TIGER

Journal Articles: 585 results
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 GCMS 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
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
Biphenyl  Jay A. Young
Safe handling and laboratory use of biphenyl are discussed.
Young, Jay A. J. Chem. Educ. 2008, 85, 1486.
Aromatic Compounds |
Laboratory Management
A Green, Guided-Inquiry Based Electrophilic Aromatic Substitution for the Organic Chemistry Laboratory  Eric Eby and S. Todd Deal
This alternative, electrophilic aromatic substitutionan iodination reaction of salicylamide, a popular analgesicuses environmentally friendly reagents and serves as a guided-inquiry experiment in which students are asked to predict the orientation of the substitution reaction and determine the product's structure using FT-IR spectroscopy.
Eby, Eric; Deal, S. Todd. J. Chem. Educ. 2008, 85, 1426.
Aromatic Compounds |
Constitutional Isomers |
Electrophilic Substitution |
Green Chemistry |
IR Spectroscopy |
Synthesis
The Comparative Nucleophilicity of Naphthoxide Derivatives in Reactions with a Fast-Red TR Dye  Cheryl M. Mascarenhas
In this experiment, organic chemistry students perform reactions between three naphthyl acetate derivatives and the diazonium salt Fast-Red TR. Students discover under what conditions the hydrolysis and electrophilic aromatic substitution is fastest and slowest, allowing them to conclude that latter, rather than the former, is rate-limiting.
Mascarenhas, Cheryl M. J. Chem. Educ. 2008, 85, 1271.
Alcohols |
Aromatic Compounds |
Dyes / Pigments |
Esters |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography |
UV-Vis Spectroscopy
Optimizing Chromatographic Separation: An Experiment Using an HPLC Simulator  R. A. Shalliker, S. Kayillo, and G. R. Dennis
An HPLC simulator from JCE Software and Excel spreadsheets are used to help students develop an appreciation for the complexities involved in the optimization of chromatographic separation procedures. The relationship between solvent composition and retention factor is measured to determine the solvent composition for maximized separation.
Shalliker, R. A.; Kayillo, S.; Dennis, G. R. J. Chem. Educ. 2008, 85, 1265.
Aromatic Compounds |
Chromatography |
Separation Science
Förster Resonance Energy Transfer and Conformational Stability of Proteins  Katheryn M. Sanchez, Diana E. Schlamadinger, Jonathan E. Gable, and Judy E. Kim
Describes the integration of absorption spectroscopy, fluorescence spectroscopy, and Frster resonance energy transfer (FRET) measurements to probe important topics in protein folding. Comparison of conformational stabilities of cytochrome c measured via two chemical denaturants illustrates important concepts in protein folding and intermolecular interactions.
Sanchez, Katheryn M.; Schlamadinger, Diana E.; Gable, Jonathan E.; Kim, Judy E. J. Chem. Educ. 2008, 85, 1253.
Biophysical Chemistry |
Fluorescence Spectroscopy |
Proteins / Peptides |
Quantum Chemistry |
Resonance Theory |
Spectroscopy |
Thermodynamics |
UV-Vis Spectroscopy
Kinetic Study of the Heck Reaction: An Interdisciplinary Experiment  Christel Gozzi and Naoual Bouzidi
The aim of this experiment is to study and calculate the kinetic constant of a Heck reaction. Students use GC analysis to quantify the reaction's reagents and products, control the global order of the reaction, prove that the two products are formed by two parallel reactions, and calculate the rate constant for each reaction.
Gozzi, Christel; Bouzidi, Naoual. J. Chem. Educ. 2008, 85, 1126.
Aromatic Compounds |
Catalysis |
Gas Chromatography |
Kinetics |
Mechanisms of Reactions |
Organometallics |
Rate Law |
Microscale Lab
Construction of a Polyaniline Nanofiber Gas Sensor  Shabnam Virji, Bruce H. Weiller, Jiaxing Huang, Richard Blair, Heather Shepherd, Tanya Faltens, Philip C. Haussmann, Richard B. Kaner, and Sarah H. Tolbert
The objectives of this lab are to synthesize different diameter polyaniline nanofibers and compare them as sensor materials. Its advantages include simplicity and low cost, making it suitable for both high school and college students, particularly in departments with modest means.
Virji, Shabnam; Weiller, Bruce H.; Huang, Jiaxing; Blair, Richard; Shepherd, Heather; Faltens, Tanya; Haussmann, Philip C.; Kaner, Richard B.; Tolbert, Sarah H. J. Chem. Educ. 2008, 85, 1102.
Acids / Bases |
Aromatic Compounds |
Conductivity |
Hydrogen Bonding |
Oxidation / Reduction |
Oxidation State |
pH |
Polymerization |
Synthesis
Preparation of Conducting Polymers by Electrochemical Methods and Demonstration of a Polymer Battery  Hiromasa Goto, Hiroyuki Yoneyama, Fumihiro Togashi, Reina Ohta, Akitsu Tsujimoto, Eiji Kita, and Ken-ichi Ohshima
The electrochemical polymerization of aniline and pyrrole, and demonstrations of electrochromism and the polymer battery effect, are presented as demonstrations suitable for high school and introductory chemistry at the university level.
Goto, Hiromasa; Yoneyama, Hiroyuki; Togashi, Fumihiro; Ohta, Reina; Tsujimoto, Akitsu; Kita, Eiji; Ohshima, Ken-ichi. J. Chem. Educ. 2008, 85, 1067.
Aromatic Compounds |
Conductivity |
Electrochemistry |
Materials Science |
Oxidation / Reduction |
Polymerization
Acid-Catalyzed Enolization of β-Tetralone  Brahmadeo Dewprashad, Anthony Nesturi, and Joel Urena
This experiment allows students to use 1H NMR to compare the rates of substitution of benzylic and non-benzylic a hydrogens of -tetralone and correlate their findings with predictions made by resonance theory.
Dewprashad, Brahmadeo; Nesturi, Anthony; Urena, Joel. J. Chem. Educ. 2008, 85, 829.
Aldehydes / Ketones |
Isotopes |
Mechanisms of Reactions |
NMR Spectroscopy |
Reactive Intermediates |
Resonance Theory |
Synthesis
Determination of Hammett Equation Rho Constant for the Hydrolysis of p-Nitrophenyl Benzoate Esters  Sheue L. Keenan, Karl P. Peterson, Kelly Peterson, and Kyle Jacobson
In this experiment, seven p-nitrophenyl benzoate esters are synthesized and characterized. Students then measure the rate constants for the base hydrolysis of these esters using UV-vis spectrophotometry and determine the Hammett equation constant for this hydrolysis reaction.
Keenan, Sheue L.; Peterson, Karl P.; Peterson, Kelly; Jacobson, Kyle. J. Chem. Educ. 2008, 85, 558.
Aromatic Compounds |
Esters |
IR Spectroscopy |
Kinetics |
Synthesis |
UV-Vis Spectroscopy
"Greening Up" the Suzuki Reaction  Evangelos Aktoudianakis, Elton Chan, Amanda R. Edward, Isabel Jarosz, Vicki Lee, Leo Mui, Sonya S. Thatipamala, and Andrew P. Dicks
This article describes the green synthesis of a biaryl compound via a Pd(0)-catalyzed Suzuki cross-coupling reaction in water. The methodology exposes students to purely aqueous microscale organic reactivity and showcases topical research regarding an industrial process.
Aktoudianakis, Evangelos; Chan, Elton; Edward, Amanda R.; Jarosz, Isabel; Lee, Vicki; Mui, Leo; Thatipamala, Sonya S.; Dicks, Andrew P. J. Chem. Educ. 2008, 85, 555.
Aromatic Compounds |
Catalysis |
Green Chemistry |
Microscale Lab |
Phenols |
Water / Water Chemistry
Supramolecular Inclusion in Cyclodextrins: A Pictorial Spectroscopic Demonstration  Basudeb Haldar, Arabinda Mallick, and Nitin Chattopadhyay
Presents a spectroscopic experiment to reveal that the hydrophobically end-modified, water-soluble, polymeric fluorophore, pyrene end-capped poly(ethylene oxide) interacts differently with alpha, beta, and gamma-cyclodextrins to form supramolecular inclusion complexes.
Haldar, Basudeb; Mallick, Arabinda; Chattopadhyay, Nitin. J. Chem. Educ. 2008, 85, 429.
Aqueous Solution Chemistry |
Aromatic Compounds |
Fluorescence Spectroscopy |
Noncovalent Interactions |
Photochemistry |
Physical Properties |
Spectroscopy |
UV-Vis Spectroscopy
Synthesis and Characterization of 9-Hydroxyphenalenone Using 2D NMR Techniques  Benjamin Caes and Dell Jensen Jr.
The synthesis of 9-Hydroxyphenalenone produces a planar multicyclic beta-ketoenol, the tautomerization of which results in C2v symmetry on the NMR time scale, thus simplifying the spectra and providing a unique structure for teaching 2D NMR spectroscopy.
Caes, Benjamin; Jensen, Dell, Jr. J. Chem. Educ. 2008, 85, 413.
Alcohols |
Aldehydes / Ketones |
Aromatic Compounds |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis
Six Pillars of Organic Chemistry  Joseph J. Mullins
This article focuses on a core set of conceptselectronegativity, polar covalent bonding, inductive and steric effects, resonance, and aromaticitythe proper application of which can explain and predict a wide variety of chemical, physical, and biological properties of molecules and conceptually unite important features of general, organic, and biochemistry.
Mullins, Joseph J. J. Chem. Educ. 2008, 85, 83.
Bioorganic Chemistry |
Covalent Bonding |
Hydrogen Bonding |
Mechanisms of Reactions |
Periodicity / Periodic Table |
Reactive Intermediates |
Resonance Theory
Predicting the Shifts of Absorption Maxima of Azulene Derivatives Using Molecular Modeling and ZINDO CI Calculations of UV–Vis Spectra  Wyona C. Patalinghug, Maharlika Chang, and Joanne Solis
Computational semiempirical methods using ZINDO CI are used to model azulene and azulene derivatives and to calculate their UVvis spectra. The calculated spectra are used to show the trends in absorption band shifts upon addition of electron-donating or electron-withdrawing groups at various carbon positions in azulene.
Patalinghug, Wyona C.; Chang, Maharlika; Solis, Joanne. J. Chem. Educ. 2007, 84, 1945.
Aromatic Compounds |
Computational Chemistry |
MO Theory |
Molecular Modeling |
Quantum Chemistry |
UV-Vis Spectroscopy
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
Probing the Rate-Determining Step of the Claisen–Schmidt Condensation by Competition Reactions  Kendrew K. W. Mak, Wing-Fat Chan, Ka-Ying Lung, Wai-Yee Lam, Weng-Cheong Ng, and Siu-Fung Lee
This article describes a physical organic experiment to identify the rate-determining step of the ClaisenSchmidt condensation of benzaldehyde and acetophenone by studying the linear free energy relationship.
Mak, Kendrew K. W.; Chan, Wing-Fat; Lung, Ka-Ying; Lam, Wai-Yee; Ng, Weng-Cheong; Lee, Siu-Fung. J. Chem. Educ. 2007, 84, 1819.
Aldehydes / Ketones |
Aromatic Compounds |
Gas Chromatography |
Kinetics |
Mechanisms of Reactions |
Synthesis
Synthesis of Triarylmethane and Xanthene Dyes Using Electrophilic Aromatic Substitution Reactions  James V. McCullagh and Kelly A. Daggett
In this experiment, electrophilic aromatic substitution reactions are used to synthesize several triarylmethane and xanthene dyes (fluorescein, erythrosin B, thymolphthalein, and rhodamine B) using common equipment while avoiding often troublesome, hydroscopic Lewis acids. Subsequent UVvis analysis produce spectra that match commercially available dye samples.
McCullagh, James V.; Daggett, Kelly A. J. Chem. Educ. 2007, 84, 1799.
Acids / Bases |
Aromatic Compounds |
Dyes / Pigments |
Electrophilic Substitution |
Equilibrium |
Synthesis |
UV-Vis Spectroscopy
Dancing Crystals: A Dramatic Illustration of Intermolecular Forces  Donald W. Mundell
Crystals of naphthalene form on the surface of an acetone solution and dance about in an animated fashion illustrating surface tension, crystallization, and intermolecular forces. Additional experiments reveal the properties of the solution and previous demonstrations of surface motion are explored.
Mundell, Donald W. J. Chem. Educ. 2007, 84, 1773.
Aromatic Compounds |
Liquids |
Molecular Mechanics / Dynamics |
Molecular Properties / Structure |
Physical Properties |
Surface Science |
Noncovalent Interactions
Discovering Electronic Effects of Substituents in Nitrations of Benzene Derivatives Using GC–MS Analysis  Malgorzata M. Clennan and Edward L. Clennan
Describes an organic lab in which students pool mass spectral data to identify the distribution of isomer products generated by the nitration of six benzene derivatives whose substituents differ in their electronic effects. Students also determine which substituents direct nitration predominantly to the ortho- or para- and to the meta positions.
Clennan, Malgorzata M.; Clennan, Edward L. J. Chem. Educ. 2007, 84, 1679.
Aromatic Compounds |
Constitutional Isomers |
Electrophilic Substitution |
Gas Chromatography |
Mass Spectrometry
The Aromaticity of Pericyclic Reaction Transition States  Henry S. Rzepa
Presents an approach that combines two fundamental concepts in organic chemistry, chirality and aromaticity, into a simple rule for stating selection rules for pericyclic reactions in terms of achiral Hckel-aromatic and chiral Mbius-aromatic transition states.
Rzepa, Henry S. J. Chem. Educ. 2007, 84, 1535.
Alkanes / Cycloalkanes |
Alkenes |
Aromatic Compounds |
Mechanisms of Reactions |
Stereochemistry
Reaction-Map of Organic Chemistry  Steven Murov
The Reaction-Map of Organic Chemistry has been designed to provide an overview of most of the reactions needed for the organic chemistry course and should help students develop synthetic routes from one functional group to another.
Murov, Steven. J. Chem. Educ. 2007, 84, 1224.
Addition Reactions |
Electrophilic Substitution |
Elimination Reactions |
Nucleophilic Substitution |
Oxidation / Reduction |
Periodicity / Periodic Table |
Reactions |
Synthesis |
Enrichment / Review Materials
Imidazole as a pH Probe: An NMR Experiment for the General Chemistry Laboratory  William J. Hagan, Jr., Dennis L. Edie, and Linda B. Cooley
An experiment is described that employs the 1H-NMR signal of aqueous imidazole to determine the pH of an unknown solution. The procedure involves the preparation of a calibration curve, which is then used for the analysis of the unknown(s).
Hagan, William J., Jr.; Edie, Dennis L.; Cooley, Linda B. J. Chem. Educ. 2007, 84, 1188.
Acids / Bases |
Aqueous Solution Chemistry |
Aromatic Compounds |
Calibration |
NMR Spectroscopy |
pH
Getting the Weights of Lewis Structures out of Hückel Theory: Hückel–Lewis Configuration Interaction (HL-CI)  Stéphane Humbel
A method to obtain the weights of Lewis structures from Hckel calculations is presented and tested against established ab initio methods.
Humbel, Stéphane. J. Chem. Educ. 2007, 84, 1056.
Computational Chemistry |
Lewis Structures |
Theoretical Chemistry |
Quantum Chemistry |
Resonance Theory |
Valence Bond Theory
Oxidation of Aromatic Aldehydes Using Oxone  Rajani Gandhari, Padma P. Maddukuri, and Thottumkara K. Vinod
Describes an eco-friendly procedure for the oxidation of aldehydes to carboxylic acids in water or a water-ethanol mixture using Oxone as the oxidant. The use of eco-friendly solvents, a non-toxic reagent, and the elimination of extraction solvents in the procedure demonstrate important green chemistry themes to students.
Gandhari, Rajani; Maddukuri, Padma P.; Vinod, Thottumkara K. J. Chem. Educ. 2007, 84, 852.
Aldehydes / Ketones |
Aromatic Compounds |
Aqueous Solution Chemistry |
Carboxylic Acids |
Green Chemistry |
Mechanisms of Reactions |
NMR Spectroscopy |
Oxidation / Reduction
Aromatic Bagels: An Edible Resonance Analogy  Shirley Lin
Describes a classroom demonstration involving the use of a bagel and cream cheese as an analogy for benzene that emphasizes the deficiencies of using a single Lewis structure to describe this structure.
Lin, Shirley. J. Chem. Educ. 2007, 84, 779.
Aromatic Compounds |
Lewis Structures |
Resonance Theory |
Molecular Properties / Structure
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
Competitive Nitration of Benzene–Fluorobenzene and Benzene–Toluene Mixtures: Orientation and Reactivity Studies Using HPLC  Ronald L. Blankespoor, Stephanie Hogendoorn, and Andrea Pearson
In this experiment for the first-year organic laboratory, mixtures of benzenetoluene and benzenefluorobenzene are competitively nitrated to determine the reactivity and orientation effects of CH3 and F. HPLC is used to analyze the reaction mixtures.
Blankespoor, Ronald L.; Hogendoorn, Stephanie; Pearson, Andrea. J. Chem. Educ. 2007, 84, 697.
Aromatic Compounds |
Constitutional Isomers |
Electrophilic Substitution |
HPLC
Electrochemical Quartz Crystal Microbalance Monitoring of the Cyclic Voltammetric Deposition of Polyaniline. A Laboratory Experiment for Undergraduates  Qingji Xie, Zhili Li, Chunyan Deng, Meiling Liu, Youyu Zhang, Ming Ma, Shaoxi Xia, Xiaoming Xiao, Dulin Yin, and Shouzhuo Yao
Describes a laboratory experiment for fourth-year undergraduates in which an electrochemical quartz crystal microbalance is used to monitor the cyclic voltammetric deposition of a conducting polyaniline thin film on an Au electrode.
Xie, Qingji; Li, Zhili; Deng, Chunyan; Liu, Meiling; Zhang, Youyu; Ma, Ming; Xia, Shaoxi; Xiao, Xiaoming; Yin, Dulin; Yao, Shouzhuo. J. Chem. Educ. 2007, 84, 681.
Aromatic Compounds |
Electrochemistry |
Oxidation / Reduction |
Polymerization
Chlorobenzene  Jay A. Young
Safety precautions for handling chlorobenzene are discussed.
Young, Jay A. J. Chem. Educ. 2007, 84, 590.
Aromatic Compounds |
Laboratory Management
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
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
o-Dichlorobenzene  Jay A. Young
The hazards of o-dichlorobenzene are discussed.
Young, Jay A. J. Chem. Educ. 2006, 83, 1754.
Laboratory Management |
Aromatic Compounds
Microwave-Mediated Synthesis of Lophine: Developing a Mechanism To Explain a Product   R. David Crouch, Jessica L. Howard, Jennifer L. Zile, and Kathryn H. Barker
Describes the microwave-mediated preparation of lophine (2,4,5-triphenylimidazole). The experiment also provides an opportunity for students to employ the principles of carbonyl chemistry in devising a mechanism to explain the formation of the product.
Crouch, R. David; Howard, Jessica L.; Zile, Jennifer L.; Barker, Kathryn H. J. Chem. Educ. 2006, 83, 1658.
Aldehydes / Ketones |
Amines / Ammonium Compounds |
Aromatic Compounds |
Microscale Lab |
Molecular Modeling |
Synthesis |
NMR Spectroscopy
Changing the Laboratory: Effects of a Laboratory Course on Students' Attitudes and Perceptions  Melanie M. Cooper and Timothy S. Kerns
In this study, students in an open-ended, project-based organic chemistry laboratory were compared with others in a more conventional, "cookbook" laboratory. Those in the experimental sections were more likely to view the lab as a place to experiment and make mistakes, while those in the conventional sections were more likely to adopt a passive role.
Cooper, Melanie M.; Kerns, Timothy S. J. Chem. Educ. 2006, 83, 1356.
Electrophilic Substitution |
Learning Theories |
Student-Centered Learning
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 hostguest interaction.
Shriver, James A.; Westphal, Scott G. J. Chem. Educ. 2006, 83, 1330.
Aromatic Compounds |
Hydrogen Bonding |
Molecular Recognition |
Synthesis |
Thin Layer Chromatography
More on the Nature of Resonance  Robert C. Kerber
The author continues to find the use of delocalization preferable to resonance.
Kerber, Robert C. . J. Chem. Educ. 2006, 83, 1291.
Aromatic Compounds |
Covalent Bonding |
Molecular Properties / Structure |
Resonance Theory |
Nomenclature / Units / Symbols
More on the Nature of Resonance  William B. Jensen
Supplements a recent article on the interpretation of resonance theory with three additional observationsone historical and two conceptual.
Jensen, William B. J. Chem. Educ. 2006, 83, 1290.
Aromatic Compounds |
Covalent Bonding |
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Resonance Theory
Purification and Modification of Fullerene C60 in the Undergraduate Laboratory  Tracey Spencer, Barney Yoo, and Kent Kirshenbaum
Describes an experiment for the extraction and column purification of buckminsterfullerene from fullerene-rich soot followed by a one-pot 1,3-dipolar cycloaddition of an azomethine ylide. Characterization of the starting material and product can be performed by UVVis, MS, 1H NMR, and 13C NMR.
Spencer, Tracey; Yoo, Barney; Kirshenbaum, Kent. J. Chem. Educ. 2006, 83, 1218.
Aromatic Compounds |
Chromatography |
NMR Spectroscopy |
UV-Vis Spectroscopy |
Synthesis |
Nanotechnology |
Reactions
Evaluating the Internal Charge-Transfer in Benzylidene Derivatives of N,N′-Dimethylbarbituric Acid  Marcos Caroli Rezende, Francisco Jara, and Moisés Domínguez
Four benzylidene derivatives of N,N'-dimethylbarbituric acid are prepared and their UVvisible and 1H NMR spectra used to characterize the molecular internal charge-transfer in the molecules.
Rezende, Marcos Caroli; Jara, Francisco; Domínguez, Moisés. J. Chem. Educ. 2006, 83, 937.
Aqueous Solution Chemistry |
Aromatic Compounds |
Dyes / Pigments |
Molecular Properties / Structure |
NMR Spectroscopy |
Synthesis |
UV-Vis Spectroscopy
Correction to "Determination of Hypochlorite in Bleaching Products with Flower Extracts To Demonstrate the Principles of Flow Injection Analysis" ( J. Chem. Ed. 2005, 82, 1815–1819)  
The article Determination of Hypochlorite in Bleaching Products with Flower Extracts To Demonstrate the Principles of Flow Injection Analysis (J. Chem. Educ. 2005, 82, 18151819)contains an incorrect equation on page 1815.
J. Chem. Educ. 2006, 83, 703.
Dyes / Pigments |
Natural Products |
Quantitative Analysis |
pH |
Aromatic Compounds |
UV-Vis Spectroscopy
Incorporation of Microwave Synthesis into the Undergraduate Organic Laboratory  Alan R. Katritzky, Chunming Cai, Meghan D. Collins, Eric F. V. Scriven, Sandeep K. Singh, and E. Keller Barnhardt
Describes a simple way to effectively implement microwave synthesis into the undergraduate organic laboratory curriculum.
Katritzky, Alan R.; Cai, Chunming; Collins, Meghan D.; Scriven, Eric F. V.;Singh, Sandeep K.; Barnhardt, E. Keller. J. Chem. Educ. 2006, 83, 634.
Aromatic Compounds |
Laboratory Equipment / Apparatus |
Reactions |
Synthesis
A Multistep Synthesis for an Advanced Undergraduate Organic Chemistry Laboratory  Chang Ji and Dennis G. Peters
Presents a three-step procedure for the synthesis of 5-(2-sulfhydrylethyl)salicylaldehyde employing a Grignard reagent as a critical reactant.
Ji, Chang; Peters, Dennis G. J. Chem. Educ. 2006, 83, 290.
Aromatic Compounds |
Chromatography |
IR Spectroscopy |
Mass Spectrometry |
NMR Spectroscopy |
Synthesis |
Grignard Reagents
Convenient Microscale Synthesis of a Coumarin Laser Dye Analog  Evangelos Aktoudianakis and Andrew P. Dicks
Describes the Knoevenagel synthesis of 3-acetyl-7-(diethylamino)-2H-1-benzopyran-2-one, a fluorescent coumarin laser dye analog.
Aktoudianakis, Evangelos; Dicks, Andrew P. J. Chem. Educ. 2006, 83, 287.
Aromatic Compounds |
Fluorescence Spectroscopy |
IR Spectroscopy |
Microscale Lab |
Synthesis |
NMR Spectroscopy |
UV-Vis Spectroscopy
Assaying α-Dicarbonyl Compounds in Wine: A Complementary GC–MS, HPLC, and Visible Spectrophotometric Analysis  Tammy J. Dwyer and Jeremiah D. Fillo
A facile, aqueous reaction coupled with gas chromatographymass spectrometry, visible spectrophotometry, and high performance liquid chromatography is used to quantify the amounts of a-dicarbonyl compounds in wine samples.
Dwyer, Tammy J.; Fillo, Jeremiah D. J. Chem. Educ. 2006, 83, 273.
Aromatic Compounds |
Chromatography |
Food Science |
HPLC |
Mass Spectrometry |
Quantitative Analysis |
Synthesis |
UV-Vis Spectroscopy
If It's Resonance, What Is Resonating?  Robert C. Kerber
This article reviews the origin of the terminology associated with the use of more than one Lewis-type structure to describe delocalized bonding in molecules and how the original usage has evolved to reduce confusion
Kerber, Robert C. . J. Chem. Educ. 2006, 83, 223.
Aromatic Compounds |
Covalent Bonding |
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Resonance Theory
Determination of Hypochlorite in Bleaching Products with Flower Extracts To Demonstrate the Principles of Flow Injection Analysis  Luiz Antônio Ramos, Kátia Roberta Prieto, Éder Tadeu Gomes Cavalheiro, and Carla Cristina Schmitt Cavalheiro
Proposes the use of crude flower extracts and a bleaching reaction between hypochlorite and anthocyanins to teach the principles of flow injection procedures.
