| Journal Articles: 153 results |
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Assessing Nitration Products of Benzene Derivatives Using TLC Analysis Rita K. Hessley
Thin layer chromatography is applied to an earlier published, guided discovery experiment using GCMS analyses to identify isomers formed by the nitration of mono-substituted benzenes.
Hessley, Rita K. J. Chem. Educ. 2008, 85, 1623.
Thin Layer Chromatography |
Gas Chromatography |
Mass Spectrometry |
Aromatic Compounds
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A More Challenging Interpretative Nitration Experiment Employing Substituted Benzoic Acids and Acetanilides Edward M. Treadwell and Tung-Yin Lin
An experiment is described involving the nitration of ortho or meta, monosubstituted benzoic acids and monochlorinated acetanilides with nitric acid to evaluate the regioselectivity of addition through computational methods and 1H NMR spectroscopy.
Treadwell, Edward M.; Lin, Tung-Yin. J. Chem. Educ. 2008, 85, 1541.
Aromatic Compounds |
Computational Chemistry |
Electrophilic Substitution |
Molecular Modeling |
NMR Spectroscopy |
Synthesis
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A Green, Guided-Inquiry Based Electrophilic Aromatic Substitution for the Organic Chemistry Laboratory Eric Eby and S. Todd Deal
This alternative, electrophilic aromatic substitutionan iodination reaction of salicylamide, a popular analgesicuses 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
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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
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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
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The Aromaticity of Pericyclic Reaction Transition States Henry S. Rzepa
Presents an approach that combines two fundamental concepts in organic chemistry, chirality and aromaticity, into a simple rule for stating selection rules for pericyclic reactions in terms of achiral Hckel-aromatic and chiral Mbius-aromatic transition states.
Rzepa, Henry S. J. Chem. Educ. 2007, 84, 1535.
Alkanes / Cycloalkanes |
Alkenes |
Aromatic Compounds |
Mechanisms of Reactions |
Stereochemistry
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Toluene Jay A. Young
Safety precautions for handling toluene are discussed.
Young, Jay A. J. Chem. Educ. 2007, 84, 760.
Aromatic Compounds |
Laboratory Computing / Interfacing
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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 benzenetoluene and benzenefluorobenzene 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
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Electronic Structure Principles and Aromaticity P. K. Chattaraj, U. Sarkar, and D. R. Roy
Electronic structure principles dictate that aromatic molecules are associated with low energy, polarizability, and electrophilicity but high hardness values, while antiaromatic molecules possess the opposite characteristics. These relationships are demonstrated through B3LYP/6-311G** calculations on benzene and cyclobutadiene.
Chattaraj, P. K.; Sarkar, U.; Roy, D. R. J. Chem. Educ. 2007, 84, 354.
Aromatic Compounds |
Molecular Properties / Structure |
Quantitative Analysis |
Theoretical Chemistry |
Alkenes |
Quantum Chemistry
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p-Dichlorobenzene Jay A. Young
The hazards of p-dichlorobenzene are discussed.
Young, Jay A. J. Chem. Educ. 2006, 83, 1755.
Laboratory Management |
Aromatic Compounds
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Calix[4]pyrrole: Synthesis and Anion-Binding Properties. An Organic Chemistry Laboratory Experiment James A. Shriver and Scott G. Westphal
Simple calixpyrrole macrocycles provide an easy-to-synthesize example of an anion-binding agent that can be included in the undergraduate laboratory curriculum. The inclusion of a test for anion binding also makes this procedure suitable for a more advanced audience and supplies a bridge for the introduction of supramolecular chemistry and a typical hostguest interaction.
Shriver, James A.; Westphal, Scott G. J. Chem. Educ. 2006, 83, 1330.
Aromatic Compounds |
Hydrogen Bonding |
Molecular Recognition |
Synthesis |
Thin Layer Chromatography
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Benzene Jay A. Young
The hazards of benzene are discussed.
Young, Jay A. J. Chem. Educ. 2005, 82, 1769.
Laboratory Management |
Aromatic Compounds
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Quantitative Thermodynamic Descriptions of Aromaticity. A Computational Exercise for the Organic Chemistry Laboratory Terrence Gavin
This article describes an exercise that enables students to establish a quantitative scale of aromaticity via computer-driven quantum mechanical calculations using Spartan software. The method utilizes a group of analogous isodesmic reactions from which the energy difference between two isomeric cyclic polyenes is calculated from their optimized geometries. The energy differences found are used to characterize structures as aromatic, nonaromatic, or antiaromatic depending on the value obtained. A representative group of structures, including hydrocarbons, hydrocarbon ions, and heterocycles are studied.
Gavin, Terrence. J. Chem. Educ. 2005, 82, 953.
Aromatic Compounds |
Computational Chemistry |
Heterocycles |
Molecular Modeling |
Thermodynamics
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A Discovery-Based Friedel–Crafts Acylation Experiment: Student-Designed Experimental Procedure Anne McElwee Reeve
A discovery-based FriedelCrafts acylation experiment that includes a student-designed procedure, spectroscopic analysis of an unknown aromatic product, and molecular modeling is described. Students design the synthetic procedure and workup for the acylation of an unknown aromatic starting material in an instructor-guided classroom discussion that integrates concepts from the first semester of organic lab into a new context.
Reeve, Anne McElwee. J. Chem. Educ. 2004, 81, 1497.
Aromatic Compounds |
Chromatography |
IR Spectroscopy |
Molecular Modeling |
NMR Spectroscopy |
Synthesis
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The Electrophilic Aromatic Substitution of Fluorobenzene Addison Ault
Joel Rosenthal and David Schuster published a paper entitled The Anomalous Reactivity of Fluorobenzene in Electrophilic Aromatic Substitution and Related Phenomena. The authors and the reviewers, apparently, were not aware of my publication in this Journal in 1966 entitled The Activating Effect of Fluorine in Electrophilic Aromatic Substitution.
Ault, Addison. J. Chem. Educ. 2004, 81, 644.
Aromatic Compounds |
Mechanisms of Reactions |
Synthesis
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Microscale Synthesis and Spectroscopic Analysis of Flutamide, an Antiandrogen Prostate Cancer Drug Ryan G. Stabile and Andrew P. Dicks
The synthesis involves N-acylation of a trisubstituted aromatic compound, 3-trifluoromethyl-4-nitroaniline. The procedure is easily adapted to generate structural analogues of flutamide. A significant feature is the curricular flexibility afforded by this experiment.
Stabile, Ryan G.; Dicks, Andrew P. J. Chem. Educ. 2003, 80, 1439.
Drugs / Pharmaceuticals |
IR Spectroscopy |
Mechanisms of Reactions |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Aromatic Compounds
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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
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The Anomalous Reactivity of Fluorobenzene in Electrophilic Aromatic Substitution and Related Phenomena Joel Rosenthal and David I. Schuster
Extensive analysis of the reactivity of fluorobenzene (electrophilic substitution); includes resonance and other inductive effects, acidities of fluorinated aromatic compounds, and properties of other organofluorine compounds.
Rosenthal, Joel; Schuster, David I. J. Chem. Educ. 2003, 80, 679.
Aromatic Compounds |
Mechanisms of Reactions |
Synthesis |
Electrophilic Substitution |
Enrichment / Review Materials |
Resonance Theory
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Dendrimers: Branching Out of Polymer Chemistry Eric E. Simanek and Sergio O. Gonzalez
Addresses synthetic concepts surrounding dendrimers including the use of protecting groups, functional group interconversions, and convergent and divergent synthetic strategies.
Simanek, Eric E.; Gonzalez, Sergio O. J. Chem. Educ. 2002, 79, 1222.
