TIGER

Journal Articles: 410 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
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
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
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
Computational Analysis of Stereospecificity in the Cope Rearrangement  Laura Glish and Timothy W. Hanks
Experimental product distributions from the Cope rearrangement of disubstituted 1,5-hexadienes can be readily understood by computer modeling of the various possible transitions states. Visual analysis of these geometries allow students to interpret the computational results by analogy to the familiar chair and boat conformations of substituted cyclohexanes.
Glish, Laura; Hanks, Timothy W. J. Chem. Educ. 2007, 84, 2001.
Alkenes |
Computational Chemistry |
Conformational Analysis |
Medicinal Chemistry |
MO Theory |
Molecular Modeling |
Mechanisms of Reactions
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
Introducing the Practical Aspects of Computational Chemistry to Undergraduate Chemistry Students  Jason K. Pearson
Presents a laboratory exercise in which students use traditional second-year concepts such as the rigid rotor and harmonic oscillator approximations in conjunction with Gaussian 03 to reinforce practical aspects of computational chemistry.
Pearson, Jason K. J. Chem. Educ. 2007, 84, 1323.
Computational Chemistry |
MO Theory |
Quantum Chemistry |
Theoretical Chemistry
The Mechanism of Covalent Bonding: Analysis within the Hückel Model of Electronic Structure  Sture Nordholm, Andreas Bäck, and George B. Bacskay
Hckel molecular orbital theory is shown to be uniquely useful in understanding and interpreting the mechanism of covalent bonding. Using the Hckel model it can be demonstrated that the dynamical character of the molecular orbitals is related simultaneously to the covalent bonding mechanism and to the degree of delocalization of the electron dynamics.
Nordholm, Sture; Bäck, Andreas; Bacskay, George B. J. Chem. Educ. 2007, 84, 1201.
Covalent Bonding |
MO Theory |
Quantum Chemistry |
Theoretical Chemistry
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
On the Role of d Orbital Hybridization in the Chemistry Curriculum  John Morrison Galbraith
The use of d-orbital hybridization to describe hypervalent molecules should be removed from the general chemistry curriculum. The case of bonding in sulfur hexaflouride can illustrate that no theory provides all the right answers all the time.
Galbraith, John Morrison. J. Chem. Educ. 2007, 84, 783.
Computational Chemistry |
MO Theory |
Valence Bond Theory
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
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
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
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
A Sequence of Linked Experiments, Suitable for Practical Courses of Inorganic, Organic, Computational Chemistry, and NMR Spectroscopy  Grigoriy A. Sereda
A sequence of investigations associated with the iodochlorination of styrene and 1-hexene is described. The sequence is flexible enough to be used in inorganic, organic, computational, and instrumental courses.
Sereda, Grigoriy A. J. Chem. Educ. 2006, 83, 931.
Alkenes |
Computational Chemistry |
Constitutional Isomers |
MO Theory |
NMR Spectroscopy |
Synthesis
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
Why the Lower-Energy Term of Singlet Dioxygen Has a Doubly Occupied π* Orbital  Terry S. Carlton
The singlet term of dioxygen with one doubly occupied p* orbital has lower energy than the singlet term with two singly occupied p* orbitals even though single occupancy is favored in the aufbau of atoms. A simple physical explanation based on orbital angular momentum explains this double occupancy.
Carlton, Terry S. J. Chem. Educ. 2006, 83, 477.
MO Theory |
Quantum Chemistry
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
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 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
The Evolution of a Green Chemistry Laboratory Experiment: Greener Brominations of Stilbene  Lallie C. McKenzie, Lauren M. Huffman, and James E. Hutchison
We describe two new greener alkene bromination reactions that offer enhanced laboratory safety and convey important green chemistry concepts, in addition to illustrating the chemistry of alkenes. The two alternative reactions, one involving pyridinium tribromide and a second using hydrogen peroxide and hydrobromic acid, are compared to the traditional bromination of stilbene through the application of green metrics, including atom economy, percent experimental atom economy, E factor, and effective mass yield.
McKenzie, Lallie C.; Huffman, Lauren M.; Hutchison, James E. J. Chem. Educ. 2005, 82, 306.
Synthesis |
Green Chemistry |
Aromatic Compounds |
Addition Reactions |
Alkenes
A 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
Moving Beyond the Single Center—Ways To Reinforce Molecular Orbital Theory in an Inorganic Course  Marion E. Cass and William E. Hollingsworth
Rather than ending the discussion of molecular orbital (MO) theory in an inorganic chemistry course with molecules such as octahedral ML6 or square planar ML4, we suggest moving beyond the single-atom center to include the MO diagram of ethene (C2H4).
Cass, Marion E.; Hollingsworth, William E. J. Chem. Educ. 2004, 81, 997.
MO Theory |
Molecular Modeling
A Unified Approach to Electron Counting in Main-Group Clusters  John E. McGrady
A unified approach to electron counting in main-group cluster chemistry is presented, wherein the different classes, electron-rich, electron-precise, and electron-deficient, are viewed simply as different regions of a continuum defined by two variables, vertex count and valence electron count.
McGrady, John E. J. Chem. Educ. 2004, 81, 733.
Main-Group Elements |
MO Theory
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
The Singlet States of Molecular Oxygen   Jean-Pierre Puttemans and Georges Jannes
Although the purpose of the article The Visible Spectrum of Liquid Oxygen in the General Chemistry Laboratory is an analysis of the two-moleculesone-photon absorption spectrum of oxygen, it nevertheless assigns arrangements of the electrons in an energy diagram to the two singlet states of molecular oxygen which do not seem to be correct in our opinion.
Puttemans, Jean-Pierre; Jannes, Georges. J. Chem. Educ. 2004, 81, 639.
Molecular Properties / Structure |
MO Theory |
UV-Vis Spectroscopy
The Singlet States of Molecular Oxygen   Jean-Pierre Puttemans and Georges Jannes
Although the purpose of the article The Visible Spectrum of Liquid Oxygen in the General Chemistry Laboratory is an analysis of the two-moleculesone-photon absorption spectrum of oxygen, it nevertheless assigns arrangements of the electrons in an energy diagram to the two singlet states of molecular oxygen which do not seem to be correct in our opinion.
