TIGER

Journal Articles: 431 results
Study of Molecular-Shape Selectivity of Zeolites by Gas Chromatography  Pei-Yu Chao, Yao-Yuan Chuang, Grace Hsiuying Ho, Shiow-Huey Chuang, Tseng-Chang Tsai, Chi-Young Lee, Shang-Tien Tsai, and Jun-Fu Huang
This analytical or physical chemistry sorption experiment uses hexane isomers as probe molecules to demonstrate the "molecular-shape selectivity" behavior of zeolites. Students can also modify the sorption protocol to build their own experiments.
Chao, Pei-Yu; Chuang, Yao-Yuan; Ho, Grace Hsiuying; Chuang, Shiow-Huey; Tsai, Tseng-Chang; Lee, Chi-Young; Tsai, Shang-Tien; Huang, Jun-Fu. J. Chem. Educ. 2008, 85, 1558.
Alkanes / Cycloalkanes |
Constitutional Isomers |
Gas Chromatography |
Molecular Properties / Structure |
Physical Properties |
Separation Science |
Solid State Chemistry |
Molecular Recognition
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
Percy Julian, Robert Robinson, and the Identity of Eserethole  Addison Ault
The Nova production Percy JulianForgotten Genius, which included the very public disagreement over the identity of "eserethole," the key intermediate for the synthesis of the alkaloid physostigmine, left three important chemical questions unanswered.
Ault, Addison. J. Chem. Educ. 2008, 85, 1524.
Constitutional Isomers |
Enantiomers |
Natural Products |
Stereochemistry |
Synthesis
A Green, Guided-Inquiry Based Electrophilic Aromatic Substitution for the Organic Chemistry Laboratory  Eric Eby and S. Todd Deal
This alternative, electrophilic aromatic substitutionan iodination reaction of salicylamide, a popular analgesicuses environmentally friendly reagents and serves as a guided-inquiry experiment in which students are asked to predict the orientation of the substitution reaction and determine the product's structure using FT-IR spectroscopy.
Eby, Eric; Deal, S. Todd. J. Chem. Educ. 2008, 85, 1426.
Aromatic Compounds |
Constitutional Isomers |
Electrophilic Substitution |
Green Chemistry |
IR Spectroscopy |
Synthesis
The Laser Synthesis of Linear Polyynes: The Particle in a Box Revisited  Bruce D. Anderson and Christopher M. Gordon
In this experiment, suitable for inclusion in a standard physical chemistry course or other upper-level laboratory where the principles of quantum mechanics are studied, linear polyynes are synthesized and then the predictions of a one-dimensional, particle in a box are used to calculate the quantum mechanical box length for the polyynes.
Anderson, Bruce D.; Gordon, Christopher M. J. Chem. Educ. 2008, 85, 1279.
Alkenes |
Lasers |
Mass Spectrometry |
Quantum Chemistry |
Synthesis |
UV-Vis Spectroscopy
Liebig–Wöhler Controversy and the Concept of Isomerism  Soledad Esteban
The conflict between Liebig and Whler regarding their analyses of fulminates and cyanates marked the beginning of a long friendship between the two, led Berzelius to recognize the phenomenon of isomerism, and can provide interesting anecdotal material to increase interest in lectures.
Esteban, Soledad. J. Chem. Educ. 2008, 85, 1201.
Constitutional Isomers |
Enrichment / Review Materials
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
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
A Nitration Reaction Puzzle for the Organic Chemistry Laboratory  Milton J. Wieder and Russell Barrows
Treatment of phenylacetic acid with different concentrations of nitric acid yields two different products. Using 1H NMR and IR spectral data, students are asked to deduce the structures of the two products, thus illustrating fundamental concepts in electrophilic aromatic substitution while posing an interesting structure elucidation puzzle.
Wieder, Milton J.; Barrows, Russell. J. Chem. Educ. 2008, 85, 549.
Constitutional Isomers |
Mass Spectrometry |
NMR Spectroscopy |
Synthesis |
Titration / Volumetric Analysis
Extensions of a Basic Laboratory Experiment: [4+2] and [2+2] Cycloadditions  Hazem Y. Amarne, Alex D. Bain, Karen Neumann, and Paul M. Zelisko
Describes an extended third-year undergraduate chemistry laboratory exercise in which a number of techniques and concepts are applied to the photochemical and thermal cycloadditions of -nitrostyrene and 2,3-dimethylbutadiene. The exercises include synthesis, NMR spectroscopy, and computer-based molecular modeling.
Amarne, Hazem Y.; Bain, Alex D.; Neumann, Karen; Zelisko, Paul M. J. Chem. Educ. 2008, 85, 104.
Alkenes |
Conformational Analysis |
MO Theory |
NMR Spectroscopy |
Quantum Chemistry |
Spectroscopy
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
A Bright Spark: Open Teaching of Science Using Faraday's Lectures on Candles  Mark Walker, Martin Gröger, Kirsten Schlüter, and Bernd Mosler
Faraday's famous lecture series, "The Natural History of the Candle," has been adapted for use in a student-centered setting, where students decide the meaning of what they see and do.
Walker, Mark; Gröger, Martin; Schlüter, Kirsten; Mosler, Bernd. J. Chem. Educ. 2008, 85, 59.
Alkanes / Cycloalkanes |
Learning Theories |
Constructivism |
Student-Centered Learning
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
Synthesis and Catalytic Activity of Ruthenium–Indenylidene Complexes for Olefin Metathesis  Ted M. Pappenfus, David L. Hermanson, Daniel P. Ekerholm, Stacie L. Lilliquist, and Megan L. Mekoli
Presents a series of experiments that focus on the design of rutheniumindenylidene complexes for olefin metathesis. Included are the syntheses of two such complexes that display very different catalytic activity in a ring-closing metathesis reaction. Students also utilize several analytical methods in characterizing the complexes and quantifying their catalytic activity.
Pappenfus, Ted M.; Hermanson, David L.; Ekerholm, Daniel P.; Lilliquist, Stacie L.; Mekoli, Megan L. J. Chem. Educ. 2007, 84, 1998.
Alkenes |
Catalysis |
Coordination Compounds |
Gas Chromatography |
Mass Spectrometry |
Microscale Lab |
NMR Spectroscopy |
Organometallics
Nobel Chemistry in the Laboratory: Synthesis of a Ruthenium Catalyst for Ring-Closing Olefin Metathesis  George E. Greco
An experiment is described in which students synthesize a ruthenium olefin metathesis catalyst and then use the catalyst to carry out the ring-closing metathesis of diethyl diallylmalonate. The olefin metathesis reaction was the subject of the 2005 Nobel Prize in chemistry.
Greco, George E. J. Chem. Educ. 2007, 84, 1995.
Alkynes |
Catalysis |
Coordination Compounds |
NMR Spectroscopy |
Organometallics |
Synthesis |
Transition Elements |
Alkenes
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
Zeroing In on Electrophilic Aromatic Substitution  David C. Forbes, Mohini Agarwal, Jordan L. Ciza, and Heather A. Landry
Presents a unique and novel illustration of reactivity trends in the formation of trisubstituted benzene derivatives from disubstituted systems using electrophilic aromatic substitution reactions.
Forbes, David C.; Agarwal, Mohini; Ciza, Jordan L.; Landry, Heather A. J. Chem. Educ. 2007, 84, 1878.
Aromatic Compounds |
Constitutional Isomers |
Electrophilic Substitution |
Reactions
Gas Clathrate Hydrates Experiment for High School Projects and Undergraduate Laboratories  Melissa P. Prado, Annie Pham, Robert E. Ferazzi, Kimberly Edwards, and Kenneth C. Janda
Presents a procedure for preparing and studying propane clathrate hydrate. This experiment introduces students to this unusual solid while stimulating a discussion of the interplay of intermolecular forces, thermodynamics, and solid structure.
Prado, Melissa P.; Pham, Annie; Ferazzi, Robert E.; Edwards, Kimberly; Janda, Kenneth C. J. Chem. Educ. 2007, 84, 1790.
Alkanes / Cycloalkanes |
Applications of Chemistry |
Calorimetry / Thermochemistry |
Gases |
Phases / Phase Transitions / Diagrams |
Thermodynamics |
Water / Water Chemistry |
Hydrogen Bonding
Discovering Electronic Effects of Substituents in Nitrations of Benzene Derivatives Using GC–MS Analysis  Malgorzata M. Clennan and Edward L. Clennan
Describes an organic lab in which students pool mass spectral data to identify the distribution of isomer products generated by the nitration of six benzene derivatives whose substituents differ in their electronic effects. Students also determine which substituents direct nitration predominantly to the ortho- or para- and to the meta positions.
Clennan, Malgorzata M.; Clennan, Edward L. J. Chem. Educ. 2007, 84, 1679.
Aromatic Compounds |
Constitutional Isomers |
Electrophilic Substitution |
Gas Chromatography |
Mass Spectrometry
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
The Quartz-Crystal Microbalance in an Undergraduate Laboratory Experiment  Vladimir Tsionsky
Describes a typical student experiment on the determination of the viscosity of liquids using a quartz-crystal microbalance.
Tsionsky, Vladimir. J. Chem. Educ. 2007, 84, 1337.
Alcohols |
Alkanes / Cycloalkanes |
Laboratory Equipment / Apparatus |
Liquids |
Physical Properties |
Solutions / Solvents
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
Quantitative Comparison of Three Standardization Methods Using a One-Way ANOVA for Multiple Mean Comparisons  Russell D. Barrows
In this experiment, students determine the concentrations of three long-chain hydrocarbons through gas chromatography using a procedure of their own design and three standardization methodsan external calibration curve, standard addition, and an internal standard. They then test their success by performing a one-way ANOVA statistical analysis.
Barrows, Russell D. J. Chem. Educ. 2007, 84, 839.
Alkanes / Cycloalkanes |
Gas Chromatography |
Quantitative Analysis |
Statistical Mechanics |
Student-Centered Learning
Competitive Nitration of Benzene–Fluorobenzene and Benzene–Toluene Mixtures: Orientation and Reactivity Studies Using HPLC  Ronald L. Blankespoor, Stephanie Hogendoorn, and Andrea Pearson
In this experiment for the first-year organic laboratory, mixtures of benzenetoluene and benzenefluorobenzene are competitively nitrated to determine the reactivity and orientation effects of CH3 and F. HPLC is used to analyze the reaction mixtures.
Blankespoor, Ronald L.; Hogendoorn, Stephanie; Pearson, Andrea. J. Chem. Educ. 2007, 84, 697.
Aromatic Compounds |
Constitutional Isomers |
Electrophilic Substitution |
HPLC
Sudoku Puzzles for First-Year Organic Chemistry Students  Alice L. Perez and G. Lamoureux
Sudoku puzzles are used to help the students learn the correspondence between the names of amino acids, their abbreviations, and codes; and the correspondence between the names of functional groups, their structures, and abbreviations.
Perez, Alice L.; Lamoureux, G. J. Chem. Educ. 2007, 84, 614.
Alcohols |
Aldehydes / Ketones |
Alkanes / Cycloalkanes |
Alkenes |
Alkylation |
Amines / Ammonium Compounds |
Amino Acids |
MO Theory |
Nomenclature / Units / Symbols |
Student-Centered Learning |
Alkynes |
Amides
Nuclear Overhauser Effect Spectroscopy. An Advanced Undergraduate Experiment  Michael T. Huggins and Freida Billimoria
Describes an advanced laboratory experiment in which students prepare a set of compounds to study both the configuration of a newly formed double bond (E or Z) and the conformation of the molecule.
Huggins, Michael T.; Billimoria, Freida. J. Chem. Educ. 2007, 84, 471.
Alkenes |
Conformational Analysis |
Molecular Modeling |
NMR Spectroscopy |
Stereochemistry |
Synthesis |
Molecular Properties / Structure |
Chirality / Optical Activity
Introduction of Differential Scanning Calorimetry in a General Chemistry Laboratory Course: Determination of Thermal Properties of Organic Hydrocarbons  Ronald DAmelia, Thomas Franks, and William F. Nirode
Differential scanning calorimetry (DSC) is a rugged, easy-to-use instrumental method for thermal analysis determinations. The work described herein discusses the use of DSC in a general chemistry laboratory course to determine thermal properties such as melting points, ?fusionH, ?fusionS, and introduce the concept of polymorphism for organic hydrocarbons.
DAmelia, Ronald; Franks, Thomas; Nirode, William F. J. Chem. Educ. 2007, 84, 453.
Alkanes / Cycloalkanes |
Instrumental Methods |
Physical Properties |
Thermal Analysis |
Thermodynamics |
Calorimetry / Thermochemistry
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
Greening Wittig Reactions: Solvent-Free Synthesis of Ethyl trans-Cinnamate and trans-3-(9-Anthryl)-2-Propenoic Acid Ethyl Ester  Kim Chi Nguyen and Haim Weizman
Presents solvent-free alternatives to published procedures of Wittig reactions. Spectral data provide a basis for an inquiry-based discussion of (i) the factors influencing the chemical shifts of alkenyl proton, (ii) the analysis of NMR spectrum containing a mixture, and (iii) the role of strong dipoledipole interactions in dictating the stereochemical outcome of the Wittig reaction.
Nguyen, Kim Chi; Weizman, Haim. J. Chem. Educ. 2007, 84, 119.
Aldehydes / Ketones |
Alkenes |
NMR Spectroscopy |
Green Chemistry
Photochemical Synthesis and Ligand Exchange Reactions of Ru(CO)4(η²-alkene) Compounds  Jason Cooke, David E. Berry, and Kelli L. Fawkes
Irradiation of Ru3(CO)12 in the presence of either methyl acrylate (CH2=CHCO2CH3) or ethylene generates labile Ru(CO)4(?2-alkene) species that readily react with other two-electron donor ligands, such as triphenylphosphine or the more p-acidic alkene dimethyl fumarate (trans-CH3CO2CH=CHCO2CH3), to produce thermally stable Ru(CO)4L compounds.
Cooke, Jason; Berry, David E.; Fawkes, Kelli L. J. Chem. Educ. 2007, 84, 115.
Alkenes |
IR Spectroscopy |
Microscale Lab |
Organosulfur Compounds |
Photochemistry |
Synthesis |
Organometallics
Entropy and the Shelf Model: A Quantum Physical Approach to a Physical Property  Arnd H. Jungermann
A quantum physical approach relying on energy quantization leads to three simple rules which are the key to understanding the physical property described by molar entropy values.
Jungermann, Arnd H. J. Chem. Educ. 2006, 83, 1686.
Alcohols |
Alkanes / Cycloalkanes |
Carboxylic Acids |
Covalent Bonding |
Ionic Bonding |
Physical Properties |
Quantum Chemistry |
Thermodynamics
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
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
Synthesis of Chromophore-Labeled Polymers and Their Molecular Weight Determination Using UV–Vis Spectroscopy  Eric S. Tillman, Amanda C. Roof, Steven M. Palmer, Beth Ann Zarko, Caton C. Goodman, and Alissa M. Roland
Polystyrene quantitatively end-labeled with fluorene is produced via atom transfer radical polymerization. Molecular weight characterization of the polymers is performed using UVvis spectroscopy, and BeerLambert's law is used to determine the molarity of the fluorene-labeled polymers.
Tillman, Eric S.; Roof, Amanda C.; Palmer, Steven M.; Zarko, Beth Ann; Goodman, Caton C.; Roland, Alissa M. J. Chem. Educ. 2006, 83, 1215.
Polymerization |
Alkenes |
Free Radicals |
Reactions |
UV-Vis Spectroscopy
Colorful Chemical Demonstrations on the Extraction of Anionic Species from Water into Ether Mediated by Tricaprylylmethylammonium Chloride (Aliquat 336), a Liquid–Liquid Phase-Transfer Agent  Anil Joseph Pezhathinal, Kerensa Rocke, Louis Susanto, Derek Handke, Roch Chan-Yu-King, and Patrick Gordon
Provides a list of safe and easy experiments to demonstrate the extraction of colorful, water-soluble reagents by Aliquat 336 into ether. The demonstrations simulate the preliminary extractive step of an ionic species in liquidliquid phase transfer-catalyzed reactions and introduce various undergraduate chemistry concepts and principles to students.
Pezhathinal, Anil Joseph; Rocke, Kerensa; Susanto, Louis; Handke, Derek; Chan-Yu-King, Roch; Gordon, Patrick. J. Chem. Educ. 2006, 83, 1161.
Alkanes / Cycloalkanes |
Amines / Ammonium Compounds |
Catalysis |
Dyes / Pigments |
Reactions |
Mechanisms of Reactions
Was Markovnikov's Rule an Inspired Guess?  Peter Hughes
A study of 19th century literature shows that neither Markovnikov nor any of his contemporaries carried out the reactions often attributed to himthe addition of hydrogen bromide or hydrogen chloride to propene. Since there is little evidence for Markovnikov's rule in his 1870 article, it is likely that it was more of an inspired guess than a rational conclusion.
Hughes, Peter. J. Chem. Educ. 2006, 83, 1152.
Addition Reactions |
Alkenes |
Mechanisms of Reactions
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
Reactivity of the Monoterpenoid Nerol with p-Toluenesulfonic and Chlorosulfonic Acids: Selective Syntheses of α-Terpineol and α-Cyclogeraniol. An Activity for the Undergraduate Organic Lab  Pablo J. Linares-Palomino, Sofía Salido, Joaquín Altarejos, Manuel Nogueras, and Adolfo Sánchez
Describes the selective syntheses of the cyclic monoterpenoids a-terpineol or a-cyclogeraniol from the acyclic monoterpenoid nerol using p-toluenesulfonic acid or chlorosulfonic acid as cyclizing agents.
Linares-Palomino, Pablo J.; Salido, Sofía; Altarejos, Joaquín; Nogueras, Manuel; Sánchez, Adolfo. J. Chem. Educ. 2006, 83, 1052.
Alcohols |
Carbocations |
Gas Chromatography |
Mechanisms of Reactions |
Microscale Lab |
Synthesis |
Natural Products |
Alkenes
Semiempirical and DFT Investigations of the Dissociation of Alkyl Halides  Jack R. Waas
Enthalpy changes corresponding to the gas phase heats of dissociation of 12 organic halides were calculated using two semiempirical methods, the HartreeFock method, and two DFT methods. All five methods agreed generally with the expected empirically known trends in the dissociation of alkyl halides.
Waas, Jack R. J. Chem. Educ. 2006, 83, 1017.