Ramos, Luiz Antônio; Prieto, Kátia Roberta; Cavalheiro, Éder Tadeu Gomes; Cavalheiro, Carla Cristina Schmitt. J. Chem. Educ. 2005, 82, 1815.
Dyes / Pigments |
Natural Products |
pH |
Quantitative Analysis |
UV-Vis Spectroscopy |
Aromatic Compounds
Acid-Catalyzed Isomerization of Carvone to Carvacrol  Richard A. Kjonaas and Shawn P. Mattingly
Describes the acid-catalyzed isomerization of carvone (oil of spearmint) to carvacrol (oil of origanum). The experiment demonstrates several important concepts including formation of a carbocation by protonation of an alkene, rearrangement of a carbocation, deprotonation of a carbocation, acid-catalyzed enolization, and aromaticity.
Kjonaas, Richard A.; Mattingly, Shawn P. J. Chem. Educ. 2005, 82, 1813.
Aromatic Compounds |
Medicinal Chemistry |
Natural Products |
NMR Spectroscopy
Benzaldehyde  Jay A. Young
The hazards of benzaldehyde are discussed.
Young, Jay A. J. Chem. Educ. 2005, 82, 1770.
Laboratory Management |
Aromatic Compounds
Benzene  Jay A. Young
The hazards of benzene are discussed.
Young, Jay A. J. Chem. Educ. 2005, 82, 1769.
Laboratory Management |
Aromatic Compounds
Benzidine  Jay A. Young
The hazards of benzidine are discussed.
Young, Jay A. J. Chem. Educ. 2005, 82, 1768.
Laboratory Management |
Aromatic Compounds
The Introduction of High-Throughput Experimentation Methods for Suzuki–Miyaura Coupling Reactions in University Education  Richard Hoogenboom, Michael A. R. Meier, and Ulrich S. Schubert
To prepare students to work with novel techniques in their future careers, a "classical" SuzukiMiyaura coupling reaction is performed and subsequently converted into a step-by-step procedure suitable for fully automated parallel synthesis robots.
Hoogenboom, Richard; Meier, Michael A. R.; Schubert, Ulrich S. J. Chem. Educ. 2005, 82, 1693.
Combinatorial Chemistry |
Instrumental Methods |
Aromatic Compounds |
Laboratory Equipment / Apparatus |
Synthesis |
Fluorescence Spectroscopy |
NMR Spectroscopy
Azulene Chemistry  
The months Featured Molecules illustrate some of the chemistry of a substituted azulene, a structural isomer of naphthalene.
J. Chem. Educ. 2005, 82, 1688.
Molecular Properties / Structure |
Molecular Modeling |
Aromatic Compounds
An Azulene-Based Discovery Experiment: Challenging Students To Watch for the "False Assumption"  Charles M. Garner
Abundant inconsistencies between the "expected" structure of a product and its observed color, solubility, polarity, and NMR spectra causes students to be much more observant and critical of their results, particularly with respect to interpretation of NMR spectra.
Garner, Charles M. J. Chem. Educ. 2005, 82, 1686.
Aromatic Compounds |
NMR Spectroscopy |
Microscale Lab |
Reactions |
Synthesis |
Chromatography
The Quantitative Determination of Butylated Hydroxytoluene in Chewing Gum Using GC–MS  A. E. Witter
An undergraduate experiment for the quantitative determination of the synthetic antioxidant butylated hydroxytoluene (BHT) in chewing gum is described. A simple extraction procedure was used that did not require sample derivatization for analysis.
Witter, A. E. J. Chem. Educ. 2005, 82, 1538.
Food Science |
Free Radicals |
Instrumental Methods |
Mass Spectrometry |
Quantitative Analysis |
Aromatic Compounds |
Chromatography |
Consumer Chemistry |
Gas Chromatography
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
Formation of α-Tetralone by Intramolecular Friedel–Crafts Acylation  Michael S. Holden, R. David Crouch, and Kathryn A. Barker
A microscale procedure is described for the formation of the industrially-important compound alpha-tetralone. This is an example of an intramolecular FriedelCrafts acylation, utilizing 4-phenylbutanoic acid and a proton source. The title reaction demonstrates the concept of ring-forming reactions and highlights the use of carboxylic acids as an electrophile precursor in electrophilic aromatic substitution reactions.
Holden, Michael S.; Crouch, R. David; Barker, Kathryn A. J. Chem. Educ. 2005, 82, 934.
Aromatic Compounds |
Microscale Lab |
Synthesis |
Carboxylic Acids |
IR Spectroscopy |
NMR Spectroscopy
A Green Starting Material for Electrophilic Aromatic Substitution for the Undergraduate Organic Laboratory  T. Michelle Jones-Wilson and Elizabeth A. Burtch
Traditional experiments in the undergraduate organic chemistry laboratory involve the use of hazardous organic materials. Substitution of alternative green procedures wherever possible reduces organic waste and allows students to consider the need for environmentally sound chemistry. A green electrophilic aromatic substitution reaction (EAS), nitration of tyrosine, has been developed for use in the undergraduate laboratory. This reaction allows students to consider the varied aspects of EAS including activating and deactivating groups and o, p, m directors in a green environment.
Jones-Wilson, T. Michelle; Burtch, Elizabeth A. J. Chem. Educ. 2005, 82, 616.
Amino Acids |
Aromatic Compounds |
Green Chemistry |
Synthesis |
Electrophilic Substitution
"You're Repulsive!"Teaching VSEPR in a Not-So-Elegant Way  Robert S. H. Liu
Valence shell electron pair repulsive (VSEPR) interaction is an important concept particularly in discussing structural properties of molecules. In this article we showed five organic examples not commonly associated with VSEPR but yet all involving repulsive interactions of valence electrons, which provides ready explanations for altered chemical reactivity and spectroscopic properties of organic compounds. The ready catchy phrase Youre Repulsive! is the common thread used throughout these five examples.
Liu, Robert S. H. J. Chem. Educ. 2005, 82, 558.
Mechanisms of Reactions |
UV-Vis Spectroscopy |
Reactions |
Addition Reactions |
Electrophilic Substitution
Comments on Purser's Article: "Lewis Structures are Models for Predicting Molecular Structure, Not Electronic Structure"   Gordon H. Purser
Weinhold makes four major criticisms of my article. I shall address each of these criticisms.
Purser, Gordon H. J. Chem. Educ. 2005, 82, 528.
Molecular Properties / Structure |
Lewis Structures |
Resonance Theory |
MO Theory
Comments on Purser's Article: "Lewis Structures are Models for Predicting Molecular Structure, Not Electronic Structure"  Frank Weinhold
Some time ago in this Journal, Purser expressed strong views on the proper teaching of Lewis structures, as summarized in the quoted title. Because his criticisms are based on substantial factual misrepresentations and errors, it seemed desirable to call attention to a few of the conspicuous misstatements in order that readers may judge the opinions and conclusions from a more informed perspective.
Weinhold, Frank. J. Chem. Educ. 2005, 82, 527.
Molecular Properties / Structure |
Lewis Structures |
Resonance Theory |
MO Theory
The Evolution of a Green Chemistry Laboratory Experiment: Greener Brominations of Stilbene  Lallie C. McKenzie, Lauren M. Huffman, and James E. Hutchison
We describe two new greener alkene bromination reactions that offer enhanced laboratory safety and convey important green chemistry concepts, in addition to illustrating the chemistry of alkenes. The two alternative reactions, one involving pyridinium tribromide and a second using hydrogen peroxide and hydrobromic acid, are compared to the traditional bromination of stilbene through the application of green metrics, including atom economy, percent experimental atom economy, E factor, and effective mass yield.
McKenzie, Lallie C.; Huffman, Lauren M.; Hutchison, James E. J. Chem. Educ. 2005, 82, 306.
Synthesis |
Green Chemistry |
Aromatic Compounds |
Addition Reactions |
Alkenes
Rotor-shaped Cyclopentadienyltetraphenylcyclobutadienecobalt. An Advanced Inorganic Experiment  Darren K. MacFarland and Rebecca Gorodetzer
An advanced laboratory experiment involving the synthesis of the title compound is described. The suitability of the compound for teaching inert-atmosphere techniques and the stability of the product are discussed. The compound has interesting structural features that pique student interest.
MacFarland, Darren K.; Gorodetzer, Rebecca. J. Chem. Educ. 2005, 82, 109.
Aromatic Compounds |
Synthesis |
IR Spectroscopy |
NMR Spectroscopy |
Organometallics
A Discovery-Based Friedel–Crafts Acylation Experiment: Student-Designed Experimental Procedure  Anne McElwee Reeve
A discovery-based FriedelCrafts 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
Coumarin, Naphthalene, and Additional Polycyclic Aromatic Hydrocarbons  William F. Coleman
Fully manipulative Chime versions of these molecules are available online.
Coleman, William F. J. Chem. Educ. 2004, 81, 912.
Aromatic Compounds |
Molecular Modeling |
Molecular Properties / Structure
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
Developing Investigation Skills in an Introductory Multistep Synthesis Using Fluorene Oxidation and Reduction  Mark G. Stocksdale, Steven E. S. Fletcher, Ian Henry, Paul J. Ogren, Michael A. G. Berg, Roy D. Pointer, and Barrett W. Benson
A two-step reaction sequence in the beginning organic laboratory provides a useful introduction to the importance of multistep synthesis. In addition to introducing several common synthetic methods and techniques, a two-step preparation can quickly establish the importance of testing alternative reactions in order to optimize intermediate yields.
Stocksdale, Mark G.; Fletcher, Steven E. S.; Henry, Ian; Ogren, Paul J.; Berg, Michael A. G.; Pointer, Roy D.; Benson, Barrett W. J. Chem. Educ. 2004, 81, 388.
Chromatography |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Aromatic Compounds |
Oxidation / Reduction
Polycyclic Aromatic Hydrocarbons  William F. Coleman
The Featured Molecules for the month of February are a number of polycyclic aromatic hydrocarbons (PAHs) discussed in the article Fluorescence, Absorption, and Excitation Spectra of Polycyclic Aromatic Hydrocarbons as a Tool for Quantitative Analysis.
Coleman, William F. J. Chem. Educ. 2004, 81, 245.
Molecular Modeling |
Molecular Properties / Structure |
Aromatic Compounds
Fluorescence, Absorption, and Excitation Spectra of Polycyclic Aromatic Hydrocarbons as a Tool for Quantitative Analysis  A. M. Rivera-Figueroa, K. A. Ramazan, and B. J. Finlayson-Pitts
An experiment suitable for college junior or senior students in the analytical instrumental analysis laboratory that demonstrates the analysis of PAHs (benzo[a]anthracene, benzo[k]fluoranthene, benzo[a]pyrene, chrysene, and phenanthrene) using absorption and fluorescence spectroscopy is described.
Rivera-Figueroa, A. M.; Ramazan, K. A.; Finlayson-Pitts, B. J. J. Chem. Educ. 2004, 81, 242.
Fluorescence Spectroscopy |
Molecular Properties / Structure |
Quantitative Analysis |
UV-Vis Spectroscopy |
Aromatic Compounds |
Photochemistry
Steam Hydrocarbon Cracking and Reforming  Michael Golombok
We examine steam hydrocarbon reforming and steam hydrocarbon cracking as an example of two processes that operate under different chemical reactivity regimes: equilibrium determined and kinetically determined, respectively. The feed streams and reaction conditions are similar, but the products are different. The role of catalysis for the two processes is compared and the effects on the kinetics are discussed.
Golombok, Michael. J. Chem. Educ. 2004, 81, 228.
Aromatic Compounds |
Equilibrium |
Gases |
Industrial Chemistry |
Kinetics
Microscale Synthesis of 1-Bromo-3-chloro-5-iodobenzene: An Improved Deamination of 4-Bromo-2-chloro-6-iodoaniline  Michael W. Pelter, Libbie S.W. Pelter, Dusanka Colovic, and Regina Strug
Overall, we find this procedure to be advantageous to the published methods owing to its requirement of less starting material, higher product yields, and a greatly simplified procedure.
Pelter, Michael W.; Pelter, Libbie S.W.; Colovic, Dusanka; Strug, Regina. J. Chem. Educ. 2004, 81, 111.
Microscale Lab |
Synthesis |
Aromatic Compounds |
Amines / Ammonium Compounds
An Acid Hydrocarbon: A Chemical Paradox  Jeffrey T. Burke
This article explores the use of paradox as a teaching and learning strategy. Specifically, students observe the acid-like paradoxical behavior of the hydrocarbon cyclopentadiene. This observation then serves as a springboard to an understanding of the non-benzenoid aromatics.
Burke, Jeffrey T. J. Chem. Educ. 2004, 81, 65.
Acids / Bases |
Aromatic Compounds
Analytical Spectroscopy Using Modular Systems  Brian M. Patterson, Neil D. Danielson, Gary A. Lorigan, and André J. Sommer
This article describes the development of three analytical spectroscopy experiments that compare the determination of salicylic acid (SA) content in aspirin tablets. The experiments are based on UVvis, fluorescence, and Raman spectroscopies and utilize modular spectroscopic components. Students assemble their own instruments, optimize them with respect to signal-to-noise, generate calibration curves, determine the SA content in retail aspirin tablets, and assign features in the respective spectra to functional groups within the active material.
Patterson, Brian M.; Danielson, Neil D.; Lorigan, Gary A.; Sommer, André J. J. Chem. Educ. 2003, 80, 1460.
Fluorescence Spectroscopy |
Laboratory Equipment / Apparatus |
Quantitative Analysis |
Raman Spectroscopy |
UV-Vis Spectroscopy |
Aromatic Compounds |
Esters |
Carboxylic Acids |
Alcohols
A Polymer-Supported Organic Reaction: Seeing Is Believing  E. Hailstone, N. Huther, and A. F. Parsons
In this laboratory experiment, an amide-coupling reaction is carried out on a polymer support, and the reaction is monitored using different chemical stains. This effectively demonstrates, through color changes, the reaction of a polymer-supported amine that provides students with valuable practical experience of this important and modern advance in organic chemistry methodology.
Hailstone, E.; Huther, N.; Parsons, A. F. J. Chem. Educ. 2003, 80, 1444.
Drugs / Pharmaceuticals |
Dyes / Pigments |
Solid State Chemistry |
Synthesis |
Aromatic Compounds
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
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
Photoinduced Oxidative DNA Damage Revealed by an Agarose Gel Nicking Assay: A Biophysical Chemistry Laboratory Experiment  Vladimir Shafirovich, Carolyn Singh, and Nicholas E. Geacintov
This article describes the design of several simple experiments to explore DNA damage initiated by photoinduced electron-transfer reactions sensitized by the acridine derivative, proflavine (PF). A supercoiled DNAagarose gel nicking assay is employed as a sensitive probe of DNA strand cleavage.
Shafirovich, Vladimir; Singh, Carolyn; Geacintov, Nicholas E. J. Chem. Educ. 2003, 80, 1297.
Biophysical Chemistry |
Drugs / Pharmaceuticals |
Photochemistry |
Aromatic Compounds |
Nucleic Acids / DNA / RNA
A Nonlinear Optical Experiment: Stimulated Raman Scattering in Benzene and Deuterated Benzene  Stéphanie Melin and Joseph W. Nibler
A sampling arrangement is described that results in strong stimulated Raman emission involving symmetric CC and CH(CD) stretching modes in both C6H6 and C6D6. The wavelengths of the coherent beams are easily measured with a simple transmission grating and meter stick. Observations of both collinear and conical stimulated Raman beams are made and the reasons for these discussed.
Melin, Stéphanie; Nibler, Joseph W. J. Chem. Educ. 2003, 80, 1187.
Aromatic Compounds |
Lasers |
Spectroscopy |
Raman Spectroscopy
The Base-Induced Reaction of Salicylaldehyde with 1-Bromobutane in Acetone: Two Related Examples of Chemical Problem Solving  Holly D. Bendorf and Chriss E. McDonald
Each student performs his or her own experimental work, running one of the two reactions, and acquiring the proton and carbon NMR, IR, and mass spectra. The students work in groups to propose structures for the products and mechanisms for their formation. The students are also asked to address why the reactions take different courses.
Bendorf, Holly D.; McDonald, Chriss E. J. Chem. Educ. 2003, 80, 1185.
Chromatography |
Mass Spectrometry |
NMR Spectroscopy |
Aromatic Compounds |
Aldehydes / Ketones |
Ethers |
Phenols |
IR Spectroscopy
Writing Electron Dot Structures   Kenneth R. Magnell
Drill with feedback for students learning to write electron dot structures.
Magnell, Kenneth R. J. Chem. Educ. 2003, 80, 711.
Covalent Bonding |
Lewis Structures |
Resonance Theory |
Enrichment / Review Materials
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
Spiral Puzzle for Organic Chemistry Students  Ender Erdik
Puzzle to review organic reactions and their reagents.
Erdik, Ender. J. Chem. Educ. 2003, 80, 428.
Synthesis |
Learning Theories |
Enrichment / Review Materials |
Addition Reactions |
Alkylation |
Electrophilic Substitution |
Elimination Reactions |
Reactions |
Nucleophilic Substitution |
Mechanisms of Reactions |
Grignard Reagents
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
Featured Molecules: Enantiomers of Guaifenesin  William F. Coleman and Randall J. Wildman
Fully manipulable Chime versions of guaifenesin or 3-(2-methoxyphenoxy)-1,2-propanediol, an aromaric ether, for the article "Semi-Microscale Williamson Ether Synthesis and Simultaneous Isolation of an Expectorant from Cough Tablets"
Coleman, William F.; Wildman, Randall J. J. Chem. Educ. 2003, 80, 315.
Molecular Modeling |
Molecular Properties / Structure |
Aromatic Compounds |
Esters
Semi-Microscale Williamson Ether Synthesis and Simultaneous Isolation of an Expectorant from Cough Tablets  Ryan G. Stabile and Andrew P. Dicks
Procedure for synthesis of the active ingredient in many well-known, over-the-counter cough syrups - 3-(2-methoxyphenoxy)-1,2-propanediol, an aromaric ether.
Stabile, Ryan G.; Dicks, Andrew P. J. Chem. Educ. 2003, 80, 313.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Mathematics / Symbolic Mathematics |
Microscale Lab |
Synthesis |
Stereochemistry |
Applications of Chemistry |
Ethers |
Aromatic Compounds |
Medicinal Chemistry
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
A General Chemistry Laboratory Theme: Spectroscopic Analysis of Aspirin  Houston Byrd and Stephen E. O’Donnell
A laboratory sequence designed for introductory chemistry students that focusses on the synthesis and spectroscopic (IR and NMR) and chromatographic (HPLC) analysis of aspirin as an alternative to traditional general chemistry laboratories.
Byrd, Houston; O’Donnell, Stephen E. J. Chem. Educ. 2003, 80, 174.
Drugs / Pharmaceuticals |
Chromatography |
NMR Spectroscopy |
UV-Vis Spectroscopy |
Aromatic Compounds |
Atomic Spectroscopy |
Instrumental Methods
Chemical Recycling of Pop Bottles: The Synthesis of Dibenzyl Terephthalate from the Plastic Polyethylene Terephthalate  Craig J. Donahue, Jennifer A. Exline, and Cynthia Warner
Procedure in which students depolymerize a common plastic (PET from 2-L pop bottles) under mild conditions using nontoxic chemicals to produce monomer building blocks.
Donahue, Craig J.; Exline, Jennifer A.; Warner, Cynthia. J. Chem. Educ. 2003, 80, 79.
Industrial Chemistry |
Synthesis |
Aromatic Compounds |
Polymerization
Featured Molecule: Dibenzyl Terephthalate  William F. Coleman and Randall J. Wildman
Fully manipulable Chime version of dibenzyl terephthalate.
Coleman, William F.; Wildman, Randall J. J. Chem. Educ. 2003, 80, 75.
Molecular Modeling |
Molecular Properties / Structure |
Aromatic Compounds
Triboluminescent Crystals from the Microwave Oven  Bruce W. Baldwin and David M. Wilhite
Procedure for producing triboluminescent crystals in a microwave oven.
Baldwin, Bruce W.; Wilhite, David M. J. Chem. Educ. 2002, 79, 1344.
Aromatic Compounds |
Crystals / Crystallography |
Synthesis |
Photochemistry
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
Preparing Students for Research: Synthesis of Substituted Chalcones as a Comprehensive Guided-Inquiry Experience  James R. Vyvyan, Donald L. Pavia, Gary M. Lampman, and George S. Kriz Jr.
An aldol condensation of substituted benzaldehydes with substituted acetophones to produce substituted benzalacetophenones (chalcones) in a guided-inquiry approach.
Vyvyan, James R.; Pavia, Donald L.; Lampman, Gary M.; Kriz, George S., Jr. J. Chem. Educ. 2002, 79, 1119.
Medicinal Chemistry |
Microscale Lab |
Natural Products |
NMR Spectroscopy |
Synthesis |
Aromatic Compounds |
Aldehydes / Ketones
Teaching Molecular Applications of the Particle-in-a-Ring Model Using Azulene  Miguel A. R. B. Castanho
Using azulene as a 2-D, circular equivalent to the particle-in-a-box model.
Castanho, Miguel A. R. B. J. Chem. Educ. 2002, 79, 1092.
Molecular Properties / Structure |
UV-Vis Spectroscopy |
Aromatic Compounds |
Molecular Modeling
1H NMR Measurement of the Trans–Cis Photoisomerization of Cinnamic Acid Derivatives  Basil Danylec and Magdy N. Iskander
Procedure that illustrates trans-cis photoisomerization.
Danylec, Basil; Iskander, Magdy N. J. Chem. Educ. 2002, 79, 1000.
NMR Spectroscopy |
Photochemistry |
Stereochemistry |
Aromatic Compounds |
Alcohols |
Esters |
Alkenes |
Molecular Properties / Structure
A Structure–Activity Investigation of Photosynthetic Electron Transport. An Interdisciplinary Experiment for the First-Year Laboratory  Kerry K. Karukstis, Gerald R. Van Hecke, Katherine A. Roth, and Matthew A. Burden
Investigation in which students measure the effect of several inhibitors (herbicides) on the electron transfer rate in chloroplasts and formulate a hypothesis between the inhibitor's activity and its structure as a means of using a physical technique to measure a chemical process in a biological system.
Karukstis, Kerry K.; Van Hecke, Gerald R.; Roth, Katherine A.; Burden, Matthew A. J. Chem. Educ. 2002, 79, 985.
Biophysical Chemistry |
Electrochemistry |
Noncovalent Interactions |
Molecular Properties / Structure |
UV-Vis Spectroscopy |
Aromatic Compounds |
Plant Chemistry
Aqueous-Phase Palladium-Catalyzed Coupling. A Green Chemistry Laboratory Experiment  Brandy A. Harper, J. Chance Rainwater, Kurt Birdwhistell, and D. Andrew Knight
Synthesis of triphenylphosphine monosulfonate, and its use in the aqueous-phase palladium-catalyzed coupling of iodobenzene with diethyl phosphite to give diethyl phenylphosphonate.
Harper, Brandy A.; Rainwater, J. Chance; Birdwhistell, Kurt; Knight, D. Andrew. J. Chem. Educ. 2002, 79, 729.
Catalysis |
NMR Spectroscopy |
Water / Water Chemistry |
Green Chemistry |
Aromatic Compounds
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
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
Keto-Enol Tautomers in a Carbonyl Phosphonium Salt  David E. Berry and G. W. Patenaude
Observations of keto-enol tautomers of a phosphonium ion.
Berry, David E.; Patenaude, G. W. J. Chem. Educ. 2002, 79, 498.
Synthesis |
NMR Spectroscopy |
Organometallics |
Resonance Theory
The Electrophilic Bromination of Toluene: Determination of the Ortho, Meta, and Para Ratios by Quantitative FTIR Spectrometry  Ross E. Smith IV, James R. McKee, and Murray Zanger
Determining the ratio of ortho:meta:para bromotoluenes when an electrophilic aromatic substitution is carried out on a monosubstituted benzene.
Smith, Ross E., IV; McKee, James R.; Zanger, Murray. J. Chem. Educ. 2002, 79, 227.
Instrumental Methods |
IR Spectroscopy |
Microscale Lab |
Synthesis |
Quantitative Analysis |
Electrophilic Substitution |
Aromatic Compounds
The Mechanism of Aqueous Hydrolysis of Nitro Derivatives of Phenyl Phenylmethanesulfonate. An Organic Laboratory Experiment  S. D. Mulder, B. E. Hoogenboom, and A. G. Splittgerber
Synthesis, purification, and characterization of three esters.
Mulder, S. D.; Hoogenboom, B. E.; Splittgerber, A. G. J. Chem. Educ. 2002, 79, 218.
Mechanisms of Reactions |
Molecular Properties / Structure |
Resonance Theory |
Reactive Intermediates |
Equilibrium |
Esters |
Aromatic Compounds |
Brønsted-Lowry Acids / Bases
Colorful Azulene and Its Equally Colorful Derivatives  Robert S. H. Liu
Analysis of azulene and related compounds for an explanation of their respective colors.
Liu, Robert S. H. J. Chem. Educ. 2002, 79, 183.
Atomic Properties / Structure |
MO Theory |
UV-Vis Spectroscopy |
Aromatic Compounds |
Alkenes
Synthesis of Quinolines and Their Characterization by 2-D NMR Spectroscopy  Pamela J. Seaton, R. Thomas Williamson, Abhijit Mitra, and Ali Assarpour
Synthesis of quinolines and their characterization by 2-D NMR spectroscopy.
Seaton, Pamela J.; Williamson, R. Thomas; Mitra, Abhijit; Assarpour, Ali. J. Chem. Educ. 2002, 79, 106.