Puttemans, Jean-Pierre; Jannes, Georges. J. Chem. Educ. 2004, 81, 639.
Molecular Properties / Structure |
MO Theory |
UV-Vis Spectroscopy
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
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
Why Chemical Reactions Happen (James Keeler and Peter Wothers)  John Krenos
By concentrating on a limited number of model reactions, this book presents chemistry as a cohesive whole by tying together the fundamentals of thermodynamics, chemical kinetics, and quantum chemistry, mainly through the use of molecular orbital interpretations.
Krenos, John. J. Chem. Educ. 2004, 81, 201.
Mechanisms of Reactions |
Thermodynamics |
Kinetics |
Quantum Chemistry |
MO Theory
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
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
The Excited States of Molecular Oxygen  David Tudela and Vicente Fernández
There is a mistake in the electronic structure of the first two excited states.
Tudela, David; Fernández, Vicente. J. Chem. Educ. 2003, 80, 1381.
MO Theory |
UV-Vis Spectroscopy
Using Hydrocarbon Acidities To Demonstrate Principles of Organic Structure and Bonding  Andrew P. Dicks
This article demonstrates the utility of hydrocarbon acidity as a teaching tool within the undergraduate classroom. Acidities of compounds containing only hydrogen and carbon vary by at least 50 orders of magnitude. Differences in acidities are rationalized by invoking principles of hybridization, resonance, induction, and aromaticity.
Dicks, Andrew P. J. Chem. Educ. 2003, 80, 1322.
Acids / Bases |
Aromatic Compounds |
Alkanes / Cycloalkanes
The 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
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
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
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
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
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
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
How We Teach Molecular Structure to Freshmen  Michael O. Hurst
Examination of how textbooks discuss various aspects of molecular structure; conclusion that much of general chemistry is taught the way it is for historical and not pedagogical reasons.
Hurst, Michael O. J. Chem. Educ. 2002, 79, 763.
Covalent Bonding |
Atomic Properties / Structure |
Molecular Properties / Structure |
Lewis Structures |
VSEPR Theory |
Valence Bond Theory |
MO Theory
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
The Visible Spectrum of Liquid Oxygen in the General Chemistry Laboratory  Frazier Nyasulu, John Macklin, and William Cusworth III
Examination of the spectrum of liquid oxygen and testing several hypotheses to explain the pattern of spectral lines observed.
Nyasulu, Frazier; Macklin, John; Cusworth, William, III. J. Chem. Educ. 2002, 79, 356.
MO Theory |
UV-Vis Spectroscopy |
Molecular Properties / Structure
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
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
Structure and Bonding (by Jack Barrett)  Michael Laing
Tutorial chemistry text.
Laing, Michael. J. Chem. Educ. 2001, 78, 1600.
Molecular Properties / Structure |
MO Theory |
Atomic Properties / Structure |
Group Theory / Symmetry |
Covalent Bonding |
VSEPR Theory
The Role of Lewis Structures in Teaching Covalent Bonding  S. R. Logan
Difficulties with the Lewis theory of covalent bonding and upgrading it to the Molecular Orbital theory.
Logan, S. R. J. Chem. Educ. 2001, 78, 1457.
Covalent Bonding |
MO Theory |
Nonmajor Courses |
Learning Theories |
Lewis Structures |
Molecular Properties / Structure
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
Orbitals in Chemistry: A Modern Guide for Students
by Victor M. Gil
  David Hanson
Analysis of atomic and molecular orbitals.
Hanson, David. J. Chem. Educ. 2001, 78, 1184.
MO Theory |
Molecular Properties / Structure |
Quantum Chemistry |
Atomic Properties / Structure |
Covalent Bonding
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
Have Orbitals Really Been Observed? (re J. Chem. Educ. 2000, 77, 1492-1494)  John C. H. Spence, M. O'Keefe, and J. M. Zuo
Clarification of work described in a previous article.
Spence, John C. H.; O'Keefe, M.; Zuo, J. M. J. Chem. Educ. 2001, 78, 877.
Computational Chemistry |
MO Theory |
Quantum Chemistry |
Theoretical Chemistry
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
An Idea Whose Time Has Come?
(re
J. Chem. Educ. 1999, 76, 1718-1722)  David E. Lewis
Unoccupied orbitals as the major arbiters of reactivity have been long ignored in teaching introductory organic chemistry courses.
Lewis, David E. J. Chem. Educ. 2001, 78, 727.
Covalent Bonding |
Mechanisms of Reactions |
MO Theory
An Idea Whose Time Has Come?
(re
J. Chem. Educ. 1999, 76, 1718-1722)  William B. Jensen
Past classifications related to the nine-category classification of organic electrophilic-nucleophilic reactions based on the bonding and symmetry characteristics of the reactants' frontier orbitals of the author.
Jensen, William B. J. Chem. Educ. 2001, 78, 727.
Covalent Bonding |
Mechanisms of Reactions |
MO Theory
An Idea Whose Time Has Come?
(re
J. Chem. Educ. 1999, 76, 1718-1722)  William B. Jensen
Past classifications related to the nine-category classification of organic electrophilic-nucleophilic reactions based on the bonding and symmetry characteristics of the reactants' frontier orbitals of the author.
Jensen, William B. J. Chem. Educ. 2001, 78, 727.
Covalent Bonding |
Mechanisms of Reactions |
MO Theory
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
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
Hybridization and Structural Properties
(re
J. Chem. Educ. 1998, 75, 888-890)  Victor M. S. Gil
Clarifying cause-effect relationships between orbital hybridization and structural properties.
Gil, Victor M. S. J. Chem. Educ. 2001, 78, 31.
MO Theory |
Instrumental Methods |
NMR Spectroscopy |
Molecular Properties / Structure
Hybridization and Structural Properties
(re
J. Chem. Educ. 1998, 75, 888-890)  Victor M. S. Gil
Clarifying cause-effect relationships between orbital hybridization and structural properties.
Gil, Victor M. S. J. Chem. Educ. 2001, 78, 31.
MO Theory |
Instrumental Methods |
NMR Spectroscopy |
Molecular Properties / Structure
Have Orbitals Really Been Observed?  Eric R. Scerri
Recent reports claiming to have observed textbook d orbitals are analyzed and it is argued that what was observed indirectly, and not for the first time, was actually electron density. It is also suggested that the tendency to use the terms electron density and orbital to mean the same thing will give rise to confusion in chemical education.