Alkanes / Cycloalkanes |
Computational Chemistry |
Mechanisms of Reactions |
Molecular Modeling |
Reactions |
Reactive Intermediates |
Thermodynamics |
Elimination Reactions |
Nucleophilic Substitution
An Exploration of a Photochemical Pericyclic Reaction Using NMR Data  Sara M. Hein
This inexpensive, small-scale experiment for advanced organic students describes the unambiguous identification of a photochemical dimerization product from eleven possible candidates.
Hein, Sara M. J. Chem. Educ. 2006, 83, 940.
Addition Reactions |
Alkanes / Cycloalkanes |
Alkenes |
Carboxylic Acids |
Conformational Analysis |
NMR Spectroscopy |
Photochemistry |
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
Enhancements on the Photochromism of 2-(2,4-Dinitrobenzyl)pyridine: Molecular Modeling, NMR Spectrometry, Photo- and Solvent-Bleaching  Ernest C. McGoran, Kevin Hintz, Kristin Hoffman, and Ramon Iovin
Describes molecular-modeling studies on the photochromism of 2-(2,4-dinitrobenzyl)pyridine (a-DNBP) that focus on the hydrogen atom migratory distances and the energies for the two very different tautomers arising from the photo-induced proton transfers.
McGoran, Ernest C.; Hintz, Kevin; Hoffman, Kristin; Iovin, Ramon. J. Chem. Educ. 2006, 83, 923.
Constitutional Isomers |
Molecular Modeling |
NMR Spectroscopy |
Photochemistry
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
Octachem Model: Organic Chemistry Nomenclature Companion  Joaquin Palacios
The Octachem model is an educational physical model designed to guide students in the identification, classification, and naming of the chemical structures of organic compounds. In this article the basic concepts of Octachem model are presented, and the physical model and contents are described.
Palacios, Joaquin. J. Chem. Educ. 2006, 83, 890.
Alcohols |
Aldehydes / Ketones |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes |
Amines / Ammonium Compounds |
Esters |
Ethers |
Nomenclature / Units / Symbols
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
Study of an AB System within the 1H NMR Spectrum of a Maleamic Acid: Application of Chemical Exchange between Acid–Base Conjugates  Pierre Fellman, Alain Gevertz, and Christine Cordier
The 1H NMR spectrum of the system of two coupled protons shows two dissymmetric doublets; the frequency and intensity of the four lines are defined by calculations in the field of quantum chemistry. This article presents an experimental verification of these results employing two vicinal olefinic protons.
Fellman, Pierre; Gevertz, Alain; Cordier, Christine. J. Chem. Educ. 2006, 83, 432.
Acids / Bases |
Alkenes |
Fourier Transform Techniques |
Molecular Mechanics / Dynamics |
NMR Spectroscopy |
Quantum Chemistry |
Spectroscopy
A Laboratory Assignment in 1H NMR Spectroscopy: A Comparative Analysis of Calculated and Experimental 1H NMR Chemical Shifts  Susan D. Van Arnum
A computer program is used to determine the proton NMR chemical shifts of endo- and exo-norbornenyl ketones and these values are compared to empirical results.
Van Arnum, Susan D. J. Chem. Educ. 2006, 83, 429.
Constitutional Isomers |
NMR Spectroscopy |
Photochemistry
Propanol to Propane: An Advanced Laboratory Experiment Using Heterogeneous Catalysts for Two Successive Gas-Phase Reactions  Bruce Mattson, Martin Hulce, Wes Cheng, Jaclyn Greimann, Trisha Hoette, and Peter Menzel
This article describes two organic reactions involving gas-phase heterogeneous catalysis. In the first reaction, 2-propanol is converted to propene using heated alumina beads as the catalyst. In the second, the propene is hydrogenated to propane using a palladium catalyst.
Mattson, Bruce; Hulce, Martin; Cheng, Wes; Greimann, Jaclyn; Hoette, Trisha; Menzel, Peter. J. Chem. Educ. 2006, 83, 421.
Alcohols |
Alkenes |
Catalysis |
Gases |
Microscale Lab |
NMR Spectroscopy |
Synthesis
Experiments on Heterogeneous Catalysis Using a Simple Gas Chromatograph  Flávia Cristina Camilo Moura, Frederico Garcia Pinto, Eduardo Nicolau dos Santos, Luis Otávio Fagundes do Amaral, and Rochel Montero Lago
A catalyst is placed inside a gas chromatograph injector liner and the reactants injected, vaporized, and led through the catalyst bed by the carrier gas for reaction. By controlling the GC injector temperature, varying the carrier gas, its flow rate, and injecting different quantities of the reactant, several parameters in heterogeneous catalysis can be determined.
Moura, Flávia Cristina Camilo; Pinto, Frederico Garcia; dos Santos, Eduardo Nicolau; Fagundes do Amaral, Luis Otávio; Lago, Rochel Montero. J. Chem. Educ. 2006, 83, 417.
Alkenes |
Catalysis |
Gas Chromatography |
Quantitative Analysis |
Reactions |
Separation Science |
Chromatography
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
Diastereoselectivity in the Reduction of α-Hydroxyketones. An Experiment for the Chemistry Major Organic Laboratory  David B. Ball
Describes a research type, inquiry-based project where students synthesize racemic ahydroxyketones using umpolung, a polarity-reversal approach; investigate chelating versus non-chelating reducing agents; and determine the diastereoselectivity of these reducing processes by NMR spectroscopy.
Ball, David B. J. Chem. Educ. 2006, 83, 101.
Addition Reactions |
Aldehydes / Ketones |
Chirality / Optical Activity |
Chromatography |
Conferences |
Constitutional Isomers |
Enantiomers |
NMR Spectroscopy |
Stereochemistry |
Synthesis |
Conformational Analysis
Further Analysis of Boiling Points of Small Molecules, CHwFxClyBrz  Guy Beauchamp
Multiple linear regression analysis has proven useful in selecting predictor variables that could significantly clarify the boiling point variation of the CHwFxClyBrz molecules.
Beauchamp, Guy. J. Chem. Educ. 2005, 82, 1842.
Chemometrics |
Physical Properties |
Hydrogen Bonding |
Molecular Properties / Structure |
Alkanes / Cycloalkanes
Determination of the Rotational Barrier in Ethane by Vibrational Spectroscopy and Statistical Thermodynamics  Gianfranco Ercolani
The finite-difference boundary-value method is used to determine, in combination with vibrational spectroscopy and statistical thermodynamics, the torsional potential in ethane.
Ercolani, Gianfranco. J. Chem. Educ. 2005, 82, 1703.
IR Spectroscopy |
Molecular Properties / Structure |
Quantum Chemistry |
Statistical Mechanics |
Alkanes / Cycloalkanes |
Conformational Analysis |
Heat Capacity |
Thermodynamics
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
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
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
Conversion of an Aziridine to an Oxazolidinone Using a Salt and Carbon Dioxide in Water  Justin R. Wallace, Deborah L. Lieberman, Matthew T. Hancock, and Allan R. Pinhas
An undergraduate laboratory experiment that allows for optimization of experimental reaction conditions for the conversion of a readily-available aziridine to the corresponding oxazolidinone using only carbon dioxide and a salt in water is discussed. A variety of salts were used to determine their effect on the reaction. In all cases, either no reaction occurred or a high yield of product was obtained. Ring opening of the less substituted carbonnitrogen bond predominates. This experiment allows students to optimize reaction conditions to obtain predominantly one of two regioisomers.
Wallace, Justin R.; Lieberman, Deborah L.; Hancock, Matthew T.; Pinhas, Allan R. J. Chem. Educ. 2005, 82, 1229.
Heterocycles |
Synthesis |
Aqueous Solution Chemistry |
Constitutional Isomers |
Mechanisms of Reactions |
NMR Spectroscopy |
Quantitative Analysis
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
Quantitative Determination of the Rotameric Energy Differences of 1,2-Dihaloethanes Using Raman Spectroscopy. An Experimental Project for the Physical Chemistry Laboratory  Mark D. Young, Natalia C. Borjemscaia, and Brian D. Wladkowski
The effects of structure and environment on the rotameric energy difference between gauche and trans conformations of 1,2-disubtitutedethanes are determined quantitatively through the use of Raman spectroscopy. Two 1,2-dihaloethanes (chloro- and bromo-) were analyzed in the condensed phase (pure liquid, carbon tetrachloride, and acetonitrile solutions). Since the gauche conformation of these molecules has a nonzero dipole, dissolving the compounds in solvents with increasing dielectric constant causes a stabilization of the gauche conformation, thus decreasing the absolute energy difference between the rotamers. The major factor governing the intrinsic stability is that of steric hindrance.
Young, Mark D.; Borjemscaia, Natalia C.; Wladkowski, Brian D. J. Chem. Educ. 2005, 82, 912.
Instrumental Methods |
IR Spectroscopy |
Quantitative Analysis |
Raman Spectroscopy |
Alkanes / Cycloalkanes |
Conformational Analysis |
Stereochemistry
DielsAlder Cycloadditions: A MORE Experiment in the Organic Laboratory Including A Diene Identification Exercise Involving NMR Spectroscopy and Molecular Modeling  Roosevelt Shaw, Ashika Severin, Miguel Balfour, and Columbus Nettles
The MORE (microwave-induced organic reaction enhancement) technique has been used successfully to prepare two DielsAlder [p2 + p4] cycloaddition adducts, racemic exo, endo-2,3-dibenzoylbicyclo[2.2.1]hept-5-ene and racemic exo, endo-2,3-dibenzoylbicyclo[2.2.2]octa-5-ene, in high purity and good yields. Microwave synthesis of these two dienes serves as an excellent organic laboratory experiment to demonstrate the rate enhancement advantage of using microwave heating over conventional heating in preparing selected DielsAlder cycloaddition products.
Shaw, Roosevelt; Severin, Ashika; Balfour, Miguel; Nettles, Columbus. J. Chem. Educ. 2005, 82, 625.
Addition Reactions |
Molecular Modeling |
NMR Spectroscopy |
Alkenes
Testing for Genetically Modified Foods Using PCR  Ann Taylor and Samin Sajan
The polymerase chain reaction (PCR) is a powerful technique used to detect and amplify a specific DNA sequence. In this experiment, DNA is isolated from commercially available corn meal and corn-muffin mixes, then a sequence unique to transgenic plants is amplified by PCR. The amplified sequence is identified by its size (192 base pairs) by agarose gel electrophoresis. This experiment could be used in either a biochemistry course or in an analytical chemistry course in a curriculum that integrates biochemistry throughout the course work.
Taylor, Ann; Sajan, Samin. J. Chem. Educ. 2005, 82, 597.
Agricultural Chemistry |
Constitutional Isomers |
Biotechnology |
Plant Chemistry |
Consumer Chemistry |
Nucleic Acids / DNA / RNA
The Evolution of a Green Chemistry Laboratory Experiment: Greener Brominations of Stilbene  Lallie C. McKenzie, Lauren M. Huffman, and James E. Hutchison
We describe two new greener alkene bromination reactions that offer enhanced laboratory safety and convey important green chemistry concepts, in addition to illustrating the chemistry of alkenes. The two alternative reactions, one involving pyridinium tribromide and a second using hydrogen peroxide and hydrobromic acid, are compared to the traditional bromination of stilbene through the application of green metrics, including atom economy, percent experimental atom economy, E factor, and effective mass yield.
McKenzie, Lallie C.; Huffman, Lauren M.; Hutchison, James E. J. Chem. Educ. 2005, 82, 306.
Synthesis |
Green Chemistry |
Aromatic Compounds |
Addition Reactions |
Alkenes
A Methane Balloon Inflation Chamber  Curtis J. Czerwinski and Tanya J. Cordes
While several lecture demonstrations are possible using methane-filled balloons, it is often inconvenient to prepare these balloons since the pressure from standard laboratory and lecture hall gas nozzles is too low. As a solution to this problem, a methane balloon inflation chamber, prepared from a translucent 3.5-gallon pail and an aspirator or house-vacuum, provides an inexpensive and convenient method for inflating balloons in laboratories or lecture halls. Prepared in this way, methane-filled balloons can be used to demonstrate the effects of vacuum, the lifting power of low-density gases, and the explosive combustion of methane.
Czerwinski, Curtis J.; Cordes, Tanya J. J. Chem. Educ. 2005, 82, 248.
Alkanes / Cycloalkanes |
Calorimetry / Thermochemistry |
Gases |
Oxidation / Reduction |
Reactions
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
A Set of Hands-On Exercises on Conformational Analysis  Silvina C. Pellegrinet and Ernesto G. Mata
This article describes a set of comprehensive exercises on conformational analysis that employs a hands-on approach by the use of molecular modeling kits. In addition, the exercises provide illustrations of other topics such as nomenclature, functional groups, and isomerism, and introduce some notions of chirality.
Pellegrinet, Silvina C.; Mata, Ernesto G. J. Chem. Educ. 2005, 82, 73.
Alkanes / Cycloalkanes |
Conformational Analysis |
Constitutional Isomers |
Molecular Properties / Structure |
Stereochemistry
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
Studying Current–Potential Curves Using Bipotentiometric Iodometric Back-Titration for the Determination of Ascorbic Acid in Fruits and Vegetables  Roxana A. Verdini and Claudia M. Lagier
A method for the determination of the ascorbic acid content in fruits and vegetables was used to introduce the principles of voltammetry. The procedure combines an iodometric back-titration with voltammetric (bipotentiometric) end point detection, which minimizes the risk of ascorbic acid oxidation, allowing for a rapid and efficient quantification of vitamin C in fruits and vegetables. A better understanding of the titration curve is achieved by analyzing the schematic currentpotential curves of the anodic and cathodic half-cell reactions during the titration.
Verdini, Roxana A.; Lagier, Claudia M. J. Chem. Educ. 2004, 81, 1482.
Constitutional Isomers |
Electrochemistry |
Food Science |
Instrumental Methods |
Oxidation / Reduction |
Titration / Volumetric Analysis |
Vitamins |
Consumer 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
Molecular Modeling of Non-Trivial Cyclohexane Derivatives: A Discovery Approach  Gail Horowitz
An experiment is described that utilizes molecular modeling to study the effects of sp2 hybridization, bond elongation, and heteroatom substitution upon the stabilities of the axial and equatorial conformers of cyclohexane.
Horowitz, Gail. J. Chem. Educ. 2004, 81, 1006.
Molecular Modeling |
Alkanes / Cycloalkanes |
Computational Chemistry |
Molecular Properties / Structure
The Origin of Vinyl  William B. Jensen
In response to a reader query, the column traces the origins of the word "vinyl" back to the Latin term, vinum, meaning "wine".
Jensen, William B. J. Chem. Educ. 2004, 81, 464.
Alkenes |
Alcohols |
Polymerization
Alkene Isomerization Using a Solid Acid as Activator and Support for a Homogeneous Catalyst  Andrew J. Seen
The experiment illustrates how immobilization of reagents and catalysts on solid supports provides the opportunity to develop more environmentally acceptable processes by removing potentially corrosive and toxic reagents or catalysts from solution.
Seen, Andrew J. J. Chem. Educ. 2004, 81, 383.
Catalysis |
Coordination Compounds |
Green Chemistry |
Ion Exchange |
Alkenes
Vibrational Analysis for C60 and Other Fullerenes  Frank Rioux
Nakamoto and McKinney provided a symmetry analysis of the vibrational modes of C60 and other fullerenes. I would like to supplement their presentation with another approach, in widespread use, which records the number of atoms that are unmoved by each symmetry operation, yielding the reducible representation Guma.
Rioux, Frank. J. Chem. Educ. 2003, 80, 1380.
Chirality / Optical Activity |
Group Theory / Symmetry |
IR Spectroscopy |
NMR Spectroscopy |
Raman Spectroscopy |
Alkenes
Vibrational Analysis for C60 and Other Fullerenes  Frank Rioux
Nakamoto and McKinney provided a symmetry analysis of the vibrational modes of C60 and other fullerenes. I would like to supplement their presentation with another approach, in widespread use, which records the number of atoms that are unmoved by each symmetry operation, yielding the reducible representation Guma.
Rioux, Frank. J. Chem. Educ. 2003, 80, 1380.
Chirality / Optical Activity |
Group Theory / Symmetry |
IR Spectroscopy |
NMR Spectroscopy |
Raman Spectroscopy |
Alkenes
Using Hydrocarbon Acidities To Demonstrate Principles of Organic Structure and Bonding  Andrew P. Dicks
This article demonstrates the utility of hydrocarbon acidity as a teaching tool within the undergraduate classroom. Acidities of compounds containing only hydrogen and carbon vary by at least 50 orders of magnitude. Differences in acidities are rationalized by invoking principles of hybridization, resonance, induction, and aromaticity.
Dicks, Andrew P. J. Chem. Educ. 2003, 80, 1322.
Acids / Bases |
Aromatic Compounds |
Alkanes / Cycloalkanes
The Study of Elimination Reactions Using Gas Chromatography: An Experiment for the Undergraduate Organic Laboratory  Devin Latimer
This article describes an investigation of elimination reactions of alkyl halides. 1-Bromopentane or 2-bromopentane are reacted with either sodium ethoxide or potassium tert-butoxide. Gas chromatography is used to monitor the relative amounts of 1-pentene, (E)-2-pentene, and (Z)-2-pentene produced.
Latimer, Devin. J. Chem. Educ. 2003, 80, 1183.
Chromatography |
Instrumental Methods |
Synthesis |
Gas Chromatography |
Elimination Reactions |
Mechanisms of Reactions |
Alkenes |
Stereochemistry
Organic Functional Group Playing Card Deck  Michael J. Welsh
Organic functional group playing card deck used for review of the name and structure of organic functional groups that can be used to play any game that a normal deck of cards is used for.
Welsh, Michael J. J. Chem. Educ. 2003, 80, 426.
Nomenclature / Units / Symbols |
Nonmajor Courses |
Enrichment / Review Materials |
Alcohols |
Aldehydes / Ketones |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes |
Amides |
Amines / Ammonium Compounds |
Aromatic Compounds |
Carboxylic Acids |
Esters |
Ethers |
Mechanisms of Reactions |
Synthesis
C–H and C–D Bonds: An Experimental Approach to the Identity of C–H Bonds by Their Conversion to C–D Bonds  Alex T. Rowland
Three experiments that allow students to determine the relative reactivity of C-H bonds that are aliphatic, alpha, benzylic, or aromatic by the ease of substitution of deuterium for oxygen.
Rowland, Alex T. J. Chem. Educ. 2003, 80, 311.
Acids / Bases |
IR Spectroscopy |
Isotopes |
NMR Spectroscopy |
Undergraduate Research |
Alkanes / Cycloalkanes |
Aromatic Compounds |
Carboxylic Acids
1H NMR Measurement of the Trans–Cis Photoisomerization of Cinnamic Acid Derivatives  Basil Danylec and Magdy N. Iskander
Procedure that illustrates trans-cis photoisomerization.