Materials Science |
Synthesis |
Molecular Properties / Structure |
Addition Reactions |
Aromatic Compounds |
Alkylation |
Nucleophilic Substitution
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Fractional Distillation and GC Analysis of Hydrocarbon Mixtures Craig J. Donahue
Separating and identifying the components of a three-hydrocarbon mixture through fractional distillation and gas chromatography.
Donahue, Craig J. J. Chem. Educ. 2002, 79, 721.
Chromatography |
Gas Chromatography |
Separation Science |
Alkanes / Cycloalkanes |
Alkenes |
Aromatic Compounds |
IR Spectroscopy |
NMR Spectroscopy |
Qualitative Analysis
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A New Approach to Understanding Oxidation-Reduction of Compounds in Organic Chemistry Abdullah Menzek
Teaching oxidation-reduction in introductory organic chemistry.
Menzek, Abdullah. J. Chem. Educ. 2002, 79, 700.
Aromatic Compounds |
Oxidation / Reduction |
Oxidation State
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Effect of Anisotropy on the Chemical Shift of Vinyl Protons in trans- and cis-1,2-Dibenzoylethylenes. A Small-Group or Recitation Activity Roosevelt Shaw, David Roane, and Sean Nedd
Procedure to help students explain chemical shift differences for vinyl protons in alkene diastereomers.
Shaw, Roosevelt; Roane, David; Nedd, Sean. J. Chem. Educ. 2002, 79, 67.
Magnetic Properties |
NMR Spectroscopy |
Undergraduate Research |
Diastereomers |
Aromatic Compounds |
Alkenes |
Photochemistry |
Molecular Properties / Structure
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Discovery-Oriented Approach To Organic Synthesis: Tandem Aldol Condensation-Michael Addition Reactions. Identifying Diastereotopic Hydrogens in an Achiral Molecule by NMR Spectroscopy Nanette Wachter-Jurcsak and Kendra Reddin
Procedure illustrating aldol condensation and Michael addition reactions.
Wachter-Jurcsak, Nanette; Reddin, Kendra. J. Chem. Educ. 2001, 78, 1264.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Aromatic Compounds |
Aldehydes / Ketones |
Addition Reactions |
Mechanisms of Reactions
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Suzuki Cross-Coupling Reactions: Synthesis of Unsymmetrical Biaryls in the Organic Laboratory Christopher S. Callam and Todd L. Lowary
Laboratory that exposes students to organometallic chemistry and application of the Suzuki reaction.
Callam, Christopher S.; Lowary, Todd L. J. Chem. Educ. 2001, 78, 947.
Aromatic Compounds |
Metals |
Synthesis |
Organometallics |
Transition Elements |
Mechanisms of Reactions
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The Bullvalene Story. The Conception of Bullvalene, a Molecule That Has No Permanent Structure Addison Ault
Properties and chemistry of bullvalene, C10H10, a hydrocarbon with no permanent carbon-carbon bonds.
Ault, Addison. J. Chem. Educ. 2001, 78, 924.
Molecular Properties / Structure |
Aromatic Compounds
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The Oxidation of Alkylbenzenes: Using Data Pooling in the Organic Laboratory to Illustrate Research in Organic Chemistry James C. Adrian Jr. and Leslie A. Hull
Student groups are assigned the task of oxidizing various substituted alkylbenzenes with potassium permanganate in basic solution; by pooling the results from all groups it is possible to illustrate how a research project in chemistry can be used to answer simple questions - What happens when your individual alkylbenzene is oxidized?
Adrian, James C., Jr.; Hull, Leslie A. J. Chem. Educ. 2001, 78, 529.
Synthesis |
Chemometrics |
Oxidation / Reduction |
Mechanisms of Reactions |
Aromatic Compounds
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Determination of the Regiochemistry of Disubstituted Arenes Generated by Addition of a Carbanion to the (h6-Anisole)Cr(CO)3 Complex Ashfaq A. Bengali, Cindy Samet, and Samantha B. Charlton
A laboratory activity that integrates fundamental concepts of organic and organometallic chemistry and then employs standard instrumental techniques (GC) and molecular modeling to justify the results.
Bengali, Ashfaq A.; Samet, Cindy; Charlton, Samantha B. J. Chem. Educ. 2001, 78, 68.
Aromatic Compounds |
Synthesis |
Organometallics |
Gas Chromatography |
Molecular Modeling
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A Phthalocyanine Synthesis Group Project for General Chemistry Darren K. MacFarland, Christopher M. Hardin, and Michael J. Lowe
A group experiment synthesizing phthalocyanine dyes in one step from commercially available starting materials is described. The importance of a metal template is explored. The experiment is suitable for a second-semester general chemistry course.
MacFarland, Darren K.; Hardin, Christopher M.; Lowe, Michael J. J. Chem. Educ. 2000, 77, 1484.
Aromatic Compounds |
Synthesis |
Organometallics |
UV-Vis Spectroscopy |
Aromatic Compounds
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Visible Aromatic Electronic Effects Using a Series of Substituted Copper Phthalocyanines Darren K. MacFarland, Solomon Lieb, and Jessica Oswald
Phthalocyanines provide an opportunity to directly observe electronic effects in an aromatic system through color changes that are dependent on the nature of peripheral substituents. Simple, reliable syntheses of electron-poor and electron-rich phthalocyanines are reported, along with corresponding UV-visible spectra.
MacFarland, Darren K.; Lieb, Solomon; Oswald, Jessica. J. Chem. Educ. 2000, 77, 1482.
Aromatic Compounds |
Synthesis |
Organometallics |
UV-Vis Spectroscopy |
Aromatic Compounds
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Displacement of the Benzene Solvent Molecule from Cr(CO)5(benzene) by Piperidine: A Laser Flash Photolysis Experiment Ashfaq A. Bengali and Samantha B. Charlton
This laboratory experiment utilizes a nitrogen laser to investigate the chemistry of the Cr(CO)5(benzene) complex on the microsecond time scale. The unique capabilities of a laser and the chemistry made possible by its use is demonstrated.
Bengali, Ashfaq A.; Charlton, Samantha B. J. Chem. Educ. 2000, 77, 1348.
Kinetics |
Lasers |
Spectroscopy |
Organometallics |
Photochemistry |
Aromatic Compounds |
Reactions
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Two Faces of Alkaloids Jirí Dostál
The article discusses and compares the salts and free bases of six well-known alkaloids: nicotine, morphine, cocaine, sanguinarine, allocryptopine, and magnoflorine. Relevance for the biological and medical uses of these compounds is emphasized.
Dostál, Jirí. J. Chem. Educ. 2000, 77, 993.
Acids / Bases |
Bioorganic Chemistry |
Drugs / Pharmaceuticals |
Natural Products |
Aromatic Compounds |
Medicinal Chemistry
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The Discovery Approach to NMR: Development of Chemical-Shift Additivity Tables and Application to Product Identification Eric Bosch
A discovery-based approach to the preparation and application of chemical-shift additivity tables is presented to give students insight into the development of NMR spectral prediction software.
Bosch, Eric. J. Chem. Educ. 2000, 77, 890.
Laboratory Computing / Interfacing |
NMR Spectroscopy |
Aromatic Compounds |
Molecular Properties / Structure
|
Melting Point and Molecular Symmetry R. J. C. Brown and R. F. C. Brown
In 1882 Thomas Carnelley observed that high molecular symmetry is associated with high melting point. The application of the rule to a number of different molecular crystals is discussed. The rule applies to different categories of crystal for different reasons, which can be explained by thermodynamic analysis.
Brown, R. J. C.; Brown, R. F. C. J. Chem. Educ. 2000, 77, 724.