NMR Spectroscopy |
Synthesis |
Mechanisms of Reactions |
Aromatic Compounds |
Heterocycles
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
Kinetic Derivations for Thermal Isomerizations of Monodeuterio Cyclic 1,3-Dienes through 1,5-Hydrogen Shifts  John E. Baldwin, Phyllis A. Leber, and Tamara W. Lee
Explicit derivations of equations defining relative concentrations versus time for five sets of monodeuterio cyclic 1,3-dienes.
Baldwin, John E.; Leber, Phyllis A.; Lee, Tamara W. J. Chem. Educ. 2001, 78, 1394.
Isotopes |
Kinetics |
Aromatic Compounds |
Alkenes
The Combined Effects of pH and Percent Methanol on the HPLC Separation of Benzoic Acid and Phenol  Seema M. Joseph and John A. Palasota
Investigating the combined effects of pH and percent methanol on the HPLC separation of benzoic acid and phenol.
Joseph, Seema M.; Palasota, John A. J. Chem. Educ. 2001, 78, 1381.
Chromatography |
Instrumental Methods |
Separation Science |
Carboxylic Acids |
Aromatic Compounds |
Phenols
Synthesis and Analysis of a Solvatochromic Dye, 1-(p-Dimethylaminophenyl)-2-nitroethylene. An Advanced Undergraduate Laboratory Experiment  Dana L. Richter-Egger, Aaron Tesfai, Spencer J. Flamm, and Sheryl A. Tucker
Synthesis and analysis of 1-(p-dimethylaminophenyl)-2-nitroethylene.
Richter-Egger, Dana L.; Tesfai, Aaron; Flamm, Spencer J.; Tucker, Sheryl A. J. Chem. Educ. 2001, 78, 1375.
Fluorescence Spectroscopy |
Synthesis |
Undergraduate Research |
UV-Vis Spectroscopy |
Dyes / Pigments |
Amines / Ammonium Compounds |
Aromatic Compounds |
Alkenes
Synthesis and Use of Jacobsen's Catalyst: Enantioselective Epoxidation in the Introductory Organic Laboratory  John Hanson
Laboratory series to introduce students to an important synthetic method and many common techniques used in running reactions, purifying products, and characterizing compounds.
Hanson, John. J. Chem. Educ. 2001, 78, 1266.
Catalysis |
Chirality / Optical Activity |
Synthesis |
Organometallics |
Stereochemistry |
Epoxides |
Enantiomers |
Aromatic Compounds
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
Using a Molecular Modeling Program to Calculate Electron Paramagnetic Resonance Hyperfine Couplings in Semiquinone Anion Radicals  Alice Haddy
Estimating hyperfine couplings to aromatic hydrogens based on hydrogen atom electron populations using HyperChem or other molecular modeling programs.
Haddy, Alice. J. Chem. Educ. 2001, 78, 1206.
Laboratory Computing / Interfacing |
MO Theory |
Computational Chemistry |
EPR / ESR Spectroscopy |
Molecular Modeling |
Aromatic Compounds
Binary Solid-Liquid Phase Diagrams of Selected Organic Compounds. A Complete Listing of 15 Binary Phase Diagrams  Jürgen Gallus, Qiong Lin, Andreas Zumbühl, Sebastian D. Friess, Rudolf Hartmann, and Erich C. Meister
A simple and low-cost apparatus that allows accurate and reproducible phase measurements in a broad temperature range; fifteen solid-liquid phase diagrams of binary systems that result from the systematic combination of six aromatic hydrocarbons are summarized.
Gallus, J¨rgen; Lin, Qiong; Zumb¨hl, Andreas; Friess, Sebastian D.; Hartmann, Rudolf; Meister, Erich C. J. Chem. Educ. 2001, 78, 961.
Equilibrium |
Laboratory Equipment / Apparatus |
Phases / Phase Transitions / Diagrams |
Thermal Analysis |
Thermodynamics |
Aromatic Compounds
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
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
Isolation and Spectral Analysis of Naturally Occurring Thiarubrine A  Juan Reyes, Melita Morton, Kelsey Downum, and Kevin E. O'Shea
An experiment in which students isolate (from ragweed) and characterize thiarubrine A; thiarubrines are an important class of compounds which have recently received attention because of their unusual reactivity, unique biological activity, and potential medicinal applications.
Reyes, Juan; Morton, Melita; Downum, Kelsey; O'Shea, Kevin E. J. Chem. Educ. 2001, 78, 781.
Aromatic Compounds |
IR Spectroscopy |
Natural Products |
NMR Spectroscopy |
UV-Vis Spectroscopy |
Medicinal Chemistry
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
Simulating How a Virus Spreads through a Population: An Introduction to Acid-Base Chemistry in the Organic Chemistry Laboratory  Ronald M. Jarret
The traditional lab exercise that achieves separation of a mixture of 4-aminoacetophenone and benzoic acid by chemically active extraction has been expanded to include an exercise that uses materials from the extraction experiment to simulate how a virus spreads through a population.
Jarret, Ronald M. J. Chem. Educ. 2001, 78, 525.
Acids / Bases |
Separation Science |
Solutions / Solvents |
Aromatic Compounds |
Carboxylic Acids
A Strategy for Incorporating Hands-On GC-MS into the General Chemistry Lecture and Laboratory Courses  Perry C. Reeves and Kim L. Pamplin
Students use the GC-MS to obtain spectra of the various halobenzenes. This vividly illustrates the differences in isotopic distributions of the halogens and the complications these differences present in calculating molar masses of compounds. The isotopic distribution of iron is then obtained from the mass spectrum of Fe(CO)5, and the students calculate the atomic mass of iron from this data.
Reeves, Perry C.; Pamplin, Kim L. J. Chem. Educ. 2001, 78, 368.
Chromatography |
Isotopes |
Mass Spectrometry |
Gas Chromatography |
Aromatic Compounds
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
An EPR Experiment for the Undergraduate Physical Chemistry Laboratory  R. A. Butera and D. H. Waldeck
An experiment that illustrates the principles of electron paramagnetic resonance spectroscopy in the undergraduate physical chemistry laboratory is described. Students measure the value of g for DPPH and use it to determine the value of g for two inorganic complexes, Cu(acac)2 and VO(acac)2.
Butera, Richard A.; Waldeck, David H. J. Chem. Educ. 2000, 77, 1489.
EPR / ESR Spectroscopy |
Laboratory Equipment / Apparatus |
Aromatic Compounds
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
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
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
Analysis of Common Household Cleaner-Disinfectants by Capillary Electrophoresis  William P. Gardner and James E. Girard
Capillary electrophoresis analysis for benzalkonium compounds in common household cleaners and disinfectants.
Gardner, William P.; Girard, James E. J. Chem. Educ. 2000, 77, 1335.
Electrophoresis |
Instrumental Methods |
Quantitative Analysis |
Separation Science |
Aromatic Compounds |
Consumer Chemistry
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
Organic Acids without a Carboxylic Acid Functional Group  G. V. Perez and Alice L. Perez
This paper presents several organic molecules that have been labeled as acids but do not contain a carboxylic acid functional group. Various chemical principles such as pKa, tautomerization, aromaticity, conformation, resonance, and induction are explored.
Perez, G. V.; Perez, Alice L. J. Chem. Educ. 2000, 77, 910.
Acids / Bases |
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Phenols |
Carboxylic Acids |
Aromatic Compounds
A Practical Procedure for the Solid-Phase Synthesis of Azo Compounds in the Undergraduate Organic Laboratory  Cailan Wang, Yulu Wang, Xiaoyang Wang, Xiaoxia Wang, and Hong Wang
A new solid-phase reaction method used to synthesize a new type of azo compound is described. The procedure is short, safe, and simple enough to serve as a laboratory exercise for undergraduate students in the middle weeks of a course when azo compounds or synthesis methods have been discussed in the lecture.
Wang, Cailan; Wang, Yulu; Wang, Xiaoyang; Wang, Xiaoxia; Wang, Hong. J. Chem. Educ. 2000, 77, 903.
Synthesis |
Undergraduate Research |
Aromatic Compounds
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
Molecular Orbital Animations for Organic Chemistry  Steven A. Fleming, Greg R. Hart, and Paul B. Savage
Introduces the application of highest occupied and lowest unoccupied molecular orbitals (HOMOs and LUMOs) in animated form.
Fleming, Steven A.; Hart, Greg R.; Savage, Paul B. J. Chem. Educ. 2000, 77, 790.
MO Theory |
Molecular Modeling |
Mathematics / Symbolic Mathematics |
Mechanisms of Reactions |
Electrophilic Substitution |
Nucleophilic Substitution
The Heck Reaction: A Microscale Synthesis Using a Palladium Catalyst  William B. Martin and Laura J. Kateley
The microscale synthesis described uses a reaction between a bromoiodobenzene and acrylic acid to produce a bromocinnamic acid. Structure verification for the product uses IR and 1H NMR spectroscopy.
Martin, William B.; Kateley, Laura J. J. Chem. Educ. 2000, 77, 757.
Catalysis |
Microscale Lab |
Synthesis |
IR Spectroscopy |
NMR Spectroscopy |
Aromatic Compounds |
Mechanisms of Reactions
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
Isolation of Curcumin from Turmeric  Andrew M. Anderson, Matthew S. Mitchell, and Ram S. Mohan
The active ingredient in turmeric is curcumin, which is approximately 2% by weight of the root of turmeric. We have developed two simple procedures for isolation of curcumin from turmeric, making this a new and interesting natural product isolation experiment.
Anderson, Andrew M.; Mitchell, Matthew S.; Mohan, Ram S. J. Chem. Educ. 2000, 77, 359.
Chromatography |
Medicinal Chemistry |
Natural Products |
Synthesis |
Separation Science |
Aromatic Compounds
Synthesis of the Sweetener Dulcin from the Analgesic Tylenol  Brian D. Williams, Birute Williams, and Louise Rodino
A sequence suitable for the synthesis of the sweetener dulcin from the analgesic acetaminophen. The analgesic phenacetin is isolated during the synthesis as an intermediate and consequently the experiment can be adopted as a multistep synthesis or as either of two single-period transformations.
Williams, Brian D.; Williams, Birute; Rodino, Louise. J. Chem. Educ. 2000, 77, 357.
Synthesis |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Aromatic Compounds
Microwave Irradiation Reactions: Synthesis of Analgesic Drugs  Gholam A. Mirafzal and Jolene M Summer
Over-the-counter analgesics such as aspirin, acetanilide, phenacetin, and acetaminophen are conveniently prepared in a microwave at 30% power for five minutes. Recrystallization from appropriate solvents results in solid products in good to excellent yields.
Mirafzal, Gholam A.; Summer, Jolene M. J. Chem. Educ. 2000, 77, 356.
Drugs / Pharmaceuticals |
Synthesis |
Medicinal Chemistry |
Aromatic Compounds |
Amines / Ammonium Compounds |
Esters
Experiments with Aspirin  Londa L. Borer and Edward Barry
Experiments include (i) synthesis, purification, and characterization of aspirin by mp and TLC, (ii) percentage composition of a commercial aspirin tablet by titration, (iii) kinetics of the hydrolysis of aspirin to salicylic acid under various conditions, (iv) synthesis and characterization of copper(II) aspirinate and copper(II) salicylate, and (v) reaction of copper(II) aspirinate in aqueous solution.
Borer, Londa L.; Barry, Edward. J. Chem. Educ. 2000, 77, 354.
Synthesis |
Kinetics |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Aromatic Compounds
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
Amino Acids, Aromatic Compounds, and Carboxylic Acids: How Did They Get Their Common Names?  Sam H. Leung
This article provides a brief survey of the origins of the common names of some amino acids, aromatic compounds, and carboxylic acids.
Leung, Sam H. J. Chem. Educ. 2000, 77, 48.
Amino Acids |
Aromatic Compounds |
Nomenclature / Units / Symbols |
Carboxylic Acids
Trigonometric Basis Set Functions: Their Application to the C-H Stretching and Deformation Motions of Benzene and to Orbital Symmetry  G. Bor and Sidney F. A. Kettle
The unifying power of the use of trigonometric basis functions in group character tables is demonstrated. Additionally, these functions provide a simple way of generating pictures of symmetry coordinates. This is illustrated for the in-plane stretch and out-of-plane deformation motions of the C-H bonds in benzene. Their application to orbital symmetry applications is also indicated.
Bor, G.; Kettle, Sidney F. A. J. Chem. Educ. 1999, 76, 1723.
Group Theory / Symmetry |
Molecular Modeling |
Stereochemistry |
Molecular Properties / Structure |
Aromatic Compounds |
Spectroscopy |
IR Spectroscopy |
Raman Spectroscopy |
UV-Vis Spectroscopy
Synthesis of Derivatives of (1R)-(-)- and (1S)-(+)-10-Camphorsulfonic Acid  Steven C. Cermak and David F. Wiemer
The preparation of optically active (camphorsulfonyl)oxaziridines from commercially available (1R)-(-) and/or (1S)-(+)10-camphorsulfonic acid provides a clear demonstration of the lack of relationship between absolute configuration and optical rotation. The parent sulfonic acid can be converted to the corresponding acid chloride and then to the sulfonamide, sulfonylimine, and finally to an oxaziridine in a series of practical organic laboratory experiments.
Cermak, Steven C.; Wiemer, David F. J. Chem. Educ. 1999, 76, 1715.
Stereochemistry |
Synthesis |
Aromatic Compounds |
Ethers |
Alcohols |
Aldehydes / Ketones |
Acids / Bases
Separation of Polyaromatic Hydrocarbons Using 2-Dimensional Thin-Layer Chromatography. An Environmental Chemistry Experiment  Geoffrey T. Crisp and Natalie M. Williamson
Students are given a soil sample from which they extract two (previously added) polyaromatic hydrocarbons (PAHs) using a Soxhlet apparatus. They determine the identity of the unknown PAHs by comparing the 2-dimensional thin-layer chromatograms of the soil sample extract and a standard solution, both of which they must run themselves.
Crisp, Geoffrey T.; Williamson, Natalie M. J. Chem. Educ. 1999, 76, 1691.
Aromatic Compounds |
Chromatography |
Thin Layer Chromatography |
Separation Science
Selection of an Analysis Wavelength: An Interesting Example Involving Solvatochromism and the Zwitterionic Dimroth-Reichardt's Betaine ET-30 Dye  Taihe Deng and William E. Acree Jr.
By spectrophotometric measurements, students determine the analysis wavelength for ET-30 dissolved in solvents of varying polarity. The five solvents selected for study give solutions that appear wine-red, violet, blue, green, and yellowish-green. Student observations afford an excellent opportunity for detailed discussions of how solvent polarity affects spectral transitions, which expands the presentation given in most analytical textbooks.
Deng, Taihe; Acree, William E., Jr. J. Chem. Educ. 1999, 76, 1555.
Solutions / Solvents |
Dyes / Pigments |
Aromatic Compounds
Geometry of Benzene from the Infrared Spectrum  Elisabetta Cané, Andrea Miani, and Agostino Trombetti
The structure of benzene is fully determined once the interatomic distances rcc and rCH are obtained from experimental data. This infrared spectroscopy experiment allows the determination of rcc and rCH from the rotational analysis of an infrared active band of C6H6 and one of its isotopomers, C6D6.
Can, Elisabetta; Miani, Andrea; Trombetti, Agostino. J. Chem. Educ. 1999, 76, 1288.
IR Spectroscopy |
Molecular Properties / Structure |
Aromatic Compounds
Electrophilic Substitution in Naphthalene: Kinetic vs Thermodynamic Control  Leslie D. Field, Sever Sternhell, and Howard V. Wilton
Deuterium-protium exchange in naphthalene effected by trifluoroacetic acid and aluminium tris-trifluoroacetate was followed by proton NMR spectroscopy. These results are a potential "textbook" example of kinetic versus thermodynamic control, which is much clearer than the usually quoted reversible sulfonation of naphthalene.
Field, Leslie D.; Sternhell, Sever; Wilton, Howard V. J. Chem. Educ. 1999, 76, 1246.
Kinetics |
Thermodynamics |
Mechanisms of Reactions |
NMR Spectroscopy |
Electrophilic Substitution
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
Chemical Bonding as a Superposition Phenomenon  Frank Weinhold
The characteristic phenomena of chemistry-covalent and coordinate bonding, resonance delocalization, aromaticity, H-bonding, hyperconjugation-can also be seen as special cases of a central superposition paradigm: the "donor-acceptor" interaction between filled and unfilled orbitals.
Weinhold, Frank. J. Chem. Educ. 1999, 76, 1141.
Covalent Bonding |
Quantum Chemistry |
Aromatic Compounds |
Noncovalent Interactions |
Quantum Chemistry |
MO Theory
Quantitative Determination of PAHs in Diesel Engine Exhausts by GC-MS  Paul Fleurat-Lessard, Karine Pointet, and Marie-France Renou-Gonnord
A gas chromatography-mass spectrometry (GC-MS) analytical protocol for quantitation of PAHs in diesel exhaust particles, adapted for a single laboratory period, is proposed. Gravitational chromatography is first used to isolate aromatic compounds. Then quantitative determination of PAHs (polycyclic aromatic hydrocarbons) is performed by GC-MS, using deuterated PAHs as internal standards.
Fleurat-Lessard, Paul; Pointet, Karine; Renou-Gonnord, Marie-France. J. Chem. Educ. 1999, 76, 962.
Mass Spectrometry |
Chromatography |
Quantitative Analysis |
Instrumental Methods |
Learning Theories |
Aromatic Compounds |
Gas Chromatography
A Simple and Convenient Method for Generation and NMR Observation of Stable Carbanions  Hamid S. Kasmai
A simple and convenient method for the generation and NMR study of stable carbanions is described. The data and sample spectra illustrate that reliable and good quality NMR spectra of stable carbanions may be obtained. The experiments described provide a good opportunity for students to apply the basic principles of 1H and 13C NMR spectrometry and the interesting topic of the exchange phenomenon in NMR.
Kasmai, Hamid S. J. Chem. Educ. 1999, 76, 830.
Acids / Bases |
Reactive Intermediates |
NMR Spectroscopy |
Aromatic Compounds
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
The "Big Dog-Puppy Dog" Analogy for Resonance  Todd P. Silverstein
In this analogy, puppy dogs are restricted to a specific dog run; they represent s-bond electron pairs. Big dogs are allowed to roam freely over several consecutive dog runs; they represent delocalized p-bond electron pairs. By adding a bunny rabbit who is chased by the big dog, the analogy can be expanded to account for delocalized formal charge in a resonance hybrid.
Silverstein, Todd P. J. Chem. Educ. 1999, 76, 206.
Covalent Bonding |
Learning Theories |
Resonance Theory |
Molecular Properties / Structure
John Norman Collie: Chemist and Mountaineer  Ronald Bentley
Chemical career and contributions of John Norman Collie (1859-1942).
Bentley, Ronald. J. Chem. Educ. 1999, 76, 41.
Aromatic Compounds |
Bioorganic Chemistry |
Natural Products |
Bioinorganic Chemistry
Conformation Interchange in Nuclear Magnetic Resonance Spectroscopy  Keith C. Brown, Randy L. Tyson, and John A. Weil
Intramolecular dynamics are readily discernible by use of nuclear magnetic resonance spectrometry. A relatively simple laboratory tutorial experiment demonstrating such motion, an internal interchange of conformations, in a readily available nitroaromatic hydrazine (2,2-diphenyl-1-picrylhydrazine in liquid solution) is presented and discussed.
Brown, Keith C.; Tyson, Randy L.; Weil, John A. J. Chem. Educ. 1998, 75, 1632.
Magnetic Properties |
Molecular Properties / Structure |
NMR Spectroscopy |
Stereochemistry |
Aromatic Compounds
Quantitative HPLC Analysis of a Psychotherapeutic Medication: Simultaneous Determination of Amitriptyline Hydrochloride and Perphenazine  Glenda K. Ferguson
A quantitative high-performance liquid chromatography (HPLC) laboratory experiment which entails the isocratic separation and simultaneous determination of the two active components of a commercial antipsychotic tablet has been developed.
Ferguson, Glenda K. J. Chem. Educ. 1998, 75, 1615.
Chromatography |
Instrumental Methods |
Aromatic Compounds |
HPLC |
Medicinal Chemistry |
Quantitative Analysis
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
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
Polycyclic Aromatic Hydrocarbons (by Ronald G. Harvey)  C. F. Murray
This text is a timely and welcome addition to the ever-growing literature on polycyclic aromatic hydrocarbon (PAH) chemistry and an essential addition to the chemist's library. It is the most comprehensive and complete account of the synthesis and chemical properties of polyarenes to date.
Murray, C. F. J. Chem. Educ. 1998, 75, 1392.
Aromatic Compounds
Naphthalene and Azulene I: Semimicro Bomb Calorimetry and Quantum Mechanical Calculations  Carl Salter and James B. Foresman
A novel H2O physical chemistry experiment is proposed in which the heats of combustion of naphthalene and azulene are measured using bomb calorimetry, and then the energy difference between the two molecules is computed using Gaussian 94W.
Salter, Carl; Foresman, James B. J. Chem. Educ. 1998, 75, 1341.
Computational Chemistry |
Thermodynamics |
Calorimetry / Thermochemistry |
Aromatic Compounds
Use of Theoretical Chemistry To Explain Baeyer-Villiger Oxidations of Methoxy Aromatic Aldehydes  N. Anoune, H. Hannachi, P. Lantéri, R. Longeray, and C. Arnaud
This is a project for advanced students in two parts. First: A study of the Baeyer-Villiger reaction on para-methoxybenzaldehyde. Such a reaction is commonly used to oxidize ketones into esters. Second: The experiment is extended to various polymethoxybenzaldehydes and theoretical calculations are used to explain their particular behaviors.
Anoune, N.; Hannachi, H.; Lantéri, P.; Longeray, R.; Arnaud, Christian. J. Chem. Educ. 1998, 75, 1290.
Mechanisms of Reactions |
Theoretical Chemistry |
Aldehydes / Ketones |
Aromatic Compounds
A Modified Synthesis of the Insect Repellent DEET  Peter H. Knoess and Edward G. Neeland
In the preparation of the insect repellent DEET, lab procedures prepare the intermediate m-toluoyl chloride by heating m-toluic acid with thionyl chloride for times ranging from 15 to 45 minutes. The acid chloride is then worked up under Schotten-Baumann conditions to yield DEET.
Knoess, Peter H.; Neeland, Edward G. J. Chem. Educ. 1998, 75, 1267.
Synthesis |
Aromatic Compounds |
Carboxylic Acids
Synthesis of NMP, a Fluoxetine (Prozac) Precursor, in the Introductory Organic Laboratory  Daniel M. Perrine, Nathan R. Sabanayagam, and Kristy J. Reynolds
A synthesis of the immediate precursor of the widely used antidepressant fluoxetine (Prozac) is described. The procedure is short, safe, and simple enough to serve as a laboratory exercise for undergraduate students in the second semester of introductory organic chemistry and is one which will be particularly interesting to those planning a career in the health sciences.
Perrine, Daniel M.; Sabanayagam, Nathan R.; Reynolds, Kristy J. J. Chem. Educ. 1998, 75, 1266.
Drugs / Pharmaceuticals |
Industrial Chemistry |
Medicinal Chemistry |
Synthesis |
Aromatic Compounds
Synthesis of Aspirin: A General Chemistry Experiment  John A. Olmsted III
An experiment is described that is suitable for the early portion of the laboratory in a general chemistry course and integrates organic examples. It is the two-step synthesis of aspirin starting from oil of wintergreen. The mechanism for this synthesis provides examples of three major classes of chemical reactions: hydrolysis, condensation, and proton transfer.
Olmsted, John A., III. J. Chem. Educ. 1998, 75, 1261.
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Mechanisms of Reactions |
Aromatic Compounds |
Carboxylic Acids |
Aldehydes / Ketones
The Chemistry behind Carbonless Copy Paper  Mary Anne White
Carbonless copy paper, used to make countless copies of forms, is a 1,000,000,000 kg business annually. Copies are made when the pressure of a pen ruptures microcapsules that contain a dye precursor, initiating a chemical reaction between the dye precursor in the top page and an acid source in the bottom page.
White, Mary Anne. J. Chem. Educ. 1998, 75, 1119.
Acids / Bases |
Materials Science |
Applications of Chemistry |
Aromatic Compounds
Cinnamaldehyde by Steam Distillation of Cinnamon  Douglass F. Taber and Andrew J. Weiss
Powdered cinnamon foams badly on attempted steam distillation. It has been demonstrated that preliminary iterative evacuation of the aqueous mixture allows smooth distillation of cinnamaldehyde (I).
Taber, Douglass F.; Weiss, Andrew J. J. Chem. Educ. 1998, 75, 633.
Aldehydes / Ketones |
Aromatic Compounds
Nanosecond Time-Resolved Fluorescence Spectroscopy in the Physical Chemistry Laboratory: Formation of the Pyrene Excimer in Solution  David A. Van Dyke, Brian A. Pryor, Philip G. Smith, and Michael R. Topp
Students are introduced to nanosecond-domain transient spectroscopy in fluid solution by using a pulsed-laser apparatus to make direct measurements of the effects of these variables. They become familiar with the operation of a nitrogen laser and an associated apparatus for fluorescence spectra and lifetime measurements, including the optical and electronic hardware and the computer software used to acquire and analyze the data.
Van Dyke, David A.; Pryor, Brian A.; Smith, Philip G.; Topp, Michael R. J. Chem. Educ. 1998, 75, 615.
Fluorescence Spectroscopy |
Kinetics |
Lasers |
Spectroscopy |
Aromatic Compounds
The Pi-Electron-System of Monocyclic Polyenes C2nH2n with Alternating Single and Double Bonds  J. J. C. Mulder
The question asked is whether (in)stability towards distortion away from a symmetric geometry is a {pi}-electron property or, on the contrary, primarily connected to the {sigma}-skeleton.