Danylec, Basil; Iskander, Magdy N. J. Chem. Educ. 2002, 79, 1000.
NMR Spectroscopy |
Photochemistry |
Stereochemistry |
Aromatic Compounds |
Alcohols |
Esters |
Alkenes |
Molecular Properties / Structure
Fractional Distillation and GC Analysis of Hydrocarbon Mixtures  Craig J. Donahue
Separating and identifying the components of a three-hydrocarbon mixture through fractional distillation and gas chromatography.
Donahue, Craig J. J. Chem. Educ. 2002, 79, 721.
Chromatography |
Gas Chromatography |
Separation Science |
Alkanes / Cycloalkanes |
Alkenes |
Aromatic Compounds |
IR Spectroscopy |
NMR Spectroscopy |
Qualitative Analysis
Colorful Azulene and Its Equally Colorful Derivatives  Robert S. H. Liu
Analysis of azulene and related compounds for an explanation of their respective colors.
Liu, Robert S. H. J. Chem. Educ. 2002, 79, 183.
Atomic Properties / Structure |
MO Theory |
UV-Vis Spectroscopy |
Aromatic Compounds |
Alkenes
Effect of Anisotropy on the Chemical Shift of Vinyl Protons in trans- and cis-1,2-Dibenzoylethylenes. A Small-Group or Recitation Activity  Roosevelt Shaw, David Roane, and Sean Nedd
Procedure to help students explain chemical shift differences for vinyl protons in alkene diastereomers.
Shaw, Roosevelt; Roane, David; Nedd, Sean. J. Chem. Educ. 2002, 79, 67.
Magnetic Properties |
NMR Spectroscopy |
Undergraduate Research |
Diastereomers |
Aromatic Compounds |
Alkenes |
Photochemistry |
Molecular Properties / Structure
Preparation of a D-Glucose-Derived Alkene. An E2 Reaction for the Undergraduate Organic Chemistry Laboratory  Peter Norris and Andrew Fluxe
Synthesis of four carbohydrate derivatives that highlight techniques such as inert atmosphere work, rotary evaporators, and flash column chromatography.
Norris, Peter; Fluxe, Andrew. J. Chem. Educ. 2001, 78, 1676.
Carbohydrates |
NMR Spectroscopy |
Synthesis |
Alkenes |
Elimination Reactions |
Chromatography
Further Information on the Hazards of n-Hexane (re J. Chem. Educ. 2001, 78, 587)  Jay A. Young
Consideration of a flammable liquid above its flash point.
Young, Jay A. J. Chem. Educ. 2001, 78, 1593.
Alkanes / Cycloalkanes |
Laboratory Management
Further Information on the Hazards of n-Hexane (re J. Chem. Educ. 2001, 78, 587)  J. C. Jones
Consideration of a flammable liquid above its flash point.
Jones, J. C. J. Chem. Educ. 2001, 78, 1593.
Alkanes / Cycloalkanes |
Laboratory Management
Further Information on the Hazards of n-Hexane (re J. Chem. Educ. 2001, 78, 587)  J. C. Jones
Consideration of a flammable liquid above its flash point.
Jones, J. C. J. Chem. Educ. 2001, 78, 1593.
Alkanes / Cycloalkanes |
Laboratory Management
The Hydrogenation of Cyclododecene by Lithium Naphthalenide and Nickel Chloride Dihydrate  Francisco Alonso and Miguel Yus
Transformation of cyclododecene into cyclododecane in the absence of external hydrogen as an alternative to the normal method of catalytic hydrogenation.
Alonso, Francisco; Yus, Miguel. J. Chem. Educ. 2001, 78, 1517.
Synthesis |
Alkanes / Cycloalkanes |
Alkenes |
Metals
Kinetic Derivations for Thermal Isomerizations of Monodeuterio Cyclic 1,3-Dienes through 1,5-Hydrogen Shifts  John E. Baldwin, Phyllis A. Leber, and Tamara W. Lee
Explicit derivations of equations defining relative concentrations versus time for five sets of monodeuterio cyclic 1,3-dienes.
Baldwin, John E.; Leber, Phyllis A.; Lee, Tamara W. J. Chem. Educ. 2001, 78, 1394.
Isotopes |
Kinetics |
Aromatic Compounds |
Alkenes
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
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
Correction to Chemical Laboratory Information Profile: n-Hexane (J. Chem. Educ. 2001, 78, 587)  Jay A. Young
Corrected formula for n-hexane.
Young, Jay A. J. Chem. Educ. 2001, 78, 1021.
Alkanes / Cycloalkanes |
Laboratory Management |
Physical Properties
A Method for Drawing the Cyclohexane Ring and Its Substituents  Veljko Dragojlovic
A simple method for drawing cyclohexanes.
Dragojlovic, Veljko. J. Chem. Educ. 2001, 78, 923.
Molecular Properties / Structure |
Stereochemistry |
Alkanes / Cycloalkanes
Chemical Laboratory Information Profile: n-Hexane  Jay A. Young
Properties, hazards, and storage requirements for n-hexane.
Young, Jay A. J. Chem. Educ. 2001, 78, 587.
Alkanes / Cycloalkanes |
Laboratory Management |
Physical Properties
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
The Discovery-Oriented Approach to Organic Chemistry. 3. Rearrangement of cis- and trans-Stilbene Oxides with Boron Trifluoride Etherate. An Exercise in 1H NMR Spectroscopy for Sophomore Organic Laboratories  Erik A. Sgariglia, Regina Schopp, Kostas Gavardinas, and Ram S. Mohan
A discovery-oriented laboratory experiment that involves the rearrangement of both cis- and trans-stilbene oxides with boron trifluoride etherate.
Sgariglia, Erik A.; Schopp, Regina; Gavardinas, Kostas; Mohan, Ram S. J. Chem. Educ. 2000, 77, 79.
Mechanisms of Reactions |
NMR Spectroscopy |
Constitutional Isomers
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
The Calculation of Standard Enthalpies of Formation of Alkanes: Illustrating Molecular Mechanics and Spreadsheet Programs  Eric Leigh Hawk
How group increment methods may be used to predict standard enthalpies of formation of alkanes is outlined as an undergraduate computational chemistry experiment. The experiment requires input and output data sets. Although users may create their own data sets, both sets are provided.
Hawk, Eric Leigh. J. Chem. Educ. 1999, 76, 278.
Computational Chemistry |
Molecular Modeling |
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Calorimetry / Thermochemistry
Recycling Solvent Mixtures of Ethyl Acetate and Hexanes  Timothy J. Wilkinson
A method to recycle ethyl acetate-hexanes mixtures from thin-layer or column chromatography experiments is described. The procedure consists of co-distillation of the mixture followed by estimation of the composition by reference to an Rf vs percent composite graph. The mixture is then diluted with the appropriate solvent to achieve the desired composition.
Wilkinson, Timothy J. J. Chem. Educ. 1998, 75, 1640.
Chromatography |
Separation Science |
Solutions / Solvents |
Esters |
Alkanes / Cycloalkanes
Rotational Barriers in Push-Pull Ethylenes: An Advanced Physical-Organic Project Including 2D EXSY and Computational Chemistry  Tammy J. Dwyer, Julia E. Norman, and Paul G. Jasien
An integrated upper-division physical-organic experiment for chemistry majors has been developed. It involves the determination and mechanistic interpretation of the C=C and CN rotational barriers in a push-pull ethylene. In the course of the experiment students will synthesize an organic compound, acquire variable temperature 1D and 2D NMR spectra, and use computational quantum chemistry to gain a deeper understanding of the unique electronic features of the molecule.
Dwyer, Tammy J.; Norman, Julia E.; Jasien, Paul G. J. Chem. Educ. 1998, 75, 1635.
Kinetics |
NMR Spectroscopy |
Molecular Properties / Structure |
Computational Chemistry |
Alkenes
Photodimerization of Maleic Anhydride  Zhang, Zhijun
Why the photodimerization of maleic anhydride produces the cis, tans, cis product.
Zhang, Zhijun J. Chem. Educ. 1998, 75, 1515.
Photochemistry |
Stereochemistry |
Molecular Properties / Structure |
Alkenes
Resolution of trans-Cyclohexane-1,2-diamine and Determination of the Enantiopurity Using Chiral Solid-Phase HPLC Techniques and Polarimetry  Patrick J. Walsh, Diane K. Smith, and Chris Castello
The experiment is designed to reinforce and broaden the students' understanding of the relationship between enantiomers and diasteriomers and of diasteriomeric interactions. Additionally, it illustrates the differences in physical properties (solubility and melting range) between a racemic mixture and the same compound in highly resolved form.
Walsh, Patrick J.; Smith, Diane K.; Castello, Chris. J. Chem. Educ. 1998, 75, 1459.
Chromatography |
Synthesis |
Separation Science |
Stereochemistry |
HPLC |
Alkanes / Cycloalkanes |
Amines / Ammonium Compounds |
Chirality / Optical Activity
A Strategy for Incorporating 13C NMR into the Organic Chemistry Lecture and Laboratory Courses  Perry C. Reeves and Chris P. Chaney
The use of spectroscopy in establishing the structures of molecules is an important component of the first course in Organic Chemistry. However, the point in the course at which these techniques are best introduced remains uncertain. We suggest that carbon nuclear magnetic resonance spectroscopy should be introduced at an early stage of the lecture course, specifically while studying the alkanes, and used extensively for structure determination throughout the course.
Reeves, Perry C.; Chaney, Chris P. J. Chem. Educ. 1998, 75, 1006.
Instrumental Methods |
NMR Spectroscopy |
Fourier Transform Techniques |
Alkanes / Cycloalkanes |
Molecular Properties / Structure
A Simple Molecular Orbital Treatment of the Barrier to Internal Rotation in the Ethane Molecule  Derek W. Smith
The origin of the barrier to internal rotation in the ethane molecule is explored in terms of elementary molecular orbital (MO) considerations. Emphasis is placed on the antibonding effect, i.e. the result that an antibonding MO is more destabilized than its bonding counterpart is stabilized, relative to the parent atomic orbitals (AOs). It is shown that, in the case of two equivalent AOs, this effect is approximately proportional to the square of the overlap integral.
Smith, Derek W. J. Chem. Educ. 1998, 75, 907.
Covalent Bonding |
MO Theory |
Stereochemistry |
Theoretical Chemistry |
Alkanes / Cycloalkanes
The Energy Profile for Rotation about the C-C Bond in Substituted Ethanes: A Multi-Part Experimental Computational Project for the Physical Chemistry Laboratory  Luther E. Erickson and Kevin F. Morris
This paper describes a multi-part project for the physical chemistry lab that includes both experimental and computational approaches to the investigation of the energy profile for internal rotation in substituted ethanes. Experimental approaches include dipole moment determinations, high-resolution nmr spectroscopy (including coupling constant determinations from the analysis of C-13 satellites), and infrared spectral analysis, all directed toward the goal of determining the relative populations - and thereby the relative energies - of low energy rotamers of a substituted ethane as a function of substituent, temperature and solvent composition.
Erickson, Luther E.; Morris, Kevin F. J. Chem. Educ. 1998, 75, 900.
Theoretical Chemistry |
Computational Chemistry |
Stereochemistry |
Alkanes / Cycloalkanes
Intermolecular Forces in Introductory Chemistry Studied by Gas Chromatography, Computer Models, and Viscometry  Jonathan C. Wedvik, Charity McManaman, Janet S. Anderson, and Mary K. Carroll
Students performing gas chromatographic (GC) analyses of mixtures of n-alkanes and samples that simulate crime scene evidence discover that liquid mixtures can be separated rapidly into their components based upon intermolecular forces. Each group of students is given a liquid sample that simulates one collected at an arson scene, and the group is required to determine the identity of the accelerant. Students also examine computer models to better visualize how molecular structure affects intermolecular forces: London forces, dipole-dipole interactions, and hydrogen bonding.
Wedvik, Jonathan C.; McManaman, Charity; Anderson, Janet S.; Carroll, Mary K. J. Chem. Educ. 1998, 75, 885.
Theoretical Chemistry |
Chromatography |
Noncovalent Interactions |
Gas Chromatography |
Molecular Modeling |
Forensic Chemistry |
Alkanes / Cycloalkanes |
Hydrogen Bonding |
Molecular Properties / Structure
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
The Pi-Electron-System of Monocyclic Polyenes C2nH2n with Alternating Single and Double Bonds  J. J. C. Mulder
The question asked is whether (in)stability towards distortion away from a symmetric geometry is a {pi}-electron property or, on the contrary, primarily connected to the {sigma}-skeleton.
Mulder, J. J. C. J. Chem. Educ. 1998, 75, 594.
Alkenes |
Aromatic Compounds |
Molecular Properties / Structure
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
Alkanes in Motion (Program for Mac OS-Compatible Computers: J. Chem. Educ. Software Vol. 9C, No. 1)  Jae Hyun Kim
To improve students' understanding of molecular motion, Alkanes in Motion, a collection of clip animations generated from molecular dynamics calculations, was produced. It depicts the molecular motion of hydrocarbons in the gas phase.
Kim, Jae Hyun. J. Chem. Educ. 1997, 74, 1015.
Molecular Modeling |
Alkanes / Cycloalkanes
A Three-Dimensional Energy Surface for the Conformational Inversion of Cyclohexane  Nicholas Leventis*, Samir B. Hanna, Chariklia Sotiriou-Leventis
While it is well known that chair forms of cyclohexane can interconvert without passing through the boat conformation, the same statement frequently comprises a source of confusion regarding the location of the boat conformation on the energy surface of the conformational inversion of cyclohexane. To alleviate this problem, a novel three-dimensional energy diagram has been introduced showing explicitly how the chair forms of cyclohexane interconvert.
Leventis, Nicholas; Hanna , Samir B. ; Sotiriou-Leventis, Chariklia . J. Chem. Educ. 1997, 74, 813.
Learning Theories |
Mechanisms of Reactions |
Stereochemistry |
Alkanes / Cycloalkanes |
Conformational Analysis |
Molecular Properties / Structure
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
Aromaticity Today: Energetic and Structural Criteria  Mikhail Glukhovtsev
The present paper addresses current controversies in development and applications of the two main criteria of aromaticity, namely, energetic and structural criteria. Various types of resonance energy with an emphasis on homodesmotic and isodesmic stabilization energies are discussed. Reliability of such structural criteria of aromaticity as equalization of carbon-carbon bond lengths and stability with respect to out-of-plane distortions of a molecular structure are analyzed using various examples.
Glukhovtsev, Mikhail . J. Chem. Educ. 1997, 74, 132.
Aromatic Compounds |
Alkenes |
Molecular Properties / Structure
The Wittig Reaction: Generation, Observation and Reactivity of a Phosphorous Ylide Intermediate. An Experiment for the Advanced Organic Chemistry Laboratory Course  Gary W. Breton
An experiment has been devised that illustrates three important concepts in organic chemistry: the synthesis of an alkene via the Wittig reaction, characterization of a reactive intermediate by 1H NMR, and site - specific deuterium labeling.
Breton, Gary W. J. Chem. Educ. 1997, 74, 114.
Synthesis |
Alkenes |
NMR Spectroscopy
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
Four Programs for Windows: Abstract of Volume 4D, Number 2: Alkanes in Motion  Jae Hyun Kim
Alkanes in Motion depicts the molecular motion of hydrocarbons in the gas phase. Four animations from the collection are presented here. These four animations consist of two animations each of hexane and octadecane, one animation calculated to show translational motion and one to show vibrational motion.
Kim, Jae Hyun. J. Chem. Educ. 1996, 73, 1079.
Molecular Modeling |
Alkanes / Cycloalkanes |
Molecular Properties / Structure |
Gases
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
An Alternative Derivation of the Energy Levels of the "Particle on a Ring" System  Alan Vincent
If the linear box is bent round into a ring, acceptable wave functions are those which are continuous at the 'join'. On this model some acceptable linear functions become unacceptable for the ring and some unacceptable cosine functions become acceptable. This approach can be used to produce a straightforward derivation of the energy levels and wave functions of the particle on a ring.
Vincent, Alan. J. Chem. Educ. 1996, 73, 1001.
Alkenes |
Quantum Chemistry
The Heats of Combustion of Gaseous Cyclotetradecane and trans-Stilbene - a Tale of Long-standing Confusion   Ernest L. Eliel and Jan J. Engelsman
This paper embodies the belated publication of a thesis submitted by JJE to the Free University of Amsterdam in 1955; heretofore the data were available only in a printed version of the thesis. In conjunction with a subsequent determination of the heat of combustion of solid cyclotetradecane, this led to the conclusion that the compound was strain-free.
J. Chem. Educ. 1996, 73, 903.
Alkanes / Cycloalkanes |
Physical Properties |
Calorimetry / Thermochemistry
A Conceptually Simple Approach to the Analysis of Aromaticity in Pericyclic Transition States  Richard Francis Langler
Aromatic Mbius cyclobutadiene is shown to be an artifact of Hckel theory. It is then shown that transition states may be classified as aromatic / antiaromatic / non-aromatic by exploiting both the extent of orbital overlap which develops in competing transition states and Hckel's rule.
J. Chem. Educ. 1996, 73, 899.
Molecular Modeling |
Aromatic Compounds |
Alkenes |
Molecular Properties / Structure
The Curiously Intertwined Histories of Benzene and Cyclohexane  E. W. Warnhoff
The first reduction of benzene, which was done by means of hydrogen iodide in the middle of the 19th century, led to a saturated hydrocarbon initially thought to be hexane and later to be hexahydrobenzene (cyclohexane).
Warnhoff, E. W. J. Chem. Educ. 1996, 73, 494.
Alkanes / Cycloalkanes |
Aromatic Compounds
A Rapid Way of Computing the Number of Rings Present in a Polycyclic Organic Compound  A. Srikrishna
This article discusses how by counting the number of quaternary and tertiary atoms present, the number of rings in a polycyclic organic compound can be deduced.
Srikrishna, A. J. Chem. Educ. 1996, 73, 428.
Alkanes / Cycloalkanes
Disconnect by the Numbers: Protocol for the Synthesis of Alkanes  Michael B. Smith
This addendum gives a method to convert an alkane to a functionalized precursor and that new molecule can be analyzed in the normal manner. --------------------------------------------------------------------------------
Smith, Michael B. J. Chem. Educ. 1996, 73, 304.
Alkanes / Cycloalkanes |
Synthesis
Relative Stabilities and Reactivities of Isolated Versus Conjugated Alkenes: Reconciliation Via a Molecular Orbital Approach  Chariklia Sotiriou-Leventis, Samir B. Hanna, and Nicholas Leventis
The well-accepted practice of generating a pair of molecular orbitals, one of lower energy and another of higher energy than the original pair of overlapping atomic orbitals, and the concept of a particle in a one-dimensional box are implemented in a simplified, nonmathematical method that explains the relative stabilities and reactivities of alkenes with conjugated versus isolated double bonds.