Liquids |
Molecular Properties / Structure |
Phases / Phase Transitions / Diagrams |
Solids |
Thermodynamics |
Physical Properties |
Aromatic Compounds |
Crystals / Crystallography
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Keep Going with Cyclooctatetraene! Addison Ault
This paper shows how some simple properties of cyclooctatetraene can indicate important ideas about the structure of cyclooctatetraene.
Ault, Addison. J. Chem. Educ. 2000, 77, 55.
Aromatic Compounds |
NMR Spectroscopy |
Mechanisms of Reactions |
Molecular Properties / Structure
|
Comments on the Treatment of Aromaticity and Acid-Base Character of Pyridine and Pyrrole in Contemporary Organic Chemistry Textbooks Hugh J. Anderson and Ludwig Bauer
Presentations of aromaticity and acid-base character of pyridine and pyrrole in 18 contemporary organic chemistry textbooks were surveyed.
Anderson, Hugh J.; Bauer, Ludwig. J. Chem. Educ. 1999, 76, 1151.
Acids / Bases |
Aromatic Compounds
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Preparation and Identification of Benzoic Acids and Benzamides: An Organic "Unknown" Lab Douglass F. Taber, Jade D. Nelson, and John P. Northrop
The reaction of an unknown substituted benzene derivative with oxalyl chloride and aluminum chloride gives the acid chloride. Hydrolysis of the acid chloride gives the acid, and reaction of the acid with concentrated aqueous ammonia gives the benzamide. The equivalent weight of the acid can be determined by titration; given this information and the melting points of the acid and the benzamide, it is possible to deduce the structure of the initial unknown.
Taber, Douglass F.; Nelson, Jade D.; Northrop, John P. J. Chem. Educ. 1999, 76, 828.
Qualitative Analysis |
Aromatic Compounds |
Carboxylic Acids
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Chromatography, Absorption, and Fluorescence: A New Instrumental Analysis Experiment on the Measurement of Polycyclic Aromatic Hydrocarbons in Cigarette Smoke Lisa M. Wingen, Jason C. Low, and Barbara J. Finlayson-Pitts
An experiment suitable for an undergraduate junior/senior-level instrumental analysis laboratory which illustrates the principles of high-performance liquid chromatography (HPLC) and its application to the identification and measurement of polycyclic aromatic hydrocarbons (PAH) in tobacco smoke.
Wingen, Lisa M.; Low, Jason C.; Finlayson-Pitts, Barbara J. J. Chem. Educ. 1998, 75, 1599.
Instrumental Methods |
Chromatography |
Qualitative Analysis |
Quantitative Analysis |
Fluorescence Spectroscopy |
Aromatic Compounds
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A New GC-MS Experiment for the Undergraduate Instrumental Analysis Laboratory in Environmental Chemistry: Methyl-t-butyl Ether and Benzene in Gasoline Dinh T. Quach, Nancy A. Ciszkowski, and Barbara J. Finlayson-Pitts
In addition to illustrating the fundamentals of GC and MS, this experiment demonstrates (i) the use of internal standards to improve precision; (ii) the application of the method of standard additions; and (iii) the importance of techniques such as selected ion extraction/monitoring in the identification and measurement of specific highly volatile organic compounds in complex environmental mixtures.
Quach, Dinh T.; Ciszkowski, Nancy A.; Finlayson-Pitts, Barbara J. J. Chem. Educ. 1998, 75, 1595.
Instrumental Methods |
Chromatography |
Mass Spectrometry |
Quantitative Analysis |
Gas Chromatography |
Aromatic Compounds |
Ethers
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Photodimerization of Anthracene Gary W. Breton and Xoua Vang
The laboratory experiment of the photodimerization of anthracene is given.
Breton, Gary W.; Vang, Xoua. J. Chem. Educ. 1998, 75, 81.
Photochemistry |
UV-Vis Spectroscopy |
Aromatic Compounds |
Synthesis
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On the Disproportionations of Cyclohexene and Related Compounds Alex Bunjes, Ingo Eilks, Manfred Pahlke, and Bernd Ralle*
The catalytic hydrogenation of liquid hydrocarbons is easy to realize in a simple laboratory experiment using a palladium catalyst. In the case of hydrogenation cyclohexen or cyclohexadiene in addition to the expected finding of cyclohexane among the hydrogenation products, the formation of benzene can be observed. In absence of hydrogen, the disproportionation of both starting materials to cyclohexane and benzene takes place.
Bunjes, Alex; Eilks, Ingo; Pahlke, Manfred; Ralle, Bernd. J. Chem. Educ. 1997, 74, 1323.
Alkanes / Cycloalkanes |
Aromatic Compounds |
Alkenes |
Synthesis
|
Vanillin: Synthetic Flavoring from Spent Sulfite Liquor Martin B. Hocking
The isolation and preparation of vanillin, its commercial preparation from lignin, and environmental concerns.
Hocking, Martin B. J. Chem. Educ. 1997, 74, 1055.
Consumer Chemistry |
Industrial Chemistry |
Food Science |
Natural Products |
Applications of Chemistry |
Aromatic Compounds |
Synthesis
|
Correction
Correction in equation 1.
J. Chem. Educ. 1997, 74, 480.
Aromatic Compounds |
Molecular Properties / Structure
|
GC/MS Analysis of the Aromatic Composition of Gasoline Keith S. Kostecka, Ashraf Rabah, and Charles F. Palmer, Jr.
Procedure for examining 11 aromatics species in three unleaded regular-grade commercial fuels using GC/MS analysis; includes sample data.
Kostecka, Keith S.; Rabah, Ashraf; Palmer, Charles F., Jr. J. Chem. Educ. 1995, 72, 853.
Chromatography |
Mass Spectrometry |
Aromatic Compounds |
Separation Science |
Gas Chromatography
|
Characterizing Resins According to Organic Ion Exchange and Chelating Ion Exchange Quigley, Michael N.; Vernon, Frederick
Procedure for characterizing ion-exchange materials.
Quigley, Michael N.; Vernon, Frederick J. Chem. Educ. 1995, 72, 553.
Ion Exchange |
Aromatic Compounds
|
Resonance Analogy Using Cartoon Characters Starkey, Ronald
Using Charlie Brown and Dennis the Menace as an analogy for resonance hybrids (specifically benzene).
Starkey, Ronald J. Chem. Educ. 1995, 72, 542.
Covalent Bonding |
Aromatic Compounds |
Molecular Properties / Structure
|
An Attention-Getting Model for Atomic Orbitals Kiefer, Edgar F.
Tapping a spoon on a coffee mug to illustrate the circular orbitals of benzene.
Kiefer, Edgar F. J. Chem. Educ. 1995, 72, 500.
MO Theory |
Aromatic Compounds
|
Microwave Synthesis of Tetraphenylcyclopentadienone and Dimethyl Tetraphenylphthalate Elder, John W.
Procedure for using a microwave to synthesize tetraphenylcyclopentadienone and dimethyl tetraphenylphthalate.
Elder, John W. J. Chem. Educ. 1994, 71, A142.
Microscale Lab |
Laboratory Equipment / Apparatus |
Synthesis |
Aromatic Compounds |
Esters |
Amines / Ammonium Compounds
|
Dinitration of 2-Benzylpyyridine: Microscale Synthesis of a Photochromic Compound Gilfillan, Elizabeth D.; Pelter, Michael W.
Microscale synthesis of 2-[(2,4-dinitrophenyl)methyl]pyridine, which is tan in the absence of light but turns blue when exposed to light.
Gilfillan, Elizabeth D.; Pelter, Michael W. J. Chem. Educ. 1994, 71, A4.