Scerri, Eric R. J. Chem. Educ. 2000, 77, 1492.
Computational Chemistry |
MO Theory |
Quantum Chemistry |
Theoretical Chemistry
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
Reply to Coulombic Models in Chemical Bonding  Smith, Derek W.
Coulombic vs molecular orbital models for explaining the molecular shapes of ionic molecules.
Smith, Derek W. J. Chem. Educ. 2000, 77, 445.
Ionic Bonding |
Molecular Modeling |
Molecular Properties / Structure |
MO Theory
Coulombic Models in Chemical Bonding  Sacks, Lawrence J.
Coulombic vs molecular orbital models for explaining the molecular shapes of ionic molecules.
Sacks, Lawrence J. J. Chem. Educ. 2000, 77, 445.
Ionic Bonding |
Molecular Modeling |
Molecular Properties / Structure |
MO Theory
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
Organizing Organic Reactions: The Importance of Antibonding Orbitals  David E. Lewis
It is proposed that unoccupied molecular orbitals arbitrate much organic reactivity, and that they provide the basis for a reactivity-based system for organizing organic reactions. Such a system is proposed for organizing organic reactions according to principles of reactivity, and the system is discussed with examples of the frontier orbitals involved.
Lewis, David E. J. Chem. Educ. 1999, 76, 1718.
Covalent Bonding |
Mechanisms of Reactions |
MO Theory
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
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
Lewis Structures Are Models for Predicting Molecular Structure, Not Electronic Structure  Gordon H. Purser
This article argues against a close relationship between Lewis dot structures and electron structure obtained from quantum mechanical calculations. Lewis structures are a powerful tool for structure prediction, though they are classical models of bonding and do not predict electronic structure.
Purser, Gordon H. J. Chem. Educ. 1999, 76, 1013.
Molecular Properties / Structure |
Covalent Bonding |
Computational Chemistry |
Quantum Chemistry |
MO Theory |
Learning Theories |
Lewis Structures |
Molecular Modeling
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
Pericyclic Reactions: FMO Approach-Abstract of Issue 9904M  Albert W. M. Lee, C. T. So, C. L. Chan, and Y. K. Wu
Pericyclic Reactions: FMO Approach is a program for Macintosh computers in which the frontier molecular orbital approaches to electrocyclic and cycloaddition reactions are animated. The bonding or antibonding interactions of the frontier molecular orbital(s) determine whether the reactions are thermally or photochemically allowed or forbidden.
Lee, Albert W. M.; So, C. T.; Chan, C. L.; Wu, Y. K. J. Chem. Educ. 1999, 76, 720.
MO Theory |
Mechanisms of Reactions
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
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
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
A Simple Qualitative Molecular-Orbital/Valence-Bond Description of the Bonding in Main Group "Hypervalent" Molecules  Owen J. Curnow
A multicenter valence-bond/molecular-orbital bonding scheme for main group "hypervalent" molecules is proposed which extends the 3-center-4-electron (3c-4e) bonding model of Rundle and Pimentel to include 4c-6e, 5c-8e, and 6c-10e bonds. This model allows the determination of bond orders and a rationalisation of bond distances.
Curnow, Owen J. J. Chem. Educ. 1998, 75, 910.
Covalent Bonding |
MO Theory |
Theoretical Chemistry |
Main-Group Elements |
Molecular Properties / Structure
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
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
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
Correction  
Correction in equation 1.
J. Chem. Educ. 1997, 74, 480.
Aromatic Compounds |
Molecular Properties / Structure
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
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
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
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
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
Relative Stabilities and Reactivities of Isolated Versus Conjugated Alkenes: Reconciliation Via a Molecular Orbital Approach  Chariklia Sotiriou-Leventis, Samir B. Hanna, and Nicholas Leventis
The well-accepted practice of generating a pair of molecular orbitals, one of lower energy and another of higher energy than the original pair of overlapping atomic orbitals, and the concept of a particle in a one-dimensional box are implemented in a simplified, nonmathematical method that explains the relative stabilities and reactivities of alkenes with conjugated versus isolated double bonds.
Sotiriou-Leventis, Chariklia; Hanna, Samir B.; Leventis, Nicholas. J. Chem. Educ. 1996, 73, 295.
Alkenes |
MO Theory
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
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
Huckel Calculations using Mathematica  Healy, Eamonn F.
Using Mathematica software to simplify and elucidate the application of the Huckel theory in the calculation of molecular energies and orbital coefficients.
Healy, Eamonn F. J. Chem. Educ. 1995, 72, A120.
MO Theory |
Mathematics / Symbolic Mathematics
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
The Conformational Behavior of n-Pentane: A Molecular Mechanics and Molecular Dynamics Experiment  Mencarelli, Paolo
174. Use of HyperChem to investigate the conformational behavior of n-pentane.
Mencarelli, Paolo J. Chem. Educ. 1995, 72, 511.
MO Theory |
Chirality / Optical Activity |
Molecular Properties / Structure |
Conformational Analysis |
Alkanes / Cycloalkanes |
Molecular Mechanics / Dynamics |
Molecular Modeling
Non-Koopmans' Molecules  Duke, Brian J.; O'Leary, Brian
Analysis of the validity of the molecular orbital description of the ionization process.
Duke, Brian J.; O'Leary, Brian J. Chem. Educ. 1995, 72, 501.
MO Theory |
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
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
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
Electrophilic Aromatic Substitution, Promoted by Bentonitic Clay  Angeles, Enrique; Ramirez, Alberto; Martinez, Ignacio; Moreno, Enrique
Experiment that uses bentonitic clay as a catalyst instead of the conventional Lewis acid in the chlorination and bromination of benzene and dimerization of toluene.
Angeles, Enrique; Ramirez, Alberto; Martinez, Ignacio; Moreno, Enrique J. Chem. Educ. 1994, 71, 533.
Aromatic Compounds |
Electrophilic Substitution |
Catalysis
Isomers of Benzene  Gutman, I.; Potgieter, J. H.
Summary of isomers and valence isomers of benzene.
Gutman, I.; Potgieter, J. H. J. Chem. Educ. 1994, 71, 222.