Mulder, J. J. C. J. Chem. Educ. 1998, 75, 594.
Alkenes |
Aromatic Compounds |
Molecular Properties / Structure
Mechanism Templates: Lecture Aids for Effective Presentation of Mechanism in Introductory Organic Chemistry  Brian J. McNelis
To promote active student learning of mechanism in introductory organic chemistry, hand-outs have been developed with incomplete structures for reaction processes depicted, which are called mechanism templates. The key to these lecture aids is to provide only enough detail in the diagram to facilitate notetaking, ensuring that these templates are dynamic learning tools that must be utilized by an engaged and alert student.
Brian J. McNelis. J. Chem. Educ. 1998, 75, 479.
Learning Theories |
Mechanisms of Reactions |
Reactions |
Addition Reactions |
Acids / Bases |
Electrophilic Substitution |
Nucleophilic Substitution
Stepwise Equilibria in Gas-Phase Reactions: The Alkylation of Benzene  Eugen E. Weltin
The method to calculate the equilibrium composition of a stepwise attachment of a ligand to a central species is extended to equilibria in a stepwise gas-phase reactions and applied to the alkylation of benzene. For given initial amounts and given total pressure the equilibrium composition for four groups of isomers are evaluated.
Weltin, Eugen E. J. Chem. Educ. 1998, 75, 370.
Learning Theories |
Gases |
Equilibrium |
Thermodynamics |
Aromatic Compounds |
Coordination Compounds
A Grignard-like Organic Reaction in Water  Gary W. Breton and Christine A. Hughey
A known Grignard-like reaction between allyl bromide and benzaldehyde mediated by zinc metal in aqueous media. The procedure retains the desirable features of the traditional Grignard reaction, while eliminating some of the commonly encountered difficulties.
Breton, Gary W.; Hughey, Christine A. J. Chem. Educ. 1998, 75, 85.
Microscale Lab |
Aromatic Compounds |
Aldehydes / Ketones |
Alcohols |
Synthesis |
Mechanisms of Reactions
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
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
Regioselective Hydrochlorination: An Experiment for the Undergraduate Laboratory  Philip Boudjouk, Beon-Kyu Kim, and Byung-Hee Han
A simple and convenient procedure for the addition of hydrogen chloride to a variety of olefins is described. Conventional glassware is used and product isolation is straightforward using distillation techniques.
Boudjouk, Philip; Kim, Beon-Kyu; Han, Byung-Hee. J. Chem. Educ. 1997, 74, 1223.
Learning Theories |
NMR Spectroscopy |
Synthesis |
Electrophilic Substitution
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
Reduction of Chlorinated Dibenzodioxin and Dibenzofuran Formation in the Beilstein Test  Theodore D. Goldfarb and Sabine G. Fontana
In this paper we describe the results of studies designed to increase the safety of the Beilstein test by minimizing the production of these toxins. Simple adjustments in Bunsen burner temperature and the length of time the copper test loop is exposed to the flame were found to be ineffective.
Goldfarb, Theodore D.; Fontana, Sabine G. . J. Chem. Educ. 1997, 74, 838.
Qualitative Analysis |
Aromatic Compounds
Synthesis of 4-Nitro-1-Pentynylbenzene: An Example of Transitional Metal-Mediated Cross-Coupling  Ronald G. Brisbois, William G. Batterman, and Scott R. Kragerud
Synthesis of the target compound exemplifies contemporary Pd-mediated cross-coupling methodologies. In this regard, several fundamental mechanistic aspects of catalytic organometallic chemistry are illustrated, including oxidative addition, transmetallation, and reductive elimination.
Brisbois, Ronald G. ; Batterman, William G.; Kragerud, Scott R. J. Chem. Educ. 1997, 74, 832.
Synthesis |
Microscale Lab |
Organometallics |
Transition Elements |
Aromatic Compounds
Making Organic Concepts Visible  Robert S. H. Liu and Alfred E. Asato
Graphic illustrations, with a Hawaiian flavor, have been introduced to clarify the following concepts encountered in introductory organic chemistry: functional groups, resonance structures, polarizability, ionization in mass spectroscopy and difference in reactivities between alkyl and vinyl halides
Liu, Robert S. H.; Asato, Alfred E. J. Chem. Educ. 1997, 74, 783.
Mechanisms of Reactions |
Resonance Theory
Applications of Luminescent Transition Metal Complexes to Sensor Technology and Molecular Probes  J. N. Demas and B. A. DeGraff
An overview of the applications of luminescent transition metal complexes to sensor technology is presented. In addition to general considerations, a number of specific systems are discussed including oxygen, pH, carbon dioxide, temperature, and immunoassay sensors.
Demas, J. N.; DeGraff, B. A. J. Chem. Educ. 1997, 74, 690.
Materials Science |
Photochemistry |
Metals |
Transition Elements |
Coordination Compounds |
Aromatic Compounds
Determination of the Enantiomeric Purity of Naproxen: An Organic Chemistry Laboratory Experiment  Thomas D. Walsh and Curtis S. Koontz
Recent availability of and publicity surrounding the antiinflammatory drug naproxen presents an opportunity for an organic chemistry laboratory experiment of great up-to-the-minute interest.
Walsh, Thomas D.; Koontz, Curtis S. . J. Chem. Educ. 1997, 74, 585.
Stereochemistry |
Drugs / Pharmaceuticals |
Molecular Properties / Structure |
Aromatic Compounds |
Carboxylic Acids
Effect of Dielectric Constant and Ionic Strength Variation on the Fading of N,N-Dimethylaminophenolphthalein in Alkaline Medium  M. Dakkouri and W. Bodenmuller
A modified route for the preparation of DMAPP as well as the procedure for the performance of the fading experiment have been described. Furthermore, the results obtained from students' experiments demonstrating the influence of I and e of the solvent on the rate constant k have been presented and discussed.
Dakkouri, M.; Bodenmuller, W. . J. Chem. Educ. 1997, 74, 556.
Electrochemistry |
Kinetics |
Solutions / Solvents |
Aromatic Compounds
Correction  
Correction in equation 1.
J. Chem. Educ. 1997, 74, 480.
Aromatic Compounds |
Molecular Properties / Structure
Photochemistry of Benzophenone in 2-Propanol: An Easy Experiment for Undergraduate Physical Chemistry Courses  M. S. Churio and M. A. Grela
In this article we describe a laboratory experiment for undergraduate physical chemistry courses dealing with the photophysics and photochemistry of benzophenone in 2-propanol. This is an easy-to-perform experiment aimed to introduce the basic concepts of photochemistry which may help to achieve a systematic approach to the subject, incorporating related topics of chemical kinetics and molecular spectroscopy.
Churo, M. S.; Grela, M. A. J. Chem. Educ. 1997, 74, 436.
Photochemistry |
Aromatic Compounds
An Example of a Human Topological Rubber Glove Act  Yock Chai Toong and Shih Yung Wang
A hitherto unreported human body narcissistic inversion which is an example of the rubber glove act has been uncovered from a Chinese acrobatic performance. This inversion is related to the unimolecular enantiomerizations of chiral molecules, a topological figure and a rubber glove via chiral pathway.
Toong, Yock Chai; Wang, Shih Yung. J. Chem. Educ. 1997, 74, 403.
Chirality / Optical Activity |
Enantiomers |
Stereochemistry |
Aromatic Compounds
The Use of MO Calculations to Teach Students Some Concepts of Aromatic Substitution Reactions  Petrus Zeegers
The experiments described here are an attempt to help students unify the theoretical and practical aspects of their studies in organic chemistry. Simple aromatic compounds (4-X-phenols) have been used to illustrate the relationship between theoretical molecular orbital calculations and an industrially useful multi step organic synthesis.
Zeegers, Petrus. J. Chem. Educ. 1997, 74, 299.
MO Theory |
Aromatic Compounds |
Phenols
A History of the Structural Theory of Benzene - The Aromatic Sextet Rule and Hückel's Rule  Shigeaki Kikuchi
This paper shows why the aromatic sextet rule rapidly lost significance in the 1930s and why it has been reevaluated since the 1950s.
Kikuchi, Shigeaki. J. Chem. Educ. 1997, 74, 194.
Aromatic Compounds
Aromaticity Today: Energetic and Structural Criteria  Mikhail Glukhovtsev
The present paper addresses current controversies in development and applications of the two main criteria of aromaticity, namely, energetic and structural criteria. Various types of resonance energy with an emphasis on homodesmotic and isodesmic stabilization energies are discussed. Reliability of such structural criteria of aromaticity as equalization of carbon-carbon bond lengths and stability with respect to out-of-plane distortions of a molecular structure are analyzed using various examples.
Glukhovtsev, Mikhail . J. Chem. Educ. 1997, 74, 132.
Aromatic Compounds |
Alkenes |
Molecular Properties / Structure
Reactions of Bromine with Diphenylethylenes: an Introduction to Electrophilic Substitution  Ronald M. Jarret, Jamie New, and Kalliopi Karaliolios
Pooling the results obtained from the reaction between bromine and the cis and trans isomers of 1,2-diphenylethylenes allows students to discover the mechanism of anti addition which is common to most situations. Expansion of this experiment to include 1,1-diphenylethylene allows students the opportunity to discover the electrophilic substitution reaction. This serves as an excellent springboard for follow-up experiments on, and discussion of, electrophilic aromatic substitution.
Jarret, Ronald M.; New, Jamie; Karaliolios, Kalliopi . J. Chem. Educ. 1997, 74, 109.
Electrophilic Substitution |
Aromatic Compounds
Reduction of Carboxylic Acids with Sodium Borohydride and an Electrophile  Jan William Simek, Thad Tuck, and Kelly Courter Bush
Integration of new reduction conditions into a procedure applicable to the first-year organic chemistry laboratory, where reduction of the carboxylic acid group has remained an obstacle, notwithstanding the use of borane or LiAlH4 (2) on the microscale. The NaBH4 method with either electrophile can be modified to any scale; in our hands, the use of I2 as the electrophile performed better at the semimicro scale than the H2SO4 method.
Simek, Jan William; Tuck, Thad; Bush, Kelly Courter . J. Chem. Educ. 1997, 74, 107.
Carboxylic Acids |
Aromatic Compounds |
Oxidation / Reduction
Use of Infrared Spectroscopy in Monitoring a New Method for the Preparation of Sulotroban, an Antithrombotic Drug: A Medicinal Chemistry Experiment  Alain Nuhrich, Martine Varache-Lembège, Fabrice Martin, Guy Devaux,
The chemical experimental procedures given integrate an infrared spectroscopy technique for monitoring the chromatographic purification processes used in this synthesis. The purpose of the proposed manipulations is to reflect in a concrete manner the reality of doing research on and preparing drugs of chemical origin.
Nuhrich, Alain; Varache-Lembège, Martine; Lacan, Fabrice; Devaux, Guy. J. Chem. Educ. 1996, 73, 1185.
IR Spectroscopy |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Synthesis |
Aromatic Compounds
The Chemistry of Paper Preservation Part 3. The Strengthening of Paper  Henry A. Carter
The following study describes the parylene and graft copolymerization processes that have been developed to strengthen fragile or brittle paper artifacts.
Carter, Henry A. J. Chem. Educ. 1996, 73, 1160.
Aromatic Compounds |
Industrial Chemistry |
Applications of Chemistry
Microscale Preparation of Difluorenylidene and trans-2,3-Dibenzoylspiro[cyclopropane-1-99-fluorene]  Fred H. Greenberg
The synthetic sequence involving the oxidation of fluorene to fluorenone and the reduction of fluorenone to fluorenol can be extended by preparing the title compounds via the intermediate 9-chlorofluorene. The latter is obtained by heating fluorenol in methanol with conc. hydrochloric acid.
Greenberg, Fred H. J. Chem. Educ. 1996, 73, 1043.
Synthesis |
Aromatic Compounds
Mini-scale Oxidation/Reduction in Organic Laboratory Course: 4-Nitrobenzaldehyde/ 4-Nitrobenzyl Alcohol  Douglass F. Taber, Yanong Wang, Sebastian Liehr
Oxidation of an alcohol to the aldehyde or ketone, and corresponding reduction back to the alcohol, are two of the most common transformations of preparative organic chemistry. We have found a much more satisfactory combination in 4-nitrobenzyl alcohol and 4-nitrobenzaldehyde: both are crystalline, neither is volatile, and both are strongly UV-absorbing, so they visualize well on TLC.
Taber, Douglass F.; Wang, Yanong; Liehr, Sebastian. J. Chem. Educ. 1996, 73, 1042.
Microscale Lab |
Oxidation State |
Alcohols |
Aldehydes / Ketones |
Aromatic Compounds
A Conceptually Simple Approach to the Analysis of Aromaticity in Pericyclic Transition States  Richard Francis Langler
Aromatic Mbius cyclobutadiene is shown to be an artifact of Hckel theory. It is then shown that transition states may be classified as aromatic / antiaromatic / non-aromatic by exploiting both the extent of orbital overlap which develops in competing transition states and Hckel's rule.
J. Chem. Educ. 1996, 73, 899.
Molecular Modeling |
Aromatic Compounds |
Alkenes |
Molecular Properties / Structure
Molecular Orbital (Hückel) Theory and Linus Pauling: A Historical Perspective  Brahama D. Sharma
This short article offers evidence contrary to the belief that Linus Pauling was somehow opposed to Hckel-type calculations and that he therefore provided little or no support to the school of scientists in the '60s who were engaged in these semi empirical calculations.
Sharma, Brahama D. J. Chem. Educ. 1996, 73, 746.
Aromatic Compounds |
MO Theory
The Nitrogen-Laser Excited Luminescence of Pyrene: A Student Laboratory Study of Excimer Dynamics  John S. Muenter and John L. Deutsch
The resulting luminescence is studied as a function of wavelength, time, and pyrene concentration to observe the dynamics of both the excited pyrene monomer and the pyrene excimer.
Muenter, John S.; Deutsch, John L. J. Chem. Educ. 1996, 73, 580.
Aromatic Compounds |
Kinetics |
Rate Law |
Lasers
Azo dyes  Stick, Robert V.; Mocerino, Mauro
This "Tested Demonstration" describes the preparation of various azo dyes from p-nitroaniline and phenol, 1-naphthol or 2-naphthol, utilizing the overhead projector.
Stick, Robert V.; Mocerino, Mauro J. Chem. Educ. 1996, 73, 540.
Dyes / Pigments |
Aromatic Compounds
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
Iron(III) Chloride as a Lewis Acid in the Friedel-Crafts Acylation Reaction  William H. Miles, Charles F. Nutaitis, and Christian A. Anderton
The Friedel-Crafts reaction receives extensive coverage in sophomore organic chemistry. The most widely used Lewis acid for the Friedel-Crafts reaction is aluminum chloride. The safety and handling problems associated with using aluminum chloride prompted us to examine iron(III) chloride as an alternative Lewis acid for the Friedel-Crafts acylation reaction.
Miles, William H.; Nutaitis, Charles F.; Anderton, Christian A. J. Chem. Educ. 1996, 73, 272.
Aromatic Compounds |
Nucleophilic Substitution
Bromination of Acetanilide  Paul F. Schatz
A general procedure for bromination of aromatic compounds activated with electron donating substituents such as acetamido, hydroxyl, or ether groups is described.
Schatz, Paul F. J. Chem. Educ. 1996, 73, 267.
Aromatic Compounds
Synthesis of Ethyl Salicylate Using Household Chemicals  Sally Solomon, Chinhyu Hur, Alan Lee, and Kurt Smith
Ethyl salicylate is synthesized, isolated, and characterized in a three-step process using simple equipment and household chemicals.
Solomon, Sally; Hur, Chinyu; Lee, Alan; Smith, Kurt. J. Chem. Educ. 1996, 73, 173.
Synthesis |
Aromatic Compounds |
Carboxylic Acids
An Efficient Microscale Procedure for the Preparation of 3,5-Dinitrobenzoates  Smith, Richard F.; Cristalli, Gaetano M.
Efficient and simple microscale preparation of 3,5-dinitrobenzoates.
Smith, Richard F.; Cristalli, Gaetano M. J. Chem. Educ. 1995, 72, A164.
Synthesis |
Qualitative Analysis |
Laboratory Management |
Microscale Lab |
Aromatic Compounds |
Esters
Microscale Electrophilic Aromatic Substitution of p-Toluidine  Kady, Ismail O.
Experimental procedure for first-year organic chemistry students to apply the principles of group protection and study the effect of ring substituents on reaction orientation.
Kady, Ismail O. J. Chem. Educ. 1995, 72, A9.
Synthesis |
Mechanisms of Reactions |
Aromatic Compounds |
Microscale Lab |
Electrophilic Substitution
Thin-Layer Chromatography of Analgesics--An Update  John W. Elder
Procedure for identifying ibuprofen, naproxen sodium, acetominaphen, aspirin, and caffeine on commercial chromatography sheets containing a fluorescent indicator.
Elder, John W. J. Chem. Educ. 1995, 72, 1049.
Chromatography |
Separation Science |
Drugs / Pharmaceuticals |
Thin Layer Chromatography |
Qualitative Analysis |
Aromatic Compounds
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
Charge Distribution in 1,1-Dicyano-2-Arylethenes: An Undergraduate Organic Experiment Utilizing the Knoevenagel Condensation and NMR Spectroscopy  Rowland, Alex T.
Organic synthesis illustrating the effect of ring substituents on an aromatic ring.
Rowland, Alex T. J. Chem. Educ. 1995, 72, 548.
Mechanisms of Reactions |
Synthesis |
NMR Spectroscopy |
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
Steric Hindrance by Bromination of Alkylbenzenes: Experimental Demonstration  Cooley, James H.; Abobaker, Nagib M.
Procedure to illustrate the influence of steric hindrance on organic chemistry in which students must decide what data to collect and how to interpret it.
Cooley, James H.; Abobaker, Nagib M. J. Chem. Educ. 1995, 72, 463.
Molecular Properties / Structure |
Synthesis |
Chirality / Optical Activity |
Aromatic Compounds |
Stereochemistry
Bromination of Disubstituted Arenes: Kinetics and Mechanism: GC/MS Experiments for the Instrumental Analysis and Organic Chemistry Labs  Annis, D. Allen; Collard, David M.; Bottomley, Lawrence A.
Experimental procedure using gas chromatography and mass spectroscopy to trace the progression of a reaction over time and determine the several possible steps of its mechanism; sample data and analysis included.
Annis, D. Allen; Collard, David M.; Bottomley, Lawrence A. J. Chem. Educ. 1995, 72, 460.
Synthesis |
Mechanisms of Reactions |
Kinetics |
Chromatography |
Mass Spectrometry |
Separation Science |
Gas Chromatography |
Instrumental Methods |
Aromatic Compounds
Electrophilic Aromatic Substitution Discovery Lab  Jarret, Ronald M.; New, Jamie; Patraitis, Cynthia
An organic chemistry lab for introductory chemistry in which students must determine the reaction mechanism of an organic synthesis; includes sample data and analysis.
Jarret, Ronald M.; New, Jamie; Patraitis, Cynthia J. Chem. Educ. 1995, 72, 457.
Synthesis |
Mechanisms of Reactions |
Electrophilic Substitution
Hydrogen-Bonding Equilibrium in Phenol Analyzed by NMR Spectroscopy  Lessinger, Leslie
Experimental procedure for determining the equilibrium constant for the hydrogen-bonding equilibrium of phenol in carbon tetrachloride solution; data and analysis included.
Lessinger, Leslie J. Chem. Educ. 1995, 72, 85.
Equilibrium |
Noncovalent Interactions |
NMR Spectroscopy |
Hydrogen Bonding |
Aromatic Compounds |
Alcohols
Boiling Point and the Refraction (Polarizability) of Exposed Atoms  Rich, Ronald L.
Technique for using the refraction of light to determine the boiling points of a variety of organic and inorganic substances; includes data and analysis.
Rich, Ronald L. J. Chem. Educ. 1995, 72, 9.
Physical Properties |
Aromatic Compounds |
Organometallics
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
A More Affordable Undergraduate Experiment on the Reduction of Acetophenone by Yeast  Lee, Moses; Huntington, Martha
Preparation of Mosher's esters through the reduction of acetophenone with baker's yeast.
Lee, Moses; Huntington, Martha J. Chem. Educ. 1994, 71, A62.
Microscale Lab |
Aromatic Compounds |
Aldehydes / Ketones |
Oxidation / Reduction |
Stereochemistry |
Chirality / Optical Activity |
Esters |
Synthesis
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
Synthesis and Spectroscopic Study of Plant Growth Regulators Phenylpyridylureas: An "Agrorganic" Undergraduate Laboratory Experiment  Hocquet, Alexandre; Tohier, Jacques; Fournier, Josette
This lab could represent an undergraduate comparative synthesis and analysis of biologically active molecules, suitable for an introductory lab session.
Hocquet, Alexandre; Tohier, Jacques; Fournier, Josette J. Chem. Educ. 1994, 71, 1092.
Agricultural Chemistry |
Drugs / Pharmaceuticals |
Aldehydes / Ketones |
Aromatic Compounds |
Synthesis
The Hydrolysis of p-Nitrophenyl Acetate: A Versatile Reaction To Study Enzyme Kinetics  Anderson, J.; Byrne, T.; Woelfel, K. J.; Meany, J. E.; Spyridis, G. T.; Pocker,Y.
Simple kinetic assay methods to determine the specific and molecular activities of carbonic anhydrase, alpha-chymotrypsin, and acetylcholinesterase.
Anderson, J.; Byrne, T.; Woelfel, K. J.; Meany, J. E.; Spyridis, G. T.; Pocker,Y. J. Chem. Educ. 1994, 71, 715.
Aromatic Compounds |
Enzymes |
Kinetics
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
Computer Assisted Molecular Modeling Exercises for Undergraduates: II. Aromaticity in Hetorcyclic Molecules  Box, Vernon G. S.
159. Bits and pieces, 51. Using a molecular modeling program to design at least six mono- or bicyclic heterocyclic structures that obey Huckel's rules.
Box, Vernon G. S. J. Chem. Educ. 1994, 71, 236.
Molecular Modeling |
Aromatic Compounds |
Heterocycles
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
New Developments in Instant Photography  Simon, Myron S.
Account of the efforts to improve instant photography.
Simon, Myron S. J. Chem. Educ. 1994, 71, 132.
Applications of Chemistry |
Photochemistry |
Dyes / Pigments |
Aromatic Compounds
Cases of Two Chemical Criminals: Drug-Induced Hypertension and Respiratory Paralysis: Two Ironic Examples of How Chemicals Have Been Used To Harm and to Help  Labianca, Dominick A.
Chemistry and circumstances of two cases in which health-care workers used prescription drugs to harm individuals without being detected for some time.
Labianca, Dominick A. J. Chem. Educ. 1994, 71, 16.
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Aromatic Compounds |
Applications of Chemistry |
Enrichment / Review Materials |
Toxicology
A New Approach To Teaching Organic Chemical Mechanisms  Wentland, Stephen H.
Describing the mechanisms of organic reactions using five simple steps or operations.
Wentland, Stephen H. J. Chem. Educ. 1994, 71, 3.
Mechanisms of Reactions |
Addition Reactions |
Nucleophilic Substitution |
Electrophilic Substitution |
Elimination Reactions |
Resonance Theory |
Molecular Properties / Structure
GC/MS experiments for the organic laboratory: II. Friedel-Crafts alkylation of p-xylene   Novak, Michael; Heinrich, Julie
Experiments for the sophomore organic chemistry laboratory that make use of capillary gas chromatography (GC) and mass spectroscopy(MS), teach the use of MS fragmentation patterns in structure determination, and also illustrate the effects of reaction conditions on the product distribution in well-known reactions.
Novak, Michael; Heinrich, Julie J. Chem. Educ. 1993, 70, A150.
Mass Spectrometry |
Gas Chromatography |
Aromatic Compounds |
Alkylation
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
Using Infrared Spectroscopy Measurements To Study Intermolecular Hydrogen Bonding: Calculating the Degree of Association, Equilibrium Constant, and Bond Energy for Hydrogen Bonding in Benzyl Alcohol and Phenol  Frohlich, H.
This paper presents simple IR spectroscopy experiments that the author has used for two years in a third-year course, which covers spectroscopy and binding.
Frohlich, H. J. Chem. Educ. 1993, 70, A3.
Hydrogen Bonding |
IR Spectroscopy |
Aromatic Compounds |
Equilibrium |
Covalent Bonding
Nitration of phenols: A two-phase system  Zeegers, Petrus J.
Nitration of phenols is often overlooked in undergraduate organic chemistry courses.
Zeegers, Petrus J. J. Chem. Educ. 1993, 70, 1036.
Phenols |
Aromatic Compounds |
Reactions |
Quantitative Analysis |
Mechanisms of Reactions |
Chromatography |
NMR Spectroscopy
Do our students really understand the Hammett equation?   Schwan, Adrian L.
In this author's experience, many students can proceed through text questions dealing with the Hammett equation without having a full understanding of the Hammett analysis. He offers a question that enables students to gain a better appreciation of this concept.
Schwan, Adrian L. J. Chem. Educ. 1993, 70, 1001.
Chemometrics |
Resonance Theory |
Constitutional Isomers
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 quantitative organic analysis using carbon magnetic resonance: A study in enamine isomer distribution and relative stabilities  Cook, A. Gilbert
An experiment that utilizes the 13C capabilities of FT-NMR spectrometers.
Cook, A. Gilbert J. Chem. Educ. 1993, 70, 865.
Fourier Transform Techniques |
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
Kinetics of the reaction of p-nitrobenzyl chloride with cyanide ion: An undergraduate organic chemistry experiment  Hurst, Michael O.; Hill, John W.
The title reaction is used to develop an undergraduate organic kinetics experiment in which the student determines the order and rate constant of the reaction, as well as the effect of solvent upon the rate of the reaction.