Microscale Lab |
Synthesis |
Photochemistry |
Aromatic Compounds
|
Electrophilic Aromatic Substitution, Promoted by Bentonitic Clay Angeles, Enrique; Ramirez, Alberto; Martinez, Ignacio; Moreno, Enrique
Experiment that uses bentonitic clay as a catalyst instead of the conventional Lewis acid in the chlorination and bromination of benzene and dimerization of toluene.
Angeles, Enrique; Ramirez, Alberto; Martinez, Ignacio; Moreno, Enrique J. Chem. Educ. 1994, 71, 533.
Aromatic Compounds |
Electrophilic Substitution |
Catalysis
|
Isomers of Benzene Gutman, I.; Potgieter, J. H.
Summary of isomers and valence isomers of benzene.
Gutman, I.; Potgieter, J. H. J. Chem. Educ. 1994, 71, 222.
Aromatic Compounds |
Diastereomers |
Covalent Bonding
|
The Blue Bottle Experiment Revisited: How Blue? How Sweet? Cook, A. Gilbert; Tolliver, Randi M.; Williams, Janelle E.
Determining whether other colors and carbohydrates are possible with the "Blue Bottle" reaction.
Cook, A. Gilbert; Tolliver, Randi M.; Williams, Janelle E. J. Chem. Educ. 1994, 71, 160.
Aromatic Compounds |
Reactions |
Rate Law |
Mechanisms of Reactions |
Carbohydrates |
Oxidation / Reduction
|
A kinetic study of the isomerization of eugenol: The quantitative use of NMR, GC, and HPLC in a single organic laboratory experiment that demonstrates alternative approaches to solving a problem Peterson, Thomas H.; Bryan, James H.; Keevil, Thomas A.
Description of an experiment that allows students to be aware that there is often more than one approach to designing an experiment,and that the quality of the experimental results often depend on the proper choice of instrument(s).
Peterson, Thomas H.; Bryan, James H.; Keevil, Thomas A. J. Chem. Educ. 1993, 70, A96.
Aromatic Compounds |
NMR Spectroscopy |
Alcohols |
Kinetics
|
Organometallic benzene complexes Maslowsky, Edward, Jr.
A look at benzene's flexibility and subsequent interactions with metal atoms.
Maslowsky, Edward, Jr. J. Chem. Educ. 1993, 70, 980.
Organometallics |
Diastereomers |
Aromatic Compounds
|
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
|
Don't stop with benzene! The educational value of the cyclooctatetraene (C8H8) molecule Samet, Cindy
Educators often ignore larger molecular ring systems, suggesting to students that benzene covers all the important aspects of the chemistry of annulenes.
Samet, Cindy J. Chem. Educ. 1993, 70, 291.
Aromatic Compounds
|
Benzene isomers? (the author replies) Potgieter, J. H.
Additional isomers of benzene.
Potgieter, J. H. J. Chem. Educ. 1992, 69, 859.
Aromatic Compounds |
Alkenes |
Diastereomers
|
Benzene isomers? Reinecke, Manfred G.
Additional isomers of benzene.
Reinecke, Manfred G. J. Chem. Educ. 1992, 69, 859.
Aromatic Compounds |
Diastereomers |
Alkenes
|
Phenol and the importance of dose. Crute, Thomas D.
Phenol is highly toxic, but the active ingredient in Chloraseptic lozenges.
Crute, Thomas D. J. Chem. Educ. 1992, 69, 553.
Phenols |
Aromatic Compounds |
Alcohols |
Toxicology |
Consumer Chemistry |
Medicinal Chemistry
|
A new method for the oxidation of 4-phenylurazole to 4-phenyltriazolinedione. Mallakpour, Shadpour E.
The procedures describe the synthesis of 4-phenyl-urazole from ethyl carbazate and then the oxidation of the urazole with NO2-N2O4 to yield 4-phenyl-1,2,4-trizoline-3,5-dione.
Mallakpour, Shadpour E. J. Chem. Educ. 1992, 69, 238.
Oxidation / Reduction |
Aldehydes / Ketones |
Synthesis |
Aromatic Compounds
|
A simple preparation of 1,4-di-tert-butylbenzene without AICI3: An undergraduate organic chemistry experiment Castrillon, Jose
Alkylation of benzene with tert-butyl chloride and aluminum chloride has been very popular in first year organic chemistry courses, but it releases HCl gas fumes. This problem has lead to a replacement preparation using tert-butyl acetate, which provides better yield and eliminated the fumes.
Castrillon, Jose J. Chem. Educ. 1991, 68, 793.
Alkylation |
Aromatic Compounds |
Alcohols |
Microscale Lab
|
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
|
Friedel-Crafts alkylation products Kolb, Kenneth E.; Field, Kurt W.
Comments on how two recent papers could compliment one and another.
Kolb, Kenneth E.; Field, Kurt W. J. Chem. Educ. 1991, 68, 86.
Alkylation |
Gas Chromatography |
Diastereomers |
Aromatic Compounds
|
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
|
NMR analysis of product mixtures in electrophilic aromatic substitution Clark, Mary Ann; Duns, Glenn; Golberg, Danny; Karwowska, Anna; Turgeon, Andree; Turley, Jolanda
Use of mole fraction analysis permits precise quantitative product mixture analysis, a large improvement over qualitative and semiquantitative techniques.
Clark, Mary Ann; Duns, Glenn; Golberg, Danny; Karwowska, Anna; Turgeon, Andree; Turley, Jolanda J. Chem. Educ. 1990, 67, 802.
NMR Spectroscopy |
Electrophilic Substitution |
Aromatic Compounds |
Quantitative Analysis
|
A new approach to the generation of sigma complex structures Young, Joseph G.
An alternative to the electron pushing approach for determining intermediate resonance structures for electrophilic aromatic substitutions.
Young, Joseph G. J. Chem. Educ. 1990, 67, 550.
Aromatic Compounds |
Electrophilic Substitution |
Resonance Theory |
Mechanisms of Reactions
|
An effective and facile demonstration of organic photochemistry Brown, Trevor M.; Dronsfield, Alan T.; Cooksey, Christopher J.; Crich, David
The number of experiments that illustrate photochemically induced change and are suitable for student use is limited. The photolysis experiment described here is carried out very quickly using tungsten-filament lamp irradiation.
Brown, Trevor M.; Dronsfield, Alan T.; Cooksey, Christopher J.; Crich, David J. Chem. Educ. 1990, 67, 434.
Photochemistry |
Aromatic Compounds
|
Nucleophilic aromatic substitution: A microscale organic experiment Avila, Walter B.; Crow, Jeffrey L.; Utermoehlen, Clifford M.
This experiment demonstrates one feasible route in preparing ortho-substituted benzoic acids and is also an example of nucleophilic aromatic substitution chemistry.
Avila, Walter B.; Crow, Jeffrey L.; Utermoehlen, Clifford M. J. Chem. Educ. 1990, 67, 350.
Nucleophilic Substitution |
Aromatic Compounds |
Microscale Lab |
Carboxylic Acids
|
Laboratory experiments on phase-transfer-catalyzed reactions of neutral molecules Mathur, Nawal K.; Narang, Chander K.
In order to illustrate the application of a phase transfer catalyst (PTC), the preparation of benzophenone oxime was attempted under different conditions.
Mathur, Nawal K.; Narang, Chander K. J. Chem. Educ. 1990, 67, 273.
Catalysis |
Aromatic Compounds |
Aldehydes / Ketones |
Phases / Phase Transitions / Diagrams
|
Aromatic pi cloud availability: Formation of colored charge-transfer complexes Kolb, Kenneth E.
One way to demonstrate the variance of pi electron availability in the benzene ring is to observe the color of the charge-transfer complex formed between an aromatic compound and tetracyanoethylene.