Sotiriou-Leventis, Chariklia; Hanna, Samir B.; Leventis, Nicholas. J. Chem. Educ. 1996, 73, 295.
Alkenes |
MO Theory
Olefin Metathesis Polymerization: The Unexpected Role of Carbenoid Species in Formation of Macromolecules  Donald M. Snyder
One particularly interesting topic still rarely seen outside of the research literature is the subject of metathesis polymerization. This article is intended to present the interested reader with a brief introduction to the mechanism of this unique process, its historical background, and some recent developments in the field.
Snyder, Donald M. J. Chem. Educ. 1996, 73, 155.
Polymerization |
Alkenes |
Mechanisms of Reactions
Nitroalkenes: Conjugate Nitro Compounds (Perekalin, V. V.; Lipina, E. S.; Berestovitskaya, V. M.; Efremov, D. A.)  
Monograph.
J. Chem. Educ. 1995, 72, A93.
Alkenes
A Ternary Phase Diagram for a Less Hazardous System  Barbara A. Udale and John D. Wells
Using a n-propanol-n-heptane-water system to generate data for construction of a ternary phase diagram.
Udale, Barbara A.; Wells, John D. J. Chem. Educ. 1995, 72, 1106.
Phases / Phase Transitions / Diagrams |
Aqueous Solution Chemistry |
Alcohols |
Alkanes / Cycloalkanes |
Solutions / Solvents
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
Regioselective Methoxybromination of Styrene Using TBABr3 in Methanol: An Organic Laboratory Experiment   Jacques Berthelot, Yamina Benammar, and Catherine Lange
Methoxybromination of styrene using TBABr3 in methanol.
Bertholet, Jacques; Benammar, Yamina; Lange, Catherine. J. Chem. Educ. 1995, 72, 850.
Synthesis |
Mechanisms of Reactions |
Alkenes |
Addition Reactions
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
One-Pot Iodosulfonylation Dehydroiodination of Alkenes: (E)-beta-Tosylstyrene: An Experiment for Undergraduate Organic Chemistry Laboratory   Carme Nájera, José M. Sansano, and Miguel Yus
Method for a one-pot preparation of a vinylic sulfone starting from an acrylamide by a tandem iodosulfonylation-dehydroiodination process.
Njera, Carmen; Sansano, Jos M.; Yus, Miguel. J. Chem. Educ. 1995, 72, 664.
Free Radicals |
Alkenes
The Conformational Behavior of n-Pentane: A Molecular Mechanics and Molecular Dynamics Experiment  Mencarelli, Paolo
174. Use of HyperChem to investigate the conformational behavior of n-pentane.
Mencarelli, Paolo J. Chem. Educ. 1995, 72, 511.
MO Theory |
Chirality / Optical Activity |
Molecular Properties / Structure |
Conformational Analysis |
Alkanes / Cycloalkanes |
Molecular Mechanics / Dynamics |
Molecular Modeling
The Distribution of Cyclohexanone between Cyclohexane and Water  Worley, John D.
A microscale experiment that may be used to demonstrate extraction, spectrophotometric analysis, and the determination of a distribution constant.
Worley, John D. J. Chem. Educ. 1994, 71, A145.
Microscale Lab |
Aqueous Solution Chemistry |
Aldehydes / Ketones |
Alkanes / Cycloalkanes |
Separation Science |
Spectroscopy
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
Haloallenes: Chiral Compounds without Chiral Carbon Atoms  Novak, Igor
Four questions regarding the structure, stereochemistry, and symmetry of haloallenes.
Novak, Igor J. Chem. Educ. 1994, 71, 579.
Chirality / Optical Activity |
Group Theory / Symmetry |
Stereochemistry |
Molecular Properties / Structure |
Alkenes
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
Deprotonation of Nitroalkanes: Semiempirical Determination of Solvation Effects on a Simple Reaction Coordinate  Pietro, William J.
161. Using computational chemistry to arrive at mechanistic and kinetic information for nitromethane and its deprotonated anion.
Pietro, William J. J. Chem. Educ. 1994, 71, 416.
Alkanes / Cycloalkanes |
Computational Chemistry |
Molecular Properties / Structure |
Mechanisms of Reactions |
Kinetics
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
Do our students really understand the Hammett equation?   Schwan, Adrian L.
In this author's experience, many students can proceed through text questions dealing with the Hammett equation without having a full understanding of the Hammett analysis. He offers a question that enables students to gain a better appreciation of this concept.
Schwan, Adrian L. J. Chem. Educ. 1993, 70, 1001.
Chemometrics |
Resonance Theory |
Constitutional Isomers
Cyclooctane conformational analysis via mechanical and computational models  Fitzgerald, Jeffrey P.
Description of an exercise in which students use both mechanical and computational models to identify and quantify various types of strains in different conformations of a molecule.
Fitzgerald, Jeffrey P. J. Chem. Educ. 1993, 70, 988.
Molecular Modeling |
Alkanes / Cycloalkanes |
Diastereomers
The enumeration of isomers-With special reference to the stereoisomers of decane  Whyte, J. R. C.; Clugston, M. J.
Structural isomers predicted through algorithms.
Whyte, J. R. C.; Clugston, M. J. J. Chem. Educ. 1993, 70, 874.
Alkanes / Cycloalkanes |
Stereochemistry |
Diastereomers
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
An Application of Linear Transformations to Thermodynamics  Hughes, Elvin, Jr.
Article describes a problem in thermodynamics that can be simplified using linear transformations, thus exposing physical chemistry students to this experience prior to their typical first encounters in group theory or quantum mechanics.
Hughes, Elvin, Jr. J. Chem. Educ. 1993, 70, 93.
Chemometrics |
Thermodynamics |
Alkanes / Cycloalkanes
The Relation Between the Ionization Potential and the Molecular Electronegativity of Organic Homologs  Chenzhong, Cao.
A quantitative correlation of the molecular electronegativity with first ionization potential of organic homologs that can be a great help to students (especially those without any quantum chemistry background) in understanding the change rule of electron activity.
Chenzhong, Cao. J. Chem. Educ. 1993, 70, 25.
Molecular Properties / Structure |
Aromatic Compounds |
Alkenes |
Alkynes
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
Microscale synthesis of azulene  Brieger, Gottfried
Procedure for the microscale synthesis of azulene.
Brieger, Gottfried J. Chem. Educ. 1992, 69, A262.
Microscale Lab |
Synthesis |
Aromatic Compounds |
Alkenes |
Dyes / Pigments |
Mechanisms of Reactions
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
A simple and colorful demonstration of light-catalyzed bromination of an alkane  Stevens, Malcolm P.
Light-catalyzed bromination of an alkane.
Stevens, Malcolm P. J. Chem. Educ. 1992, 69, 1028.
Catalysis |
Alkanes / Cycloalkanes |
Photochemistry |
Reactions
An easily constructed model: The boat form of a six-membered ring composed of six distorted tetrahedral penetrating each other  Yamana, Shukichi
Instructions for constructing a model of the boat form of a six-membered ring using six empty envelopes.
Yamana, Shukichi J. Chem. Educ. 1992, 69, 964.
Molecular Modeling |
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Stereochemistry
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 simple quantum mechanical model that illustrates the Jahn-Teller effect  Senn, Peter
The Jahn-Teller distortion applied to cyclobutadiene.
Senn, Peter J. Chem. Educ. 1992, 69, 819.
Quantum Chemistry |
Alkenes
Of men and marigolds: Counting the quaterthienyls  Perrine, Daniel M.; VandeVelde, J. Richard
Description of branched quaterthienyls and their isomers.
Perrine, Daniel M.; VandeVelde, J. Richard J. Chem. Educ. 1992, 69, 719.
Alkenes |
Molecular Properties / Structure |
Stereochemistry |
Diastereomers
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
A paper-pattern system for the construction of fullerene molecular models  Beaton, John M.
Paper cut-out models of C60, C70, C80, and C76 with Td and D2 symmetry.
Beaton, John M. J. Chem. Educ. 1992, 69, 610.
Molecular Properties / Structure |
Molecular Modeling |
Alkenes |
Group Theory / Symmetry
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
Replacing carbon tet: Other alternatives.  Ackermann, Martin N.
Using a mixture of hexanes in the traditional experiment to determine the equilibrium constant for the formation of I3-.
Ackermann, Martin N. J. Chem. Educ. 1992, 69, 602.
Equilibrium |
Alkanes / Cycloalkanes |
Toxicology
The synthesis of E-beta-bromostyrene: An experiment illustrating the use of IR bending modes to distinguish E and Z isomers and the concept of kinetic and thermodynamic controlled reactions.  Strom, Laura A.; Anderson, James R.; Gandler, Joseph R.
An experiment illustrating the concept of thermodynamic and kinetically controlled reactions to produce E and Z isomers (respectively); the use of IR to distinguish E and Z isomers; and the different properties of E and Z isomers (only the E isomer has a pleasant odor).
Strom, Laura A.; Anderson, James R.; Gandler, Joseph R. J. Chem. Educ. 1992, 69, 588.
Synthesis |
IR Spectroscopy |
Stereochemistry |
Kinetics |
Thermodynamics |
Alkenes |
Diastereomers |
Mechanisms of Reactions |
Molecular Properties / Structure
A source of isomer-drawing assignments  Kjonaas, Richard A.
A comprehensive source from which instructors can choose a wide variety of good isomer drawing examples to use as homework assignments and exam questions.
Kjonaas, Richard A. J. Chem. Educ. 1992, 69, 452.
Stereochemistry |
Alcohols |
Alkanes / Cycloalkanes |
Alkenes |
Aldehydes / Ketones |
Ethers |
Esters |
Alkynes
An expanded Fieser model suitable for a large classroom  Levinson, Alfred S.; Zupan, Rudolph
In organic chemistry, one area in which models are indispensable is in introducing the conformational analysis of cyclopentane and cyclohexane rings.
Levinson, Alfred S.; Zupan, Rudolph J. Chem. Educ. 1992, 69, 369.
Alkanes / Cycloalkanes |
Molecular Modeling |
Molecular Properties / Structure
Understanding the fate of petroleum hydrocarbons in the subsurface environment  Chen, Chien T.
This article reviews our current understanding and then specifies the requirements for research that will improve our ability to detect hydrocarbons and predict their fate in the subsurface environment.
Chen, Chien T. J. Chem. Educ. 1992, 69, 357.
Alkanes / Cycloalkanes |
Phases / Phase Transitions / Diagrams
Ethylene-An unusual plant hormone  Ainscough, Eric W.; Brodie, Andrew M.; Wallace, Anna L.
This article discusses some of the early historical observations about this ethylene, the production and concentration of ethylene in plants, the ethylene biosynthesis pathway, and the possible site of ethylene action.
Ainscough, Eric W.; Brodie, Andrew M.; Wallace, Anna L. J. Chem. Educ. 1992, 69, 315.
Alkenes |
Plant Chemistry |
Biosynthesis
The addition of hydrogen bromide to unsymmetrical alkenes   Weiss, Hilton M.
The original article was valuable in pointing out the utility of HBr in acetic acid for the addition of HBr to alkenes.
Weiss, Hilton M. J. Chem. Educ. 1992, 69, 172.
Alkenes
Higher order cycloaddition reactions of adamantyl isobenzofulvene and isobenzofuran: A microscale synthesis illustrating the involvement of highly reactive intermediates and a simple FMO treatment of their cycloaddition periselectivities  Russell, Richard A.; Longmore, Robert W.; Warrener, Ronald N.
The authors have developed an undergraduate laboratory experiment to illustrate a cycloaddition reaction using a simple mathematical approach.
Russell, Richard A.; Longmore, Robert W.; Warrener, Ronald N. J. Chem. Educ. 1992, 69, 164.
Microscale Lab |
Alkenes |
Synthesis |
MO Theory
Addition of IBr to fatty acids on the overhead projector   Solomon, Sally; Fulep-Poszmik, Annamaria; Kulp, Gary; Yu, Heung
The interhalogen compound IBr dissolved in CCl4 is added to petroleum ether solutions of fatty acids to test for unsaturation.
Solomon, Sally; Fulep-Poszmik, Annamaria; Kulp, Gary; Yu, Heung J. Chem. Educ. 1992, 69, 66.
Alkanes / Cycloalkanes |
Alkenes
Fluorocarbon bubbler fluids for reactive gases   Brown, Alan B.; Kosmeder, J. W.; Gaska, Paul D.; Chronister, Chris W.; Barthel-Rosa, Luis
Perfluorodecalin is a suitable bubbler fluid for measuring small flow rates of Cl2, SO2, or HCl.
Brown, Alan B.; Kosmeder, J. W.; Gaska, Paul D.; Chronister, Chris W.; Barthel-Rosa, Luis J. Chem. Educ. 1991, 68, A298.
Microscale Lab |
Gases |
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
Discovering stereoselectivity: Synthesis of exo- and endobrevicomin using a tunable hydride reduction: A program of organic synthesis experiments for advanced undergraduate students  Richardson, David P.; Wilson, Whitney; Mattson, Rebecca J.; Powers, Dawn M.; Dolan, Brian T.
With their low molecular weights and modest structural complexity, insect pheromones have proven to be especially fruitful for advanced undergraduate organic synthesis laboratory exercises.
Richardson, David P.; Wilson, Whitney; Mattson, Rebecca J.; Powers, Dawn M.; Dolan, Brian T. J. Chem. Educ. 1991, 68, 951.
Natural Products |
Diastereomers |
Enantiomers |
Stereochemistry |
Aldehydes / Ketones |
Alcohols |
Gas Chromatography |
Alkanes / Cycloalkanes
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
A visual presentation of the relationships between the enthalpies of a reaction and the nature of the transition states  Nyquist, H. LeRoy
An apparatus that illustrates the potential energy diagram for the chlorination of alkanes and another for the bromination of alkanes.
Nyquist, H. LeRoy J. Chem. Educ. 1991, 68, 731.
Thermodynamics |
Alkanes / Cycloalkanes
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
A projection for bond location in chair cyclohexane and related structures  Woolf, A. A.
Benefits and drawbacks of 2D representations for chair cyclohexane and related structures.
Woolf, A. A. J. Chem. Educ. 1991, 68, 646.
Alkanes / Cycloalkanes |
Diastereomers |
Enantiomers |
Constitutional Isomers
Decarboxylative elimination of 2,3-dibromo-3-phenylpropanoic acid to E or Z 1-bromo-2-phenylethylene (Beta-Bromostyrene): An experiment illustrating solvent effect on the stereochemical course of a reaction  Mestdagh, Helene; Puechberty, Anne
An experiment illustrating solvent effect on the stereochemical course of a reaction.
Mestdagh, Helene; Puechberty, Anne J. Chem. Educ. 1991, 68, 515.
Elimination Reactions |
Alkenes |
Stereochemistry |
Solutions / Solvents
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
Representing isomeric structures  Thall, Edwin
"Representing isomeric structures" is the name of a technique this author has developed to help students learn to draw molecular structures of isomers in their first organic chemistry class.
Thall, Edwin J. Chem. Educ. 1991, 68, 190.
Constitutional Isomers |
Diastereomers
The synthesis of 2'-bromostyrene  Corvari, Linda; McKee, James R.; Zanger, Murray
Organic chemistry laboratories need not be the repositories of foul smells. This synthesis produces an aroma akin to hyacinth.
Corvari, Linda; McKee, James R.; Zanger, Murray J. Chem. Educ. 1991, 68, 161.
Synthesis |
NMR Spectroscopy |
IR Spectroscopy |
Stereochemistry |
Alkenes
Polarity and selectivity of ionic stationary phases used in gas chromatography: Evaluation of commercial detergents containing anionic surfactants as column packings  Furton, Kenneth G.; Mantilla, Adriana
Evaluation of commercial detergents containing anionic surfactants as column packings.
Furton, Kenneth G.; Mantilla, Adriana J. Chem. Educ. 1991, 68, 74.
Consumer Chemistry |
Gas Chromatography |
Physical Properties |
Alkanes / Cycloalkanes |
Quantitative Analysis |
Covalent Bonding |
Solutions / Solvents
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
Polymers in the physical chemistry laboratory: An integrated experimental program  Hardgrove, George L.; Tarr, Donald L.; Miessler, Gary L.
Procedure for polymerizing mixtures of styrene and methylmethacrylate.
Hardgrove, George L.; Tarr, Donald L.; Miessler, Gary L. J. Chem. Educ. 1990, 67, 979.
Polymerization |
Alkenes |
Aromatic Compounds |
IR Spectroscopy |
NMR Spectroscopy |
Chromatography
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
Reaction of bromine with hydrocarbons on the overhead, real or simulated  Solomon, Sally; Gregory, Michael; Padmanabhan, Sandeep; Smith, Kurt
A simulation that looks like the addition of bromine to hydrocarbons but is not (the bromine is simulated using a mixture of food colorings).
Solomon, Sally; Gregory, Michael; Padmanabhan, Sandeep; Smith, Kurt J. Chem. Educ. 1990, 67, 961.
Alkanes / Cycloalkanes |
Aromatic Compounds |
Addition Reactions
Keeping track of directions of atomic orbitals: A useful device in organic chemistry  Talaty, Erach R.
The usefulness of keeping track of the directions of atomic orbitals.
Talaty, Erach R. J. Chem. Educ. 1990, 67, 655.
Atomic Properties / Structure |
Alkenes |
Alkynes
The stereochemistry of additions to trans-anethole  McGahey, Lawrence
Trans-anethole is brominated with pyridinium bromide perbromide in dichloromethane.
McGahey, Lawrence J. Chem. Educ. 1990, 67, 554.
Addition Reactions |
Stereochemistry |
Mechanisms of Reactions |
Alkenes |
Diastereomers |
Enantiomers
The addition of hydrogen bromide to unsymmetrical alkenes: Introductory experiments in NMR spectroscopy and mechanistic chemistry  Brown, Trevor M.; Dronsfield, Alan T.; Ellis, Robert
As an introduction to NMR the authors center their work around the addition of hydrogen bromide to unsymmetrical alkenes and use the coupling patterns in the proton NMR spectra to establish whether the addition product is consistent with the Markovnikov rule.
Brown, Trevor M.; Dronsfield, Alan T.; Ellis, Robert J. Chem. Educ. 1990, 67, 518.
NMR Spectroscopy |
Alkenes |
Mechanisms of Reactions
Hydroboration for the large organic laboratory  Pickering, Miles
This paper reports an experiment in hydroboration without large hood space requirements, without special glassware requirements, and without inert atmospheric precautions.
