maximizing profits in equilibrium processes  Rish, Ronald J.
Provides the student with an example in which both chemical principles and calculus are applied to a realistic industrial situation where profits are a must.
Rish, Ronald J. J. Chem. Educ. 1975, 52, 441.
Equilibrium |
Industrial Chemistry |
Chemometrics
Chemists in industry. A minisemester course  Tomkins, R. P. T.; Moore, J. A.
Outlines a four-week course for "Chemists in Industry."
Tomkins, R. P. T.; Moore, J. A. J. Chem. Educ. 1975, 52, 334.
Industrial Chemistry
Chemistry careers in industry: Accent the positive  Hill, Brenda W.
Considers what college faculties can do to acquaint students with industrial careers.
Hill, Brenda W. J. Chem. Educ. 1975, 52, 224.
Industrial Chemistry |
Student / Career Counseling
Synthesis of sulfuric acid by the contact process. A student laboratory experiment  Martin, J. A.; Baudot, P.; Monal, J. L.; Lejaille, M. F.
Experimental apparatus and details for the synthesis of sulfuric acid by the contact process.
Martin, J. A.; Baudot, P.; Monal, J. L.; Lejaille, M. F. J. Chem. Educ. 1975, 52, 188.
Synthesis |
Catalysis |
Oxidation / Reduction |
Industrial Chemistry
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
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
An experiment sequence involving potassium trioxalatoferrate(III) trihydrate  Brooks, David W.
This procedure explores the synthesis, analysis, and photochemical reactions of potassium trioxalatoferrate(III) trihydrate.
Brooks, David W. J. Chem. Educ. 1973, 50, 218.
Industrial Chemistry |
Synthesis |
Photochemistry
Beyond the Conventional Classroom. Session II-A: Continuing education  Heikkinen, Henry; Zuehlke, Rick; Alexander, John
Combating technical obsolescence; rent o prof; water, man and chemistry; and an undergraduate-graduate research collaboration program.
Heikkinen, Henry; Zuehlke, Rick; Alexander, John J. Chem. Educ. 1973, 50, 18.
Conferences |
Professional Development |
Industrial Chemistry |
Water / Water Chemistry |
Undergraduate Research
Partial analysis of vinyl-asbestos floor tile. A tlc experiment for beginning organic chemistry  Foreman, William A.; Paulson, Donald R.
This laboratory introduces thin-layer chromatography while presenting the student with a typical industrial analysis problem.
Foreman, William A.; Paulson, Donald R. J. Chem. Educ. 1972, 49, 572.
Industrial Chemistry |
Thin Layer Chromatography |
Separation Science
What an industrial laboratory desires in the preparation of science graduates  Rossiter, B. W.
Elaborates on six characteristics that an industrial laboratory desires in the preparation of science graduates: the abilities to think, achieve objectives, and communicate, as well as possessing interdisciplinary interests, energy and enthusiasm, and a proper attitude and understanding of industrial research.
Rossiter, B. W. J. Chem. Educ. 1972, 49, 388.
Student / Career Counseling |
Industrial Chemistry
Ten-year experiment with chemistry students  Meszaros, L.
The author shares an account of a program in which students are engaged in practical operations as a part of their training to become professional employees in the chemical industry.
Meszaros, L. J. Chem. Educ. 1970, 47, 767.
Industrial Chemistry |
Student / Career Counseling
Heavy, heavy (metals) hang over our heads  Brasted, Robert C.
The author presents his attempts to relate the chemistry of the elements, industrial chemistry, and the chemistry of living systems through an examination of chlorine-caustic production using mercury cells and the toxicity of heavy metals.
Brasted, Robert C. J. Chem. Educ. 1970, 47, 756.
Metals |
Toxicology |
Descriptive Chemistry |
Applications of Chemistry |
Industrial Chemistry
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
Industrial chemistry for teachers: Applied research in the development of anticaries dentifrices  Cooley, William E.
Describes applied chemical research related to the development of anticaries dentifrices.