Kolb, Kenneth E. J. Chem. Educ. 1989, 66, 853.
Aromatic Compounds
|
ESR studies and HMO calculations on benzosemiquinone radical anions: A physical chemistry experiment Beck, Rainer; Nibler, Joseph W.
For this laboratory study, several benzosemiquinone radical anions were chosen since they are long-lived and are easily made from inexpensive source materials. The effects of molecular symmetry and of different substituents attached to the aromatic ring system are also readily seen.
Beck, Rainer; Nibler, Joseph W. J. Chem. Educ. 1989, 66, 263.
Spectroscopy |
MO Theory |
Aromatic Compounds
|
The correlation of multinuclear spectral data for selectively fluorinated organic compounds Everett, T. Stephen
This article presents a general discussion of fluorine-19 NMR spectroscopy, spectral data for two series of selectively fluorinated compounds, and the detailed correlation of multinuclear data for one specific compound.
Everett, T. Stephen J. Chem. Educ. 1988, 65, 422.
Aromatic Compounds |
NMR Spectroscopy |
Isotopes
|
Molecular vibration demonstrations Turrell, George; Demol, Robert
Two dynamic models that illustrate the normal-mode vibrations of the water and benzene molecules.
Turrell, George; Demol, Robert J. Chem. Educ. 1987, 64, 1025.
Group Theory / Symmetry |
Water / Water Chemistry |
Aromatic Compounds |
Molecular Properties / Structure |
Molecular Modeling
|
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
|
Relative activating ability of various ortho, para-directors Zaezek, Norbert M.; Tyszkiewicz, Robert B.
The authors saw a need to develop an experiment for students to comprehensively learn about electrophilic aromatic substitution.
Zaezek, Norbert M.; Tyszkiewicz, Robert B. J. Chem. Educ. 1986, 63, 510.
Aromatic Compounds |
Reactions |
Diastereomers |
Stereochemistry
|
Graphics drill and game programs for benzene synthesis Flash, Patrick J.
65. Bits and pieces, 26. "Benzene Synthesis Drill", a game format program that drills students on multistep conversions involving benzene.
Flash, Patrick J. J. Chem. Educ. 1985, 62, 1028.
Enrichment / Review Materials |
Aromatic Compounds |
Synthesis
|
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
|
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
|
Molecular formulas of organic compounds: the nitrogen rule and degree of unsaturation Pellegrin, Valdo
This article wishes to demonstrate the nitrogen rule and the formula for calculating the number of rings plus double bonds of any common organic compound.
Pellegrin, Valdo J. Chem. Educ. 1983, 60, 626.
Heterocycles |
Aromatic Compounds |
Free Radicals
|
The synthesis of 4,6,8-trimethylazulene: an organic laboratory experiment Garst, Michael E.; Hochlowski, Jill; Douglass, III, James G.; Sasse, Scott
A procedure for a two-step synthesis of 4,6,8-trimethylazulene.
Garst, Michael E.; Hochlowski, Jill; Douglass, III, James G.; Sasse, Scott J. Chem. Educ. 1983, 60, 510.
Synthesis |
Heterocycles |
Aromatic Compounds |
Resonance Theory |
Chromatography
|
A quick and simple conversion of carboxylic acids into their anilides of heating with phenyl isothiocyanate Ram, Ram N.; Kumar, Pradeep; Mukerjee, Arya K.
In this article, the authors report a quick and easy procedure using phenyl isothiocyanate, which is ideally suited to students.
Ram, Ram N.; Kumar, Pradeep; Mukerjee, Arya K. J. Chem. Educ. 1983, 60, 508.
Carboxylic Acids |
Aromatic Compounds |
Phenols |
Reactions
|
A phase transfer catalyzed permanganate oxidation: preparation of vanillin from isoeugenol acetate Lampman, Gary M.; Sharpe, Steven D.
There are several attractive features in this reaction sequence for the undergraduate laboratory. These include (1) use of a protecting acetate group, (2) use of a familiar "textbook" oxidant, potassium permanganate, (3) use of phase transfer catalyst, (4) preparing of an aldehyde, (5) short reaction period, and (6) the laboratory has a pleasant aroma.
Lampman, Gary M.; Sharpe, Steven D. J. Chem. Educ. 1983, 60, 503.
Oxidation / Reduction |
Catalysis |
Natural Products |
Synthesis |
Aldehydes / Ketones |
Alcohols |
Aromatic Compounds
|
The synthesis of 4,4'-di-tertbutyl biphenyl: a sophomore organic chemistry experiment Horne, Deane A.
A brief note providing a sequence of experiments for an introductory organic course that is inexpensive and does not pose a health hazard.
Horne, Deane A. J. Chem. Educ. 1983, 60, 246.
Acids / Bases |
Aromatic Compounds |
Catalysis |
Alkylation |
Solutions / Solvents
|
The misuse of the circle notation to represent aromatic rings Belloli, Robert C.
This chemistry educator has noticed confusion and erroneous conclusions resulting from the overuse and misuse of the circle notation to represent aromaticity in polycyclic aromatic hydrocarbons.
Belloli, Robert C. J. Chem. Educ. 1983, 60, 190.
Aromatic Compounds |
Molecular Properties / Structure
|
Production of aromatic hydrocarbons according to extractive distillation process Molinier, J.; Malmary, G.; Constrasti, J.
A theme that deals with the study of the recovery of benzene from petroleum hydrocarbon mixture by means of an extractive distillation processes emerges from a pilot project that has been proposed to the graduating students.
Molinier, J.; Malmary, G.; Constrasti, J. J. Chem. Educ. 1983, 60, 148.
Separation Science |
Aromatic Compounds
|
Nitration of naphthol: A laboratory experiment Mowery, Dwight F.
The nitration of beta-naphthol to produce pyrotechnic snakes and the nitration of alpha-naphthol to produce Martius yellow dye.
Mowery, Dwight F. J. Chem. Educ. 1982, 59, 689.
Aromatic Compounds
|
Begone odious benzene, carbon tet, and chloroform Carlton, Terry S.
Using benzene, carbon tet and chloroform safely and substituting them with safer solvents.
Carlton, Terry S. J. Chem. Educ. 1982, 59, 530.
Aromatic Compounds
|
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
|
A novel bomb calorimetric determination of the resonance energy of benzene Pickering, Miles
Improvements to an earlier experimental procedure.
Pickering, Miles J. Chem. Educ. 1982, 59, 318.
Aromatic Compounds
|
Was there a conspiracy when Kekul's first German benzene-structure paper was frequently listed as published in 1865? Wotiz, John H.; Rudofsky, Susanna
The question of whether Kekul was deliberately ambiguous cannot be answered without a search through editorial files and personal correspondence.
Wotiz, John H.; Rudofsky, Susanna J. Chem. Educ. 1982, 59, 23.
Aromatic Compounds |
Molecular Properties / Structure
|
An undergraduate laboratory program project involving photocyclizations in independent syntheses of novel chrysenes and phenanthrenes Letcher, R. M.
This experiment attempts to fulfill such objectives as providing meaningful and viable preparative reactions, providing an opportunity for independent laboratory work within a project framework and under conditions of nearly equal opportunity and experience.
Letcher, R. M. J. Chem. Educ. 1981, 58, 1020.
Undergraduate Research |
Synthesis |
Aromatic Compounds |
Photochemistry |
Diastereomers |
NMR Spectroscopy |
Alcohols |
Thin Layer Chromatography
|
Structure-resonance theory for pericyclic transition states Herndon, William C.
The purpose of this article is to show that structure-resonance theory can be used to understand the effects of structure or substituents on the rates of thermal pericyclic reactions.