Pickering, Miles J. Chem. Educ. 1990, 67, 436.
Oxidation / Reduction |
Alkenes |
Alcohols |
Qualitative Analysis
A vapor pressure demonstration   Sears, Jerry A.
The fact that all liquids exert a vapor pressure is an abstract concept that many students have difficulty understanding. The following demonstration offers dramatic, visual evidence of the pressure exerted by the vapor of a liquid.
Sears, Jerry A. J. Chem. Educ. 1990, 67, 427.
Alkanes / Cycloalkanes |
Phases / Phase Transitions / Diagrams |
Liquids
Kinetics of pentaamminenitritocobalt(III) to pentaaminenitrocobalt(III) linkage isomerization, revisited  Phillips, Wanda M.; Choi, Sunhee; Larrabee, James A.
A rigorous kinetics analysis experiment using infared and visible absorption spectroscopy is feasible for an advanced undergraduate student and leads to the determination of the forward rate constant, reverse rate constant, and equilibrium constant in both the solid and solution phase reactions.
Phillips, Wanda M.; Choi, Sunhee; Larrabee, James A. J. Chem. Educ. 1990, 67, 267.
IR Spectroscopy |
Kinetics |
Spectroscopy |
Constitutional Isomers |
Rate Law
The preparation of Indanthrene Scarlet GG: A vat dye experiment for the introductory organic chemistry laboratory  Lutz, Wilson B.
The vat dye Indanthrene Scarlet GG can easily be synthesized and applied to cloth within a single two hour laboratory period.
Lutz, Wilson B. J. Chem. Educ. 1990, 67, 71.
Synthesis |
Dyes / Pigments |
Alkenes
A Diels-Alder reaction for the overhead projector  Kolb, Kenneth E.
Reacting the strong dienophile tetracyanothylene with anthracene as the diene.
Kolb, Kenneth E. J. Chem. Educ. 1989, 66, 955.
Alkenes |
Mechanisms of Reactions
A valence isomer trapping procedure for introductory organic laboratory: Synthesis of a homobarrelene derivative  Kurtz, David W.; Johnson, Richard P.
Norcaradiene is trapped out of its cycloheptatriene valence isomer in a Diels-Alder reaction with maleic anhydride.
Kurtz, David W.; Johnson, Richard P. J. Chem. Educ. 1989, 66, 873.
Alkenes |
Mechanisms of Reactions
Isomerization of dimethyl maleate to dimethyl fumarate: An undergraduate experiment utilizing high performance liquid chromatography  Ledlie, David B.; Wenzel, Thomas J.; Hendrickson, Susan M.
Introduces students to liquid chromatography, the stereoisomerization of alkenes, certain aspects of free radical chemistry, and thermodynamics.
Ledlie, David B.; Wenzel, Thomas J.; Hendrickson, Susan M. J. Chem. Educ. 1989, 66, 781.
HPLC |
Mechanisms of Reactions |
Esters |
Stereochemistry |
Free Radicals |
Alkenes |
Thermodynamics
Alkenes and their derivatives: The alchemists' dream come true  Seymour, Raymond B.
History and applications of alkenes and their polymeric derivatives (rubber and plastics).
Seymour, Raymond B. J. Chem. Educ. 1989, 66, 670.
Alkenes |
Polymerization |
Applications of Chemistry
Organic chemistry on postage stamps  Schreck, James O.
Various organic chemistry topics on stamps, including hydrocarbons, benzene, Fischer projection, structural formulas, polymers, fermentation, Leibig condenser, molecular curiosities, and the organic chemical industry.
Schreck, James O. J. Chem. Educ. 1989, 66, 624.
Alkanes / Cycloalkanes |
Aromatic Compounds
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
Drawing different views of the chair form of substituted cyclohexanes  Richardson, W. S.
A set of rules to instruct students in a method for drawing chair structures of cyclohexane after rotation about the central axis.
Richardson, W. S. J. Chem. Educ. 1989, 66, 478.
Alkanes / Cycloalkanes |
Molecular Properties / Structure |
Stereochemistry
C167H336 is the smallest alkane with more realizable isomers than the observed universe has "particles"  Davies, Robert E.; Freyd, Peter J.
The number of stereoisomers of C167H336 that can exist, though not all at the same time, is greater than the classical figure for the number of particles in the observed universe.
Davies, Robert E.; Freyd, Peter J. J. Chem. Educ. 1989, 66, 278.
Alkanes / Cycloalkanes |
Stereochemistry
A classroom demonstration of aliphatic substitution   Perina, Ivo; Mihanovic, Branka
Substitution of an alkane by a halogen can be demonstrated effectively on the stage of an overhead projector using a compartmentalized Petri dish or a transparent Conway dish covered by a glass plate
Perina, Ivo; Mihanovic, Branka J. Chem. Educ. 1989, 66, 257.
Reactions |
Alkanes / Cycloalkanes
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
Bromination of a hydrocarbon   Deck, Eva; Deck, Charles
The authors have developed a simple one-hour student experiment that demonstrates photochemical halogen substitution in a quantitative way using heptane, bromine, and water.
Deck, Eva; Deck, Charles J. Chem. Educ. 1989, 66, 75.
Reactions |
Photochemistry |
Quantitative Analysis |
Alkanes / Cycloalkanes
Alkanes: Abundant, pervasive, important, and essential   Seymour, Raymond B.
Some of the most useful alkanes are high-molecular weight molecules obtained by the polymerization of ethylene.
Seymour, Raymond B. J. Chem. Educ. 1989, 66, 59.
Alkanes / Cycloalkanes |
Polymerization
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
Stereochemistry of cyclic hydrocarbons   Perkins, Robert R.
The topic of stereochemistry always poses great difficulties for many students in introductory organic chemistry. The following problems can be used as a tutorial question after having introduced the various terms associated with stereochemistry. The question requires skills at the applications level in the Bloom taxonomy.
Perkins, Robert R. J. Chem. Educ. 1988, 65, 860.
Alkanes / Cycloalkanes |
Chirality / Optical Activity |
Stereochemistry |
Diastereomers |
Constitutional Isomers
The preparation of 4-hydroxy-2,3,4,5-tetraphenyl-2-cyclopenten-1-one and its base catalyzed conversion into 2,3,4,5-tetraphenycyclopentadienone: An organic laboratory experiment   Harrison, Ernest A., Jr.
An organic laboratory experiment that permits direct observation of a pedagogically interesting transformation.
Harrison, Ernest A., Jr. J. Chem. Educ. 1988, 65, 828.
Aldehydes / Ketones |
Phenols |
Alkanes / Cycloalkanes |
IR Spectroscopy |
Synthesis
Chemical applications of graph theory. Part II. Isomer enumeration  Hansen, Peter J.; Jurs, Peter C.
An in-depth look at the study of isomer enumeration.
Hansen, Peter J.; Jurs, Peter C. J. Chem. Educ. 1988, 65, 661.
Chemometrics |
Constitutional Isomers |
Alkanes / Cycloalkanes
Arylation of carbon carbon double bonds catalyzed by palladium salts  Lauron, Helene; Mallet, Jean-Maurice; Mestdagh, Helene; Ville, Guy
A more advanced synthetic project that incorporates reactions and materials with real-world significance.
Lauron, Helene; Mallet, Jean-Maurice; Mestdagh, Helene; Ville, Guy J. Chem. Educ. 1988, 65, 632.
Applications of Chemistry |
Synthesis |
Alkenes |
Alkanes / Cycloalkanes |
Catalysis
Drawing the chair conformers of cyclohexane  Shaw, David G.
This author argues that much of the difficulty of sketching chair conformers of cyclohexane stems from the sequence in which the lines forming the chair are drawn.
Shaw, David G. J. Chem. Educ. 1988, 65, 587.
Alkanes / Cycloalkanes |
Molecular Modeling
The thermochemistry of catenation in silanes versus alkanes  Smith, Derek W.
The purpose of this paper is to clarify (not resolve) the issues behind the questions, "Why are catenated silanes less numerous and apparently less stable than the analogous alkanes?"
Smith, Derek W. J. Chem. Educ. 1988, 65, 414.
Alkanes / Cycloalkanes |
Periodicity / Periodic Table |
Thermodynamics
The effect of a catalyst on the thermodynamic properties and partition functions of a group of isomers  Alberty, Robert A.
The authors' analysis of the effect of a catalyst on the thermodynamic properties and partition functions of a group of isomers.
Alberty, Robert A. J. Chem. Educ. 1988, 65, 409.
Thermodynamics |
Equilibrium |
Alkenes |
Alkanes / Cycloalkanes |
Constitutional Isomers
The number of alkanes having n carbons and a longest chain of length d: An application of a theorem of Polya  Balaban, Alexandru T.; Kennedy, John W.; Quintas, Louis
This paper tackles the problem of determining the number of structural isomers of an alkane. The primitive algorithm that is usually taught to students is confusing and generates redundancies.
Balaban, Alexandru T.; Kennedy, John W.; Quintas, Louis J. Chem. Educ. 1988, 65, 304.
Constitutional Isomers |
Alkanes / Cycloalkanes |
Chemometrics
Alkane activation with mercury vapor   Brown, Steven B.; Crabtree, Robert H.
This paper explores the progress made by chemists in activating small molecules (CO,CO2,CH4,C2H4, etc.) with metals or metal compounds.
Brown, Steven B.; Crabtree, Robert H. J. Chem. Educ. 1988, 65, 290.
Metals |
Organometallics |
Reactions |
Catalysis |
Alkanes / Cycloalkanes
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
On the boiling points of the alkyl halides  Correla, John
Most textbooks spend some time discussing the relationship between boiling point and molecular structure, however, their reasons behind this relationship differ. This variation among textbooks warrants further investigation and discussion in order to uncover which of the factors are the major contributors to the variation of boiling point.
Correla, John J. Chem. Educ. 1988, 65, 62.
Alkanes / Cycloalkanes |
Physical Properties |
Noncovalent Interactions |
Molecular Properties / Structure
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
Hydroformylation of 1-hexene utilizing homogeneous rhodium catalysts: Regioselectivity as a function of conversion  Hanson, Brian E.; Davis, Mark E.
Possible reaction pathways for isomerization, hydroformylation, and hydrogenation of 1-alkenes using HRh(CO)L3 catalyst precursors.
Hanson, Brian E.; Davis, Mark E. J. Chem. Educ. 1987, 64, 928.
Catalysis |
Alkenes |
Mechanisms of Reactions
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
A convenient demonstration of combustion and explosion  Fenster, Ariel E.; Harpp, David N.; Schwarcz, Joseph A.
Demonstrating the correct molar ratio between propane and oxygen.
Fenster, Ariel E.; Harpp, David N.; Schwarcz, Joseph A. J. Chem. Educ. 1987, 64, 894.
Stoichiometry |
Alkanes / Cycloalkanes |
Oxidation / Reduction
From shadows to three dimensions: Stereographic images using Dreiding models and the Macintosh  Strauss, Michael J.; Gribble, Gordon
Printing stereographic images using ChemDraw.
Strauss, Michael J.; Gribble, Gordon J. Chem. Educ. 1987, 64, 850.
Alkanes / Cycloalkanes |
Stereochemistry |
Molecular Modeling |
Molecular Properties / Structure
Generation of cyclopentadiene  Ruekberg, Benjamin P.
Procedure and apparatus for generating cyclopentadiene.
Ruekberg, Benjamin P. J. Chem. Educ. 1987, 64, 726.
Alkenes |
Synthesis
Kinetic hydrogen isotope effects: An organic/physical laboratory experiment  McGuiggan, Patricia; Eliason, Robert; Anderson, Ben; Botch, Beatrice
Investigating the difference in the rate constant of a reaction due to isotopic substitution of a hydrogen atom involved in the rate-determining step of a reaction.
McGuiggan, Patricia; Eliason, Robert; Anderson, Ben; Botch, Beatrice J. Chem. Educ. 1987, 64, 718.
Isotopes |
Rate Law |
Kinetics |
Catalysis |
Alkenes |
Ethers
Counting halomethanes  Namhi, Parthasarathy
Asking the question "How many halomethanes are there?" illustrates the range of molecular species that can be derived by substituting the hydrogens of an alkane by halogens.
Namhi, Parthasarathy J. Chem. Educ. 1987, 64, 678.
Alkanes / Cycloalkanes
Molecular structure: Property relationships  Seybold, Paul G.; May, Michael; Bagal, Ujjvala A.
How molecular structure can be represented mathematically and how this can lead to a better understanding of the connection between molecular structures and properties.
Seybold, Paul G.; May, Michael; Bagal, Ujjvala A. J. Chem. Educ. 1987, 64, 575.
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Alcohols
Use of polar maps in conformational analysis  Ounsworth, James P.; Weller, Larry
A relatively simple procedure to identify different or similar conformations of large ring structures (generating polar maps of torsional angles).
Ounsworth, James P.; Weller, Larry J. Chem. Educ. 1987, 64, 568.
Conformational Analysis |
Molecular Properties / Structure |
Alkanes / Cycloalkanes
A simple formula for the number of rings in a cyclic molecule  Reddy, P. Anantha
A simple formula that determines the number of rings from the number of ring atoms and bonds present in a cyclic system.
Reddy, P. Anantha J. Chem. Educ. 1987, 64, 400.
Molecular Properties / Structure |
Alkanes / Cycloalkanes
A safe, convenient method of generating bromine for qualitative analysis  Slayden, Suzauee W.; Do, Thuy H.; Smiley, Kimberly Y.; Nelson, Donna J.
A safe, convenient method of generating bromine used as a qualitative test for unsaturation, active methylene groups, phenols, and amines.
Slayden, Suzauee W.; Do, Thuy H.; Smiley, Kimberly Y.; Nelson, Donna J. J. Chem. Educ. 1987, 64, 368.
Qualitative Analysis |
Alkenes |
Phenols |
Amines / Ammonium Compounds |
Laboratory Management
Concerning dehydration of 2-methycyclohexanol  Feigenbaum, A.
One half of class dehydrates 2-methycyclohexanol, the other half dehydrates 1-methycyclohexanol; gas chromatography retention times are then compared for the two product mixtures.
Feigenbaum, A. J. Chem. Educ. 1987, 64, 273.
Alcohols |
Alkenes |
Stereochemistry |
Constitutional Isomers |
Gas Chromatography
Addition of iodine to alkenes: A pseudo-first-, second-, or third-order kinetics experiment  Field, Kurt W.; Wilder, Deborah; Utz, Arthur; Kolb, Kenneth E.
A simple, inexpensive, class-tested experiment for determining the kinetics of iodine addition to various alkenes in several solvents.
Field, Kurt W.; Wilder, Deborah; Utz, Arthur; Kolb, Kenneth E. J. Chem. Educ. 1987, 64, 269.
Alkenes |
Kinetics
Voltammetric monitoring of Br- and Br3- concentrations during the bromination of styrene by Br3-: A laboratory experiment  Desbene Monvernay, Annie; Berthelot, Jacques; Desbene, Paul-Louis
Electrochemical titration of Br- and Br3- and voltammetric monitoring of styrene bromination by TBEBr3.
Desbene Monvernay, Annie; Berthelot, Jacques; Desbene, Paul-Louis J. Chem. Educ. 1987, 64, 86.
Electrochemistry |
Titration / Volumetric Analysis |
Alkenes |
Reactions
Comparison of chemical oxidation of alkanes, alkenes, and alcohols on the overhead projector  Kolb, Kenneth E.
This overhead projector demonstration utilizes two classical oxidants, permanganates and dichromate, to distinguish between alkanes, alkenes, and primary, secondary, and tertiary alcohols.
Kolb, Kenneth E. J. Chem. Educ. 1986, 63, 977.
Alcohols |
Alkanes / Cycloalkanes |
Alkenes |
Oxidation / Reduction |
Qualitative Analysis
Microscale organic laboratory: IV: A simple and rapid procedure for carrying out Wittig reactions  Pike, R. M.; Mayo, D. W.; Butcher, D. W.; Butcher, S. S.; Hinkle, R. J.
This paper offers two examples that illustrate a new synthetic method. This synthesis is the first feasible preparation of a particular group available for the introductory organic laboratory.
Pike, R. M.; Mayo, D. W.; Butcher, D. W.; Butcher, S. S.; Hinkle, R. J. J. Chem. Educ. 1986, 63, 917.
Synthesis |
Aromatic Compounds |
Heterocycles |
Alkenes |
Alcohols
Another look at reduction of cyclohexanone with sodium borohydride in aqueous alkaline solution  Zaezek, Norbert M.
The method presented here for the reduction of cyclohexane to cyclohexanol in aqueous alkaline solution is less time consuming and uses considerably less alkaline solution and ether.
Zaezek, Norbert M. J. Chem. Educ. 1986, 63, 909.
Alkanes / Cycloalkanes |
Oxidation / Reduction |
Aqueous Solution Chemistry
Cis, trans isomerism and polarity of molecules   Krishnan, C. V.
In this experiment, two liquids of identical molecular formula show that differences in the spatial arrangements of atoms affects molecular polarity.
Krishnan, C. V. J. Chem. Educ. 1986, 63, 601.
Constitutional Isomers |
Diastereomers |
Enantiomers |
Physical Properties |
Solutions / Solvents
Coulombic models in chemical bonding. III: Barrier to internal rotation in ethane  Sacks, Lawrence J.
In this paper, a problem of long standing will be considered: the barrier to internal rotation in ethane.
Sacks, Lawrence J. J. Chem. Educ. 1986, 63, 487.
Alkanes / Cycloalkanes |
Covalent Bonding |
Electrochemistry |
MO Theory |
Chemometrics |
Molecular Properties / Structure
Synthesis with ultrasonic waves  Boudjouk, Philip
A historical overview of the use of ultrasonic waves for chemical synthesis.
Boudjouk, Philip J. Chem. Educ. 1986, 63, 427.
Synthesis |
Aromatic Compounds |
Alkanes / Cycloalkanes |
Reactions |
Catalysis
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
The arithmetic of aromaticity  Glidewell, Christopher; Lloyd, Douglas
In this article, the authors explore an aspect of conjugated systems that have received little attention, namely polycyclic hydrocarbons.
Glidewell, Christopher; Lloyd, Douglas J. Chem. Educ. 1986, 63, 306.
Alkanes / Cycloalkanes |
Resonance Theory |
Aromatic Compounds
Application of organometallic catalysis to the commercial production of L-DOPA  Knowles, W. S.
This paper describes the application of a novel technology to the commercial preparation of L-DOPA.
Knowles, W. S. J. Chem. Educ. 1986, 63, 222.