Aromatic Compounds |
Diastereomers |
Covalent Bonding
The Blue Bottle Experiment Revisited: How Blue? How Sweet?  Cook, A. Gilbert; Tolliver, Randi M.; Williams, Janelle E.
Determining whether other colors and carbohydrates are possible with the "Blue Bottle" reaction.
Cook, A. Gilbert; Tolliver, Randi M.; Williams, Janelle E. J. Chem. Educ. 1994, 71, 160.
Aromatic Compounds |
Reactions |
Rate Law |
Mechanisms of Reactions |
Carbohydrates |
Oxidation / Reduction
The Lewis Structure: An Expanded Perspective  Reed, James L.
A simple bridge between the molecular orbital and valence bond models.
Reed, James L. J. Chem. Educ. 1994, 71, 98.
Lewis Structures |
Covalent Bonding |
MO Theory |
Molecular Properties / Structure
Models of 2-Butanone: Using Graphics To Illustrate Complementary Approaches to Molecular Structure and Reactivity  Hanks, T. W.
157. Ways in which a graphics workstation can be used to illustrate various concepts of molecular structure.
Hanks, T. W. J. Chem. Educ. 1994, 71, 62.
Aldehydes / Ketones |
Molecular Properties / Structure |
Molecular Modeling |
Molecular Mechanics / Dynamics |
Stereochemistry |
Quantum Chemistry |
MO Theory
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
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
The generation of 2-D and 3-D electron density maps using high performance computing technology   Denniston, Michael L.
Describes a method for producing computer-generated images that show the buildup of electron density at any position within a molecular structure.
Denniston, Michael L. J. Chem. Educ. 1993, 70, A76.
MO Theory |
Quantum Chemistry
Spectroscopic Analysis of Semiconductor Colloids: An Experiment in Materials Science for the Advanced Inorganic or Physical Chemistry Laboratory  Chandler, Robin R.; Bigham, Shelli R.; Coffer, Jeffery L.
While the study of clusters and the materials derived from them is rapidly expanding, little attention is paid to them in undergraduate chemistry. The authors describe an appropriate undergraduate activity.
Chandler, Robin R.; Bigham, Shelli R.; Coffer, Jeffery L. J. Chem. Educ. 1993, 70, A7.
Colloids |
Semiconductors |
MO Theory |
Metalloids / Semimetals |
Solid State Chemistry |
UV-Vis Spectroscopy |
Micelles |
Metals |
Materials Science |
Metallic Bonding
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
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
Photodegradation of methylene blue: Using solar light and semiconductor (TiO2)  Nogueira, Raquel F. P.; Jardim, Wilson F.
An experiment that can be used to introduce or explore concepts such as photochemistry, semiconductors, and kinetics.
Nogueira, Raquel F. P.; Jardim, Wilson F. J. Chem. Educ. 1993, 70, 861.
Semiconductors |
Photochemistry |
Kinetics |
Catalysis |
MO Theory
Experiments illustrating metal-insulator transitions in solids  Keller, Steven W.; Mallouk, Thomas E.
Experiments and demonstrations to expose undergraduate students to electronic properties of solids.
Keller, Steven W.; Mallouk, Thomas E. J. Chem. Educ. 1993, 70, 855.
Crystals / Crystallography |
Semiconductors |
MO Theory |
Materials Science
The Caltech chemistry animation project   Lewis, Nathan S.
Animations are being produced on subjects such as: atomic and molecular orbitals, lattices, VSPER, nucleophilic substitution, stereochemistry, sigma and pi bonding, and many more.
Lewis, Nathan S. J. Chem. Educ. 1993, 70, 739.
Stereochemistry |
Atomic Properties / Structure |
Molecular Modeling |
MO Theory |
Crystals / Crystallography
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
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
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
The nature of the chemical bond-Once more (1).  Edmiston, Clyde.
The original article is a classic case of incorrect conclusions drawn from largely correct facts.
Edmiston, Clyde. J. Chem. Educ. 1992, 69, 600.
Quantum Chemistry |
MO Theory
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
Semitopological representation of electronic structure of complex boron hydrides and ions using styx numbers  Dikshit, S. K.; Singh, Ramsharan
The equations of balance for boron hydrides do not always give unequivocal answers, but do assist by limiting the structure considered.
Dikshit, S. K.; Singh, Ramsharan J. Chem. Educ. 1992, 69, 274.
Molecular Properties / Structure |
MO Theory
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
Higher order cycloaddition reactions of adamantyl isobenzofulvene and isobenzofuran: A microscale synthesis illustrating the involvement of highly reactive intermediates and a simple FMO treatment of their cycloaddition periselectivities  Russell, Richard A.; Longmore, Robert W.; Warrener, Ronald N.
The authors have developed an undergraduate laboratory experiment to illustrate a cycloaddition reaction using a simple mathematical approach.
Russell, Richard A.; Longmore, Robert W.; Warrener, Ronald N. J. Chem. Educ. 1992, 69, 164.
Microscale Lab |
Alkenes |
Synthesis |
MO Theory
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
A simple preparation of 1,4-di-tert-butylbenzene without AICI3: An undergraduate organic chemistry experiment  Castrillon, Jose
Alkylation of benzene with tert-butyl chloride and aluminum chloride has been very popular in first year organic chemistry courses, but it releases HCl gas fumes. This problem has lead to a replacement preparation using tert-butyl acetate, which provides better yield and eliminated the fumes.
Castrillon, Jose J. Chem. Educ. 1991, 68, 793.
Alkylation |
Aromatic Compounds |
Alcohols |
Microscale Lab
The relative energies of molecular orbitals for second-row homonuclear diatomic molecules: The effect of s-p mixing  Haim, Albert
This paper attempts to point out an error usually committed when illustrating the molecular orbitals for earlier diatomic molecules (B-N) versus later ones (O and F).
Haim, Albert J. Chem. Educ. 1991, 68, 737.
MO Theory
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
There are no such things as orbitals-Act two!  Simons, Jack
What is the role of molecular orbital theory in chemistry instruction?
Simons, Jack J. Chem. Educ. 1991, 68, 131.
MO Theory |
Atomic Properties / Structure |
Quantum Chemistry
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
Superoxide dismutase and the Briggs-Rauscher reaction  Franz, David A.
