TIGER

Journal Articles: 182 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
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
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
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 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
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
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
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
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
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
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
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
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
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 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
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
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
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
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
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
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 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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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 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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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 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
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
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
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
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
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
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
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
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
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
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
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
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
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