Industrial Chemistry |
Enantiomers |
Stereochemistry |
Aromatic Compounds |
Alkenes |
Heterocycles |
Mechanisms of Reactions |
Catalysis |
Organometallics |
Alcohols
Selective oxidation and ammoxidation of olefins by heterogeneous catalysis  Grasselli, Robert K.
In this symposium paper, the author shows how the complex process of the ammoxidation of olefins can be understood in terms of free radicals and surface bound organometallic intermediates.
Grasselli, Robert K. J. Chem. Educ. 1986, 63, 216.
Organometallics |
Oxidation / Reduction |
Catalysis |
Amines / Ammonium Compounds |
Aromatic Compounds |
Alkenes |
Mechanisms of Reactions
The production and recovery of C2-C4 olefins from syngas  Murchison, C. H.; Weiss, R. L.; Stowe, R. A.
Authors from Dow Chemical present ways of preparing C2-C4 alkenes from synthesis gas using heterogeneous catalysis.
Murchison, C. H.; Weiss, R. L.; Stowe, R. A. J. Chem. Educ. 1986, 63, 213.
Alkenes |
Synthesis |
Gases
Shell higher olefins process  Lutz, E. F.
The author shows how olefin isomerization and the exotic olefin metathesis reactions can be harnessed in industrial processes.
Lutz, E. F. J. Chem. Educ. 1986, 63, 202.
Alkenes |
Mechanisms of Reactions |
Industrial Chemistry |
Organometallics |
Catalysis
Steric and electronic effects in olefin hydrocyanation at Du Pont: A scientific and industrial success story  Tolman, C. A.
An outline of the mechanistic studies that made the development of an important technology possible.
Tolman, C. A. J. Chem. Educ. 1986, 63, 199.
Organometallics |
Coordination Compounds |
Molecular Properties / Structure |
Catalysis |
Mechanisms of Reactions |
Alkenes
Reduction of cyclohexanone with sodium borohydride in aqueous alkaline solution: a beginning organic chemistry experiment  Hudak, Norman J.; Sholes, Anne H.
A beginning organic chemistry experiment that involves the reduction of cyclohexanone with sodium borohydride in aqueous alkaline solution.
Hudak, Norman J.; Sholes, Anne H. J. Chem. Educ. 1986, 63, 161.
Alkanes / Cycloalkanes |
Aqueous Solution Chemistry |
Acids / Bases |
Alcohols
The Curtin-Hammett principle and the Winstein-Holness equation: new definition and recent extensions to classical concepts  Seeman, Jeffery I.
The author briefly demonstrates that the C-H principle and the W-H equation have values far exceeding those originally intended.
Seeman, Jeffery I. J. Chem. Educ. 1986, 63, 42.
Alkanes / Cycloalkanes |
Aromatic Compounds |
Kinetics |
Equilibrium
Identification of the stable conformer of cyclohexane by vibrational spectroscopy  Garcia, M. V.; Redondo, M. I.
A laboratory experiment that uses group theory to help interpret infrared and Raman spectra of cyclohexane.
Garcia, M. V.; Redondo, M. I. J. Chem. Educ. 1985, 62, 887.
Alkanes / Cycloalkanes |
Spectroscopy |
Stereochemistry |
IR Spectroscopy |
Raman Spectroscopy |
Conformational Analysis |
Molecular Properties / Structure |
Group Theory / Symmetry
Chemical properties of commonly available hydrocarbons  Perina, Ivo
Studying the properties of saturated hydrocarbons using natural gas.
Perina, Ivo J. Chem. Educ. 1985, 62, 864.
Alkanes / Cycloalkanes
The pyrolysis of cyclopropane: A gas phase kinetic experiment for the undergraduate laboratory  O'Grady, B. V.
Presents a "pulsed-flow" reaction system that allows data for the pyrolysis of cyclopropane to propene to be gathered quickly to develop the theory of unimolecular reactions.
O'Grady, B. V. J. Chem. Educ. 1985, 62, 709.
Alkanes / Cycloalkanes |
Kinetics
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
Preparation of the bromohydrin of 3-sulfolene  Greenberg, Fred H.
Reaction of N-bromosuccinimide with 3-sulfolene.
Greenberg, Fred H. J. Chem. Educ. 1985, 62, 638.
Synthesis |
Alkenes
Measuring the atomic or molecular mass of a gas with a tire gauge and a butane lighter fluid can  Bodner, George M.; Magginnis, Lenard J.
Also demonstrating the mass of air and the dependence of the pressure of a gas on the mass of the sample.
Bodner, George M.; Magginnis, Lenard J. J. Chem. Educ. 1985, 62, 434.
Atomic Properties / Structure |
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Gases
An introduction to conformational analysis of ethane and butane  Flash, Patrick J.
60. Bits and pieces, 23. Introduces students to some conventions for drawing molecules and provides a brief tutorial and extensive drill work on the conformations of ethane and butane.
Flash, Patrick J. J. Chem. Educ. 1985, 62, 412.
Conformational Analysis |
Alkanes / Cycloalkanes |
Enrichment / Review Materials
Electronic structure in pi systems. Part I. Huckel theory with electron repulsion  Fox, Marye Anne; Matsen, F. A.
A simple conceptual framework in which two-electron theory can be presented to students; the pi-CI theory is applied to ethylene.
Fox, Marye Anne; Matsen, F. A. J. Chem. Educ. 1985, 62, 367.
Molecular Properties / Structure |
MO Theory |
Alkenes
A short set of 13C-NMR correlation tables  Brown, D. W.
The object of these tables is to enable a student to calculate rapidly approximate d values for 13C nuclei in as wide a variety of compounds as possible.
Brown, D. W. J. Chem. Educ. 1985, 62, 209.
NMR Spectroscopy |
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes |
Aromatic Compounds |
Amides |
Carboxylic Acids |
Esters
A method for drawing cyclohexane chairs  Cheer, Clair J.
A method for drawing cyclohexane chairs.
Cheer, Clair J. J. Chem. Educ. 1984, 61, 947.
Molecular Properties / Structure |
Alkanes / Cycloalkanes
Preparation of 2-bromopentane  Howell, B. A.; Kohrman, R. E.
The conversion of 2-pentanol to 2-bromopentane offers a good illustration of the problems associated with substitution in secondary systems.
Howell, B. A.; Kohrman, R. E. J. Chem. Educ. 1984, 61, 932.
Synthesis |
Alkanes / Cycloalkanes
Schemes and transformations in the (CH)2k series: Valence isomers of [8]- and [10]annulene  Balaban, Alexandru T.; Banciu, Mircea
Possible and known valence isomers of (CH)10.
Balaban, Alexandru T.; Banciu, Mircea J. Chem. Educ. 1984, 61, 766.
Molecular Properties / Structure |
Constitutional Isomers
Eugene Houdry, catalytic cracking and World War II aviation gasoline  Moseley, Charles G.
An important factor in the Allied victory in World War II was their ability to mass produce an aviation gasoline that was superior to that of the Axis nations.
Moseley, Charles G. J. Chem. Educ. 1984, 61, 655.
Catalysis |
Alkanes / Cycloalkanes |
Applications of Chemistry
Concertedness of 1,3-dipolar cycloadditions  Haque, M. Serajul
The 1,3-dipolar cycloaddition is the union of a 1,3-dipole with a multiple bond system (a dipolarophile) to form a five-membered ring; the process is regarded as one of the most general methods for the synthesis of five-membered heterocycles.
Haque, M. Serajul J. Chem. Educ. 1984, 61, 490.
Addition Reactions |
Alkanes / Cycloalkanes |
Mechanisms of Reactions |
Heterocycles |
Synthesis |
MO Theory
Who is anti-Markovnikov?  Tedder, J. M.
What are the factors that control the rate and orientation of free radical addition to alkenes?
Tedder, J. M. J. Chem. Educ. 1984, 61, 237.
Mechanisms of Reactions |
Addition Reactions |
Free Radicals |
Alkenes
The evaluation of strain and stabilization in molecules using isodesmic reactions  Fuchs, Richard
The stabilities of cyclic hydrocarbons are analyzed using isodesmic and metathetical isodesmic reactions.
Fuchs, Richard J. Chem. Educ. 1984, 61, 133.
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Alkenes |
Aromatic Compounds
Safety in the laboratory: 1,1,1-trichloroethane   Rothchild, Robert
For safety reasons, it is necessary to find a substitute for 1,1,1-trichloroethane in the academic chemistry lab.
Rothchild, Robert J. Chem. Educ. 1983, 60, A228.
Alkanes / Cycloalkanes |
Laboratory Management
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
Synthetic petroleum from coal hydrogenation: its history and present state of development in the United States  Stranges, Anthony N.
This author has reviewed the history of attempts to hydrogenate coal.
Stranges, Anthony N. J. Chem. Educ. 1983, 60, 617.
Alkanes / Cycloalkanes |
Synthesis |
Applications of Chemistry |
Industrial Chemistry
Free radical chlorination of methane: A demonstration  Conklin, Alfred R.; Kramme, Alan
Free radical reactions are very important and often discussed in chemistry. One of the first such reactions encountered by students of organic chemistry is the free radical chlorination of methane. This reaction serves to introduce the student to free radical reactions and chain reaction. In spite of its common occurrence, demonstrations of this reaction are uncommon.
Conklin, Alfred R.; Kramme, Alan J. Chem. Educ. 1983, 60, 597.
Alkanes / Cycloalkanes |
Free Radicals
Stability and formation of isobutylene dimers  Goldsmith, Robert H.
Isobutylene is an important bulk chemical for the petroleum industry. Dimerization and hydrogenation reactions produces the standard for fuel octane rating comparison. However, this classic chemistry is often misrepresented in modern texts. Therefore this paper attempts to correlate the physical organic principles that apply.
Goldsmith, Robert H. J. Chem. Educ. 1983, 60, 596.
Constitutional Isomers |
Alkenes |
Industrial Chemistry |
Quantitative Analysis
The photochemical isomerization of maleic to fumaric acid: an undergraduate organic chemistry experiment  Castro, Albert J.; Ellenberger, Suzanne R.; Sluka, James P.
An undergraduate organic chemistry experiment in the photochemical isomerization of maleic to fumaric acid.
Castro, Albert J.; Ellenberger, Suzanne R.; Sluka, James P. J. Chem. Educ. 1983, 60, 521.
Acids / Bases |
Photochemistry |
Constitutional Isomers
A study of stereospecificity: the Beckmann rearrangement  Stradling, S. S.; Hornick, D.; Lee, J.; Riley, J.
These authors have developed a Beckmann rearrangement which explores the concept of stereospecificity, and concurrently exposes the student to synthetic, spectrometric, and chromatographic processes for an advanced laboratory.
Stradling, S. S.; Hornick, D.; Lee, J.; Riley, J. J. Chem. Educ. 1983, 60, 502.
Synthesis |
Chromatography |
Spectroscopy |
Stereochemistry |
Aldehydes / Ketones |
NMR Spectroscopy |
Alkenes |
Phenols
Resolvability and the tetrahedral configuration of carbon  Kauffman, George B.
A popular explanation about the tetrahedral configuration of carbon is not entirely accurate.
Kauffman, George B. J. Chem. Educ. 1983, 60, 402.
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Enantiomers |
X-ray Crystallography |
Stereochemistry |
Chirality / Optical Activity
Estimating energy outputs of fuels  Baird, N. Colin
Which is the best fuel in terms of heat energy output: coal, natural gas, fuel oil, hydrogen, or alcohol? It is possible to obtain a semi quantitative estimate of the heat generated by combustion of a fuel from the balanced chemical equation alone.
Baird, N. Colin J. Chem. Educ. 1983, 60, 356.
Reactions |
Green Chemistry |
Thermodynamics |
Alcohols |
Alkanes / Cycloalkanes |
Geochemistry |
Stoichiometry |
Quantitative Analysis
Degas' dancers: an illustration for rotational isomers  Hargittai, Istvan
Two drawings by Degas provide an opportunity to introduce the concepts of staggered and eclipsed conformations of A2B-BC2 molecules in a concrete, interesting, and aesthetic way.
Hargittai, Istvan J. Chem. Educ. 1983, 60, 94.
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Constitutional Isomers |
Diastereomers
Cyclohexanol dehydration: A simple experiment in heterogeneous catalysis  Costa, A.
Catalytic synthesis of cyclohexene and various cyclopentenes from cyclohexanol.
Costa, A. J. Chem. Educ. 1982, 59, 1066.
Catalysis |
Synthesis |
Alcohols |
Alkenes
Lecture experiment in gas-liquid chromatography with a simple gas chromatograph at room temperature  Wollrah, Adalbert
Apparatus and method for separating mixtures of pentane / hexane and methyl chloride / carbon tetrachloride.
Wollrah, Adalbert J. Chem. Educ. 1982, 59, 1042.
Chromatography |
Separation Science |
Alkanes / Cycloalkanes
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
The oxidation of terminal alkenes by permanganate: A practical demonstration of the use of phase transfer agents  Brown, Keith C.; Chang, Victor S.; Dar, Fazal H.; Lamb, Shannon E.; Lee, Donald G.
An oxidative cleavage of a terminal alkene to give the corresponding carboxylic acid with one less carbon atom.
Brown, Keith C.; Chang, Victor S.; Dar, Fazal H.; Lamb, Shannon E.; Lee, Donald G. J. Chem. Educ. 1982, 59, 696.
Alkenes |
Oxidation / Reduction |
Carboxylic Acids
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
An easily conducted free radical substitution for organic chemistry courses  Pavlis, Robert R.
The photobromination of 1,2-diphenylethane into its dibromo derivative, (2R) (3S) 1,2-dibromo-1,2-diphenylethane.
Pavlis, Robert R. J. Chem. Educ. 1982, 59, 658.
Free Radicals |
Reactions |
Molecular Properties / Structure |
Stereochemistry |
Diastereomers |
Photochemistry |
Alkanes / Cycloalkanes |
Aromatic Compounds
The principle of vinylogy  Krishnamurthy, Subrahmanya
The principle of vinylogy recognizes the possibility that the inductive effect of a functional group is transmitted through a double bond or a conjugated system of double bonds.
Krishnamurthy, Subrahmanya J. Chem. Educ. 1982, 59, 543.
Molecular Properties / Structure |
Alkenes |
Esters |
Aldehydes / Ketones |
Amides |
Aromatic Compounds
Cyclopropenoid fatty acids  Greenberg, Arthur; Harris, Joseph
How do cyclopropene rings come to be in natural molecules, and what "havoc", if any, do these reactive units create in living organisms?
Greenberg, Arthur; Harris, Joseph J. Chem. Educ. 1982, 59, 539.
Alkenes |
Natural Products |
Fatty Acids
Introduction to infrared spectroscopy: A simple undergraduate experiment  Reeder, Deborah M.; Sridharan, Srinivasa
The objective is to obtain two IR spectra, one on an aliphatic compound and the other on an aromatic compound in a first-semester organic laboratory.
Reeder, Deborah M.; Sridharan, Srinivasa J. Chem. Educ. 1982, 59, 503.
Spectroscopy |
IR Spectroscopy |
Alkanes / Cycloalkanes |
Aromatic Compounds |
Molecular Properties / Structure
Pi bonding without tears  Akeroyd, F. Michael
A non-mathematical treatment of sigma-pi bonding applied to conjugation, hyperconjugation, Markovnikoff addition, aromaticity, and aromatic substitution.
Akeroyd, F. Michael J. Chem. Educ. 1982, 59, 371.
Alkenes |
Mechanisms of Reactions |
Addition Reactions |
Aromatic Compounds
The problem of syn- versus anti-addition: An organic chemistry laboratory experiment  Silversmith, Ernest F.
An experiment that allows a student to determine whether an addition to a carbon-carbon double bond proceeds in syn- or anti-fashion.
Silversmith, Ernest F. J. Chem. Educ. 1982, 59, 346.
Addition Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure |
Stereochemistry |
Synthesis |
Alkenes
The separation and identification of straight chain hydrocarbons: An experiment using gas-liquid chromatography  Benson, G. A.
Gas liquid chromatography used to separate and identify a mixture of C5 to C10 straight chain hydrocarbons.
Benson, G. A. J. Chem. Educ. 1982, 59, 344.
Separation Science |
Qualitative Analysis |
Alkanes / Cycloalkanes |
Chromatography
Molecular mechanics: Illustrations of its application  Cox, Philip J.
Applying molecular mechanics to n-butane and cyclohexane.
Cox, Philip J. J. Chem. Educ. 1982, 59, 275.
Molecular Mechanics / Dynamics |
Conformational Analysis |
Molecular Properties / Structure |
Alkanes / Cycloalkanes
The IUPAC systematic names of the regular polyhedranes: An exercise in organic chemistry nomenclature  Moyano, Albert; Serratosa, Felix; Camps, Pelayo; Drudis, Josep M.
A simple procedure to assign IUPAC systematic names to all the polyhedranes, as well as other polycyclic hydrocarbons.
Moyano, Albert; Serratosa, Felix; Camps, Pelayo; Drudis, Josep M. J. Chem. Educ. 1982, 59, 126.
Nomenclature / Units / Symbols |
Alkanes / Cycloalkanes
An early laboratory introduction to IR spectroscopy: Gaseous deuteroalkanes  Braun, Loren L.; Law, Raymond L.
The authors have found that the preparation of deuterated gaseous alkanes is a simple experiment that is a less hazardous experiment than the popular alternatives.
Braun, Loren L.; Law, Raymond L. J. Chem. Educ. 1981, 58, 79.
Isotopes |
Alkanes / Cycloalkanes |
Grignard Reagents |
Gases
Demonstrating self-acceleration or self-inhibition phenomena in chemical reactions: An experiment in alkane pyrolysis  Scacchi, G.; Foucaut, J. F.; Niclause, M.
Examines cases in which in which a reaction exhibits one or more orders and an experiment that can be interpreted from this analysis.
Scacchi, G.; Foucaut, J. F.; Niclause, M. J. Chem. Educ. 1980, 57, 748.
Alkanes / Cycloalkanes |
Kinetics |
Reactions
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
The effect of free radical stability on the rate of bromination of hydrocarbons  Doheny, Anthony J.; Loudon, G. Marc
The effect of alkyl free radical stability on the rate of free radical halogenation of hydrocarbons can be convincingly demonstrated by the comparative photobromination of the arenes toluene, ethylbenzene, and cumene.
Doheny, Anthony J.; Loudon, G. Marc J. Chem. Educ. 1980, 57, 507.
Free Radicals |
Reactions |
Alkanes / Cycloalkanes |
Photochemistry |
Molecular Properties / Structure
Bent bonds and multiple bonds  Robinson, Edward A.; Gillespie, Ronald J.