Herndon, William C. J. Chem. Educ. 1981, 58, 371.
Aromatic Compounds |
Resonance Theory |
Molecular Properties / Structure
|
Benzene, a familiar hazard? Smith, Roger M.
Reviews the hazards of benzene.
Smith, Roger M. J. Chem. Educ. 1980, 57, A85.
Aromatic Compounds |
Toxicology
|
Purple benzene revisited Doheny, Anthony J., Jr.; Ganem, Bruce
A variant of the referenced demonstration using crown ethers.
Doheny, Anthony J., Jr.; Ganem, Bruce J. Chem. Educ. 1980, 57, 308.
Aromatic Compounds |
Molecular Properties / Structure |
Ethers
|
Friedel-Crafts acylation: An experiment incorporating spectroscopic structure determination Schatz, Paul F.
Students use IR and NMR methods to determine the product of an aromatic substitution.
Schatz, Paul F. J. Chem. Educ. 1979, 56, 480.
Spectroscopy |
IR Spectroscopy |
NMR Spectroscopy |
Molecular Properties / Structure |
Aromatic Compounds
|
Chemical toxicology. Part I. Organic compounds Carter, D. E.; Fernando, Quintus
General principles of toxicology, and particular consideration of aliphatics, aromatic, and halogenated hydrocarbons; alcohols, aldehydes, esters, ethers, and ketones; sulfides, mercaptans, and carbon disulfide; nitrogen-containing compounds; and carcinogens.
Carter, D. E.; Fernando, Quintus J. Chem. Educ. 1979, 56, 284.
Toxicology |
Alcohols |
Aldehydes / Ketones |
Esters |
Ethers |
Aromatic Compounds |
Amines / Ammonium Compounds |
Lipids
|
Dealkylation-isomerization of p-di-t-butylbenzene Hawbecker, Byron L.; Kurtz, David W.; Elliott, Howard A.
The experiment described here can be conveniently used to explore several important facets of electrophilic aromatic substitution often ignored in typical laboratory programs.
Hawbecker, Byron L.; Kurtz, David W.; Elliott, Howard A. J. Chem. Educ. 1978, 55, 777.
Aromatic Compounds |
Electrophilic Substitution
|
Phase transfer catalysis. Part II: Synthetic applications Gokel, George W.; Weber, William P.
In this month's continuation of an article, the authors have catalogued a number of illustrative examples so that the range of applicability of phase transfer catalysis will be.
Gokel, George W.; Weber, William P. J. Chem. Educ. 1978, 55, 429.
Phases / Phase Transitions / Diagrams |
Catalysis |
Aromatic Compounds |
Organometallics |
Nucleophilic Substitution |
Synthesis |
Esters |
Oxidation / Reduction |
Alkylation
|
Favorskii rearrangement in bridged polycyclic compounds Chenier, Philip J.
Favorskii rearrangement in bridged polycyclic compounds: This can be classified as an intramolecular rearrangement from carbon to carbon, involving a migrating group Z moving without its electrons from migrating origin A to an electron-rich terminus B.
Chenier, Philip J. J. Chem. Educ. 1978, 55, 286.
Mechanisms of Reactions |
Carboxylic Acids |
Aldehydes / Ketones |
Aromatic Compounds
|
Sweet organic chemistry Bragg, Rose Wilson; Chow, Yvonne; Dennis, Lawrence; Ferguson, Lloyd N.; Howell, Susan; Morga, George; Ogino, Craig; Pugh, Harriet; Winters, Manque
The purpose of this paper is to examine some observed structure-taste correlation, and to explore one or two generalizations which might help elucidate the mechanism of taste stimulation. The sweetest compounds known to date are dipeptides; L-aspartyl-aminomalonic diester is reported to have relative sweetness of 22,000-33,200X.
Bragg, Rose Wilson; Chow, Yvonne; Dennis, Lawrence; Ferguson, Lloyd N.; Howell, Susan; Morga, George; Ogino, Craig; Pugh, Harriet; Winters, Manque J. Chem. Educ. 1978, 55, 281.
Food Science |
Natural Products |
Aromatic Compounds |
Enrichment / Review Materials
|
Vibronic analysis of the visible absorption and fluorescence spectra of the fluorescein dianion Kurucsev, Tomas
This laboratory exercise incorporates the study of the absorption spectrum of benzene. It is possible to demonstrate that remarkably simple interpretation may often be given to the solution spectra of quite complex organic aromatic molecules.
Kurucsev, Tomas J. Chem. Educ. 1978, 55, 128.
Aromatic Compounds |
Spectroscopy |
Fluorescence Spectroscopy
|
Substituent effects in electrophilic aromatic substitution. A laboratory in organic chemistry Gilow, Helmuth
The acid catalyzed bromination of aromatic substrates with hydrobromous acid.
Gilow, Helmuth J. Chem. Educ. 1977, 54, 450.
Molecular Properties / Structure |
Aromatic Compounds |
Electrophilic Substitution |
Mechanisms of Reactions |
Catalysis
|
Experiments with electrophilic aromatic substitution reactions Cox, B.; Kubler, D. G.; Wilson, C. A.
Comparing the bromination and nitration of benzene.
Cox, B.; Kubler, D. G.; Wilson, C. A. J. Chem. Educ. 1977, 54, 379.
Reactions |
Aromatic Compounds |
Electrophilic Substitution |
Stereochemistry |
Diastereomers
|
Purple benzene: Solubilization of anions in organic solvents Herriott, Arthur W.
Demonstrates the preference of a typical salt for solution in water rather than nonpolar benzene; a quaternary ammonium salt, though soluble in water, is more soluble in benzene.
Herriott, Arthur W. J. Chem. Educ. 1977, 54, 229.
Aromatic Compounds |
Precipitation / Solubility |
Solutions / Solvents |
Aqueous Solution Chemistry |
Molecular Properties / Structure
|
Where does resonance energy come from? A nonmathematical approach to the theory of aromaticity Sardella, D. J.
In confronting the central issue of why aromatic systems are aromatic, the author provides a verbal application of perturbational molecular orbital theory.
Sardella, D. J. J. Chem. Educ. 1977, 54, 217.
Aromatic Compounds |
MO Theory
|
The Friedel-Crafts pathway to diarylcyclopropenones. An undergraduate organic experiment Agranat, Israel; Tapuhi, Yitzhak
The authors describe a facile entry into the cyclopropenone series which may conveniently be practiced in an undergraduate organic chemistry laboratory.
Agranat, Israel; Tapuhi, Yitzhak J. Chem. Educ. 1976, 53, 531.
Aromatic Compounds |
Reactions
|
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
|
Imidazole - Versatile today, prominent tomorrow Matuszak, C. A.; Matuszak, A. J.
Imidazole chemistry has pedagogical utility for all the organic chemistry students pursing careers in the life sciences.
Matuszak, C. A.; Matuszak, A. J. J. Chem. Educ. 1976, 53, 280.
Grignard Reagents |
Aromatic Compounds |
Heterocycles |
Phenols |
Acids / Bases |
Catalysis |
Coordination Compounds |
Hydrogen Bonding
|
A simple lecture demonstration of aromatic nucleophilic substitution Smith, N. H. P.
Colors produced when various aromatic substrates are attacked by various nucleophiles (DMF, DMSO, EtOH).
Smith, N. H. P. J. Chem. Educ. 1975, 52, 238.
Aromatic Compounds |
Nucleophilic Substitution
|
The photoisomerization of cyclic ketones: An experiment in organic chemistry Haas, J. W., Jr.