Oxygen-derived species provide chemistry teachers with excellent examples for discussion of molecular-orbital theory, bond order and reactivity, redox potentials, radical reactivity, disproportionation, and enzyme activity.
Franz, David A. J. Chem. Educ. 1991, 68, 57.
Enzymes |
Biophysical Chemistry |
MO Theory |
Oxidation / Reduction |
Covalent Bonding
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
Reaction of bromine with hydrocarbons on the overhead, real or simulated  Solomon, Sally; Gregory, Michael; Padmanabhan, Sandeep; Smith, Kurt
A simulation that looks like the addition of bromine to hydrocarbons but is not (the bromine is simulated using a mixture of food colorings).
Solomon, Sally; Gregory, Michael; Padmanabhan, Sandeep; Smith, Kurt J. Chem. Educ. 1990, 67, 961.
Alkanes / Cycloalkanes |
Aromatic Compounds |
Addition Reactions
NMR analysis of product mixtures in electrophilic aromatic substitution  Clark, Mary Ann; Duns, Glenn; Golberg, Danny; Karwowska, Anna; Turgeon, Andree; Turley, Jolanda
Use of mole fraction analysis permits precise quantitative product mixture analysis, a large improvement over qualitative and semiquantitative techniques.
Clark, Mary Ann; Duns, Glenn; Golberg, Danny; Karwowska, Anna; Turgeon, Andree; Turley, Jolanda J. Chem. Educ. 1990, 67, 802.
NMR Spectroscopy |
Electrophilic Substitution |
Aromatic Compounds |
Quantitative Analysis
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
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
Crystal field theory and the angular overlap model applied to hydrides of main group elements  Moore, E. A.
How crystal field theory and the angular overlap model can be applied to very simple molecules, the di- and trihydrides of main group elements, which can then be used to introduce such concepts bonding orbitals, MO diagrams, and Walsh diagrams.
Moore, E. A. J. Chem. Educ. 1990, 67, 657.
Crystal Field / Ligand Field Theory |
Main-Group Elements |
MO Theory
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
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
MO theory made visible  Mealli, Carlo; Proserpio, Davide M.
114. The authors present an automated package of programs to perform MO calculations and their graphical illustration.
Mealli, Carlo; Proserpio, Davide M. J. Chem. Educ. 1990, 67, 399.
MO Theory
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
Independent coordinates of molecular structures and group theory  Ermer, Otto
The author describes a simple and safe group theoretical method for the systematic evaluation of the number of independent structural parameters.
Ermer, Otto J. Chem. Educ. 1990, 67, 209.
MO Theory |
Molecular Properties / Structure
Molecular electronic terms and molecular orbital configurations  Mazo, R. M.
This paper answers the question, which molecular electronic terms can arise from a given electronic configuration?
Mazo, R. M. J. Chem. Educ. 1990, 67, 135.
MO Theory |
Atomic Properties / Structure |
Molecular Properties / Structure
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
Observation of paramagnetic property of oxygen by simple method - A simple experiment for college chemistry and physics courses   Shimada, Hiroshi; Yasuoka, Takashi; Mitsuzawa, Shunmei
The authors devised a demonstration in which a bubble of gaseous oxygen is used to demonstrate the paramagnetic property of oxygen rather than liquid oxygen.
Shimada, Hiroshi; Yasuoka, Takashi; Mitsuzawa, Shunmei J. Chem. Educ. 1990, 67, 63.
MO Theory |
Magnetic Properties
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
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
Huckel theory and photoelectron spectroscopy  von Nagy-Felsobuki, Ellak I.
HMO theory and photoelectron spectroscopy; HMO interpretation of the energetic shifts in the ultraviolet photoelectron spectroscopy of mono-substituted haloamines.
von Nagy-Felsobuki, Ellak I. J. Chem. Educ. 1989, 66, 821.
Spectroscopy |
MO Theory |
Computational Chemistry
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
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
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
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
Recent advances in the concept of hard and soft acids and bases  Pearson, Ralph G.
The hard / soft acids / bases principle has been justifiably criticized because of the lack of a precise definition of hardness and the inability to quantify this property; recent developments have overcome these objections, however.
Pearson, Ralph G. J. Chem. Educ. 1987, 64, 561.
Acids / Bases |
Coordination Compounds |
MO Theory |
Oxidation / Reduction
Electron spectroscopic methods in teaching  Allan, Michael
Presents several spectra in a format suitable for teaching applications with the intention of promoting the use of electron energy-loss spectroscopy in teaching the electronic structure of atoms and molecules at an elementary level.
Allan, Michael J. Chem. Educ. 1987, 64, 418.
Spectroscopy |
Quantum Chemistry |
Photochemistry |
Atomic Properties / Structure |
Molecular Properties / Structure |
MO Theory
No rabbit ears on water. The structure of the water molecule: What should we tell the students?  Laing, Michael
Analysis of the bonding found in water and how it results in the observed geometry of the water molecule.
Laing, Michael J. Chem. Educ. 1987, 64, 124.
Molecular Properties / Structure |
MO Theory |
Covalent Bonding
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
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
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
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
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
Fractional bond order  Li, Wai-Kee
Question designed to test the students' understanding of multicenter bonding and elementary molecular orbital theory.
Li, Wai-Kee J. Chem. Educ. 1985, 62, 605.
MO Theory
A simple method to determine the geometry of triatomic systems  Thuraisingham, R. A.; Epa, V. C.
A method based on the first-order perturbation theory applied to the extended Huckel method to determine the geometry of triatomic systems.
Thuraisingham, R. A.; Epa, V. C. J. Chem. Educ. 1985, 62, 486.
Molecular Properties / Structure |
VSEPR Theory |
MO Theory
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 strain and stabilization in molecules using isodesmic reactions  Fuchs, Richard
The stabilities of cyclic hydrocarbons are analyzed using isodesmic and metathetical isodesmic reactions.
Fuchs, Richard J. Chem. Educ. 1984, 61, 133.
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Alkenes |
Aromatic Compounds
Molecular formulas of organic compounds: the nitrogen rule and degree of unsaturation  Pellegrin, Valdo
This article wishes to demonstrate the nitrogen rule and the formula for calculating the number of rings plus double bonds of any common organic compound.