Cooley, William E. J. Chem. Educ. 1970, 47, 177.
Industrial Chemistry |
Applications of Chemistry |
Consumer Chemistry
Safety manuals and handbooks  Monsanto Chemical Co. Research Center
Excerpts from Monsanto's laboratory safety guide.
Monsanto Chemical Co. Research Center J. Chem. Educ. 1969, 46, A881.
Laboratory Management |
Industrial Chemistry
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
Basic oxygen steelmaking  McGannon, Harold E.
Summarizes the fundamentals of oxygen steelmaking.
McGannon, Harold E. J. Chem. Educ. 1969, 46, 293.
Applications of Chemistry |
Industrial Chemistry
A sober dialogue toward balance  Sparks, William J.
Encourages greater cooperation between academia and industry, including in the area of polymer chemistry.
Sparks, William J. J. Chem. Educ. 1968, 45, 505.
Industrial Chemistry
Over one-half of industry's concern  Cairns, Robert W.
The separation between science and technology is an anachronistic dichotomy; includes an outline for a survey course in polymer science.
Cairns, Robert W. J. Chem. Educ. 1968, 45, 503.
Industrial Chemistry
Both students and industry have a stake  Bailey, William J.
In order to attract more polymer chemists to academic staffs, industry will have to play more than just a passive role.
Bailey, William J. J. Chem. Educ. 1968, 45, 500.
Industrial Chemistry |
Student / Career Counseling
Academic preparation for industry  Lippincott, W. T.
An area of chemical education that might be in need of attention is that related to the preparation of students for careers as industrial chemists.
Lippincott, W. T. J. Chem. Educ. 1968, 45, 149.
Student / Career Counseling |
Industrial Chemistry
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
Encyclopedia of industrial chemical analysis. Volume 1, general techniques, a-e (Snell, Foster Dee; Hilton, Clifford L.; eds.)  Van Doren, Janet B.

Van Doren, Janet B. J. Chem. Educ. 1967, 44, A359.
Industrial Chemistry
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
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
Introduction to symposium on polymer chemistry  Morton, Maurice
For many reasons, the area of polymer chemistry deserves special attention.
Morton, Maurice J. Chem. Educ. 1965, 42, 2.
Industrial Chemistry
Zone refining  Christian, John D.
Demonstrates the process of zone refining.
Christian, John D. J. Chem. Educ. 1963, 40, A409.
Separation Science |
Industrial Chemistry
Letters to the editor  Swayze, Donald R.
Examines balancing chemical equations.
Swayze, Donald R. J. Chem. Educ. 1963, 40, 269.
Stoichiometry |
Industrial Chemistry
Nitric acid: Manufacture and uses (Miles, Frank Douglas)  Sisler, Harry H.

Sisler, Harry H. J. Chem. Educ. 1962, 39, A694.
Acids / Bases |
Industrial Chemistry
Zirconium chemistry in industry  Blumenthal, Warren B.
Examines the processing of zircon; zirconium carbide, chlorides, fluorides, and sulfates; hydrous zirconia; zirconyl acetate; ammonium zirconyl carbonate; zirconium in organic chemistry; and zirconium compounds as catalysts.
Blumenthal, Warren B. J. Chem. Educ. 1962, 39, 604.
Industrial Chemistry |
Catalysis
Hydrocarbons in petroleum  Rossini, Frederick D.
Examines research and industrial processes involving the separation of petroleum into its constituent components.
Rossini, Frederick D. J. Chem. Educ. 1960, 37, 554.
Industrial Chemistry |
Applications of Chemistry |
Alkanes / Cycloalkanes |
Separation Science |
Natural Products
New horizons in elastic polymers  Fisher, Harry L.
Describes the history and future applications of natural and synthetic rubbers.
Fisher, Harry L. J. Chem. Educ. 1960, 37, 369.
Reactions |
Industrial Chemistry |
Mechanisms of Reactions |
Applications of Chemistry
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
The Role of Chemistry in Modern Metallurgical Engineering  Burr, Arthur A.