Hurst, Michael O.; Hill, John W. J. Chem. Educ. 1993, 70, 429.
Reactions |
Rate Law |
Kinetics |
Aromatic Compounds |
Alcohols |
Solutions / Solvents |
Organosulfur Compounds
Preparation of 2-aminobenzaldehyde: A fragrant component of floral odors  Foy, Brian D.; Smudde, R. Allen; Wood, William F.
This article summarizes an experimental procedure and lists spectroscopic and physical properties of the products.
Foy, Brian D.; Smudde, R. Allen; Wood, William F. J. Chem. Educ. 1993, 70, 322.
Aromatic Compounds |
Spectroscopy |
Physical Properties
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
The Relation Between the Ionization Potential and the Molecular Electronegativity of Organic Homologs  Chenzhong, Cao.
A quantitative correlation of the molecular electronegativity with first ionization potential of organic homologs that can be a great help to students (especially those without any quantum chemistry background) in understanding the change rule of electron activity.
Chenzhong, Cao. J. Chem. Educ. 1993, 70, 25.
Molecular Properties / Structure |
Aromatic Compounds |
Alkenes |
Alkynes
Preparation of 2,5-dimethyl-1-phenylpyrrole  Shaw, Dennis J.; Wood, William F.
Synthesis and characterization of 2,5-dimethyl-1-phenylpyrrole.
Shaw, Dennis J.; Wood, William F. J. Chem. Educ. 1992, 69, A313.
Heterocycles |
Synthesis |
Aromatic Compounds |
Microscale Lab
Microscale synthesis of azulene  Brieger, Gottfried
Procedure for the microscale synthesis of azulene.
Brieger, Gottfried J. Chem. Educ. 1992, 69, A262.
Microscale Lab |
Synthesis |
Aromatic Compounds |
Alkenes |
Dyes / Pigments |
Mechanisms of Reactions
Microscale reactions of vanillin   Fowler, Rosemary G.
In this paper five microscale experiments which allow first-year organic student sot study the properties and reactions of vanillin are presented.
Fowler, Rosemary G. J. Chem. Educ. 1992, 69, A43.
Aldehydes / Ketones |
Aromatic Compounds |
Phenols |
Microscale Lab |
IR Spectroscopy |
NMR Spectroscopy
Synthesis of epoxidated chalcone derivatives: A useful introductory undergraduate experiment in organic synthesis  Dixon, Christine E.; Pyne, Stephen G.
Modifications to a previously reported organic synthesis.
Dixon, Christine E.; Pyne, Stephen G. J. Chem. Educ. 1992, 69, 1032.
Synthesis |
Aromatic Compounds
Davidsoniana Jones and the cult of the curved arrow  Brisbois, Ronald G.
Puzzles to help students understand valence bond theory, resonance, and tautomerism.
Brisbois, Ronald G. J. Chem. Educ. 1992, 69, 971.
Resonance Theory
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
Synthesis of 5,6-dimethoxybenzofuroxan: An organic chemistry laboratory experiment  Eswaran, S. V.; Sajadian, S. K.
Synthesis and characterization of 5,6-dimethoxybenzofuroxan.
Eswaran, S. V.; Sajadian, S. K. J. Chem. Educ. 1992, 69, 839.
Synthesis |
Aromatic Compounds
Chemical structure-What is "she"?  Randic, Milan
Encoding molecular structures; path numbers as descriptors, selective use of descriptors, and basis descriptors.
Randic, Milan J. Chem. Educ. 1992, 69, 713.
Aromatic Compounds |
Molecular Properties / Structure |
Physical Properties |
Molecular Modeling |
Diastereomers
A graph-theoretical approach to structure-property relationships  Mihalic, Zlatko; Trinajstic, Nenad
Topological indexes, elementary graph-theoretical concepts, definitions of selected topological indices, and designing QSPR models.
Mihalic, Zlatko; Trinajstic, Nenad J. Chem. Educ. 1992, 69, 701.
Aromatic Compounds |
Molecular Properties / Structure
An example molecular orbital calculation using the Sachs graph method  Dias, Jerry Ray
Methodologies to circumvent solving large secular determinants.
Dias, Jerry Ray J. Chem. Educ. 1992, 69, 695.
Aromatic Compounds |
Molecular Properties / Structure
Aromaticity via Kekule structures and conjugated circuits  Klein, D. J.
Aromatic sextets, conjugated-circuit theory, and the adjacency-matrix computational method.
Klein, D. J. J. Chem. Educ. 1992, 69, 691.
Aromatic Compounds |
Molecular Properties / Structure
Synthesis and reactions of benzofurazan-1-oxide.  Terrian, Deborah L.; Houghtaling, Melissa A.; Ames, James R.
An elementary experiment that can be used to familiarize students with the synthesis and reactions of nitrogen heterocycles.
Terrian, Deborah L.; Houghtaling, Melissa A.; Ames, James R. J. Chem. Educ. 1992, 69, 589.
Synthesis |
Heterocycles |
Aromatic Compounds
The importance of temperature control in the preparation of phencyclone (1,3-diphenyl-2-H-cyclopenta[I]phenanthrene-2-one).  Harrison, Ernest A., Jr.
The addition of a methanolic alkali solution to the reactant mixture increases yields to 80%.
Harrison, Ernest A., Jr. J. Chem. Educ. 1992, 69, 571.
Synthesis |
Aromatic Compounds |
Aldehydes / Ketones
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
Flash photochemical measurements in the physical chemistry laboratory: Kinetics of deactivation of electronically excited aromatic molecules by oxygen  Clark, Lisa M.; Hayes, Susan E.; Hayes, David M.; McFarland, Jeffrey M.; Miller, Robin L.; Shalmi, Craig L.; Soltis, Marabeth G.; Susnow, Roberta; Strong, Robert L.
In this experiment, students examine the kinetics by which molecular oxygen deactivates the electronically excited triplet states of the polycyclic aromatic hydrocarbon phenanthrene in hexane solution.
Clark, Lisa M.; Hayes, Susan E.; Hayes, David M.; McFarland, Jeffrey M.; Miller, Robin L.; Shalmi, Craig L.; Soltis, Marabeth G.; Susnow, Roberta; Strong, Robert L. J. Chem. Educ. 1992, 69, 336.
Aromatic Compounds |
Photochemistry |
Kinetics |
Molecular Properties / Structure
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
Synthesis of trans-2-tert-butylcyclohexanol via hydroboration: A microscale organic experiment demonstrating syn addition  Wigal, Carl T.; Hopkins, William T.; Ronald, Bruce P.
This microscale experiment demonstrates the relative stereochemistry of the titled addition.
Wigal, Carl T.; Hopkins, William T.; Ronald, Bruce P. J. Chem. Educ. 1991, 68, A299.
Synthesis |
Microscale Lab |
Addition Reactions |
Aromatic Compounds |
Stereochemistry
The Wittig synthesis of alkenes by phase-transfer catalysis: The syntheses of 4,4'-dichlorostilbenes and of E, E-1,4 -diphenylbutadiene   Breuer, Stephen W.
The syntheses of 4,4'-dichlorostilbenes and of E, E-1,4 -diphenylbutadiene.
Breuer, Stephen W. J. Chem. Educ. 1991, 68, A58.
Synthesis |
Microscale Lab |
Alkenes |
Aromatic Compounds
The chemistry of modern petroleum product additives   Vartanian, Paul F.
This paper discusses modern petroleum product additives: raw materials, fuels, petroleum gas, gasoline, diesel fuel, jet fuel and kerosene, residual fuels, lubricants, and more.
Vartanian, Paul F. J. Chem. Educ. 1991, 68, 1015.
Applications of Chemistry |
Amines / Ammonium Compounds |
Surface Science |
Consumer Chemistry |
Aromatic Compounds |
Enrichment / Review Materials
Spontaneous detonation of a mixture of two odd electron gases   Briggs, Thomas S.
Instructions for safe detonation of ClO2 and NO (the fastest known reaction between two stable molecules at room temperature).
Briggs, Thomas S. J. Chem. Educ. 1991, 68, 938.
Reactions |
Resonance Theory
Hofmann's Benzene tree at the Kekule festivities  Brock, William H.; Benfey, O. Theodor; Stark, Susanne
A retranslation of Hofmann's speech in 1890.
Brock, William H.; Benfey, O. Theodor; Stark, Susanne J. Chem. Educ. 1991, 68, 887.
Aromatic Compounds |
Enrichment / Review Materials
Explaining resonance - a colorful approach  Abel, Kenton B.; Hemmerlin, William M.
An analogy using color to help students understand that a resonance molecule does not shift back and forth between Lewis Structures, but is in fact a hybrid of the two structures.
Abel, Kenton B.; Hemmerlin, William M. J. Chem. Educ. 1991, 68, 834.
Resonance Theory |
Lewis Structures |
Molecular Properties / Structure
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
Alkaloids: Isolation and purification  Maldoni, Betty
A detailed general method of isolation and purification of alkaloids in plants that can be useful for students that want to begin working in this field.
Maldoni, Betty J. Chem. Educ. 1991, 68, 700.
Natural Products |
Separation Science |
Plant Chemistry |
Aromatic Compounds |
Bioorganic Chemistry |
Chromatography
Synthetic applications of aromatic metabolites  Armstead, D. E. F.
A sequel lab to clove oil extraction.
Armstead, D. E. F. J. Chem. Educ. 1991, 68, 698.
Aromatic Compounds |
Alcohols |
Natural Products |
Synthesis
Synthesis of an isolable quinodimethane  Rosenfeld, Stuart; VanDyke, Sarah
A new lab sequence where the primary goal is to generate a situation in which students have the ability to extend knowledge independently using the tools and models available following a yearlong organic chemistry course. To accomplish this, the authors created a structured lab within a relatively poorly studied area so that some independent work could be done in a setting that is neither contrived nor too loosely defined to afford a useful experience.
Rosenfeld, Stuart; VanDyke, Sarah J. Chem. Educ. 1991, 68, 691.
Aromatic Compounds |
Undergraduate Research
The malonic ester synthesis in the undergraduate laboratory  Hoogenboom, Bernard E.; Ihrig, Phillip J.; Langsjoen, Arne N.; Linn, Carol J.; Mulder, Stephen D.
The versatile reactions of diethyl malonate represent an important lecture topic in introductory organic courses, but are only rarely performed in the lab because of several problems associated with performing these reactions. These authors present a lab the circumvents some of the typical problems.
Hoogenboom, Bernard E.; Ihrig, Phillip J.; Langsjoen, Arne N.; Linn, Carol J.; Mulder, Stephen D. J. Chem. Educ. 1991, 68, 689.
Aromatic Compounds |
Aldehydes / Ketones |
Amino Acids |
Heterocycles |
Amides
The three-step synthesis of 2,6-dinitro-4-methylaniline from p-toluidine  Todd, David
A multistep synthesis for the beginning organic chemistry lab.
Todd, David J. Chem. Educ. 1991, 68, 682.
Synthesis |
Aromatic Compounds |
Amides
Synthesis of a bicyclo[2.2.1]heptene Diels-Alder adduct: An organic chemistry experiment utilizing NMR spectroscopy to assign endo stereochemistry  Harrison, Ernest A., Jr.
An organic chemistry experiment utilizing NMR spectroscopy to assign endo stereochemistry via synthesis of a bicyclo[2.2.1]heptene Diels-Alder adduct.
Harrison, Ernest A., Jr. J. Chem. Educ. 1991, 68, 426.
Alkanes / Cycloalkanes |
Synthesis |
Alkenes |
Aromatic Compounds |
NMR Spectroscopy |
Thin Layer Chromatography
The diverse nature of the C6H6 molecule  Potgeiter, J. H.
The purpose of this discussion is to show that C6H6 describes more than just one kind of benzene.
Potgeiter, J. H. J. Chem. Educ. 1991, 68, 280.
Aromatic Compounds |
Alkenes |
Reactions |
Constitutional Isomers
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
A One-Step Synthesis of Cinnamic Acids Using Malonic Acid: The Verley-Doebner Modification of the Knoevenagel Condensation  Kolb, Kenneth E.; Field, Kurt W.; Schatz, Paul F.
With this procedure malonic acid itself, rather than its diester, can be effectively condensed with benzaldehyde to produce trans-cinnamic acid.
Kolb, Kenneth E.; Field, Kurt W.; Schatz, Paul F. J. Chem. Educ. 1990, 67, A304.
Microscale Lab |
Synthesis |
Acids / Bases |
Aromatic Compounds |
Aldehydes / Ketones |
Carboxylic Acids
The microscale synthesis and purification of N, N-diethyl-m-toluamide (Deet): An experiment for a project-oriented organic chemistry course  LeFevre, Joseph W.
Procedure for the microscale synthesis and purification of N, N-diethyl-m-toluamide (Deet).
LeFevre, Joseph W. J. Chem. Educ. 1990, 67, A278.
Microscale Lab |
Synthesis |
Aromatic Compounds
Synthesis of 5-nitrofurfural diacetate and 5-nitrofurfural semicarbazone: An undergraduate laboratory experiment  Li, Xiaorong; Liu, Qianguang; Chang, James C.
Demonstrates how to nitrate an aromatic compound having an aldehyde group that can be oxidized by nitrating agents.
Li, Xiaorong; Liu, Qianguang; Chang, James C. J. Chem. Educ. 1990, 67, 986.
Synthesis |
Aldehydes / Ketones |
Esters |
Ethers |
Electrophilic Substitution |
Aromatic Compounds |
NMR Spectroscopy
Polymers in the physical chemistry laboratory: An integrated experimental program  Hardgrove, George L.; Tarr, Donald L.; Miessler, Gary L.
Procedure for polymerizing mixtures of styrene and methylmethacrylate.
Hardgrove, George L.; Tarr, Donald L.; Miessler, Gary L. J. Chem. Educ. 1990, 67, 979.
Polymerization |
Alkenes |
Aromatic Compounds |
IR Spectroscopy |
NMR Spectroscopy |
Chromatography
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
Molecular recognition in aqueous solution: Supramolecular complexation and catalysis  Diederich, Francois
Structures of cyclophanes and their complexes with organic compounds, cyclophane complexes of aromatic guests in water, complexation of arenes in organic solvents, water-soluble optically active cyclophanes, and catalytic cyclophanes.
Diederich, Francois J. Chem. Educ. 1990, 67, 813.
Molecular Recognition |
Aqueous Solution Chemistry |
Catalysis |
Noncovalent Interactions |
Aromatic Compounds |
Chirality / Optical Activity |
Molecular Properties / Structure
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
An olfactory indicator for acid-base titrations: A laboratory technique for the visually impaired  Flair, Mark N.; Setzer, William N.
Analysis of eugenol, thymol, vanillin, and thiophenol as aromatic indicators for acid-base titrations.
Flair, Mark N.; Setzer, William N. J. Chem. Educ. 1990, 67, 795.
Acids / Bases |
Titration / Volumetric Analysis |
Minorities in Chemistry |
Aromatic Compounds
An easily implemented flash photolysis experiment for the physical chemistry laboratory: The isomerization of 4-anilino-4'-nitroazobenzene  Hair, Sally R.; Taylor, Gregg A.; Schultz, L. Wayne
In this experiment, an inexpensive electronic camera flash initiates the reaction, and a visible spectrometer monitors its progress.
Hair, Sally R.; Taylor, Gregg A.; Schultz, L. Wayne J. Chem. Educ. 1990, 67, 709.
Photochemistry |
Spectroscopy |
Aromatic Compounds |
UV-Vis Spectroscopy
A simple second-order kinetics experiment  Weiss, Hilton M.; Touchette, Kim
The reaction studied in this experiment is the (reversible) dimerization of 2,5-dimethyl-3,4-diphenylcyclopentadienone; the monomer is colored while the dimer is not, so monitoring the reaction with a simple spectrophotometer provides the concentration of the monomer and therefore the rate of its disappearance.
Weiss, Hilton M.; Touchette, Kim J. Chem. Educ. 1990, 67, 707.
Kinetics |
Spectroscopy |
Aromatic Compounds
Industrial chemistry in the organic laboratory: C4 alkylations  Teegarden, David M.; Varco-Shea, Theresa C.; Conklin, Karen T.; Markle, Cynthia A.; Anderson, Scott D.
A set of experiments to illustrate reactions of the tertiary-butyl group; the products are all compounds that occur in consumer products and have received considerable attention in the popular press (BHT, BHA, TBHQ, and MTBE).
Teegarden, David M.; Varco-Shea, Theresa C.; Conklin, Karen T.; Markle, Cynthia A.; Anderson, Scott D. J. Chem. Educ. 1990, 67, 619.
Industrial Chemistry |
Aromatic Compounds |
Phenols |
Synthesis |
Mechanisms of Reactions
Synthesis of 3-(2'-methoxy,5'-bromophenyl)-2,3-epoxy phenyl propanone, A novel epoxidated chalcone derivative: An undergraduate organic chemistry experiment  Moloney, Gerard P.
Synthesis of 3-(2'-methoxy,5'-bromophenyl)-1-phenyl-prop-2-enone and its subsequent epoxidation to 3-(2'-methoxy,5'- bromophenyl)-2,3-epoxy phenyl propanone.
Moloney, Gerard P. J. Chem. Educ. 1990, 67, 617.
Synthesis |
Aromatic Compounds |
Aldehydes / Ketones |
Ethers |
Mechanisms of Reactions
Saccharin alkylation: O vs. N substitution  Greenberg, Fred H.
Illustrates charge delocalization of an ambident anion in an SN2 reaction, the comparative deshielding of oxygen and nitrogen in proton NMR, and the use of the NMR integral in assessing isomer distribution.
Greenberg, Fred H. J. Chem. Educ. 1990, 67, 611.
Nucleophilic Substitution |
Mechanisms of Reactions |
Aromatic Compounds |
Heterocycles |
NMR Spectroscopy |
Stereochemistry
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
Grignard reagent additions to alpha, beta-ethylenic nitriles: 1,4- vs. 1,2- additions  Kulp, Stuart S.; DiConcetto, Joseph A.
The easily synthesized alpha-phenylcinnamonitrile serves as an excellent starting material to illustrate conjugate (1,4) vs. simple (1,2) addition of various reactants.
Kulp, Stuart S.; DiConcetto, Joseph A. J. Chem. Educ. 1990, 67, 271.
Grignard Reagents |
Aromatic Compounds |
IR Spectroscopy |
NMR Spectroscopy
Photohydration of pyridine: Modification of an undergraduate kinetics experiment  Morine, Gerald H.
In a previous article in this Journal an undergraduate experiment on photochemical kinetics was presented. This author is offering modifications to the original experiment.
Morine, Gerald H. J. Chem. Educ. 1990, 67, 266.
Photochemistry |
Kinetics |
Aromatic Compounds |
Amines / Ammonium Compounds |
Heterocycles
Microscale synthesis of heterocyclic compounds   Al-awar, Rima; Wahl, George H., Jr.
The authors describe microscale syntheses of four heterocyclic compounds for which large-scale versions were described previously in this Journal.
Al-awar, Rima; Wahl, George H., Jr. J. Chem. Educ. 1990, 67, 265.
Microscale Lab |
Heterocycles |
Esters |
Aromatic Compounds |
Synthesis
The stepwise nitration of toluene: A multistep microscale synthesis based on an industrial process  Russell, Richard A.; Switzer, Robert W.; Longmore, Robert W.
The stepwise synthesis of 2,4,6-trinitrotoluene is a simple but important industrial example of electrophilic aromatic substitution that reflects a decreasing reactivity accompanying the increasing degree of nitration.
Russell, Richard A.; Switzer, Robert W.; Longmore, Robert W. J. Chem. Educ. 1990, 67, 68.
Microscale Lab |
Industrial Chemistry |
Aromatic Compounds |
Synthesis |
HPLC
Friedel Crafts acylation and alkylation with acid chlorides  Jarret, Ronald M.; Keil, Nora; Allen, Susan; Cannon, Lisa; Coughlan, Julie; Cusumano, Leonarda; Nolan, Brian
A shortened Friedel-Crafts experiment; the extra time available allows for additional experiments designed to illustrate the finer points of the reaction, such as electrophile rearrangements and decarbonylation of acyl cations.
Jarret, Ronald M.; Keil, Nora; Allen, Susan; Cannon, Lisa; Coughlan, Julie; Cusumano, Leonarda; Nolan, Brian J. Chem. Educ. 1989, 66, 1056.
Electrophilic Substitution |
Aromatic Compounds |
Mechanisms of Reactions |
Microscale Lab
The diazo copying process: An example and demonstration of applied organic chemistry for the undergraduate student  Osterby, Bruce
Demonstrating the chemistry of the diazo copying process.
Osterby, Bruce J. Chem. Educ. 1989, 66, 1026.
Applications of Chemistry |
Industrial Chemistry |
Aromatic Compounds |
Dyes / Pigments
An overview of oriental lacquer: Art and chemistry of the original high-tech coating  Snyder, Donald M.
While the use of Oriental lacquer dates back thousands of years, a scientific understanding of this complex material is only now emerging.
Snyder, Donald M. J. Chem. Educ. 1989, 66, 977.
Applications of Chemistry |
Aromatic Compounds |
Phenols |
Natural Products
1H-NMR spectral analysis: Phenoxathiin-1-oxide: A classic first-order, four spin system  Klein, Robert F. X.; Svoronos, Paris D. N.; Hammer, Charles F.
Phenoxathiin-1-oxide is an ideal molecule for an introduction to four-spin data analysis.
Klein, Robert F. X.; Svoronos, Paris D. N.; Hammer, Charles F. J. Chem. Educ. 1989, 66, 870.
NMR Spectroscopy |
Aromatic Compounds |
Heterocycles
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
Borodin and the benzidine rearrangement  Shine, Henry J.
It is evident now that Borodin's work really had no impact at all on the mechanism of the benzidine rearrangement.
Shine, Henry J. J. Chem. Educ. 1989, 66, 793.
Catalysis |
Mechanisms of Reactions |
Aromatic Compounds
Evolution of the morphinan synthesis  Lednicer, Daniel
The key reaction to the preparation of morphinans is the Grewe carbocation cyclization.
Lednicer, Daniel J. Chem. Educ. 1989, 66, 718.
Synthesis |
Medicinal Chemistry |
Drugs / Pharmaceuticals |
Mechanisms of Reactions |
Aromatic Compounds
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
Selective reductions in the teaching laboratory  Jones, Alan G.
Reductions of nitrophenylethanone, aminophenylethanone, and nitrophenylethanol.
Jones, Alan G. J. Chem. Educ. 1989, 66, 611.
Aromatic Compounds |
Amines / Ammonium Compounds |
Oxidation / Reduction |
Mechanisms of Reactions |
IR Spectroscopy
A visual aid for teaching the resonance concept  Delvigne, Francis
Using "dot clouds" to represent electron densities and resonance in structures such as benzene.
Delvigne, Francis J. Chem. Educ. 1989, 66, 461.
Resonance Theory |
Aromatic Compounds
A simple qualitative technique for pattern recognition in structure-activity relationships  Roy, Glenn
Acetate Overlay Repeating Topology Assay (AORTA) provides an inexpensive way to introduce high school or college students to the ever expanding library of structure-taste relationships without the need of a computer.
Roy, Glenn J. Chem. Educ. 1989, 66, 435.
Qualitative Analysis |
Molecular Properties / Structure |
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 synthesis of methyl salicylate: Amine diazotization.  Zanger, Murray; McKee, James R.
Unlike many organic chemistry labs, this experiment does not expose students to carcinogenics, nor does it smell bad.
Zanger, Murray; McKee, James R. J. Chem. Educ. 1988, 65, 1106.
Amines / Ammonium Compounds |
Aromatic Compounds
Synthesis of azulene, a blue hydrocarbon  Lemal, David M.; Goldman, Glenn D.
A procedure of the synthesis of this simple, beautiful, and theoretically interesting compound with many unusual properties.
Lemal, David M.; Goldman, Glenn D. J. Chem. Educ. 1988, 65, 923.
MO Theory |
Aromatic Compounds |
Diastereomers |
Synthesis
Clusters: Link between molecules and solids  Jelski, Daniel A.; George, Thomas F.
In this article, the authors review some of the recent work reported with clusters of atoms, concentrating on the fundamental principles underlying cluster chemistry and physics.
Jelski, Daniel A.; George, Thomas F. J. Chem. Educ. 1988, 65, 879.
Solids |
Crystals / Crystallography |
Aromatic Compounds |
Molecular Properties / Structure |
Covalent Bonding
Disulfide interchange reactions: An enzymic case study   Kitson, Trevor M.
This article concerns the reaction known as "disulfide interchange" in which a thiol reacts with a disulfide to give a different thiol and disulfide pair as the products.
Kitson, Trevor M. J. Chem. Educ. 1988, 65, 829.
Enzymes |
Aldehydes / Ketones |
Aromatic Compounds |
Molecular Biology |
Biological Cells |
Alcohols
Microcomputer analyzed initial rate kinetics of the benzene enhanced unfolding of myoglobin: A biophysical chemistry experiment  Schuh, Merlyn D.
This paper descries an inexpensive biophysical chemistry experiment, designed to be completed in one lab period, that introduces students to the subject of globular protein conformation and microcomputer analysis of initial rate data for the unfolding of proteins appropriate for an upper-division physics or biochemistry lab.
Schuh, Merlyn D. J. Chem. Educ. 1988, 65, 740.
Biophysical Chemistry |
Proteins / Peptides |
Amino Acids |
Kinetics |
Aromatic Compounds |
Laboratory Computing / Interfacing |
pH
Example of the Robinson annulation procedure via phase transfer catalysis a beginning organic synthesis experiment  Soriano, D. S.; Lombardi, A. M.; Persichini, P. J.; Nalewajek, D.
A brief description of the procedure.
Soriano, D. S.; Lombardi, A. M.; Persichini, P. J.; Nalewajek, D. J. Chem. Educ. 1988, 65, 637.