Pellegrin, Valdo J. Chem. Educ. 1983, 60, 626.
Heterocycles |
Aromatic Compounds |
Free Radicals
The synthesis of 4,6,8-trimethylazulene: an organic laboratory experiment  Garst, Michael E.; Hochlowski, Jill; Douglass, III, James G.; Sasse, Scott
A procedure for a two-step synthesis of 4,6,8-trimethylazulene.
Garst, Michael E.; Hochlowski, Jill; Douglass, III, James G.; Sasse, Scott J. Chem. Educ. 1983, 60, 510.
Synthesis |
Heterocycles |
Aromatic Compounds |
Resonance Theory |
Chromatography
A quick and simple conversion of carboxylic acids into their anilides of heating with phenyl isothiocyanate  Ram, Ram N.; Kumar, Pradeep; Mukerjee, Arya K.
In this article, the authors report a quick and easy procedure using phenyl isothiocyanate, which is ideally suited to students.
Ram, Ram N.; Kumar, Pradeep; Mukerjee, Arya K. J. Chem. Educ. 1983, 60, 508.
Carboxylic Acids |
Aromatic Compounds |
Phenols |
Reactions
A phase transfer catalyzed permanganate oxidation: preparation of vanillin from isoeugenol acetate  Lampman, Gary M.; Sharpe, Steven D.
There are several attractive features in this reaction sequence for the undergraduate laboratory. These include (1) use of a protecting acetate group, (2) use of a familiar "textbook" oxidant, potassium permanganate, (3) use of phase transfer catalyst, (4) preparing of an aldehyde, (5) short reaction period, and (6) the laboratory has a pleasant aroma.
Lampman, Gary M.; Sharpe, Steven D. J. Chem. Educ. 1983, 60, 503.
Oxidation / Reduction |
Catalysis |
Natural Products |
Synthesis |
Aldehydes / Ketones |
Alcohols |
Aromatic Compounds
The synthesis of 4,4'-di-tertbutyl biphenyl: a sophomore organic chemistry experiment  Horne, Deane A.
A brief note providing a sequence of experiments for an introductory organic course that is inexpensive and does not pose a health hazard.
Horne, Deane A. J. Chem. Educ. 1983, 60, 246.
Acids / Bases |
Aromatic Compounds |
Catalysis |
Alkylation |
Solutions / Solvents
The misuse of the circle notation to represent aromatic rings  Belloli, Robert C.
This chemistry educator has noticed confusion and erroneous conclusions resulting from the overuse and misuse of the circle notation to represent aromaticity in polycyclic aromatic hydrocarbons.
Belloli, Robert C. J. Chem. Educ. 1983, 60, 190.
Aromatic Compounds |
Molecular Properties / Structure
Production of aromatic hydrocarbons according to extractive distillation process  Molinier, J.; Malmary, G.; Constrasti, J.
A theme that deals with the study of the recovery of benzene from petroleum hydrocarbon mixture by means of an extractive distillation processes emerges from a pilot project that has been proposed to the graduating students.
Molinier, J.; Malmary, G.; Constrasti, J. J. Chem. Educ. 1983, 60, 148.
Separation Science |
Aromatic Compounds
Nitration of naphthol: A laboratory experiment  Mowery, Dwight F.
The nitration of beta-naphthol to produce pyrotechnic snakes and the nitration of alpha-naphthol to produce Martius yellow dye.
Mowery, Dwight F. J. Chem. Educ. 1982, 59, 689.
Aromatic Compounds
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
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
Was there a conspiracy when Kekul's first German benzene-structure paper was frequently listed as published in 1865?  Wotiz, John H.; Rudofsky, Susanna
The question of whether Kekul was deliberately ambiguous cannot be answered without a search through editorial files and personal correspondence.
Wotiz, John H.; Rudofsky, Susanna J. Chem. Educ. 1982, 59, 23.
Aromatic Compounds |
Molecular Properties / Structure
An undergraduate laboratory program project involving photocyclizations in independent syntheses of novel chrysenes and phenanthrenes  Letcher, R. M.
This experiment attempts to fulfill such objectives as providing meaningful and viable preparative reactions, providing an opportunity for independent laboratory work within a project framework and under conditions of nearly equal opportunity and experience.
Letcher, R. M. J. Chem. Educ. 1981, 58, 1020.
Undergraduate Research |
Synthesis |
Aromatic Compounds |
Photochemistry |
Diastereomers |
NMR Spectroscopy |
Alcohols |
Thin Layer Chromatography
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
Structure-resonance theory for pericyclic transition states  Herndon, William C.
The purpose of this article is to show that structure-resonance theory can be used to understand the effects of structure or substituents on the rates of thermal pericyclic reactions.
Herndon, William C. J. Chem. Educ. 1981, 58, 371.
Aromatic Compounds |
Resonance Theory |
Molecular Properties / Structure
Benzene, a familiar hazard?  Smith, Roger M.
Reviews the hazards of benzene.
Smith, Roger M. J. Chem. Educ. 1980, 57, A85.
Aromatic Compounds |
Toxicology
Purple benzene revisited  Doheny, Anthony J., Jr.; Ganem, Bruce
A variant of the referenced demonstration using crown ethers.
Doheny, Anthony J., Jr.; Ganem, Bruce J. Chem. Educ. 1980, 57, 308.
Aromatic Compounds |
Molecular Properties / Structure |
Ethers
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
Toward an organic chemist's periodic table  Hall, H. K., Jr.
An analogy between electron transfer reactions of the elements and those of organic molecules.
Hall, H. K., Jr. J. Chem. Educ. 1980, 57, 49.
MO Theory |
Reactions |
Mechanisms of Reactions
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
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
The perturbational MO method for saturated systems  Herndon, William C.
Outlines a molecular orbital approach to the problem of predicting and correlating bond dissociation energies in saturated hydrocarbons.
Herndon, William C. J. Chem. Educ. 1979, 56, 448.
MO Theory |
Alkanes / Cycloalkanes |
Free Radicals |
Mechanisms of Reactions
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
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
Assigning oxidation states to some metal dioxygen complexes of biological interest  Summerville, David A.; Jones, Robert D.; Hoffman, Brian M.; Basolo, Fred
Considers the bonding of dioxygen in metal-dioxygen complexes, paying particular attention to the problems encountered in assigning conventional oxidation numbers to both the metal center and coordinated dioxygen.