A review and summary of chemistry in curricula for metallurgical engineering.
Burr, Arthur A. J. Chem. Educ. 1958, 35, 100.
Metals |
Metallurgy |
Industrial Chemistry
Tall oil and terpene derivatives  Eick, George H.
Examines the chemistry and uses of tall oil fatty acids and terpene derivatives.
Eick, George H. J. Chem. Educ. 1957, 34, 613.
Natural Products |
Plant Chemistry |
Industrial Chemistry |
Fatty Acids
Chemistry in the manufacture of modern gasoline  Kimberlin, C. N., Jr.
This paper presents a brief review of the chemistry involved in the manufacture of gasoline, particularly catalytic cracking reactions.
Kimberlin, C. N., Jr. J. Chem. Educ. 1957, 34, 569.
Industrial Chemistry |
Applications of Chemistry |
Catalysis |
Mechanisms of Reactions
Survey of methods for routine analysis of inorganic chemicals in industrial laboratories  Glasoe, Paul K.
The results of a survey to acquire information on the extent to which instrumentation is used in routine chemical analysis in industrial laboratories.
Glasoe, Paul K. J. Chem. Educ. 1956, 33, 441.
Instrumental Methods |
Industrial Chemistry |
Titration / Volumetric Analysis |
Gravimetric Analysis |
Spectroscopy
Teaching report writing to professional chemists and chemical engineers  Waldo, W. H.
Reports on research into industry's teaching report writing to professional chemists and chemical engineers.
Waldo, W. H. J. Chem. Educ. 1956, 33, 59.
Industrial Chemistry
The educational role of the technical editor  Davis, D. S.
In chemical engineering industries the technical editor. who is primarily a teacher, trains chemists and chemical engineers to write clearly and simply.
Davis, D. S. J. Chem. Educ. 1956, 33, 57.
Industrial Chemistry
Nuclear magnetic resonance spectroscopy  reprinted from the Industrial Bulletin
Briefly describes NMR spectroscopy, its use in industry, and equipment currently available.
reprinted from the Industrial Bulletin J. Chem. Educ. 1955, 32, 79.
NMR Spectroscopy |
Industrial Chemistry
Letters to the editor  Hendricks, B. Clifford
Questions what happens to the cryolite needed in the reduction of aluminum from its ore.
Hendricks, B. Clifford J. Chem. Educ. 1955, 32, 52.
Industrial Chemistry |
Oxidation / Reduction
Recent advances in petroleum refining  Shoemaker, B. H.; d'Ouville, E. L.; Marschner, Robert F.
Examines various means of separating, converting, and finishing the many compounds found in petroleum.
Shoemaker, B. H.; d'Ouville, E. L.; Marschner, Robert F. J. Chem. Educ. 1955, 32, 30.
Industrial Chemistry |
Separation Science
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
Letters to the editor  Miller, Julius Sumner
Commentary on the importance of chemistry teachers getting out of the classroom, particularly to observe relevant applications in industry.
Miller, Julius Sumner J. Chem. Educ. 1954, 31, 496.
Industrial Chemistry |
Professional Development
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
Glycerol  Weaver, Elbert C.
Describes the industrial production of glycerol.
Weaver, Elbert C. J. Chem. Educ. 1952, 29, 524.
Industrial Chemistry
Colloidal carbonInvaluable soot  Sweitzer, Carl W.
Examines the properties, production, and use of a variety of colloidal carbons.
Sweitzer, Carl W. J. Chem. Educ. 1952, 29, 493.
Colloids |
Industrial Chemistry |
Applications of Chemistry
Consulting chemistry as an example of industrial research  Snell, Cornelia T.
The author describes his work as a consulting chemist.
Snell, Cornelia T. J. Chem. Educ. 1952, 29, 100.
Industrial Chemistry
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
Industrial advertising as a source of information  Kessel, W. G.
Lists a variety of pamphlets and brochures dealing with various chemical problems.
Kessel, W. G. J. Chem. Educ. 1951, 28, 383.
Industrial Chemistry