This experiment deals with parameters such as the nature of the excited state, effect of triplet quenchers on product formation, chemical structure and reaction rate and quantum yield when cyclopentanone and cyclohexanone are irradiated at 254nm. These cyclic ketones provide a variety of photolysis information in a short time span, are conveniently analyzed by gas chromatography, and are readily available at the requisite levels of purity.
Haas, J. W., Jr. J. Chem. Educ. 1974, 51, 346.
Aldehydes / Ketones |
Aromatic Compounds |
Photochemistry |
Diastereomers |
Gas Chromatography
|
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 demonstration of charge-transfer complex formation using octachlorofulvalene West, Robert; Smith, R. Martin
A striking demonstration of charge-transfer complexation can be carried out using the unusual molecule octachlorofulvalene.
West, Robert; Smith, R. Martin J. Chem. Educ. 1973, 50, 723.
Molecular Properties / Structure |
Aromatic Compounds
|
Diphenyl ether. A versatile substance for laboratory demonstrations Cases, Jaime C.
The purification, properties, and uses of diphenyl ether in a variety of demonstrations.
Cases, Jaime C. J. Chem. Educ. 1973, 50, 420.
Ethers |
Solid State Chemistry |
Physical Properties |
Aromatic Compounds
|
Experiencing relevancy in organic chemistry. Hexachlorophene - manufacturing the great clean-all Moye, Alfred L.
Presents an experiment developed from a term paper by a student who had a serious dislike for organic chemistry.
Moye, Alfred L. J. Chem. Educ. 1972, 49, 770.
Applications of Chemistry |
Consumer Chemistry |
Aromatic Compounds |
Synthesis
|
Experimental illustration of chemical principles in organic chemistry lectures Haberfield, Paul
Lists a series of demonstrations used in the second semester of a one year organic chemistry course.
Haberfield, Paul J. Chem. Educ. 1972, 49, 702.
Electrophilic Substitution |
Aromatic Compounds |
Amines / Ammonium Compounds |
Nucleophilic Substitution
|
Preparation of 2,3-diphenyl-1-indenone and related compounds Clark, Thomas J.
The author describes a series of preparative experiments which students in organic chemistry have found enjoyable and instructive.
Clark, Thomas J. J. Chem. Educ. 1971, 48, 554.
Synthesis |
Aldehydes / Ketones |
Aromatic Compounds
|
Dewar resonance energy Baird, N. C.
In the present paper, some of the general properties of the Dewar Resonance Energy definition are developed. In particular, the DRE value for a compound is shown to be independent of the numerical values used to bond energies, and the use of DRE in judging the aromaticity of organic molecules is illustrated.
Baird, N. C. J. Chem. Educ. 1971, 48, 509.
Resonance Theory |
Aromatic Compounds |
Molecular Properties / Structure
|
Mechanism of aromatic iodination Butler, A. R.
The general halogenation process is given in inaccurate equilibrium textbooks.
Butler, A. R. J. Chem. Educ. 1971, 48, 508.
Aromatic Compounds
|
Substituent effects on aromatic electrophilic substitution. An "experimental" class exercise Fergwon, Philip R.
The exercise described here illustrates aromatic electrophilic substitution.
Fergwon, Philip R. J. Chem. Educ. 1971, 48, 405.
Electrophilic Substitution |
Aromatic Compounds
|
Nonlinear Hammett relationships Schreck, James 0.
The author provides examples of nonlinear structure-reactivity , Hammett correlation's, and summarize most of the types of reactions in which deviations due to change in mechanism or rate-controlling step occur.
Schreck, James 0. J. Chem. Educ. 1971, 48, 103.
Mechanisms of Reactions |
Aromatic Compounds
|
Fluorine compounds as teaching aids in organic theory Young, John A.
Fluorine compounds do obey the fundamental tenets of organic theory, but their frequent reversal of polarity, relative to hydrocarbon analogs, and the change in emphasis from a positive hydrogen ion to a negative fluoride ion allow the instructor to frame questions that demand reasoning rather than reiteration on the part of the student.
Young, John A. J. Chem. Educ. 1970, 47, 733.
Aromatic Compounds |
Mechanisms of Reactions
|
Aromatic nitro musk synthesis Nash, E. Gary; Nienhouse, Everett J.; Silhavy, Thomas A.; Humbert, Dale E.; Mish, Mary Jo
This synthesis involves the preparation of the nitro-musks, musk xylene and/or musk ketone, from readily available m-xylene.
Nash, E. Gary; Nienhouse, Everett J.; Silhavy, Thomas A.; Humbert, Dale E.; Mish, Mary Jo J. Chem. Educ. 1970, 47, 705.
Aromatic Compounds |
Synthesis
|
The photoaddition of maleic anhydride to benzene: A simple organic experiment in a complicated system Bozak, R. E.; Alvarez, V. E.
Presents the photochemical synthesis of benzopinacol as a pedagogical example of organic photochemistry suitable for the first-year organic course.
Bozak, R. E.; Alvarez, V. E. J. Chem. Educ. 1970, 47, 589.
Photochemistry |
Aromatic Compounds |
Synthesis
|
An integrated NMR and synthetic organic chemistry experiment Glaros, George; Cromwell, Norman H.
Presents a synthetic sequence that involves procedures of general utility and results in products illustrative of the basic principles of NMR spectroscopy.
Glaros, George; Cromwell, Norman H. J. Chem. Educ. 1969, 46, 854.
Spectroscopy |
NMR Spectroscopy |
Synthesis |
Mechanisms of Reactions |
Aromatic Compounds
|
Undergraduate experiments with tetrachlorobenzyne Heaney, H.; Marples, B. A.
Presents the preparation and experiments involving tetrachlorobenzyne.
Heaney, H.; Marples, B. A. J. Chem. Educ. 1968, 45, 801.
Aromatic Compounds |
Reactive Intermediates
|
The generation of benzyne - A warning Mich, Thomas F.; Nienhouse, Everett J.; Farino, Thomas E.; Tufariello, Joseph J.
The synthesis of benzyne by the diazotization of anthranilic acid may result in an explosion; an improved procedure to avoid this problem is presented.
Mich, Thomas F.; Nienhouse, Everett J.; Farino, Thomas E.; Tufariello, Joseph J. J. Chem. Educ. 1968, 45, 272.
Aromatic Compounds |
Synthesis
|
Letter to the editor (the author replies) Luder, W. F.
Replies to the concerns raised by the cited letter.
Luder, W. F. J. Chem. Educ. 1967, 44, 621.
Aromatic Compounds |
Covalent Bonding |
Molecular Properties / Structure
|
Letter to the editor Sementsov, A.
Questions the configuration of benzene supported by the theory discussed in the cited paper.
Sementsov, A. J. Chem. Educ. 1967, 44, 621.
Aromatic Compounds |
Covalent Bonding |
Molecular Properties / Structure
|
Teaching aromatic substitution: A molecular orbital approach Meislich, Herbert
This paper presents a way of teaching aromatic substitution using the concepts of alternate polarity and electron delocalization through extended pi-bonding.
Meislich, Herbert J. Chem. Educ. 1967, 44, 153.
Aromatic Compounds |
MO Theory |
Nucleophilic Substitution |
Covalent Bonding |
Molecular Properties / Structure
|
The activating effect of fluorine in electrophilic aromatic substitution Ault, Addison
It is demonstrated here that in certain electrophilic aromatic substitution reactions fluorine is actually an activating substituent.
Ault, Addison J. Chem. Educ. 1966, 43, 329.
Electrophilic Substitution |
Aromatic Compounds |
Mechanisms of Reactions
|
Xylene analysis: Integrated experiment in instrumental analysis Hanrahan, E. S.
Xylene containing major amounts of ethylbenzene, toluene, and three xylene isomers, is analyzed using infrared and gas chromatographic analysis.