Summerville, David A.; Jones, Robert D.; Hoffman, Brian M.; Basolo, Fred J. Chem. Educ. 1979, 56, 157.
Oxidation State |
Metals |
Covalent Bonding |
MO Theory
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
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
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
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
Project for problem-oriented undergraduate organic or integrated undergraduate laboratory  Silveira, Augustine, Jr.
This paper reports on an open-ended project which allows a great degree of flexibility in the laboratory. The project provided about a 6-week study for groups of 24 students each.
Silveira, Augustine, Jr. J. Chem. Educ. 1978, 55, 57.
Synthesis |
Undergraduate Research |
Spectroscopy |
Diastereomers |
Addition Reactions |
MO Theory |
Elimination Reactions |
Thermodynamics |
Kinetics
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
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
Novel pictorial approach to teaching MO concepts in polyatomic molecules  Hoffman, D. K.; Ruedenberg, K.; Verkade, J. G.
Methods used in a one-quarter course to familiarize students with the general applicability of delocalized and localized molecular orbitals to polyatomic systems; includes examples of delocalized and localized molecular orbitals of XeF2, C3H3+, CH4, and CO2.
Hoffman, D. K.; Ruedenberg, K.; Verkade, J. G. J. Chem. Educ. 1977, 54, 590.
MO Theory |
Atomic Properties / Structure
Substituent effects in electrophilic aromatic substitution. A laboratory in organic chemistry  Gilow, Helmuth
The acid catalyzed bromination of aromatic substrates with hydrobromous acid.
Gilow, Helmuth J. Chem. Educ. 1977, 54, 450.
Molecular Properties / Structure |
Aromatic Compounds |
Electrophilic Substitution |
Mechanisms of Reactions |
Catalysis
Experiments with electrophilic aromatic substitution reactions  Cox, B.; Kubler, D. G.; Wilson, C. A.
Comparing the bromination and nitration of benzene.
Cox, B.; Kubler, D. G.; Wilson, C. A. J. Chem. Educ. 1977, 54, 379.
Reactions |
Aromatic Compounds |
Electrophilic Substitution |
Stereochemistry |
Diastereomers
Purple benzene: Solubilization of anions in organic solvents  Herriott, Arthur W.
Demonstrates the preference of a typical salt for solution in water rather than nonpolar benzene; a quaternary ammonium salt, though soluble in water, is more soluble in benzene.
Herriott, Arthur W. J. Chem. Educ. 1977, 54, 229.
Aromatic Compounds |
Precipitation / Solubility |
Solutions / Solvents |
Aqueous Solution Chemistry |
Molecular Properties / Structure
Where does resonance energy come from? A nonmathematical approach to the theory of aromaticity  Sardella, D. J.
In confronting the central issue of why aromatic systems are aromatic, the author provides a verbal application of perturbational molecular orbital theory.
Sardella, D. J. J. Chem. Educ. 1977, 54, 217.
Aromatic Compounds |
MO Theory
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
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
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 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 LMO description of multiple bonding and multiple lone pairs  England, Walter
Examines localized molecular orbitals and the description of multiple bonds and lone pairs.
England, Walter J. Chem. Educ. 1975, 52, 427.
Covalent Bonding |
MO 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
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
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
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
A laboratory study of strike and inductive effects  Fulkrod, John E.
The authors describe a general reaction that can be successfully used to teach both strike and inductive effects in the laboratory by discovery.
Fulkrod, John E. J. Chem. Educ. 1974, 51, 115.
Constitutional Isomers |
Electrophilic Substitution |
Aromatic Compounds
A 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
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
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
A simple demonstration of O2 paramagnetism. A macroscopically observable difference between VB and MO approaches to bonding theory  Saban, G. H.; Moran, T. F.
A simple apparatus to demonstrate the paramagnetic behavior of oxygen.
Saban, G. H.; Moran, T. F. J. Chem. Educ. 1973, 50, 217.
Molecular Properties / Structure |
Magnetic Properties |
MO Theory |
Covalent Bonding
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
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
A simple demonstration model for molecular orbital theory  Druding, Leonard F.
Using two bar magnets and iron filings to demonstrate the formation of molecular bonding and anti-bonding orbitals.
Druding, Leonard F. J. Chem. Educ. 1972, 49, 617.
MO Theory
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
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
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
Models to illustrate orbital symmetry effects in organic reactions  Brown, Peter
From a pedagogic point of view, conservation of orbital symmetry is easily assimilated by students with a rudimentary knowledge of simple MO theory and of symmetry. The author has found in teaching over the past three years at both graduate and undergraduate levels that use of a simple set of orbital models as described in this article has enormous advantages as a visual aid in the construction and assignment of symmetry elements to the appropriate semi-localized Huckel-type MOs and in following their stereo chemical fate in concerned reactions.
Brown, Peter J. Chem. Educ. 1971, 48, 535.
Molecular Modeling |
MO Theory |
Group Theory / Symmetry
Dewar resonance energy  Baird, N. C.
In the present paper, some of the general properties of the Dewar Resonance Energy definition are developed. In particular, the DRE value for a compound is shown to be independent of the numerical values used to bond energies, and the use of DRE in judging the aromaticity of organic molecules is illustrated.
Baird, N. C. J. Chem. Educ. 1971, 48, 509.
Resonance Theory |
Aromatic Compounds |
Molecular Properties / Structure
Mechanism of aromatic iodination  Butler, A. R.
The general halogenation process is given in inaccurate equilibrium textbooks.
Butler, A. R. J. Chem. Educ. 1971, 48, 508.
Aromatic Compounds
Substituent effects on aromatic electrophilic substitution. An "experimental" class exercise  Fergwon, Philip R.
The exercise described here illustrates aromatic electrophilic substitution.
Fergwon, Philip R. J. Chem. Educ. 1971, 48, 405.
Electrophilic Substitution |
Aromatic Compounds
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
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
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 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
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
The electron-pair repulsion model for molecular geometry  Gmespie, R. J.
Reviews the electron-pair repulsion model for molecular geometry and examines three-centered bonds, cluster compounds, bonding among the transition elements, and exceptions to VSEPR rules.