Catalysis |
Aromatic Compounds |
Synthesis |
Aldehydes / Ketones
Stereospecific reductions of 4-cholesten-3-one: An advanced organic synthesis project.  Markgraf, J. Hodge; Davis, Howard A.; Mahan, Brian R.
A more advanced synthetic project that incorporates reactions and materials with real-world significance.
Markgraf, J. Hodge; Davis, Howard A.; Mahan, Brian R. J. Chem. Educ. 1988, 65, 635.
Administrative Issues |
Acids / Bases |
Synthesis |
Aromatic Compounds |
Hormones |
Diastereomers |
Metals |
IR Spectroscopy |
Thin Layer Chromatography
Undergraduate experiments with a long-lived radical (Fremy's salt): Synthesis of 1,4-benzoquinones by degradative oxidation of p-hydroxybenzyl alcohols  Morey, J.
The long-lived, stable radical described in this article can be prepared and stored for several months and therefore is an excellent basis for a series of experiments that the author designed for his class.
Morey, J. J. Chem. Educ. 1988, 65, 627.
Aqueous Solution Chemistry |
Free Radicals |
Alcohols |
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
Alkylation of chlorobenzene: An experiment illustrating kinetic versus thermodynamic control  Kolb, Kenneth E.; Standard, Jean M.; Field, Kurt W.
An experiment illustrating kinetic versus thermodynamic control through the alkylation of chlorobenze.
Kolb, Kenneth E.; Standard, Jean M.; Field, Kurt W. J. Chem. Educ. 1988, 65, 367.
Alkylation |
Aromatic Compounds |
Gas Chromatography
Consumer chemistry in an organic course   Miller, John A.
This paper looks at the main functional groups in organic chemistry and points out their appearance in consumer chemistry. These suggestions are especially useful for courses geared toward health science majors.
Miller, John A. J. Chem. Educ. 1988, 65, 210.
Aromatic Compounds |
Free Radicals |
Hormones |
Medicinal Chemistry |
Consumer Chemistry |
Applications of Chemistry
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
Analysis of xylene mixtures using binuclear lanthanide(III) silver(I) NMR shift reagents  Wenzel, Thomas J.; Russett, Mark D.
An alternative to IR spectroscopy for the quantification of xylene mixtures employing NMR spectroscopy and involving the use of binuclear lanthanide(III)-silver(I) NMR shift reagents.
Wenzel, Thomas J.; Russett, Mark D. J. Chem. Educ. 1987, 64, 979.
NMR Spectroscopy |
Aromatic Compounds
The Indian happiness wart in the development of photodynamic action  Neckers, Douglas C.
Review of the properties and uses of Rose Bengal and related dyes.
Neckers, Douglas C. J. Chem. Educ. 1987, 64, 649.
Aromatic Compounds |
Applications of Chemistry |
Dyes / Pigments |
Molecular Properties / Structure |
Photochemistry
The synthesis of lactones from beta-aroylpropionic acids  McGahey, Lawrence
The experiment described in this article gives students experience in a short, multistep syntheses using reactions covered in most elementary organic courses and demonstrates reactions of difunctional compounds.
McGahey, Lawrence J. Chem. Educ. 1986, 63, 1101.
Aromatic Compounds |
Synthesis
The ultraviolet spectra of benzene derivatives: A physical chemistry experiment  DiBenedetto, John S.; Joens, Jeffrey A.
This paper describes an experiment that can be carried out using only a standard UV-visible scanning spectrophotometer and commonly available chemicals that make use of the fundamental concepts in symmetry and spectroscopy.
DiBenedetto, John S.; Joens, Jeffrey A. J. Chem. Educ. 1986, 63, 1095.
Aromatic Compounds |
Spectroscopy |
Stereochemistry
Does Cu(acac)2 quench benzene fluorescence?: A physical chemistry experiment  Marciniak, Bronislaw
The quenching of benzene fluorescence is investigated in this laboratory experiment because besides the "normal" quenching process, corrections for the absorption of exciting light as well as the absorption of benzene emission by the quencher are taken into account. This way, students see how many parameters should be taken into consideration in the solution of the quenching problem.
Marciniak, Bronislaw J. Chem. Educ. 1986, 63, 998.
Photochemistry |
Coordination Compounds |
Kinetics |
Aromatic Compounds
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
Synthesis of fulvenes using phase-transfer catalysis  Hill, John W.; Jenson, Jeffrey A.; Yaritz, Joseph G.
These authors have devised a new procedure for synthesizing fulvenes from indene and fluorene using phase-transfer catalysis.
Hill, John W.; Jenson, Jeffrey A.; Yaritz, Joseph G. J. Chem. Educ. 1986, 63, 916.
Synthesis |
Aromatic Compounds |
Catalysis
Getting the acid out of your 2,4-DNPH  Behforouz, Mohammad
A method for getting the acid out of a sample of 2,4-DNPH.
Behforouz, Mohammad J. Chem. Educ. 1986, 63, 723.
Acids / Bases |
Aromatic Compounds |
Phenols |
Amines / Ammonium Compounds |
Laboratory Management
The enzymatic resolution of aromatic amino acids  Sheardy, Riehard; Liotta, L.; Steinhart, E.; Champion, R.; Rinker, J.; Planutis, M.; Salinkas, J.; Boyer, T.; Carcanague, D.
This article presents an experiment that can demonstrate as many principles of steroisomersim as possible and is also efficient in terms of time and preparation.
Sheardy, Riehard; Liotta, L.; Steinhart, E.; Champion, R.; Rinker, J.; Planutis, M.; Salinkas, J.; Boyer, T.; Carcanague, D. J. Chem. Educ. 1986, 63, 646.
Stereochemistry |
Chirality / Optical Activity |
Enantiomers |
Aromatic Compounds |
Amino Acids |
Enzymes
Teaching the concept of resonance with transparent overlays  Richardson, W. S.
The overlap method can be useful in the development of the concept of a partial charge on the atoms of an ion.
Richardson, W. S. J. Chem. Educ. 1986, 63, 518.
Resonance Theory |
Molecular Properties / Structure
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
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
Application of organometallic catalysis to the commercial production of L-DOPA  Knowles, W. S.
This paper describes the application of a novel technology to the commercial preparation of L-DOPA.
Knowles, W. S. J. Chem. Educ. 1986, 63, 222.
Industrial Chemistry |
Enantiomers |
Stereochemistry |
Aromatic Compounds |
Alkenes |
Heterocycles |
Mechanisms of Reactions |
Catalysis |
Organometallics |
Alcohols
Selective oxidation and ammoxidation of olefins by heterogeneous catalysis  Grasselli, Robert K.
In this symposium paper, the author shows how the complex process of the ammoxidation of olefins can be understood in terms of free radicals and surface bound organometallic intermediates.
Grasselli, Robert K. J. Chem. Educ. 1986, 63, 216.
Organometallics |
Oxidation / Reduction |
Catalysis |
Amines / Ammonium Compounds |
Aromatic Compounds |
Alkenes |
Mechanisms of Reactions
Mushroom odors: Student synthesis of the odoriferous compounds of the matsutake mushroom  Wood, William F.; Fesler, Mark
Matsutake mushrooms are in demand due to their pleasant and appetizing flavor or aroma. This article describes the synthesis of methyl cinnamate as an experiment for the undergraduate organic chemistry laboratory.
Wood, William F.; Fesler, Mark J. Chem. Educ. 1986, 63, 92.
Food Science |
Synthesis |
Aromatic Compounds |
Natural Products
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
And the winner is . . . A multistep synthesis for the introductory organic course  Stradling, Samuel S.; Gage, Clarke L.
A synthetic sequence with a touch of friendly competition; methyl m-nitrobenzoate is prepared via three different routes from acetophenone.
Stradling, Samuel S.; Gage, Clarke L. J. Chem. Educ. 1985, 62, 1116.
Synthesis |
Aromatic Compounds
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
Spectroscopic studies of the catechol dioxygenases  Que, Lawrence, Jr.
The catechol dioxygenases are bacterial iron-containing enzymes that catalyze the oxidative cleavage a catechols; these enzymes serve as a component of nature's mechanism for cleaving aromatic compounds in the environment. From the "State of the Art Symposium: Bioinorganic Chemistry", held at the ACS meeting, Miami, 1985.
Que, Lawrence, Jr. J. Chem. Educ. 1985, 62, 938.
Spectroscopy |
Enzymes |
Catalysis |
Raman Spectroscopy |
Molecular Properties / Structure |
Mechanisms of Reactions |
Aromatic Compounds
The preparation of benzoyl esters of phenols and benzoic anhydride by phase-transfer catalysis  Yeadon, A.; Turney, T. A.; Ramsay, G.
The procedure is sufficiently rapid to replace the Schotten-Baumann technique.
Yeadon, A.; Turney, T. A.; Ramsay, G. J. Chem. Educ. 1985, 62, 518.
Synthesis |
Catalysis |
Esters |
Phenols |
Aromatic Compounds
Frontier orbital analysis of the bathochromic shift of monosubstituted benzenes  Duben, Anthony J.
The bathochromic shift of the longest wavelength band observed when benzene is substituted can be demonstrated theoretically using a simple frontier orbital analysis.
Duben, Anthony J. J. Chem. Educ. 1985, 62, 373.
Aromatic Compounds
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
Synthesis and testing of the insecticide carbaryl  Thadeo, Peter F.; Mowery, Dwight F.
Carbaryl, 1-naphthyl-N-methylcarbamate, is synthesized from alpha-naphthol and triethylamine.
Thadeo, Peter F.; Mowery, Dwight F. J. Chem. Educ. 1984, 61, 742.
Synthesis |
Applications of Chemistry |
Aromatic Compounds |
Amines / Ammonium Compounds
Synthesis of benzoic acid using household bleach  Perkins, Robert
Conversion of acetophenone to benzoic acid (the haloform reaction) using household bleach.
Perkins, Robert J. Chem. Educ. 1984, 61, 551.
Synthesis |
Carboxylic Acids |
Aromatic Compounds
The evaluation of empirical resonance energies as reaction enthalpies with particular reference to benzene  George, Philip; Bock, Charles W.; Trachtman, Mendel
Deals with empirical resonance energy - how its magnitude depends on the choice of reference molecules from which the bond energies are derived, and how it can be evaluated much more simply, without recourse to bond energies, as the enthalpy change for a reaction predetermined by the choice of reference molecules.
George, Philip; Bock, Charles W.; Trachtman, Mendel J. Chem. Educ. 1984, 61, 225.
Aromatic Compounds |
Thermodynamics |
Molecular Properties / Structure
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
Determination of the dipole moment of polar compounds in nonpolar solvents  Janini, George M.; Katrib, Ali H.
An experiment is described in the determination of the dipole moment of polar compounds in nonpolar solvents.
Janini, George M.; Katrib, Ali H. J. Chem. Educ. 1983, 60, 1087.
Solutions / Solvents |
Noncovalent Interactions |
Liquids |
Aromatic Compounds
Aromatic substitution reactions: when you've said ortho, meta, and para you haven't said it all  Traynham, James G.
The author presents a range of examples for nucleophilic, electrophilic, and free-radical reactions where the ipso is an important, predominant, or even exclusive site of reaction.
Traynham, James G. J. Chem. Educ. 1983, 60, 937.
Nucleophilic Substitution |
Electrophilic Substitution |
Free Radicals |
Diastereomers |
Stereochemistry |
Reactions
Cyclic voltammetry experiment  Van Benschoten, James J.; Lewis, Jane Y.; Heineman, William R.; Roston, Daryl A.; Kissinger, Peter T.
This three-part experiment has been designed specifically for introducing cyclic voltammetry to students who are at the advanced undergraduate or early graduate level.
Van Benschoten, James J.; Lewis, Jane Y.; Heineman, William R.; Roston, Daryl A.; Kissinger, Peter T. J. Chem. Educ. 1983, 60, 772.
Electrochemistry |
Oxidation / Reduction |
Drugs / Pharmaceuticals |
pH |
Heterocycles |
Aromatic Compounds |
Bioanalytical Chemistry
Application of aromatic solvent induced shifts in organic chemistry  Kalyanam, Nagabushanam
This article illustrates the predictability of the movement of proton signals in the case of carbonyl compounds when the solvent is changed from a standard aliphatic solvent to an aromatic solvent.
Kalyanam, Nagabushanam J. Chem. Educ. 1983, 60, 635.
Aromatic Compounds |
Carboxylic Acids |
NMR Spectroscopy |
Solutions / Solvents
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
Raoult's law: A general chemistry experiment  Steffel, Margaret J.
A paper exercise and laboratory work make Raoult's law more meaningful to students.
Steffel, Margaret J. J. Chem. Educ. 1983, 60, 500.
Liquids |
Aromatic Compounds |
Covalent Bonding
Palladium catalyzed reduction of nitrobenzene  Mangravite, John A.
The authors present an application of palladium catalyzed reductions to the undergraduate laboratory.
Mangravite, John A. J. Chem. Educ. 1983, 60, 439.
Aromatic Compounds |
Oxidation / Reduction |
Drugs / Pharmaceuticals |
Reactions |
Catalysis |
Organometallics
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
Highly stereoselective synthesis and rearrangement of beta-amino alpha-bromo chalcones  Arnould, J. C.; Feigenbaum, A.; Henin, F.
The authors propose an experiment for advanced students which involves a sequence of easy steps illustrating important reactions and concepts of organic chemistry.
Arnould, J. C.; Feigenbaum, A.; Henin, F. J. Chem. Educ. 1983, 60, 82.
Synthesis |
Stereochemistry |
Amino Acids |
Phenols |
Synthesis |
Aromatic Compounds
The synthesis of 2-acetyl-1,4-naphthoquinone: A multi-step synthesis  Green, Ivan R.
Synthesis of the title compound is carried out through two different pathways that are then compared for their relative merits.
Green, Ivan R. J. Chem. Educ. 1982, 59, 698.
Synthesis |
Aromatic Compounds |
Mechanisms of Reactions
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
An easily conducted free radical substitution for organic chemistry courses  Pavlis, Robert R.
The photobromination of 1,2-diphenylethane into its dibromo derivative, (2R) (3S) 1,2-dibromo-1,2-diphenylethane.
Pavlis, Robert R. J. Chem. Educ. 1982, 59, 658.
Free Radicals |
Reactions |
Molecular Properties / Structure |
Stereochemistry |
Diastereomers |
Photochemistry |
Alkanes / Cycloalkanes |
Aromatic Compounds
The principle of vinylogy  Krishnamurthy, Subrahmanya
The principle of vinylogy recognizes the possibility that the inductive effect of a functional group is transmitted through a double bond or a conjugated system of double bonds.
Krishnamurthy, Subrahmanya J. Chem. Educ. 1982, 59, 543.
Molecular Properties / Structure |
Alkenes |
Esters |
Aldehydes / Ketones |
Amides |
Aromatic Compounds
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
Introduction to infrared spectroscopy: A simple undergraduate experiment  Reeder, Deborah M.; Sridharan, Srinivasa
The objective is to obtain two IR spectra, one on an aliphatic compound and the other on an aromatic compound in a first-semester organic laboratory.
Reeder, Deborah M.; Sridharan, Srinivasa J. Chem. Educ. 1982, 59, 503.
Spectroscopy |
IR Spectroscopy |
Alkanes / Cycloalkanes |
Aromatic Compounds |
Molecular Properties / Structure
Pi bonding without tears  Akeroyd, F. Michael
A non-mathematical treatment of sigma-pi bonding applied to conjugation, hyperconjugation, Markovnikoff addition, aromaticity, and aromatic substitution.
Akeroyd, F. Michael J. Chem. Educ. 1982, 59, 371.
Alkenes |
Mechanisms of Reactions |
Addition Reactions |
Aromatic Compounds
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
The preparation of lucigenin: An experiment with charm  Amiet, R. G.
The preparation of lucigenin involves both nucleophilic and electrophilic aromatic substitution, nucleophilic aliphatic substitution, reductive coupling, and oxidation reactions.
Amiet, R. G. J. Chem. Educ. 1982, 59, 163.
Synthesis |
Oxidation / Reduction |
Nucleophilic Substitution |
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
Cyclohexane as a cryoscopic solvent   Steffel, Margaret J.
The author explores options for replacing benzene in the academic laboratory.
Steffel, Margaret J. J. Chem. Educ. 1981, 58, A133.
Toxicology |
Aromatic Compounds |
Laboratory Management
Carcinogens and mutagens in the undergraduate laboratory   Melnikow, Joy; Keeffe, James R.; Bernstein, R. L.
Identifying carcinogens and suspected carcinogens; methods for identification and safe disposal; results and specific recommendations for metals, organic solvents, and others.
Melnikow, Joy; Keeffe, James R.; Bernstein, R. L. J. Chem. Educ. 1981, 58, A11.
Phenols |
Aromatic Compounds |
Toxicology |
Laboratory Management
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
High-strength/high-modulus fibers from aromatic polymers  Preston, J.
In this review, some of the lessons learned from the work on fibers from the rod-like polymers of the polyamide class will be summarized and the extensions of the early work to fibers from other rod-like polymers will be discussed.
Preston, J. J. Chem. Educ. 1981, 58, 935.
Aromatic Compounds |
Polymerization
Oxidation of cyclohexanol to cyclohexanone by sodium hypochlorite  Zuczek, Norbert M; Furth, Paul S.
A laboratory that was previously published is modified for a smaller scale in this note.
Zuczek, Norbert M; Furth, Paul S. J. Chem. Educ. 1981, 58, 824.
Oxidation / Reduction |
Alcohols |
Aromatic Compounds
What compound was discovered as a result of an insurance claim?  Julian, Maureen M.
The discovery of benzene can be attributed both to the insurance industry and to the gas-lighting industry.
Julian, Maureen M. J. Chem. Educ. 1981, 58, 793.
Aromatic Compounds |
Enrichment / Review Materials
What compound was discovered as a result of an insurance claim?  Julian, Maureen M.
The discovery of benzene can be attributed both to the insurance industry and to the gas-lighting industry.
Julian, Maureen M. J. Chem. Educ. 1981, 58, 793.
Aromatic Compounds |
Enrichment / Review Materials
Friedrich August Kekule   Lipeles, Enid S.
Kekule began his career as a student of architecture, went on to study chemistry and physics, and had a famous dream about a snake that would have stumped Freud.
Lipeles, Enid S. J. Chem. Educ. 1981, 58, 624.
Aromatic Compounds |
Enrichment / Review Materials
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
Kathleen Lonsdale and the planarity of the benzene ring  Julian, Maureen M.
Dr. Lonsdale "suspected that the departure of the crystal symmetry from hexagonal was due to packing effects involving the hydrogen atoms and made a gallant attempt to narrow down their positions; much later, Brockway and Robertson confirmed and refined her conclusions".
Julian, Maureen M. J. Chem. Educ. 1981, 58, 365.
Aromatic Compounds |
Women in Chemistry |
Enrichment / Review Materials
The Menschutkin reaction: A group experiment in a kinetic study  Barnard ,P. W. C.; Smith, B. V.
A description of a laboratory experiment that demonstrate the application of kinetic methods to nucleophilic aliphatic substitution.
Barnard ,P. W. C.; Smith, B. V. J. Chem. Educ. 1981, 58, 282.
Nucleophilic Substitution |
Aromatic Compounds |
Kinetics
Benzene-the polymer former   Wittcoff, Harold
Benzene is crucial to the petrochemical industry.
Wittcoff, Harold J. Chem. Educ. 1981, 58, 270.
Aromatic Compounds |
Industrial Chemistry
Benzene, a familiar hazard?  Smith, Roger M.
Reviews the hazards of benzene.
Smith, Roger M. J. Chem. Educ. 1980, 57, A85.
Aromatic Compounds |
Toxicology
Evolution of a process: The manufacture of diphenyl oxide  Fravel, Harold G., Jr.
An understanding of the chemistry involved in this reaction provides the basis for converting an unprofitable process and plant to a profitable business without a substantial use of capital or a major change in operating procedures.
Fravel, Harold G., Jr. J. Chem. Educ. 1980, 57, 873.
Industrial Chemistry |
Aromatic Compounds |
Synthesis
The 1A1g > 1B2u Transition of benzene: A physical chemistry experiment  Campbell, Mary K.
The group-theoretical analysis of the vibronic coupling permits the assignment of the more prominent UV spectral peaks that appear and shows the applicability of the Born-Oppenheimer approximation.
Campbell, Mary K. J. Chem. Educ. 1980, 57, 756.
Aromatic Compounds |
UV-Vis Spectroscopy
Acylation of ferrocene: Effect of temperature on reactivity as measured by reverse phase high performance liquid chromatography  McKone, Harold T.
A reverse-phase separation of the products of the Friedel-Crafts acylation of ferrocene.
McKone, Harold T. J. Chem. Educ. 1980, 57, 380.
HPLC |
Chromatography |
Aromatic Compounds |
Electrophilic Substitution |
Separation Science
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
An undergraduate organic laboratory project involving independent synthesis of novel flavones  Letcher, R. M.
each student is provided different starting materials to produce different flavones, many of which have not been described in the literature.
Letcher, R. M. J. Chem. Educ. 1980, 57, 220.
Synthesis |
Aromatic Compounds
The preparation of p-cresyl propyl ether by phase transfer catalysis  Rowe, Jeffrey E.
Modifying the referenced procedure to produce aromatics ethers.
Rowe, Jeffrey E. J. Chem. Educ. 1980, 57, 162.
Catalysis |
Synthesis |
Aromatic Compounds |
Ethers
Bioactivity in organic chemistry courses  Ferguson, Lloyd N.
Considers the antibacterial activity of hydroxy compounds, the carcinogenicity of polycyclic aromatic hydrocarbons, structure-activity correlations, and bioactivity.
Ferguson, Lloyd N. J. Chem. Educ. 1980, 57, 46.
Aromatic Compounds |
Bioorganic Chemistry |
Molecular Properties / Structure
Quantitative hydrocarbon energies from the PMO method  Cooper, Charles F.
Perturbational molecular orbital theory is used to determine the total energies for conjugated hydrocarbons.
Cooper, Charles F. J. Chem. Educ. 1979, 56, 568.
MO Theory |
Quantum Chemistry |
Aromatic Compounds
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
Synthesis of some unreported derivatives of sulfonamides: A laboratory in organic chemistry  Gilow, Helmuth
Preparation of N4-benzylsulfanilamide.
Gilow, Helmuth J. Chem. Educ. 1979, 56, 419.
Synthesis |
Amides |
Aromatic Compounds
The aromatic ring  Kolb, Doris
Historic analysis and attempts to explain the structure of benzene, the concept of resonance, Huckel's rule, polycyclic aromatic compounds, non-classical aromatic compounds, and a definition for aromaticity.
Kolb, Doris J. Chem. Educ. 1979, 56, 334.
Aromatic Compounds |
Molecular Properties / Structure |
Resonance Theory
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
Para-bond or "Dewar" benzene?  Baker, Wilson; Rouvray, Dennis H.
The name "Dewar" benzene stems from a misreading of Sir James Dewar's paper.
Baker, Wilson; Rouvray, Dennis H. J. Chem. Educ. 1978, 55, 645.
Aromatic Compounds
Schemes and transformations in the (CH)8 series. The "valence isomers" of cyclooctatetraene  Smith, Leverett R.
The authors provide a scheme for deriving valence isomers.
Smith, Leverett R. J. Chem. Educ. 1978, 55, 569.
Aromatic Compounds |
Enantiomers |
Stereochemistry |
Diastereomers
Aldol condensation: A simple teaching model for organic laboratory  Hawbecker, Byron L.; Kurtz, David W.; Putnam, Theodore D.; Ahlers, Patricia A.; Gerber, Gregory D.
The authors share a teaching model for the organic laboratory that was developed to be accomplished in a three-hour-period and clearly illustrate a number of concepts which serve to enrich the student's understanding of organic reaction chemistry.
Hawbecker, Byron L.; Kurtz, David W.; Putnam, Theodore D.; Ahlers, Patricia A.; Gerber, Gregory D. J. Chem. Educ. 1978, 55, 540.
Aldehydes / Ketones |
Alcohols |
Aromatic Compounds |
Reactions
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
Z- and E-stereoisomerism: An experiment using photochemistry  Bourelle-Wargnier, F.; Feigenbaum, A.; Muzart, J.
The authors' report on the preparation of 2-benzylidenecyclohexanone E(I).
Bourelle-Wargnier, F.; Feigenbaum, A.; Muzart, J. J. Chem. Educ. 1978, 55, 339.
Stereochemistry |
Photochemistry |
Aromatic Compounds |
Thin Layer Chromatography |
IR Spectroscopy |
Enantiomers
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
The structures of metal-cyclopentadienyl derivatives   Maslowsky, Edward, Jr.
Metal derivatives of cyclopentadiene can be classified as either ionic cyclopentadiene or covalent cyclopentadienyl. Although these structural extremes are common, other such structures also have been found; some possess dynamic structural aspects.
Maslowsky, Edward, Jr. J. Chem. Educ. 1978, 55, 276.
Metals |
Organometallics |
Aromatic Compounds |
Covalent Bonding |
Noncovalent Interactions |
Molecular Mechanics / Dynamics |
Molecular Properties / Structure
The discovery of saccharin  Wotiz, John H.
The controversy and drama behind the discovery of saccharin.
Wotiz, John H. J. Chem. Educ. 1978, 55, 161.
Aromatic Compounds |
Natural Products
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
Synthesis of caprolactam and Nylon 6  Carraher, Charles E., Jr.
This experiment allows the illustration of the Beckman rearrangement and ring opening reactions. [Debut]
Carraher, Charles E., Jr. J. Chem. Educ. 1978, 55, 51.
Aromatic Compounds
The Nitration of alkylbenzenes: A lecture demonstration   Davis, M.; Deady, L. W.; Paproth, T. G.
The firsthand experimental data provided by this experiment enriches a discussion of aromatic compounds.