Hanrahan, E. S. J. Chem. Educ. 1966, 43, 321.
Instrumental Methods |
IR Spectroscopy |
Gas Chromatography |
Aromatic Compounds
|
1-bromo-3-chloro-5-iodobenzene: An eight-step synthesis from benzene Ault, Addison; Kraig, Raymond
Presents an eight-step synthesis of 1-bromo-3-chloro-5-iodobenzene from benzene.
Ault, Addison; Kraig, Raymond J. Chem. Educ. 1966, 43, 213.
Synthesis |
Aromatic Compounds |
Mechanisms of Reactions
|
Sonnet on a benzene ring Moje, Stephen
Sonnet on a benzene ring.
Moje, Stephen J. Chem. Educ. 1966, 43, 151.
Aromatic Compounds
|
Who proposed the Dewar formula of benzene? Sementsov, A.
The bridged formula of benzene was first proposed by two German chemists in 1868.
Sementsov, A. J. Chem. Educ. 1966, 43, 151.
Aromatic Compounds
|
Aromatic substitution Duewell, H.
Reports on the use of the molecular orbit theory in a qualitative approach to the activation and orientation of substitution in aromatic systems.
Duewell, H. J. Chem. Educ. 1966, 43, 138.
Aromatic Compounds |
MO Theory |
Mechanisms of Reactions
|
A three-step synthesis: 2,4-Dinitrophenylhydrazine from benzene Ault, Addison
Presents a synthetic sequence for use in the introductory organic chemistry laboratory: the synthesis of 2,4-dinitrophenylhydrazine from benzene by way of bromobenzene and 2,4-dinitrobromobenzene.
Ault, Addison J. Chem. Educ. 1965, 42, 267.
Synthesis |
Aromatic Compounds |
Mechanisms of Reactions |
Reactions
|
The Friedel-Crafts alkylation of benzene: A first year organic laboratory experiment Dunathan, H. C.
This experiment involves the alkylation of benzene with each of the four butyl chlorides and aluminum chloride; the monobutylbenzenes from each reaction are then analyzed by vapor phase chromatography and IR spectroscopy.
Dunathan, H. C. J. Chem. Educ. 1964, 41, 278.
Aromatic Compounds |
Reactions |
Mechanisms of Reactions |
IR Spectroscopy
|
A pseudo first-order-second-order kinetics experiment: An illustration of the Guggenheim method Ahmad, Mushlaq; Hamer, Jan
The rate of one of the typical reactions of the aromatic nitroso group is determined spectrophotometrically employing the Guggenheim method.
Ahmad, Mushlaq; Hamer, Jan J. Chem. Educ. 1964, 41, 249.
Kinetics |
Rate Law |
Aromatic Compounds |
Spectroscopy
|
Benzene clathrate Bhatnagar, Vijay Mohan
Describes the properties and investigations of a benzene clathrate, [Ni(CN)2.NH3.C6H6].
Bhatnagar, Vijay Mohan J. Chem. Educ. 1963, 40, 646.
Aromatic Compounds
|
Functionally-substituted aromatic silanes Neville, Roy G.
The purpose of this article is to present a brief account of the functionally-substituted aromatic silanes.
Neville, Roy G. J. Chem. Educ. 1962, 39, 276.
Aromatic Compounds |
Organometallics
|
Structural variety of natural products Roderick, William R.
Classes of natural products examined includes alkynes; quinones; benzpyrones; small and large rings; sulfur, nitrogen, and halogen-containing compounds; and new amino acids.
Roderick, William R. J. Chem. Educ. 1962, 39, 2.
Natural Products |
Amino Acids |
Alkynes |
Aromatic Compounds
|
The chemistry of benzyne Bunnett, Joseph F.
Examines the chemistry of benzyne and alkynes.
Bunnett, Joseph F. J. Chem. Educ. 1961, 38, 278.
Aromatic Compounds |
Reactions |
Mechanisms of Reactions |
Alkynes
|
The side-chain halogenation of n-alkyl benzenes Goldwhite, H.
A number of textbooks state that in the halogenation of the side-chains of normal alkyl benzenes with elemental halogens there is a strong tendency for halogenation to take place preferentially at the carbon atom next to the aromatic nucleus; the literature does not support this conclusion.
Goldwhite, H. J. Chem. Educ. 1960, 37, 295.
Aromatic Compounds |
Alkylation |
Reactions
|
Aniline by a modified Jones reductor method Stubbs, U. Simpson, Jr.; Atkins, Cyril F.
By making certain simple modifications in the Jones reductor aniline can be prepared from nitrobenzene.
Stubbs, U. Simpson, Jr.; Atkins, Cyril F. J. Chem. Educ. 1959, 36, 611.
Synthesis |
Aromatic Compounds
|
The contributions of Fritz Arndt to resonance theory Campaigne, E.
Examines the contribution of Fritz Arndt to resonance theory and his work regarding the nature of bonds in pyrone ring systems.
Campaigne, E. J. Chem. Educ. 1959, 36, 336.
Resonance Theory |
Aromatic Compounds |
Covalent Bonding
|
Substituent effects on the benzene ring: A demonstration Lambert, Frank L.
In a series of simple experiments it can be visually demonstrated that -OH, -OR, and -NR2 powerfully activate the benzene ring.
Lambert, Frank L. J. Chem. Educ. 1958, 35, 342.
Aromatic Compounds |
Molecular Properties / Structure
|
Representation of polycyclic aromatic compounds Bieber, Theodore I.
Reviews the representation of polycyclic aromatic compounds and the matter of pi-electron sharing by adjacent sextets.
Bieber, Theodore I. J. Chem. Educ. 1958, 35, 235.
Aromatic Compounds |
Nomenclature / Units / Symbols |
Molecular Properties / Structure
|
The small scale preparation of azobenzene and of hydrazobenzene Vogel, A. I.; Watling, A.; Watling, J.
A satisfactory procedure for the preparation of azobenzene consists of the reduction of pure nitrobenzene with magnesium turnings and anhydrous methanol; hydrazobenzene may be prepared by reduction of nitrobenzene either with Devarda's alloy and sodium hydroxide solution or with excess of magnesium and anhydrous methanol.
Vogel, A. I.; Watling, A.; Watling, J. J. Chem. Educ. 1958, 35, 40.
Synthesis |
Aromatic Compounds
|
Aromatic substitution by free radicals Nelson, Peter F.
This article summarizes recent investigations upon orientation and reaction rates with respect to homolytic substitution.
Nelson, Peter F. J. Chem. Educ. 1955, 32, 606.
Free Radicals |
Aromatic Compounds |
Reactions |
Rate Law |
Molecular Properties / Structure
|
Nucleophilic substitution in aromatic systems Gillis, Richard G.
Classifies and examines various categories of nucleophilic substitution in aromatic systems.
Gillis, Richard G. J. Chem. Educ. 1955, 32, 296.
Nucleophilic Substitution |
Aromatic Compounds
|
The orientation and mechanism of electrophilic aromatic substitution Ferguson, Lloyd N.
Electrophilic aromatic substitution apparently takes place by the formation of an intermediate pentadienate cation, +ArG, where Ar is an aromatic molecule and G is a portion of the reagent.
Ferguson, Lloyd N. J. Chem. Educ. 1955, 32, 42.
Electrophilic Substitution |
Reactions |
Mechanisms of Reactions |
Aromatic Compounds
|
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
|
Kekule's theory of aromaticity Gero, Alexander
Examines what Kekule really wrote in his famous paper on the structure of benzene.
Gero, Alexander J. Chem. Educ. 1954, 31, 201.
Aromatic Compounds |
Molecular Properties / Structure |
Resonance Theory
|
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
|
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