Gmespie, R. J. J. Chem. Educ. 1970, 47, 18.
Molecular Properties / Structure |
Covalent Bonding |
MO Theory |
VSEPR Theory |
Transition Elements
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
Localized and delocalized molecular orbital description of methane  Bernett, William A.
The purpose of this article is to show that the relationship between localized and delocalized molecular orbitals can be easily demonstrated for the case of methane.
Bernett, William A. J. Chem. Educ. 1969, 46, 746.
Molecular Properties / Structure |
MO Theory
LTE. Normalization of MO's  Hecht, Charles E.
The author suggests that the cited computer program be modified to normalize molecular orbitals.
Hecht, Charles E. J. Chem. Educ. 1969, 46, 700.
MO Theory |
Molecular Properties / Structure
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
Fluid-flow simulation of molecular orbitals  Gymer, Roger G.
A simple device, the fluid mapper, is used for the simulation of molecular orbitals.
Gymer, Roger G. J. Chem. Educ. 1969, 46, 493.
MO Theory |
Molecular Modeling
Hybrid orbitals in molecular orbital theory  Cohen, Irwin; Del Bene, Janet
Reviews, for the nonspecialist, the basis of hybrid orbitals in terms of molecular orbital theory, to show how the chemical bond is most closely approximated in orbital theory, and to present some new orbital diagrams.
Cohen, Irwin; Del Bene, Janet J. Chem. Educ. 1969, 46, 487.
MO Theory |
Transition Elements
Simplified molecular orbital approach to inorganic stereochemistry  Gavin, R. M., Jr.
The purpose of this paper is to outline the simplest of the Huckel-type molecular orbital models for inorganic molecules and to explore the information on molecular geometry implicit in this model.
Gavin, R. M., Jr. J. Chem. Educ. 1969, 46, 413.
MO Theory |
Stereochemistry |
Molecular Properties / Structure |
VSEPR Theory
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
Molecular geometry: Bonded versus nonbonded interactions  Bartell, L. S.
Proposes simplified computational models to facilitate a comparison between the relative roles of bonded and nonbonded interactions in directed valence.
Bartell, L. S. J. Chem. Educ. 1968, 45, 754.
Molecular Properties / Structure |
VSEPR Theory |
Molecular Modeling |
Covalent Bonding |
Noncovalent Interactions |
Valence Bond Theory |
MO 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
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
A unified theory of bonding for cyclopropanes  Bernett, William A.
Examines various models for bonding in cyclopropanes.
Bernett, William A. J. Chem. Educ. 1967, 44, 17.
Covalent Bonding |
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
MO Theory |
Molecular Modeling
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
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
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
Hybridization in the description of homonuclear diatomic molecules  George, John W.
Presents energy levels for B2 and C2 molecules using hybrid atomic orbitals.
George, John W. J. Chem. Educ. 1965, 42, 152.
Molecular Properties / Structure |
MO Theory
Atomic orbital molecular models  Martins, George
Atomic orbital molecular models are constructed using molded white expanded polystyrene in the form of spheres and teardrops.
Martins, George J. Chem. Educ. 1964, 41, 658.
Atomic Properties / Structure |
MO Theory
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 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
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
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 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
A comparison of theories: Molecular orbital, valence bond, and ligand field  Liehr, Andrew D.
Compares the development, nature, and applications of the molecular orbital, valence bond, and ligand field theories.
Liehr, Andrew D. J. Chem. Educ. 1962, 39, 135.
MO Theory |
Covalent Bonding |
Crystal Field / Ligand Field Theory
Ionic character, polarity, and electronegativity  Wilmshurst, J. K.
This article attempts to clearly define ionic character and polarity in both the valence bond and molecular orbital approximations; the electronegativity concept is also discussed.
Wilmshurst, J. K. J. Chem. Educ. 1962, 39, 132.
Covalent Bonding |
MO Theory
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
Molecular models featuring molecular orbitals  Brumlik, George C.
Molecular models have been constructed that attempt to represent atomic and molecular orbitals as accurately as the current theories of valence and pertinent experimental evidence permit.
Brumlik, George C. J. Chem. Educ. 1961, 38, 502.
Molecular Modeling |
Atomic Properties / Structure |
MO Theory
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
Some recent developments in the theory of bonding in complex compounds of the transition metals  Sutton, Leslie E.
Examines the ligand field and the molecular orbital theories of complexes, particularly involving transition metals.
Sutton, Leslie E. J. Chem. Educ. 1960, 37, 498.
Noncovalent Interactions |
Transition Elements |
Metals |
Crystal Field / Ligand Field Theory |
Coordination Compounds |
MO Theory |
Covalent Bonding
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
The small scale preparation of azobenzene and of hydrazobenzene  Vogel, A. I.; Watling, A.; Watling, J.
A satisfactory procedure for the preparation of azobenzene consists of the reduction of pure nitrobenzene with magnesium turnings and anhydrous methanol; hydrazobenzene may be prepared by reduction of nitrobenzene either with Devarda's alloy and sodium hydroxide solution or with excess of magnesium and anhydrous methanol.
Vogel, A. I.; Watling, A.; Watling, J. J. Chem. Educ. 1958, 35, 40.
Synthesis |
Aromatic Compounds
Aromatic substitution by free radicals  Nelson, Peter F.
This article summarizes recent investigations upon orientation and reaction rates with respect to homolytic substitution.
Nelson, Peter F. J. Chem. Educ. 1955, 32, 606.
Free Radicals |
Aromatic Compounds |
Reactions |
Rate Law |
Molecular Properties / Structure
Nucleophilic substitution in aromatic systems  Gillis, Richard G.
Classifies and examines various categories of nucleophilic substitution in aromatic systems.
Gillis, Richard G. J. Chem. Educ. 1955, 32, 296.
Nucleophilic Substitution |
Aromatic Compounds
The orientation and mechanism of electrophilic aromatic substitution  Ferguson, Lloyd N.
Electrophilic aromatic substitution apparently takes place by the formation of an intermediate pentadienate cation, +ArG, where Ar is an aromatic molecule and G is a portion of the reagent.
Ferguson, Lloyd N. J. Chem. Educ. 1955, 32, 42.
Electrophilic Substitution |
Reactions |
Mechanisms of Reactions |
Aromatic Compounds
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
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
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
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