Davis, M.; Deady, L. W.; Paproth, T. G. J. Chem. Educ. 1978, 55, 34.
Aromatic Compounds
Applications of the perturbational molecular orbital method  Freeman, Fillmore
In this paper, the author shows that simple properties of AHpMO's with the PMO formulas, make qualitative calculations particularly facile.
Freeman, Fillmore J. Chem. Educ. 1978, 55, 26.
Aromatic Compounds |
MO Theory |
Quantum Chemistry
Apparent ionic charge in electrolyte and polyelectrolyte solutions  Magdelenat, H.; Turq, P.; Tivant, P.; Chemla, M.; Menez, R.; Drifford, M.
The purpose of this paper is to show how the comparison of the experimental values of the average displacement of charged particles obtained under the action of thermal motion alone with those obtained by the action of an external electric field, leads to the concept of "apparent charge". This is a good approximation of their actual structural charge in a given electrolyte solution at finite concentration and thus reflects the complexity of their structure.
Magdelenat, H.; Turq, P.; Tivant, P.; Chemla, M.; Menez, R.; Drifford, M. J. Chem. Educ. 1978, 55, 12.
Aqueous Solution Chemistry |
Solutions / Solvents |
Electrophilic Substitution |
Chemometrics |
Metals
Preparation of vanillin from eugenol and sawdust  Lampman, Gary M.; Andrews, Jennifer; Bratz, Wayne; Hanssen, Otto; Kelley, Kenneth; Perry, Dana; Ridgeway, Anthony
Two procedures are described for the conversion of eugenol to vanillin.
Lampman, Gary M.; Andrews, Jennifer; Bratz, Wayne; Hanssen, Otto; Kelley, Kenneth; Perry, Dana; Ridgeway, Anthony J. Chem. Educ. 1977, 54, 776.
Synthesis |
Consumer Chemistry |
Food Science |
Mechanisms of Reactions |
Aromatic Compounds |
Oxidation / Reduction
Pittacal - The first synthetic dyestuff  Kauffman, George B.
The story of the discovery of the first synthetic dyestuff by Karl Ludwig von Reichenbach.
Kauffman, George B. J. Chem. Educ. 1977, 54, 753.
Dyes / Pigments |
Aromatic Compounds
Phthalimide, anthranilic acid, benzyne. An undergraduate organic laboratory sequence  Dougherty, C. M.; Baumgarten, R. L.; Sweeney, A., Jr.; Concepcion, E.
A synthetic sequence: phthalic anhydride to phthalimide to anthranilic acid to methyl anthranilate or to 1,2,3,4-tetraphenylnaphthalene.
Dougherty, C. M.; Baumgarten, R. L.; Sweeney, A., Jr.; Concepcion, E. J. Chem. Educ. 1977, 54, 643.
Aromatic Compounds |
Mechanisms of Reactions |
Synthesis
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
Catalytic dehydrogenation of tetrahydrocarbazole  Van Verth, James E.; Ulmer, Simon W.
The conversion of 1,2,3,4-tetrahydrocarbazole to carbazole illustrates the synthesis of a common heterocyclic system.
Van Verth, James E.; Ulmer, Simon W. J. Chem. Educ. 1977, 54, 383.
Catalysis |
Synthesis |
Aromatic Compounds |
Heterocycles
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
Sodium perborate oxidation of an aromatic amine  Huestis, Laurence
Upon learning that the mechanism and even the nature of the oxidizing species is unknown, this reaction assumes new significance and provides an excellent opportunity for speculation on the nature of the reaction and a review of factors that affect the yield.
Huestis, Laurence J. Chem. Educ. 1977, 54, 327.
Aromatic Compounds |
Amines / Ammonium Compounds |
Oxidation / Reduction |
Synthesis |
Mechanisms of Reactions
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
Rate constant for fluorescence quenching. An undergraduate experiment using the Spectronic 20  Legenza, Michael W.; Marzzacco, Charles J.
An experiment that uses fluorescence intensity measurements to determine the rate constant for the fluorescence quenching of various aromatic hydrocarbons by CCl4 in an ethanol solvent.
Legenza, Michael W.; Marzzacco, Charles J. J. Chem. Educ. 1977, 54, 183.
Spectroscopy |
Aromatic Compounds
Teaching aromaticity, conjugation, and enolization  Schambach, Robert A.
An understanding of the delocalization of electrons in organic compounds is central knowledge. In teaching undergraduates about aromaticity, conjugation, and enoliztion, this author has found it useful to present examples of compounds in which delocalization. Effects are sustained in the presence of potentially interfering saturated carbon atoms.
Schambach, Robert A. J. Chem. Educ. 1976, 53, 711.
Aromatic Compounds |
Reactions
Micelle catalysis of an aromatic substitution reaction  Corsaro, Gerald; Smith, J. K.
This article describes an experiment which demonstrates micelle catalysis.
Corsaro, Gerald; Smith, J. K. J. Chem. Educ. 1976, 53, 589.
Micelles |
Aromatic Compounds |
Reactions |
Catalysis
Molecular design of compounds via intermolecular Diels-Alder reactions  Mehta, Goverdhan
The Diels-Alder reaction involving a cycloaddition between a diene and dienophile is one of the most versatile and useful reactions in the armory of the synthetic organic chemists.
Mehta, Goverdhan J. Chem. Educ. 1976, 53, 551.
Synthesis |
Addition Reactions |
Aromatic Compounds
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
Preparation of the sweetening agent P4000. A student project  de Koning, A. J.
The author presents the procedure for preparation of the sweetening agent P4000 that can be performed by students.
de Koning, A. J. J. Chem. Educ. 1976, 53, 521.
Synthesis |
Food Science |
Carbocations |
Aromatic Compounds
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
The scope of the Haworth synthesis  Agranat, Israel; Shih, Yu-Shan
The duality of the Haworth synthesis as revealed most conspicuously in the preparation of both anthracene and phenanthrene, widens the scope of the method. On the basis of the reversibility of Friedel-Crafts acylation in PPA, the Haworth synthesis may serve as a route to linearly annelated-as well as to angularly annelated polynuclear aromatic hydrocarbons.
Agranat, Israel; Shih, Yu-Shan J. Chem. Educ. 1976, 53, 488.
Synthesis |
Catalysis |
Aromatic Compounds |
Aldehydes / Ketones
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
An undergraduate electroanalytical experiment  Janata, Jiri
This article presents a determination of vanillin and of other aromatic aldehyde can easily be accomplished by amperometric titration with a standard solution of 2,4-dinitrophenylhydazine.
Janata, Jiri J. Chem. Educ. 1976, 53, 399.
Electrochemistry |
Aldehydes / Ketones |
Titration / Volumetric Analysis |
Aromatic Compounds |
Natural Products
Preparation of phenanthridone. A multipurpose experiment for the organic laboratory  Hawbecker, Byron L.; Radovich, David A.; Tillotson, Loyal G.
It is desirable to have a series of multipurpose reactions available which can illustrate a variety of reaction types within a single, three hour lab period.
Hawbecker, Byron L.; Radovich, David A.; Tillotson, Loyal G. J. Chem. Educ. 1976, 53, 398.
Reactions |
Aromatic Compounds |
Aldehydes / Ketones
Metal replaced hemoproteins. A review with introductory laboratory preparation of cobaltmyoglobin.  Dickinson, L. Charles.
This paper deals with a different class of metal-containing enzymes-hemoproteins- where metal replacement requires rather more chemistry related to the metal substitution in porphyrin rings.
Dickinson, L. Charles. J. Chem. Educ. 1976, 53, 381.
Aromatic Compounds |
Enzymes |
Bioinorganic Chemistry
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
Computer assisted instruction in organic synthesis  Feldman, Martin; Bishop, Marvin
The authors have used two successful Basic programs where students had practice with a series of interconversions involving alphatic and aromatic compounds.
Feldman, Martin; Bishop, Marvin J. Chem. Educ. 1976, 53, 91.
Aromatic Compounds |
Synthesis
The preparation and photochemistry of stilbenes. A synthetic organic chemistry experiment  Davy, J. R.; Jessup, P. J.; Reiss, J. A.
The synthesis of 3,6-dimethylphenanthrene.
Davy, J. R.; Jessup, P. J.; Reiss, J. A. J. Chem. Educ. 1975, 52, 747.
Photochemistry |
Aromatic Compounds |
Synthesis
A direct calorimetric demonstration of resonance energy in the benzene nucleus  van Vugt, W. H.; Mosselman, C.
This calorimetric experiment is intended as a first contact in chemical education with the aromaticity concept.
van Vugt, W. H.; Mosselman, C. J. Chem. Educ. 1975, 52, 746.
Calorimetry / Thermochemistry |
Resonance Theory
Cancer. How can chemists help?  Ferguson, Lloyd N.
A summary of cancer topics of interest to chemists, including carcinogens, cancer treatment, and designing cytotoxic agents.
Ferguson, Lloyd N. J. Chem. Educ. 1975, 52, 688.
Aromatic Compounds
The Gabriel synthesis of benzylamine: An undergraduate organic experiment  Nigh, W. G.
The Gabriel synthesis involves the reaction of the conjugate base of phthalimide and an alkyl halide to give an alkyl phthalimide which is subsequently hydrolyzed to the primary alkyl amine; the reaction is important historically for the synthesis of pure primary amines uncontaminated by secondary or tertiary by-products.
Nigh, W. G. J. Chem. Educ. 1975, 52, 670.
Synthesis |
Aromatic Compounds |
Amines / Ammonium Compounds
The selective reduction of meta- (and para-) nitroacetophenone  Jones, Alan G.
By appropriate choice of reagent and reaction conditions a nitroketone can be selectively reduced to an aminoketone or a nitroalcohol; aromatic nitro groups can be reduced to primary arylamines using various chemical reducing agents.
Jones, Alan G. J. Chem. Educ. 1975, 52, 668.
Mechanisms of Reactions |
Synthesis |
IR Spectroscopy |
Oxidation / Reduction |
Aromatic Compounds |
Amines / Ammonium Compounds
An alternative procedure to writing Lewis structures  Imkampe, Karl
Using simple molecular orbital pictures to represent all the resonance structures of larger organic molecules.
Imkampe, Karl J. Chem. Educ. 1975, 52, 429.
Lewis Structures |
Molecular Properties / Structure |
Resonance Theory
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
Preparation and color of azo-dyes  Mosher, Melvyn W.; Ansell, Jay M.
A simple experiment to relate the color of certain substituted azo-dyes to their visible absorption spectra.
Mosher, Melvyn W.; Ansell, Jay M. J. Chem. Educ. 1975, 52, 195.
Dyes / Pigments |
Synthesis |
Molecular Properties / Structure |
Aromatic Compounds |
Student-Centered Learning
The electrostatic dimension in conformational analysis  Kaloustian, Moses K.
The author presents the relevance of electrostatics in performing a conformational analysis.
Kaloustian, Moses K. J. Chem. Educ. 1974, 51, 777.
Chemometrics |
Aromatic Compounds |
Enantiomers |
Diastereomers |
Equilibrium |
Solids |
Gases
Huckel theory and aromatically  Schaad, L. J.; Hess, B. A., Jr.
After several years in disrepute, the simple Huckel molecular orbital method, when used with proper reference structure, now appears to give accurate predictions of aromatically.
Schaad, L. J.; Hess, B. A., Jr. J. Chem. Educ. 1974, 51, 640.
Aromatic Compounds |
MO Theory
A novel photochemistry experiment using a Diels-Alder reaction  Nash, E. G.
The authors present a two-step experiment incorporating a novel, but general photochemical reaction that is rapid, does not require special equipment, and which yields an interesting product worthy of further study.
Nash, E. G. J. Chem. Educ. 1974, 51, 619.
Aromatic Compounds |
Reactions |
Photochemistry
Photoelectron spectra. An experimental approach to teaching molecular orbital models  Bock, Hans; Mollere, Phillip D.
The photoelectron effect; Koopman's theorem; the argon atom; the nitrogen molecule; the correlation of AH2 molecules: Hydrogen sulfide and water; MO models for larger molecules; pi conjunction in butadiene; bond-bond interaction in polysilanes; perturbation of benzene pi system by methylio substituents; "Through space" interactions in isopropylidene norboradiene; "Through bond" interaction in diazabicyclo [2.2.2.]octane.
Bock, Hans; Mollere, Phillip D. J. Chem. Educ. 1974, 51, 506.
MO Theory |
Photochemistry |
Enrichment / Review Materials |
Aromatic Compounds
Benzene and the triumph of the octet theory  Saltzman, Martin D.
This article describes the history of understanding benzene structure.
Saltzman, Martin D. J. Chem. Educ. 1974, 51, 498.
Aromatic Compounds |
Molecular Properties / Structure |
Enrichment / Review Materials |
Atomic Properties / Structure
Conversion of a primary alcohol to an alkyl halide via a tosylate intermediate  Wiseman, Park A.; Betras, Steve; Lindley, Barry
The experiment in this article was designed primarily for and has been performed successfully by sophomore chemistry majors.
Wiseman, Park A.; Betras, Steve; Lindley, Barry J. Chem. Educ. 1974, 51, 348.
Alcohols |
Alkylation |
Reactions |
Aromatic Compounds |
NMR Spectroscopy
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
The number of possible isomers in the porphyrins  Pilgrim, R. L. C.
The author examines problems within the discussion of porphyrin compounds in biochemistry textbooks.
Pilgrim, R. L. C. J. Chem. Educ. 1974, 51, 316.
Constitutional Isomers |
Diastereomers |
Enantiomers |
Aromatic Compounds
A simple and inexpensive collector for preparative gas chromatography  Rossley, Nicci L.; Higgins, Gibson W.; Rothberg, Irvin; Friedman, H. Martin
The authors present a more simple and inexpensive collector for studying alkylation of naphthalene with alkenenes.
Rossley, Nicci L.; Higgins, Gibson W.; Rothberg, Irvin; Friedman, H. Martin J. Chem. Educ. 1974, 51, 242.
Gas Chromatography |
Aromatic Compounds |
Alkylation |
Laboratory Equipment / Apparatus
Stereochemistry of carbonyl addition reactions  Goller, Edwin J.
This article is a brief summary of some of the more important unifying concepts that have been proposed in the study of the stereo chemistry of carbonyl addition reactions.
Goller, Edwin J. J. Chem. Educ. 1974, 51, 182.
Addition Reactions |
Stereochemistry |
Aldehydes / Ketones |
Aromatic Compounds
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
An APL computer program for evaluating gas-phase kinetic reactions  Seyse, Robert J.; Rose, Timothy L.
The authors have written an APL computer program to solve the first-order rate equation. Since the general program is easily modified to take into account the stoichiometry of the reaction, it can be used for any gas phase decomposition reactions such as cyclopentene, di-tert-butylperoxide and norbornylene.
Seyse, Robert J.; Rose, Timothy L. J. Chem. Educ. 1974, 51, 112.
Gases |
Kinetics |
Aromatic Compounds |
Stoichiometry |
Laboratory Computing / Interfacing
A crossed aldol condensation for the undergraduate laboratory  Angres, Isaac; Zieger, Herman E.
This two-step experiment for undergraduate organic chemistry students illustrates three basic ideas: organic chemistry students illustrate three basic ideas (1) crossed aldol condensation; (2) the acidity of benzylic hydrogen in hydrocarbons; and (3) reduction of a double bond in hydride transfer.
Angres, Isaac; Zieger, Herman E. J. Chem. Educ. 1974, 51, 64.
Aromatic Compounds |
Aldehydes / Ketones |
Acids / Bases |
Alcohols
A simulated research project in synthetic organic chemistry: An undergraduate laboratory  Bobbitt, J. M.; Huang, Samuel J.
An undergraduate laboratory of a simulated research project in synthetic organic chemistry.
Bobbitt, J. M.; Huang, Samuel J. J. Chem. Educ. 1974, 51, 58.
Synthesis |
Aromatic Compounds
Resonance theory and the enumeration of Kekule structures  Herndon, William C.
The formulation of resonance theory as it is practiced today is explicated in the well-known books by Pauling and Wheland. Study of these texts show that resonance theory are so drastic that many theoreticians are loathe to ascribe validity to the less rigorous method.
Herndon, William C. J. Chem. Educ. 1974, 51, 10.
Resonance Theory |
Theoretical Chemistry |
Aromatic Compounds |
Molecular Properties / Structure
Aromaticity (Garratt, P. J.)  Paquette, Leo A.

Paquette, Leo A. J. Chem. Educ. 1973, 50, A598.
Aromatic Compounds
A rapid and convenient lecture demonstration of dyeing with azo colors  Smith, N. H. P.
Lists colors obtained from diazonium salts and naphthol AS analogs, as well as a procedure for a rapid and convenient lecture demonstration of dyeing with azo colors.
Smith, N. H. P. J. Chem. Educ. 1973, 50, 790.
Dyes / Pigments |
Applications of Chemistry |
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
Laboratory safety with sodium bis(2-methoxy-ethoxy) aluminum hydride  Bull, L. S.
Safety information on benzene should be included with the referenced article.
Bull, L. S. J. Chem. Educ. 1973, 50, 655.
Toxicology |
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
The synthesis and nitration of benzene-d1  Todd, David
The synthesis of labeled benzene-d1 and its conversion to meta-dinitrobenzene.
Todd, David J. Chem. Educ. 1973, 50, 366.
Aromatic Compounds |
Synthesis |
Isotopes |
IR Spectroscopy
A first-order four coupled nuclei nmr spectrum: 2-bromo-4-fluoroanisole  Canselier, J. P.
Few molecules are found to represent four magnetically non-equivalent nuclei, the chemical shifts of which are sufficiently different to allow a first-order analysis; 2-bromo-4-fluoroanisole is one such molecule.
Canselier, J. P. J. Chem. Educ. 1973, 50, 291.
NMR Spectroscopy |
Molecular Properties / Structure |
Aromatic Compounds
The determination of the resonance energy of benzene. A physical chemistry laboratory experiment  Stevenson, Gerald R.
This procedure relies on calorimetry to measure the resonance energy of benzene, a useful way to relate the concepts of aromaticity and resonance energy to experimental thermodynamics.
Stevenson, Gerald R. J. Chem. Educ. 1972, 49, 781.
Aromatic Compounds |
Resonance Theory |
Molecular Properties / Structure |
Calorimetry / Thermochemistry |
Thermodynamics
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
The bombardier beetle  Plumb, Robert C.; Erickson, Karen L.
The chemistry behind the bombardier beetle's chemical defenses illustrates the principles of reaction rates, catalysis, and laboratory safety.
Plumb, Robert C.; Erickson, Karen L. J. Chem. Educ. 1972, 49, 705.
Applications of Chemistry |
Natural Products |
Rate Law |
Catalysis |
Oxidation / Reduction |
Aromatic Compounds
Use of the Huckel molecular orbital computer programs in teaching  Duke, B. J.
Describes the use of a computer program in a quantum chemistry course for calculating theoretical properties of aromatic compounds by the Huckel molecular orbital method.
Duke, B. J. J. Chem. Educ. 1972, 49, 703.
MO Theory |
Quantum Chemistry |
Theoretical Chemistry |
Aromatic Compounds
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
The vegetable chameleons  Heines, Virginia
Summarizes the work by Tswett with natural and artificial anthocyanins, as well as subsequent efforts.
Heines, Virginia J. Chem. Educ. 1972, 49, 605.
Plant Chemistry |
Natural Products |
Dyes / Pigments |
Acids / Bases |
Aromatic Compounds
Perfumes and the art of perfumery  Grant, Nancy; Naves, Renee G.
Examines the physical and chemical properties of perfumes, as well as several examples of compounds that constitute the essence of typical perfumes.
Grant, Nancy; Naves, Renee G. J. Chem. Educ. 1972, 49, 526.
Consumer Chemistry |
Molecular Properties / Structure |
Aromatic Compounds |
Applications of Chemistry
A laboratory project in competitive aromatic nucleophilic displacement  Todd, David; Lookabaugh, Mark
The purposes of this series of experiments are to demonstrate how easily some aromatic nucleophilic substitutions can go and to introduce the competitive method of determining relative reaction rates.
Todd, David; Lookabaugh, Mark J. Chem. Educ. 1972, 49, 292.
Aromatic Compounds |
Nucleophilic Substitution |
Synthesis |
Reactions |
Thin Layer Chromatography
Selective reduction of dinitrobenzenes. An organic laboratory experiment  Idoux, John P.; Plain, Wendell
Different students are assigned different reducing agents and asked to explain why their particular selective reduction occurs as their results indicate.
Idoux, John P.; Plain, Wendell J. Chem. Educ. 1972, 49, 133.
Aromatic Compounds |
Resonance Theory |
Oxidation / Reduction
Directive effects in electrophilic aromatic substitution. An organic chemistry experiment  Beishline, Robert R.
The student is given the procedure for the monobromination of acetanilide in glacial acetic acid, but is not told where on the ring the bromine will substitute; he is required to prove the structure of the product through an independent synthesis of the preparation of a known derivative.
Beishline, Robert R. J. Chem. Educ. 1972, 49, 128.
Aromatic Compounds |
Electrophilic Substitution |
Synthesis |
Alkylation
Fragmentation mechanisms in mass spectrometry  Campbell, M. M.; Runquist, O.
Presents a precise mechanistic notation that is useful in teaching fragmentation processes.
Campbell, M. M.; Runquist, O. J. Chem. Educ. 1972, 49, 104.
Mass Spectrometry |
Alkenes |
Aromatic Compounds |
Alcohols |
Ethers |
Amines / Ammonium Compounds |
Aldehydes / Ketones |
Esters |
Amides
Guanidine, trimethylenemethane, and "Y-delocalization." Can acyclic compounds have "aromatic" stability?  Gund, Peter
It appears that the Y-shaped configuration of 6 pi electrons as found in guanidine derivatives is an exceptionally stable one.
Gund, Peter J. Chem. Educ. 1972, 49, 100.
Aromatic Compounds |
Molecular Properties / Structure |
Resonance Theory |
MO Theory
Benzoxazinone synthesis. An organic chemistry experiment  Eckroth, David R.
The preparation of 2-methyl-4H-3,1-benzoxazin-4-one and 2(2'-methanesulfonamido)phenyl-4H-3,1-benzoxazin-4-one exposes students to reactive intermediates.
Eckroth, David R. J. Chem. Educ. 1972, 49, 66.
Synthesis |
Aromatic Compounds |
Reactive Intermediates
Evidence of d pi-acceptor resonance in halogen substituents  Abdulla, Riaz F.
The association of various structural and dynamic phenomena through the postulate of d pi resonance has potential additional predictive value.
Abdulla, Riaz F. J. Chem. Educ. 1972, 49, 64.
Resonance Theory |
Mechanisms of Reactions
Liquid crystals - Synthesis and properties. An experiment for the integrated organic and physical laboratory  Verbit, Lawrence
Outlines some of the history behind the synthesis of liquid crystals, and presents a procedure for the synthesis and examination of two types of liquid crystals.
Verbit, Lawrence J. Chem. Educ. 1972, 49, 36.
Aromatic Compounds
Bridgehead reactivity. An experiment in organic chemistry  Jefford, C. W.; McCreadie, R. M.; Muller, P.; Siegfried, B.
The experiment featured in this article illustrates bridgehead reactivity.
Jefford, C. W.; McCreadie, R. M.; Muller, P.; Siegfried, B. J. Chem. Educ. 1971, 48, 708.
Reactions |
Aromatic Compounds
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
Chemical queries. Especially for introductory chemistry teachers  Young, J. A.; Malik, J. G.
(1) What is the significance of negative absolute temperatures? (2) What role do nitrogen atoms play in dyes?
Young, J. A.; Malik, J. G. J. Chem. Educ. 1971, 48, 529.
Dyes / Pigments |
Nomenclature / Units / Symbols |
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
Nitrenes  Belloli, Robert
The purpose of this article is to present some important general concepts in nitrene chemistry and to concentrate on the chemistry of more thoroughly studied nitrenes, ethoxycarbonylnitrene and cyanontirene.
Belloli, Robert J. Chem. Educ. 1971, 48, 422.
Diastereomers |
Aromatic Compounds |
Reactions |
Free Radicals
Diazonium salts as spot test and synthetic reagents  Stone, DeWitt B.
The laboratory experiment outlined in this article includes the paper chromatography of phenols, the use of p-nitrobenzenediazonium chloride to locate and identify the phenols on the chromatogram, and the use of this diazonium salt in syntheses involving coupling or replacement of the diazonium functional group.
Stone, DeWitt B. J. Chem. Educ. 1971, 48, 413.
Chromatography |
Phenols |
Aromatic Compounds |
Amines / Ammonium 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
Transannular carbene reactions. An intermediate organic laboratory experiment  Hecht, Stephen S.
The experiment described in this article has been used to integrate physical, organic, and inorganic chemistry and stresses the use of research techniques in understanding the relationship between structure and reactivity.
Hecht, Stephen S. J. Chem. Educ. 1971, 48, 340.
Spectroscopy |
Chromatography |
Aromatic Compounds |
Reactions |
Molecular Properties / Structure
Vibronic spectra and energy levels of polyatomic molecules. A physical chemistry experiment  Moomaw, William R.; Skinner, James F.
In the experiment described here, the student measures and assigns the vapor phase vibronic spectrum of an aromatic and an azaaromatic molecule.
Moomaw, William R.; Skinner, James F. J. Chem. Educ. 1971, 48, 304.
Aromatic Compounds |
Quantum Chemistry |
Gases |
Spectroscopy
Demonstration of the relative nucleophilic properties of aromatic primary amines  Yeadon, Alan
It is possible to demonstrate this simple nucleophilic substitution by examining the initial stages of the methylation of aniline and other aromatic amines.
Yeadon, Alan J. Chem. Educ. 1971, 48, 256.
Aromatic Compounds |
Amines / Ammonium Compounds |
Nucleophilic Substitution
An integrated nmr and photochemical organic chemistry experiment  Glaros, George; Cromwell, Norman H.