Considers carbon-carbon multiple bonds in terms of the bent bond model first proposed by Pauling in 1931.
Robinson, Edward A.; Gillespie, Ronald J. J. Chem. Educ. 1980, 57, 329.
Covalent Bonding |
Molecular Properties / Structure |
Molecular Modeling |
Alkenes |
Alkynes
Diphenylbutadienes syntheses by means of the Wittig reaction: Experimental introduction to the use of phase transfer catalysis  Gillois, J.; Guillerm, G.; Stephen, E.; Vo-Quang, L.
Intended as a project carried out by students at the end of introductory organic chemistry.
Gillois, J.; Guillerm, G.; Stephen, E.; Vo-Quang, L. J. Chem. Educ. 1980, 57, 161.
Synthesis |
Catalysis |
Alkenes |
Aldehydes / Ketones |
Stereochemistry
Stereochemical nonequivalence of ligands and faces (heterotopicity)  Eliel, Ernest L.
Reviews the concepts associated with stereochemical non-equivalence (heterotopicity).
Eliel, Ernest L. J. Chem. Educ. 1980, 57, 52.
Stereochemistry |
Enantiomers |
Diastereomers |
Constitutional Isomers |
Group Theory / Symmetry
Optical illusions in drawings of cyclohexane derivatives  Feldman, Martin R.
An optical illusion in the representation of chair cyclohexanes.
Feldman, Martin R. J. Chem. Educ. 1979, 56, 659.
Molecular Properties / Structure |
Stereochemistry |
Enantiomers |
Diastereomers |
Alkanes / Cycloalkanes
Report of the symposium on high school instructional interface: Modernization, restructuring and improvement of chemistry teaching  Richardson, Shirley E.

Richardson, Shirley E. J. Chem. Educ. 1979, 56, 602.
Constitutional Isomers |
Professional Development
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
Solid state photochemical isomerization: A convenient laboratory experiment  Burton, W. B.
This experiment demonstrates the novel use of benzophenone in the dual role as a solid state sensitizer in a photochemical isomerization and as an indicator in the preparative layer chromatography used for the purification of the isomeride.
Burton, W. B. J. Chem. Educ. 1979, 56, 483.
Solid State Chemistry |
Photochemistry |
Molecular Properties / Structure |
Constitutional Isomers |
Chromatography |
Thin Layer Chromatography
The perturbational MO method for saturated systems  Herndon, William C.
Outlines a molecular orbital approach to the problem of predicting and correlating bond dissociation energies in saturated hydrocarbons.
Herndon, William C. J. Chem. Educ. 1979, 56, 448.
MO Theory |
Alkanes / Cycloalkanes |
Free Radicals |
Mechanisms of Reactions
The attractive and repulsive gauche effects  Juaristi, Eusebio
Focusses on 1,2-disubstituted ethanes and cyclohexanes and 5-substituted-1,3-heterocycles.
Juaristi, Eusebio J. Chem. Educ. 1979, 56, 438.
Molecular Properties / Structure |
Conformational Analysis |
Diastereomers |
Alkanes / Cycloalkanes |
Heterocycles
Conformations of substituted ethanes  Kingsbury, Charles A.
Provides a state-of-the-art view of conformational analysis, with an emphasis on sp3 hybridized acyclic molecules.
Kingsbury, Charles A. J. Chem. Educ. 1979, 56, 431.
Molecular Properties / Structure |
Conformational Analysis |
Alkanes / Cycloalkanes |
Diastereomers
Compact Compacts  Huebner, Jay S.; Shiflett, R. B.; Blanck, Harvey F.
A collection of three suggestions regarding demonstrating the oxidation of hydrocarbons and the primary, secondary, and tertiary structure of proteins and the first law of thermodynamics as applied to air conditioning.
Huebner, Jay S.; Shiflett, R. B.; Blanck, Harvey F. J. Chem. Educ. 1979, 56, 389.
Oxidation / Reduction |
Alkanes / Cycloalkanes |
Molecular Properties / Structure |
Proteins / Peptides |
Thermodynamics
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
CHIRAL-a computer aided application of the Cahn-lngold-Prelog rules  Meyer, Edgar F., Jr.
The author describes a computer program that will generate information about isomers.
Meyer, Edgar F., Jr. J. Chem. Educ. 1978, 55, 780.
Diastereomers |
Constitutional Isomers |
Enantiomers |
Chirality / Optical Activity |
Chemometrics
Dissociation energies of p bonds in alkenes  Alyea, Hubert N.
An outline of different methods that can be used to estimate dissociation energies.
Alyea, Hubert N. J. Chem. Educ. 1978, 55, 778.
Alkenes |
MO Theory |
Diastereomers
Enumeration of permutational isomers: The porphyrins  Tapscott, R. E.; Marcovich, D.
The use of combinatorial methods permits the counting of permutational isomers in systems that are sufficiently complex that direct counting is tedious and/ or likely to be in error. The use of Polya's theorem has been illustrated for the porphyrin system, here the isomers for all possible ligand partitions have been counted.
Tapscott, R. E.; Marcovich, D. J. Chem. Educ. 1978, 55, 446.
Diastereomers |
Stereochemistry |
Enantiomers |
Constitutional Isomers |
Chemometrics |
Coordination Compounds
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
MO description of allene  Zimmerman, Howard E.
This question tests students' abilities to distinguish between Huckel and Mobius systems as well as to recognize the equivalence of the traditional model for allene and that proposed.
Zimmerman, Howard E. J. Chem. Educ. 1977, 54, 609.
MO Theory |
Alkenes
Group theory. From common objects to molecules  Herman, Michel; Lievin, Jacques
Shows a practical and visual way of how the concept of symmetry present in common objects (in this case, a tennis ball) can be extended to the quantum structure of molecules.
Herman, Michel; Lievin, Jacques J. Chem. Educ. 1977, 54, 596.
Group Theory / Symmetry |
Quantum Chemistry |
Molecular Properties / Structure |
Alkenes
Why did Adolf Baeyer propose a planar, strained cyclohexane ring?  Ramsay, O. Bertrand
Considers the question "Why did Adolf Baeyer propose a planar, strained cyclohexane ring?"
Ramsay, O. Bertrand J. Chem. Educ. 1977, 54, 563.
Alkanes / Cycloalkanes |
Molecular Properties / Structure
Photohydration of pyridine in aqueous solution. An undergraduate experiment in photochemical kinetics  Andre, J. C.; Niclause, M.; Joussot-Dubien, J.; Deglise, X.
An easy experiment that illustrates many of the physical aspects of photochemistry.
Andre, J. C.; Niclause, M.; Joussot-Dubien, J.; Deglise, X. J. Chem. Educ. 1977, 54, 387.
Photochemistry |
Kinetics |
Spectroscopy |
Alkenes |
Aldehydes / Ketones |
Mechanisms of Reactions
A Dramatic and relevant demonstration of ring strain  Kelly, T. Ross
Addition of the cyclobutane alpha-pinene to crystalline iodine results in an exceptionally exothermic reaction.
Kelly, T. Ross J. Chem. Educ. 1977, 54, 228.
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Reactions
Pathway of minimum steps for the bullvalene automerization  Bennett, Karl E.; Fisher, Allan
The minimum Cope rearrangements necessary for interconversion among various structures of bullvalene.
Bennett, Karl E.; Fisher, Allan J. Chem. Educ. 1977, 54, 166.
Alkenes |
Molecular Properties / Structure |
Stereochemistry
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
2,2-Dichlorobicyclo[4.1.0]heptane from cyclohexene and dichlorocarbene by phase transfer catalysis  Ault, Addison; Wright, Bradley
The authors have developed a procedure for the addition of dichlorocarbene to cyclohexane to give dichloronorcarane.
Ault, Addison; Wright, Bradley J. Chem. Educ. 1976, 53, 489.
Aromatic Compounds |
Alkenes |
Alkanes / Cycloalkanes |
Catalysis
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
Conformational analysis, 1869  Brescia, Frank; Mangiaracina, Pietro
This paper examines historical inaccuracies resulting from an inquiry into the conformational analysis of C2HCl5.
Brescia, Frank; Mangiaracina, Pietro J. Chem. Educ. 1976, 53, 32.
Constitutional Isomers |
Stereochemistry
Hydrocarbons in ambient air: A laboratory experiment  DiNardi, Salvatore R.; Briggs, Elaine S.
Students calibrate and the n use a gas chromatograph to analyze ambient air for hydrocarbons.
DiNardi, Salvatore R.; Briggs, Elaine S. J. Chem. Educ. 1975, 52, 811.
Alkanes / Cycloalkanes |
Quantitative Analysis |
Atmospheric Chemistry |
Gas Chromatography
Some reflections on the topological structure of covalent molecules  Rouvray, D. H.
Presents a method that involves a description of the possible topological structures a chemical species may adopt, subject to the constraints imposed by the valence.
Rouvray, D. H. J. Chem. Educ. 1975, 52, 768.
Molecular Properties / Structure |
Alkanes / Cycloalkanes
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
A case history of unplanned development of new chemistry  Roberts, John D.
Work to synthesize a cyclobutadiene derivative resulted in an unanticipated procedure.
Roberts, John D. J. Chem. Educ. 1975, 52, 708.
Alkenes |
Synthesis |
Aldehydes / Ketones
Calculation of the number of cis-trans isomers in a "symmetric" polyene  Har-zvi, Ron; Wittes, Janet Turk
A problem in which students are to derive a general expression for the number of cis-trans isomers in a "symmetric" straight chain polyene when there are n double bonds.
Har-zvi, Ron; Wittes, Janet Turk J. Chem. Educ. 1975, 52, 545.
Stereochemistry |
Molecular Properties / Structure |
Diastereomers |
Alkenes
Microbial oxidation of alkenes. An integrated organic-biology experiment  Kumler, Philip L.; DeJong, Peter J.
The conversion of an appropriate terminal alkene to a 1,2-epoxyalkane by Pseudomonas oleovorans introduces students to the techniques used in carrying out chemical conversions employing microorganisms.
Kumler, Philip L.; DeJong, Peter J. J. Chem. Educ. 1975, 52, 475.
Oxidation / Reduction |
Alkenes |
Bioorganic Chemistry |
Biotechnology |
Natural Products
A simple gas chromatograph for teaching purposes  Wollrab, Adalbert
A simple apparatus for demonstrating the separation of a mixture of pentane and hexane gas.
Wollrab, Adalbert J. Chem. Educ. 1975, 52, 200.
Chromatography |
Gas Chromatography |
Laboratory Equipment / Apparatus |
Separation Science |
Alkanes / Cycloalkanes |
Gases
Generation of vinyl cations by solvolysis reactions. A lesser known genre of carbenium ions  Subramanian, L. R.; Hanack, M.
Considers the structure and geometry of vinyl cations; modes of generation of vinyl cations; heterolysis of vinyl substrates; and mechanisms of solvolysis of vinyl substrates.
Subramanian, L. R.; Hanack, M. J. Chem. Educ. 1975, 52, 80.
Molecular Properties / Structure |
Alkenes |
Mechanisms of Reactions
Stereoisomerism about a double bond (1-3)  Fernelius, W. C.; Loening, Kurt; Adams, Roy M.
Rules for specifying E and Z configurations.
Fernelius, W. C.; Loening, Kurt; Adams, Roy M. J. Chem. Educ. 1975, 52, 60.
Stereochemistry |
Diastereomers |
Molecular Properties / Structure |
Alkenes |
Nomenclature / Units / Symbols
Exact thermodynamics of propane combustion   Yean, D. H.; Riter, J. R., Jr.
The authors have used the heterogeneous equilibria computer program featured in this note.
Yean, D. H.; Riter, J. R., Jr. J. Chem. Educ. 1974, 51, 505.
Alkanes / Cycloalkanes |
Laboratory Computing / Interfacing |
Equilibrium
The number of possible isomers in the porphyrins  Pilgrim, R. L. C.
The author examines problems within the discussion of porphyrin compounds in biochemistry textbooks.
Pilgrim, R. L. C. J. Chem. Educ. 1974, 51, 316.
Constitutional Isomers |
Diastereomers |
Enantiomers |
Aromatic Compounds
Stereospecific thermal cycloadditions and catalyzed isomerizations: An organic laboratory project  Pasto, D. J.; Duncan, J. A.; Silversmith, E. F.
The authors have prepared a sequence of experiments for their undergraduate organic chemistry laboratory concerned with the preparation of cis and trans 1,4-diphenyl-2-butene-1,4diones, their cycloadditions reactions with cyclopentandiene, and with related isomerization reactions of both the sequence, which has met with much success experimentally, clearly and collectively demonstrates certain aspects of the concepts of thermodynamics, kinetics, and stereochemistry and photochemistry.
Pasto, D. J.; Duncan, J. A.; Silversmith, E. F. J. Chem. Educ. 1974, 51, 277.
Photochemistry |
Constitutional Isomers |
Addition Reactions
A laboratory study of strike and inductive effects  Fulkrod, John E.
The authors describe a general reaction that can be successfully used to teach both strike and inductive effects in the laboratory by discovery.
Fulkrod, John E. J. Chem. Educ. 1974, 51, 115.
Constitutional Isomers |
Electrophilic Substitution |
Aromatic Compounds
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
The octane cannon experiment updated for television  Richtol, H. H.; Nelson, D. L.; Reeves, R. R.
Video recording the detonation of octane in a clear tube for frame-by-frame analysis of a rapid reaction.
Richtol, H. H.; Nelson, D. L.; Reeves, R. R. J. Chem. Educ. 1973, 50, 856.
Alkanes / Cycloalkanes |
Reactions |
Oxidation / Reduction
Demonstration of solubility of "immiscible" fluids  Koob, R. D.; Tallman, D. E.
Demonstrating that hexane is miscible in water.
Koob, R. D.; Tallman, D. E. J. Chem. Educ. 1973, 50, 724.
Solutions / Solvents |
Precipitation / Solubility |
Water / Water Chemistry |
Alkanes / Cycloalkanes
Computer program for identifying alkane structures  Davidson, Scott
A Fortran IV computer program to identify and name alkane structure having C1-C16 main chains and C1-C4 side chains is available.
Davidson, Scott J. Chem. Educ. 1973, 50, 707.
Alkanes / Cycloalkanes |
Molecular Properties / Structure |
Nomenclature / Units / Symbols
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
Attractive steric effects  Liberles, A.; Greenberg, A.; Eilers, J. E.
Attractive steric effects cause some organic structures to be more stable when bulky side-groups are closer together.
Liberles, A.; Greenberg, A.; Eilers, J. E. J. Chem. Educ. 1973, 50, 676.
Molecular Properties / Structure |
Alkenes |
Stereochemistry |
Diastereomers
The boat form of cyclohexane as viewed by Midwestern sailors (the author replies)  Hart, Harold
Possible confusion regarding the boat analogy in describing the positions of hydrogens in cyclohexane.
Hart, Harold J. Chem. Educ. 1973, 50, 656.
Molecular Properties / Structure |
Alkanes / Cycloalkanes
The boat form of cyclohexane as viewed by Midwestern sailors  Lyle, Gloria; Lyle, Robert E.
Possible confusion regarding the boat analogy in describing the positions of hydrogens in cyclohexane.
Lyle, Gloria; Lyle, Robert E. J. Chem. Educ. 1973, 50, 655.
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Nomenclature / Units / Symbols
An application of GC and IR to follow the progress of chemical reactions  Lires, O. A.; Molinari, M. A.
Two examples of preparing chloro derivatives of hydrocarbons for analysis by gas chromatography and infrared spectroscopy.
Lires, O. A.; Molinari, M. A. J. Chem. Educ. 1973, 50, 492.
Gas Chromatography |
IR Spectroscopy |
Reactions |
Addition Reactions |
Alkenes |
Alkylation
Ozone. Properties, toxicity, and applications  Leh, F.
Sources and properties, toxicity and hazards, and analytical and synthetic applications of ozone.
Leh, F. J. Chem. Educ. 1973, 50, 404.
Atmospheric Chemistry |
Alkenes
Saving a life with alcohol  Scala, A. A.
Using alcohol as a treatment for ethylene glycol poisoning.
Scala, A. A. J. Chem. Educ. 1973, 50, 365.
Alcohols |
Toxicology |
Metabolism |
Constitutional Isomers
Huckel-Mobius concept in concerted reactions  Shen, Kei-wei
Introduces the Huckel-Mobius concept and applies it to predicting the allowedness of chemical reactions.
Shen, Kei-wei J. Chem. Educ. 1973, 50, 238.
Reactive Intermediates |
Alkenes
The aspirin project. Laboratory experiments for introductory chemistry  Brown, David B.; Friedman, Lawrence B.
This laboratory project involves the synthesis, characterization, and study of some reactions of acetylsalicylic acid, and the comparison of acetylsalicylic acid with the major components of various commercial brands of aspirin tablets.
Brown, David B.; Friedman, Lawrence B. J. Chem. Educ. 1973, 50, 214.
Constitutional Isomers |
Synthesis |
Acids / Bases |
UV-Vis Spectroscopy |
Quantitative Analysis
Fragmentation mechanisms in mass spectrometry  Campbell, M. M.; Runquist, O.
Presents a precise mechanistic notation that is useful in teaching fragmentation processes.
Campbell, M. M.; Runquist, O. J. Chem. Educ. 1972, 49, 104.
Mass Spectrometry |
Alkenes |
Aromatic Compounds |
Alcohols |
Ethers |
Amines / Ammonium Compounds |
Aldehydes / Ketones |
Esters |
Amides
The Ene Synthesis  Keung, Edmund C.; Alper, Howard
Examines developments of an "indirect substitutive addition" or "ene synthesis" reaction.
Keung, Edmund C.; Alper, Howard J. Chem. Educ. 1972, 49, 97.
Synthesis |
Alkenes |
Mechanisms of Reactions |
Reactions
Dietary Chemicals vs. Dental Caries. Advances in Chemistry Series no. 94 (Gould, Robert F.)  Leicester, Henry M.

Leicester, Henry M. J. Chem. Educ. 1971, 48, A784.
Food Science |
Constitutional Isomers
Computer calculation of alkane isomers  Davis, Charles C.; Ebel, Michael
A FORTRAN IV computer program has been written which calculates the number of possible isomers of the saturated aliphatic hydrocarbons.
Davis, Charles C.; Ebel, Michael J. Chem. Educ. 1971, 48, 675.
Alkanes / Cycloalkanes |
Stereochemistry |
Diastereomers |
Constitutional Isomers
Inductive effects in the chlorination of 1-chlorobutane. An organic laboratory experiment  Reeves, Perry C.