The authors describe a photochemical experiment involving a compound that was prepared in the authors' previous paper.
Glaros, George; Cromwell, Norman H. J. Chem. Educ. 1971, 48, 204.
Aromatic Compounds |
Diastereomers
The structure and properties of choleic acids. A biologically oriented organic experiment  Jesaitis, R. G.; Krantz, A.
The experiment described here introduces students to techniques which are often not introduced in the context of a laboratory experiment.
Jesaitis, R. G.; Krantz, A. J. Chem. Educ. 1971, 48, 137.
Acids / Bases |
Aromatic Compounds |
Stoichiometry |
Quantitative Analysis |
UV-Vis Spectroscopy
Vibronic energy transfer. A physical chemistry experiment  Wettack, F. Sheldon; Bibart, C. H.
In order to familiarize chemistry majors with work in this area of physical chemistry, the authors have developed a new experiment for the third year laboratory course. This experiment involves a study of the quenching of the fluorescence of benzene by various added molecules in the gas phase, and serves to introduce the student to such concepts as excited state energy levels and energy transfer rates and to the techniques involved in measuring fluorescence in the gas phase.
Wettack, F. Sheldon; Bibart, C. H. J. Chem. Educ. 1971, 48, 126.
Photochemistry |
Aromatic Compounds |
Gases
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
The symmetries and multiplicities of electronic states in polyatomic molecules  Ellis, R. L.; Jaffe, H. H.
A simple approach has been presented for determining the symmetries and multiplicities of electronic states arising from configurations containing both equivalent and nonequivalent electrons. This method is based on the use of different "building blocks" for each set of electrons described by the same space function.
Ellis, R. L.; Jaffe, H. H. J. Chem. Educ. 1971, 48, 92.
Quantum Chemistry |
Aromatic Compounds |
MO Theory
The isomerization of xylenes. An experiment for the organic or instrumental laboratory  Harbison, Kenneth G.
This experiment illustrates both qualitative and quantitative applications of infrared spectroscopy for the analysis of mixtures, as well as providing an interesting study of the mechanism of Friedel-Crafts reactions.
Harbison, Kenneth G. J. Chem. Educ. 1970, 47, 837.
Instrumental Methods |
Aromatic Compounds |
IR Spectroscopy |
Mechanisms of Reactions |
Reactions |
Constitutional Isomers
Ultraviolet and fluorescence spectra of 2,5-diaryl-1,3,4-oxidiazoles: An organic laboratory experiment  Taber, Richard L.; Grantham, Gary D.
Reports on an experiment involving a two-step synthesis leading to a series of substituted 2,5-diaryl-1,3,4-oxidiazoles that can be used for a class study of substituent effects on absorption and emission spectra of aromatic molecules.
Taber, Richard L.; Grantham, Gary D. J. Chem. Educ. 1970, 47, 834.
UV-Vis Spectroscopy |
Fluorescence Spectroscopy |
Aromatic Compounds |
Mechanisms of Reactions |
Molecular Properties / Structure |
Synthesis
Hydrolysis of benzenediazonium ion  Sheats, John E.; Harbison, Kenneth G.
Presents a more convenient approach to studying the kinetics of the hydrolysis of benzenediazonium ion.
Sheats, John E.; Harbison, Kenneth G. J. Chem. Educ. 1970, 47, 779.
Aromatic Compounds |
Nucleophilic Substitution |
Kinetics
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
Preparation of 6-aminosaccharin  Rose, Norman C.; Rome, Sanford
This synthesis involves the substitution of a chlorosulfonyl group onto an aromatic ring at a position predictable on the basis of the directing ability of the groups already present, the oxidation of a methyl group, a cyclization that is an example of the ease with which five-membered rings are formed, and the reduction of a nitro group.
Rose, Norman C.; Rome, Sanford J. Chem. Educ. 1970, 47, 649.
Synthesis |
Aromatic Compounds |
Oxidation / Reduction
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
Inexpensive molecular models of metallocenes  Sutton, John R.
Describes the construction of sandwich compounds such a ferrocene.
Sutton, John R. J. Chem. Educ. 1970, 47, 305.
Aromatic Compounds |
Molecular Properties / Structure |
Molecular Modeling |
Coordination Compounds
The rearrangement of diazotized 4-bromobenzophenone hydrazone: A stereospecific reaction  Hawbeker, Byron L.
This procedure involves the synthesis of hydrazone and its subsequent diazotization / rearrangement to produce an anilide.
Hawbeker, Byron L. J. Chem. Educ. 1970, 47, 218.
Reactions |
Stereochemistry |
Molecular Properties / Structure |
Aromatic Compounds |
Mechanisms of Reactions |
Synthesis
An experiment to illustrate nucleophilic aromatic substitution and tautomerism  Farmer, J. L.; Haws, E. J.
Students hydrolyze 2-chloropyridine and then examine the tautomeric mixture produced using infrared spectroscopy.
Farmer, J. L.; Haws, E. J. J. Chem. Educ. 1970, 47, 41.
Nucleophilic Substitution |
Aromatic Compounds |
Synthesis |
Mechanisms of Reactions |
IR Spectroscopy
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
Oxidative coupling: A new approach to azo chemistry  Hunig, S.
By looking for the important structural features of p-phenylenediamines that constitute their ability to couple oxidatively, it was possible to construct three new systems that are also capable of undergoing this reaction. The enormous variety possible in these systems permits the syntheses of a great number of unusual azo compounds.
Hunig, S. J. Chem. Educ. 1969, 46, 734.
Aromatic Compounds |
Oxidation / Reduction |
Mechanisms of Reactions |
Synthesis
Preparation of sulfanilamide from aniline: An organic chemistry experiment  Hurdis, Everett C.; Yang, Josephine W.
Presents the preparation of sulfanilamide from aniline, a synthesis that is shorter than the tradition method.
Hurdis, Everett C.; Yang, Josephine W. J. Chem. Educ. 1969, 46, 697.
Synthesis |
Aromatic Compounds |
Mechanisms of Reactions
Chemical queries. Especially for introductory chemistry teachers  Young, J. A.; Malik, J. G.; Quagliano, James V.; Danehy, James P.
(1) Why different potential for copper/zinc cells when using nitrates vs. sulfates? Why is neither cell potential as large as predicted by Nerst equation? (2) Do elements in the zinc subgroup belong to the transition series? - answer by Quagliano. (3) How can the 2,4,5-trichloro derivative of phenoxyacetic acid be prepared? - answer by Danehy.
Young, J. A.; Malik, J. G.; Quagliano, James V.; Danehy, James P. J. Chem. Educ. 1969, 46, 227.
Electrochemistry |
Electrolytic / Galvanic Cells / Potentials |
Periodicity / Periodic Table |
Metals |
Synthesis |
Aromatic Compounds
Metalation of metallocenes  Slocum, D. W.; Engelmann, T. R.; Ernst, C.; Jennings, C. A.; Jones, W.; Koonsivitsky, B.; Lewis, J.; Shenkin, P.
Examines the metalation of unsubstituted metallocenes and the mono- and dimetalation of substituted ferrocenes.
Slocum, D. W.; Engelmann, T. R.; Ernst, C.; Jennings, C. A.; Jones, W.; Koonsivitsky, B.; Lewis, J.; Shenkin, P. J. Chem. Educ. 1969, 46, 144.
Aromatic Compounds |
Metals
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
Cross conjugation  Phelan, Nelson F.; Orchin, Milton
Although qualitative conclusions may be obtained by judicious use of simple resonance theory, even in simple systems the electron distribution and extent of conjugation between the nonconjugated centers in cross conjugation is most effectively illustrated by molecular orbital descriptions.
Phelan, Nelson F.; Orchin, Milton J. Chem. Educ. 1968, 45, 633.
Valence Bond Theory |
MO Theory |
Resonance Theory
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  Winterburn, John
Praises the usefulness of an earlier published synthesis.
Winterburn, John J. Chem. Educ. 1968, 45, 70.
Synthesis |
Aromatic Compounds
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
Letter to the editor  Neville, G. A.
Identifies a more appropriate reference for the cited article.
Neville, G. A. J. Chem. Educ. 1967, 44, 427.
Aromatic Compounds |
Nucleophilic Substitution
The electron repulsion theory of the chemical bond. II. An alternative to resonance hybrids  Luder, W. F.
The author proposes the electron repulsion theory of the chemical bond as an alternative to resonance hybrids.
Luder, W. F. J. Chem. Educ. 1967, 44, 269.
Covalent Bonding |
Resonance Theory
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
Electrophilic substitution in benzenoid compounds (Norman, R. O. C.; Taylor, R.)  Bunnett, Joseph F.

Bunnett, Joseph F. J. Chem. Educ. 1966, 43, A358.
Electrophilic Substitution |
Aromatic Compounds
An experiment in activated aromatic nucleophilic substitution  Dyall, L. K.
This experiment involves preparing the intermediates formed during activated aromatic nucleophilic substitution and a study of their decomposition on treatment with mineral acid.
Dyall, L. K. J. Chem. Educ. 1966, 43, 663.
Aromatic Compounds |
Nucleophilic Substitution |
IR Spectroscopy
Selective reduction of dinitro compounds  Weiss, Hilton M.
The selective reduction of aromatic dinitro compounds by ammonium sulfide is an opportunity to consider an open-ended question.
Weiss, Hilton M. J. Chem. Educ. 1966, 43, 384.
Oxidation / Reduction |
Aromatic Compounds |
Mechanisms of Reactions
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
Letters to the editor  Brady, Leonard E.
Notes the danger of benzene vapors.
Brady, Leonard E. J. Chem. Educ. 1965, 42, 577.
Aromatic Compounds
Qualitative test for ketones, aromatic aldehydes, and aliphatic aldehydes  Morrison, James D.
The Bordwell-Wellman solution of chromic anhydride in aqueous sulfuric acid is an excellent reagent for distinguishing aldehydes from ketones.
Morrison, James D. J. Chem. Educ. 1965, 42, 554.
Qualitative Analysis |
Aldehydes / Ketones |
Aromatic Compounds
Electronic interactions between nonconjugated groups  Ferguson, Lloyd N.; Nnadi, John C.
The purpose of this paper is to discuss some of the different molecular systems in which electronic interactions between classically nonconjugated groups are explicable in terms of molecular orbital theory as well as nonclassical resonance theory.
Ferguson, Lloyd N.; Nnadi, John C. J. Chem. Educ. 1965, 42, 529.
MO Theory |
Resonance Theory |
Molecular Properties / Structure
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
Kekule's benzene ring theory: A subject for lighthearted banter  Wilcox, David H., Jr.; Greenbaum, Frederick R.
Presents a nineteenth century analogy between benzene and six monkeys.
Wilcox, David H., Jr.; Greenbaum, Frederick R. J. Chem. Educ. 1965, 42, 266.
Aromatic Compounds
Thermally stable polymeric materials  Bruck, S. D.
The object of this article is to discuss some of the factors responsible for high thermal stability in polymers, to review a few of the most important advances that have recently been made in the synthesis of such materials, and to present some of the results of the thermal degradation of an aromatic polyimide under investigation in the author's laboratory.
Bruck, S. D. J. Chem. Educ. 1965, 42, 18.
Synthesis |
Aromatic Compounds |
Thermal Analysis
Homolytic, cationotropic, and anionotropic reactions: A mechanistic approach to organic chemistry  Hoogenboom, Bernard E.
Examines examples of radical, cationotropic, and anionotropic reactions.
Hoogenboom, Bernard E. J. Chem. Educ. 1964, 41, 639.
Mechanisms of Reactions |
Free Radicals |
Reactions |
Electrophilic Substitution |
Nucleophilic Substitution
Relative rates of electrophilic aromatic substitution  Casanova, Joseph, Jr.
An experiment involving the bromination of various aromatic substrates that covers several aspects of kinetic phenomena.
Casanova, Joseph, Jr. J. Chem. Educ. 1964, 41, 341.
Aromatic Compounds |
Electrophilic Substitution |
Rate Law |
Kinetics
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
The ultraviolet spectra of aromatic hydrocarbons: Predicting substitution and isomerism changes  Stevenson, Philip E.
Presents a theory that allows one to predict the UV spectra of many benzene derivatives and their isomers.
Stevenson, Philip E. J. Chem. Educ. 1964, 41, 234.
UV-Vis Spectroscopy |
Spectroscopy |
Aromatic Compounds
Letters  Fang, Fabian T.
Suggests corrections to an earlier published article.
Fang, Fabian T. J. Chem. Educ. 1964, 41, 170.
Aromatic Compounds
The use of the Perkin reaction in organic chemistry classes  Buckles, R. E.
Provides suggestions for student research based on an earlier article published in the Journal.
Buckles, R. E. J. Chem. Educ. 1963, 40, A139.
Undergraduate Research |
Reactions |
Aromatic Compounds |
Aldehydes / Ketones |
Amines / Ammonium Compounds
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
Rules for molecular orbital structures  Meislich, Herbert
In view of the fact that molecular orbital theory makes more correct predictions and avoids the misconceptions that arise in the minds of novice students when they are exposed to resonance theory, it would be better to use M.O. theory as much as possible in teaching organic chemistry.
Meislich, Herbert J. Chem. Educ. 1963, 40, 401.
MO Theory |
Resonance Theory
Multicenter and assisted mechanistic pathways in the reactions of organometallic compounds  Dessy, Raymond E.; Paulik, Frank
Examines a variety of nucleophilic and electrophilic, multicenter and assisted mechanistic pathways in the reactions of organometallic compounds.
Dessy, Raymond E.; Paulik, Frank J. Chem. Educ. 1963, 40, 185.
Organometallics |
Mechanisms of Reactions |
Nucleophilic Substitution |
Electrophilic Substitution
The preparation of nitrosobenzene  Young, Jay A.; Taylor, John K.
Suggests some research activities based on an article published previously in the Journal.
Young, Jay A.; Taylor, John K. J. Chem. Educ. 1962, 39, A962.
Synthesis |
Aromatic Compounds |
Undergraduate Research
The rate of iodination of aniline: A physical chemistry experiment  Brice, L. K.
The rate of iodination of aniline is determined by measuring the optical density of the reaction medium.
Brice, L. K. J. Chem. Educ. 1962, 39, 632.
Aromatic Compounds |
Kinetics |
Rate Law
The stability of the "aromatic sextet"  Waack, Richard
The calculation of the pi-electron molecular orbitals for planar monocyclic conjugated polyolefins gives an explanation for the observation that the 4n + 2 number of pi-electrons forms a highly stable aromatic molecule.
Waack, Richard J. Chem. Educ. 1962, 39, 469.
Aromatic Compounds |
Molecular Properties / Structure
The configuration of (-)-shikimic acid and certain biochemically related compounds  Hanson, Kenneth R.
Points out errors in representations of the structures of important biological derivatives of 5-dehydroquinic acid II.
Hanson, Kenneth R. J. Chem. Educ. 1962, 39, 419.
Aromatic Compounds |
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers |
Plant Chemistry
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
The electronic structures and stereochemistry of NO2+, NO2, and NO2-  Panckhurst, M. H.
A comparison of the electronic structures and stereochemistry of NO2+, NO2, and NO2-.
Panckhurst, M. H. J. Chem. Educ. 1962, 39, 270.
Stereochemistry |
Molecular Properties / Structure |
Resonance Theory
The nature of essential oils. II. Chemical constituents, analysis  Sterrett, Frances S.
Examines aliphatic and aromatic compounds, and terpenes and terpenoids.
Sterrett, Frances S. J. Chem. Educ. 1962, 39, 246.
Aromatic Compounds |
Natural Products
The acylation of aliphatic unsaturated hydrocarbons  Sharefkin, Jacob G.
Introductory organic chemistry textbooks discuss the Friedel-Crafts synthesis of aromatic ketones but usually do not treat the corresponding reaction in the aliphatic series.
Sharefkin, Jacob G. J. Chem. Educ. 1962, 39, 206.
Aromatic Compounds |
Aldehydes / Ketones |
Reactions |
Synthesis |
Mechanisms of Reactions
Chemical equilibrium: The hydrogenation of benzene  Kokes, R. J.; Dorfman, M. K.; Mathia, T.
This procedure examines the reversible reaction between benzene and hydrogen, forming cyclohexane, in the presence of a metal catalyst.
Kokes, R. J.; Dorfman, M. K.; Mathia, T. J. Chem. Educ. 1962, 39, 91.
Reactions |
Aromatic Compounds |
Equilibrium |
Catalysis
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
Substitution at elements other than carbon (Ingold, C. K.)  Reinheimer, John D.

Reinheimer, John D. J. Chem. Educ. 1961, 38, A434.
Nucleophilic Substitution |
Electrophilic Substitution |
Organometallics
Determination of saponification equivalents of phenolic esters  Tobey, Stephen W.; McGregor, S. D.; Cottrill, Sharon L.
The objective of this paper is to show that by making a few key changes in existing techniques, a procedure of saponification determination is evolved that is not only applicable to ordinary alkyl esters of carboxylic acids, but gives excellent results with a wide variety of esters of phenol and other aromatic hydroxyl compounds.
Tobey, Stephen W.; McGregor, S. D.; Cottrill, Sharon L. J. Chem. Educ. 1961, 38, 611.
Esters |
Carboxylic Acids |
Phenols |
Aromatic Compounds
Apparatus for the Friedel-Crafts reaction: For the undergraduate organic chemistry laboratory  Kremer, Chester B.; Wilen, Samuel H.
A simple and practical reaction apparatus has been designed that offers several advantages over earlier set-ups.
Kremer, Chester B.; Wilen, Samuel H. J. Chem. Educ. 1961, 38, 306.
Laboratory Equipment / Apparatus |
Electrophilic Substitution
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
A simplified preparation of anthraquinone  Wilcox, C. R., Jr.; Stevens, M.
The cyclization of ortho-benzoylbenzoic acid to anthraquinone by strong acids is an instructive reaction for elementary organic laboratory course because it is a model of the industrial preparation of the important anthraquinone dye intermediates and serves as a point of entry into the area of polycyclic aromatic chemistry.
Wilcox, C. R., Jr.; Stevens, M. J. Chem. Educ. 1959, 36, 633.
Synthesis |
Dyes / Pigments |
Aromatic Compounds
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
Peter GriessDiscoverer of diazo compounds  Heines, Sister Virginia
Summarizes the life of Peter Griess and his research with diazo compounds.
Heines, Sister Virginia J. Chem. Educ. 1958, 35, 187.
Dyes / Pigments |
Aromatic Compounds
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
August Kekule and the birth of the structural theory of organic chemistry in 1858  Benfey, O. Theodore
Translation of a speech made by Kekule in 1890 in which he discusses his development of the structural theory and the importance of creativity and imagination in scientific research.
Benfey, O. Theodore J. Chem. Educ. 1958, 35, 21.
Molecular Properties / Structure |
Aromatic Compounds |
Covalent Bonding
Ferrocene: A novel organometallic compound  Rausch, Marvin; Vogel, Martin; Rosenberg, Harold
Examines the preparation, physical properties, structure, aromatic character, reactions, and applications of ferrocene.
Rausch, Marvin; Vogel, Martin; Rosenberg, Harold J. Chem. Educ. 1957, 34, 268.
Organometallics |
Synthesis |
Physical Properties |
Aromatic Compounds
The ultraviolet absorption spectra of aromatic compounds adsorbed on silicic acid  Robin, Melvin
Presents ultraviolet absorption spectra of benzene, phenol, fluorobenzene, n-methylaniline, and their analysis.
Robin, Melvin J. Chem. Educ. 1956, 33, 526.
UV-Vis Spectroscopy |
Aromatic Compounds |
Phenols
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
Editor's outlook  Rakestraw, Norris W.
Unless the prospects of a scientific career include the spirit of freedom, we are unlikely to attract to it the kind of young men and women who in the long run will pursue it most effectively and productively.
Rakestraw, Norris W. J. Chem. Educ. 1955, 32, 343.
Student / Career Counseling |
Aromatic Compounds |
Amides
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
A sequence of synthesis in the general organic laboratory class  Lange, Erwin F.; Teranishi, Roy; Christensen, Bert E.
This synthesis involves the oxidation of p-xylene, nitration and esterfication of terephthalic acid, reduction of nitroterephthalic acid, and the preparation of 4-quinazolone-7-carboxylic acid.
Lange, Erwin F.; Teranishi, Roy; Christensen, Bert E. J. Chem. Educ. 1955, 32, 40.
Synthesis |
Aromatic Compounds |
Reactions |
Oxidation / Reduction
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
Theoretical chemistry in Russia  Hunsberger, I. Moyer
Examines contributions to organic structural theory and Russian criticisms of resonance theory.
Hunsberger, I. Moyer J. Chem. Educ. 1954, 31, 504.
Resonance 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
Predicting reactions of a resonance hybrid from minor canonical structures  Gero, Alexander
Little effort seems to have been made to set up any general rules on the relative contributions of the several structural formulas (canonical structures) used to represent a resonance hybrid to the reactions of the hybrid.
Gero, Alexander J. Chem. Educ. 1954, 31, 136.
Resonance Theory |
Mechanisms of Reactions
Letters to the editor  Ferguson, Lloyd N.
Points out an additional reference that should have been made in an earlier article.
Ferguson, Lloyd N. J. Chem. Educ. 1954, 31, 102.
Aromatic Compounds |
Electrophilic Substitution
Letters  Bent, Richard L.
Addresses issues raised regarding an earlier paper on isomerism and mesomerism.
Bent, Richard L. J. Chem. Educ. 1953, 30, 648.
Molecular Properties / Structure |
Resonance Theory |
Covalent Bonding
Letters  Ferreira, Ricardo Carvalho
Identifies some inconsistencies in an earlier paper on isomerism and mesomerism.
Ferreira, Ricardo Carvalho J. Chem. Educ. 1953, 30, 647.
Molecular Properties / Structure |
Resonance Theory |
Covalent Bonding
Letters  Wolfrom, Melville L.
The author encourages American chemists to familiarize themselves with the conventions of representing configurational formulas.
Wolfrom, Melville L. J. Chem. Educ. 1953, 30, 479.
Molecular Modeling |
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Resonance Theory
Directive influence of substituents in the benzene ring  Varshni, Yatendra Pal
The author describes a new rule regarding the directive influence of substituents in the benzene ring.
Varshni, Yatendra Pal J. Chem. Educ. 1953, 30, 465.
Molecular Properties / Structure |
Aromatic Compounds
Hlasiwetz and BarthPioneers in the structural aspects of plant products  McConnell, Virginia F.
Examines the contributions made by Heinrich Hlasiwetz and Ludwig Barth von Barthenau to uncovering the structural aspects of plant products, including resins, tannins, proteins, and benzene.
McConnell, Virginia F. J. Chem. Educ. 1953, 30, 380.
Plant Chemistry |
Natural Products |
Aromatic Compounds |
Proteins / Peptides
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
Aspects of isomerism and mesomerism. I. (a) Formulas and their meaning (b) Mesomerism  Bent, Richard L.
Examines molecular, empirical, structural, configurational, and projection formulas, as well as mesomerism (electronic isomers) and various types of resonance.
Bent, Richard L. J. Chem. Educ. 1953, 30, 220.
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Resonance Theory
The Fischer indole synthesis  Roussel, Philip A.
Examines the discovery of indole and Fischer's work to develop a means of its synthesis.
Roussel, Philip A. J. Chem. Educ. 1953, 30, 122.
Synthesis |
Mechanisms of Reactions |
Molecular Properties / Structure |
Aromatic Compounds
Letters  Brescia, Frank
The author calls for someone to invent another term for the word resonance as applied to the field of molecular structure.
Brescia, Frank J. Chem. Educ. 1952, 29, 261.
Resonance Theory |
Nomenclature / Units / Symbols |
Molecular Properties / Structure
Peter Griess and the phenylene diamines  Smith, Manning A.; Gower, William R.
Contrary to the claim made by some textbooks, Peter Griess did not isolate and decarboxylate the six diaminobenzooic acids.
Smith, Manning A.; Gower, William R. J. Chem. Educ. 1952, 29, 176.
Amines / Ammonium Compounds |
Aromatic Compounds |
Synthesis |
Molecular Properties / Structure
The concept of resonance energy in elementary organic chemistry  Gero, Alexander
The author describes an empirically-based presentation of resonance energy that is perfectly within reach of introductory organic students.
Gero, Alexander J. Chem. Educ. 1952, 29, 82.
Resonance Theory
About a machistic theory in chemistry and its propagandists  Tatevskii, V. M.; Shakhparanov, M. I.
Russian scientists attack the resonance theory and the use of resonance structures.
Tatevskii, V. M.; Shakhparanov, M. I. J. Chem. Educ. 1952, 29, 13.
Molecular Properties / Structure |
Resonance Theory
The present state of the chemical structural theory  Kursanov, D. N.; Gonikberg, M. G.; Dubinin, B. M.; Kabachnik, M. I.; Kaverzneva, E. D.; Prilezhaeva, E. N.; Sokolov, N. D.; Freidlina, R. Kh.
Several members of the Russian Academy of Sciences attack the resonance theory and resonance structures.
Kursanov, D. N.; Gonikberg, M. G.; Dubinin, B. M.; Kabachnik, M. I.; Kaverzneva, E. D.; Prilezhaeva, E. N.; Sokolov, N. D.; Freidlina, R. Kh. J. Chem. Educ. 1952, 29, 2.
Molecular Properties / Structure |
Resonance Theory
A new derivative for the identification of primary aromatic amines  Lappin, Gerald R.
Describe an investigation into the products reactions between various primary aromatic amines and ethyl ethoxymethylenemalonate as a means of identifying primary aromatic amines.
Lappin, Gerald R. J. Chem. Educ. 1951, 28, 126.
Qualitative Analysis |
Aromatic Compounds |
Amines / Ammonium Compounds |
Heterocycles |
Synthesis