The present paper describes the quantitative study of the directive effect of chlorine already present in the molecule on the orientation of incoming chlorine in the free radical halogenation of 1-chlorobutane.
Reeves, Perry C. J. Chem. Educ. 1971, 48, 636.
Alkanes / Cycloalkanes |
Molecular Properties / Structure
Conversions from cyclohexanol. An undergraduate laboratory project  Hanna, Samir B.; Wrobleski, James T.; Bohanon, Joseph T.; Peace, Bab W.
A procedure for a laboratory in conversions from cyclohexanol.
Hanna, Samir B.; Wrobleski, James T.; Bohanon, Joseph T.; Peace, Bab W. J. Chem. Educ. 1971, 48, 556.
Alkanes / Cycloalkanes |
Alcohols
Quantitative studies of conformational energies in some cyclic compounds  Wyn-Jones, E.
The authors discuss methods that have proved to be versatile in determining conformational energies especially in heterocyclic molecules and in this article the principles involved in these methods and some complimentary results will be discussed.
Wyn-Jones, E. J. Chem. Educ. 1971, 48, 402.
Alkanes / Cycloalkanes |
Thermodynamics |
Constitutional Isomers |
NMR Spectroscopy |
Equilibrium
Interconversion of the cyclohexane conformers  Strauss, Herbrt L.
It is important to develop the understanding of conformations of cyclohexane and the role it has played in understanding the conformation of saturated carbon compounds.
Strauss, Herbrt L. J. Chem. Educ. 1971, 48, 221.
Alkanes / Cycloalkanes |
Chemometrics |
Conformational Analysis
The stereospecific synthesis of trans-1,4-disubstituted cyclohexanes. An organic chemistry laboratory experiment  Monson, Richard S.
The authors present a synthetic experiment suitable for the introductory organic chemistry laboratory which the introductory organic chemistry laboratory which allows for the unambiguous preparation of trans-1,4-disubstituted cyclohexane derivatives from readily available starting materials.
Monson, Richard S. J. Chem. Educ. 1971, 48, 197.
Alkanes / Cycloalkanes |
Stereochemistry |
Reactions
Models for demonstrating overlap and intermolecular repulsions  Meek, John S.
By using magnets so that they repel rather than attract, a model demonstrating the rotational barriers in ethane has been built. By using alnico magnets and Styrofoam balls a space filling scale model has easily been prepared.
Meek, John S. J. Chem. Educ. 1971, 48, 112.
Molecular Modeling |
Molecular Properties / Structure |
Alkanes / Cycloalkanes
Separation of leucine and isoleucine by thin-layer chromatography  Gatto, Karen L.; Borders, C. L., Jr.
This experiment involves the separation of leucine and isoleucine through continuous ascending thin layer chromatography.
Gatto, Karen L.; Borders, C. L., Jr. J. Chem. Educ. 1970, 47, 840.
Separation Science |
Thin Layer Chromatography |
Chromatography |
Amino Acids |
Constitutional Isomers
The isomerization of xylenes. An experiment for the organic or instrumental laboratory  Harbison, Kenneth G.
This experiment illustrates both qualitative and quantitative applications of infrared spectroscopy for the analysis of mixtures, as well as providing an interesting study of the mechanism of Friedel-Crafts reactions.
Harbison, Kenneth G. J. Chem. Educ. 1970, 47, 837.
Instrumental Methods |
Aromatic Compounds |
IR Spectroscopy |
Mechanisms of Reactions |
Reactions |
Constitutional Isomers
Woodward-Hoffmann rules: Cycloaddition reactions  Vollmer, John J.; Servis, Kenneth L.
Applies Woodward-Hoffmann rules to a wide variety of cycloaddition reactions.
Vollmer, John J.; Servis, Kenneth L. J. Chem. Educ. 1970, 47, 491.
Mechanisms of Reactions |
Addition Reactions |
Alkenes
The two forms of cyclohexane  Dunitz, J. D.
The object of this paper is to provide a simple mathematical derivation of the flexibility of the boat form and the rigidity of the chair form of cyclohexane.
Dunitz, J. D. J. Chem. Educ. 1970, 47, 488.
Molecular Properties / Structure |
Alkanes / Cycloalkanes
Separation of bromoaniline isomers by cation-exchange chromatography  Romano, S. J.
Presents a procedure for separating o-, m-, and p-bromoaniline by ion-exchange chromatography on Sephadex C-25 CM resin.
Romano, S. J. J. Chem. Educ. 1970, 47, 478.
Chromatography |
Separation Science |
Ion Exchange |
Constitutional Isomers
Organic nomenclature, I  Liotta, Charles
It is the purpose of this article to call attention to errors and misconceptions in the application of IUPAC Rules of Organic Nomenclature.
Liotta, Charles J. Chem. Educ. 1970, 47, 471.
Nomenclature / Units / Symbols |
Alkanes / Cycloalkanes |
Alcohols |
Heterocycles
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
Computer animation of molecular vibrations: Ethane  Mortensen, Earl M.; Penick, Ronald J.
Examines the theory and calculations necessary to animate the molecular vibrations of an ethane molecule.
Mortensen, Earl M.; Penick, Ronald J. J. Chem. Educ. 1970, 47, 102.
Alkanes / Cycloalkanes |
Molecular Properties / Structure |
Molecular Modeling
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
Economics in the chemical industry. Part II  Reese, K. M.
Focusses on the production of ethylene, aspirin, nylon, DDT, and fluorocarbon-12 since WWII.
Reese, K. M. J. Chem. Educ. 1969, 46, 827.
Industrial Chemistry |
Alkenes |
Synthesis
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
Chlorination of 2,3-dimethylbutane: A quantitative organic chemistry experiment  Markgraf, J. Hodge
This paper describes the quantitative study of a free radical chlorination in which the student determines the relative reactivity of selected hydrogens.
Markgraf, J. Hodge J. Chem. Educ. 1969, 46, 610.
Quantitative Analysis |
Alkylation |
Alkanes / Cycloalkanes |
Free Radicals
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
Photochemistry of organic compounds. I, Selected aspects of olefin photochemistry  Swenton, John S.
Examines the chemistry of mono- and unconjugated olefins and conjugated dienes.
Swenton, John S. J. Chem. Educ. 1969, 46, 7.
Photochemistry |
Alkenes
Substitution products in the Hofmann elimination  Baumgarten, Ronald J.
Textbooks often state or imply that alkenes are the only products formed when tetra- alkylammonium hydroxides are heated.
Baumgarten, Ronald J. J. Chem. Educ. 1968, 45, 122.
Alkenes
3-Sulfolene: A butadiene source for a Diels-Alder synthesis: An undergraduate laboratory experiment  Sample, Thomas E., Jr.; Hatch, Lewis F.
By selecting a suitable diene cyclic sulfone, the common complication in performing a Diels-Alder experiment can be avoided.
Sample, Thomas E., Jr.; Hatch, Lewis F. J. Chem. Educ. 1968, 45, 55.
Alkenes |
Synthesis |
Mechanisms of Reactions
Dehydration of 2-methylcyclohexanol  Taber, Richard L.; Champion, William C.
This short article describes a simple alcohol dehydration that illustrates the Saytzeff Rule.
Taber, Richard L.; Champion, William C. J. Chem. Educ. 1967, 44, 620.
Alcohols |
Gas Chromatography |
Alkenes
The preparation of naphthalene-alpha-d: An experiment in organic chemistry  Ziegler, Gene R.
This procedure involves the preparation of a hydrocarbon via the Grignard reagent from the corresponding bromide.
Ziegler, Gene R. J. Chem. Educ. 1967, 44, 609.
Synthesis |
Grignard Reagents |
Alkanes / Cycloalkanes
Halogenation and olefinic nature of cyclopropane  Gordon, Arnold J.
A brief discussion of evidence for the double-bond nature of the cyclopropane ring is presented, followed by a summary of representative studies of cyclopropane halogenations and related reactions.
Gordon, Arnold J. J. Chem. Educ. 1967, 44, 461.
Alkanes / Cycloalkanes |
Molecular Properties / Structure
A unified theory of bonding for cyclopropanes  Bernett, William A.
Examines various models for bonding in cyclopropanes.
Bernett, William A. J. Chem. Educ. 1967, 44, 17.
Covalent Bonding |
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
MO Theory |
Molecular Modeling
The Hofmann Rule  Freedman, Leon D.
The statement that the decomposition of tert-butyldimethyltethylammonium hydroxide yields predominantly ethylene is mistaken.
Freedman, Leon D. J. Chem. Educ. 1966, 43, 662.
Alkanes / Cycloalkanes
Calculation of molecular geometry by vector analysis: Application to six-membered alicyclic rings  Henshall, T.
Demonstrates the calculation of molecular geometry by vector analysis through an application to cyclohexane.
Henshall, T. J. Chem. Educ. 1966, 43, 600.
Molecular Properties / Structure |
Alkanes / Cycloalkanes
Bromination of alkanes: Experiment illustrating relative reactivities and synthetic utility  Warkentin, J.
The radical halogenation of alkanes lend themselves well to the teaching of basic material such as bond dissociation energies, potential energy profiles, enthalpy of reaction, activation energy, and reaction rate.
Warkentin, J. J. Chem. Educ. 1966, 43, 331.
Electrochemistry |
Alkanes / Cycloalkanes |
Rate Law |
Kinetics |
Synthesis |
Alkenes |
Mechanisms of Reactions |
Free Radicals
The bromination of anthracene  Wright, Oscar L.; Mura, Lawrence E.
This reaction illustrates the property of anthracene of adding the halogen molecule and later losing the elements of HBr to form the monobrominated hydrocarbon.
Wright, Oscar L.; Mura, Lawrence E. J. Chem. Educ. 1966, 43, 150.
Alkanes / Cycloalkanes
Permanganate hydroxylation of alkenes  Snyder, Carl H.
Alkaline permanganate is usually a distinctly superior reagent for the conversion of alkenes to cis-glycols; neutral permanganate usually produces oxidation to ketols or cleavage to aldehydes.
Snyder, Carl H. J. Chem. Educ. 1966, 43, 141.
Alkenes |
Alcohols |
Aldehydes / Ketones
The Chemistry of Alkenes (Patai, Saul, ed.)  Miller, Sidney I.

Miller, Sidney I. J. Chem. Educ. 1965, 42, 580.
Alkenes
The synthesis of carbocyclic compound: A historical survey  Finley, K. Thomas
Reviews the development of ring closure reactions.
Finley, K. Thomas J. Chem. Educ. 1965, 42, 536.
Synthesis |
Alkanes / Cycloalkanes
Extensions in the use of plastic tetrahedral models  Fieser, Louis F.
Describes the modification of existing models to provide for the construction of specialized organic and inorganic structures and their use in teaching.
Fieser, Louis F. J. Chem. Educ. 1965, 42, 408.
Molecular Modeling |
Molecular Properties / Structure |
Alkanes / Cycloalkanes
Carbene chemistry (Kirmse, Wolfgang)  Skell, P. S.

Skell, P. S. J. Chem. Educ. 1965, 42, 346.
Alkenes
The Betachor: A new parameter for hydrocarbons  Seymour, Raymond B.; Rivera, Ezequiel R.; Smith, Faith I.
The Betachor is the product of the index of refraction, the boiling point, and the reciprocal of the density; the accompanying figure illustrates the relationship of the Betachor and carbon number for several types of hydrocarbons.
Seymour, Raymond B.; Rivera, Ezequiel R.; Smith, Faith I. J. Chem. Educ. 1965, 42, 332.
Alkanes / Cycloalkanes |
Physical Properties
Cyclobutane chemistry: A student laboratory experiment  Williams, Francis T.; Baber, S. Charles
Suggests a sequence of experiments for studying cyclobutane chemistry involving the use of tetramethyl-1,3-cyclobutanedione.
Williams, Francis T.; Baber, S. Charles J. Chem. Educ. 1964, 41, 563.
Alkanes / Cycloalkanes |
Aldehydes / Ketones
Erratum: Cyclobutane chemistry  Wilson, Armin
Corrects a mistake in a previously published article.
Wilson, Armin J. Chem. Educ. 1964, 41, 220.
Alkanes / Cycloalkanes
Cyclobutane chemistry. 2. Reactions and mechanisms  Wilson, Armin; Goldhamer, David
This discussion on synthetic approaches to cyclobutanes is intended to acquaint the reader with more recent works in this field.
Wilson, Armin; Goldhamer, David J. Chem. Educ. 1963, 40, 599.
Alkanes / Cycloalkanes |
Reactions |
Mechanisms of Reactions |
Free Radicals
Determining activity coefficients by gas chromatography: A physical chemistry experiment  Kenworthy, Susan; Miller, James; Martire, D. E.
A simple, gas-liquid chromatographic experiment is outlined for the determination of the activity coefficients of benzene, cyclohexane, and cyclohexene in dinonylphthalate.
Kenworthy, Susan; Miller, James; Martire, D. E. J. Chem. Educ. 1963, 40, 541.
Gas Chromatography |
Alkanes / Cycloalkanes |
Alkenes
Cyclobutane chemistry. 1. Structure and strain energy  Wilson, Armin; Goldhamer, David
Examines the various conformations that have been proposed for particular four-membered rings.
Wilson, Armin; Goldhamer, David J. Chem. Educ. 1963, 40, 504.
Alkanes / Cycloalkanes |
Molecular Properties / Structure
The decarboxylation of organic acid  March, Jerry
Simple aliphatic acids (except for acetic) do not give good yields of the corresponding alkanes through decarboxylation, although many organic chemistry textbooks cite this as a general method for the preparation of alkanes.
March, Jerry J. Chem. Educ. 1963, 40, 212.
Acids / Bases |
Reactions |
Synthesis |
Alkanes / Cycloalkanes |
Carboxylic Acids
Models illustrating rotational isomerism in aliphatic chains  Hayman, H. J. G.
Describes a simple modification to Fisher-Hirschfelder-Taylor models which, without abolishing the possibility of rotation, gives additional stability to the staggered configurations of aliphatic chains.
Hayman, H. J. G. J. Chem. Educ. 1963, 40, 208.
Molecular Modeling |
Molecular Properties / Structure |
Alkanes / Cycloalkanes
A versatile molecular model of cyclobutane  Wilson, Armin
Describes a versatile molecular model of cyclobutane constructed from brass tubing and used to illustrate ring strain.
Wilson, Armin J. Chem. Educ. 1962, 39, 649.
Molecular Modeling |
Molecular Properties / Structure |
Alkanes / Cycloalkanes
Lecture demonstration models of cycloalkanes  Schultz, Harry P.
Describes large, sturdy, lecture demonstration models of cycloalkanes.
Schultz, Harry P. J. Chem. Educ. 1962, 39, 648.
Molecular Modeling |
Molecular Properties / Structure |
Alkanes / Cycloalkanes
The rotational barrier in ethane  Eyring, Henry; Grant, D. M.; Hecht, H.
Reviews research regarding the rotational barrier in ethane.
Eyring, Henry; Grant, D. M.; Hecht, H. J. Chem. Educ. 1962, 39, 466.
Alkanes / Cycloalkanes |
Molecular Properties / Structure
Models illustrating types of orbitals and bonding  Baker, Wilbur L.
A short note on a model of ethylene that clarifies the nature of bonding in the molecule.
Baker, Wilbur L. J. Chem. Educ. 1961, 38, 606.
Molecular Modeling |
Alkenes |
Covalent Bonding
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
Conformational analysis in mobile systems  Eliel, Ernest L.
A review of conformational analysis and its application to mobile systems.
Eliel, Ernest L. J. Chem. Educ. 1960, 37, 126.
Conformational Analysis |
Molecular Properties / Structure |
Alkanes / Cycloalkanes
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
Motor fuel quality as related to refinery processing and antiknock compounds  Conrad, Franklin; Sabin, William W.
Examines the refinery process, estimating the cost of quality improvement, and the tetraethyllead manufacturing process.
Conrad, Franklin; Sabin, William W. J. Chem. Educ. 1957, 34, 262.
Industrial Chemistry |
Alkanes / Cycloalkanes |
Applications of Chemistry
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
Potentialities of protein isomerism  Asimov, Isaac
The permutations generated by structural isomerism in proteins could be demonstrated more convincingly and realistically if the amino acid compositions of actual proteins were taken into consideration.
Asimov, Isaac J. Chem. Educ. 1954, 31, 125.
Proteins / Peptides |
Molecular Properties / Structure |
Amino Acids |
Constitutional Isomers
Aspects of isomerism and mesomerism. III. Stereoisomerism  Bent, Richard L.
Examines the tetrahedral nature of carbon, multiple bonds, enantiomorphism, diastereoisomerism, and geometric isomerism.
Bent, Richard L. J. Chem. Educ. 1953, 30, 328.
Molecular Properties / Structure |
Enantiomers |
Diastereomers |
Constitutional Isomers
Aspects of isomerism and mesomerism. II. Structural isomerism  Bent, Richard L.
Examines the relationship between structural, optical, and geometric isomerism.
Bent, Richard L. J. Chem. Educ. 1953, 30, 284.
Molecular Properties / Structure |
Constitutional Isomers |
Enantiomers |
Diastereomers
The organization of subject matter in elementary organic chemistry  MacKenzie, Charles A.
Describes a curricular approach in which aliphatic and aromatic compounds are treated simultaneously rather than separately.
MacKenzie, Charles A. J. Chem. Educ. 1953, 30, 243.
Aromatic Compounds |
Alkanes / Cycloalkanes
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
The mechanisms of the reactions of aliphatic hydrocarbons  Schmerling, Louis
Examines the formation of carbonium ions and free radicals, the polymerization of olefins, hydrogen-halogen exchange, the condensation of haloalkanes with alkenes, the alkylation of paraffins, the condensation of paraffins with chloroolefins, the cracking of paraffins and olefins, and the isomerization of paraffins.
Schmerling, Louis J. Chem. Educ. 1951, 28, 562.
Mechanisms of Reactions |
Alkanes / Cycloalkanes |
Free Radicals |
Polymerization
The preparation of "2-bromo-naphthalene"  Wolfe, Winthrop C.; Doukas, Harry M.
Presents a procedure for the preparation of "2-bromo-naphthalene" in large or small amounts.
Wolfe, Winthrop C.; Doukas, Harry M. J. Chem. Educ. 1951, 28, 472.
Synthesis |
Alkenes
Experiments with cyclopentadiene  Wagner, E. C.; Hunt, William C.
The experiments outlined here serve to illustrate the processes of polymerization and depolymerization, the Diels-Alder reaction, and the presence of a reactive methylene group in cyclopentadiene.
Wagner, E. C.; Hunt, William C. J. Chem. Educ. 1951, 28, 309.
Alkenes |
Synthesis |
Polymerization