TIGER

Journal Articles: 95 results
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
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
Förster Resonance Energy Transfer and Conformational Stability of Proteins  Katheryn M. Sanchez, Diana E. Schlamadinger, Jonathan E. Gable, and Judy E. Kim
Describes the integration of absorption spectroscopy, fluorescence spectroscopy, and Frster resonance energy transfer (FRET) measurements to probe important topics in protein folding. Comparison of conformational stabilities of cytochrome c measured via two chemical denaturants illustrates important concepts in protein folding and intermolecular interactions.
Sanchez, Katheryn M.; Schlamadinger, Diana E.; Gable, Jonathan E.; Kim, Judy E. J. Chem. Educ. 2008, 85, 1253.
Biophysical Chemistry |
Fluorescence Spectroscopy |
Proteins / Peptides |
Quantum Chemistry |
Resonance Theory |
Spectroscopy |
Thermodynamics |
UV-Vis Spectroscopy
Acid-Catalyzed Enolization of β-Tetralone  Brahmadeo Dewprashad, Anthony Nesturi, and Joel Urena
This experiment allows students to use 1H NMR to compare the rates of substitution of benzylic and non-benzylic a hydrogens of -tetralone and correlate their findings with predictions made by resonance theory.
Dewprashad, Brahmadeo; Nesturi, Anthony; Urena, Joel. J. Chem. Educ. 2008, 85, 829.
Aldehydes / Ketones |
Isotopes |
Mechanisms of Reactions |
NMR Spectroscopy |
Reactive Intermediates |
Resonance Theory |
Synthesis
Six Pillars of Organic Chemistry  Joseph J. Mullins
This article focuses on a core set of conceptselectronegativity, polar covalent bonding, inductive and steric effects, resonance, and aromaticitythe proper application of which can explain and predict a wide variety of chemical, physical, and biological properties of molecules and conceptually unite important features of general, organic, and biochemistry.
Mullins, Joseph J. J. Chem. Educ. 2008, 85, 83.
Bioorganic Chemistry |
Covalent Bonding |
Hydrogen Bonding |
Mechanisms of Reactions |
Periodicity / Periodic Table |
Reactive Intermediates |
Resonance Theory
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
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
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
Reaction-Map of Organic Chemistry  Steven Murov
The Reaction-Map of Organic Chemistry has been designed to provide an overview of most of the reactions needed for the organic chemistry course and should help students develop synthetic routes from one functional group to another.
Murov, Steven. J. Chem. Educ. 2007, 84, 1224.
Addition Reactions |
Electrophilic Substitution |
Elimination Reactions |
Nucleophilic Substitution |
Oxidation / Reduction |
Periodicity / Periodic Table |
Reactions |
Synthesis |
Enrichment / Review Materials
Getting the Weights of Lewis Structures out of Hückel Theory: Hückel–Lewis Configuration Interaction (HL-CI)  Stéphane Humbel
A method to obtain the weights of Lewis structures from Hckel calculations is presented and tested against established ab initio methods.
Humbel, Stéphane. J. Chem. Educ. 2007, 84, 1056.
Computational Chemistry |
Lewis Structures |
Theoretical Chemistry |
Quantum Chemistry |
Resonance Theory |
Valence Bond Theory
Aromatic Bagels: An Edible Resonance Analogy  Shirley Lin
Describes a classroom demonstration involving the use of a bagel and cream cheese as an analogy for benzene that emphasizes the deficiencies of using a single Lewis structure to describe this structure.
Lin, Shirley. J. Chem. Educ. 2007, 84, 779.
Aromatic Compounds |
Lewis Structures |
Resonance Theory |
Molecular Properties / Structure
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
Changing the Laboratory: Effects of a Laboratory Course on Students' Attitudes and Perceptions  Melanie M. Cooper and Timothy S. Kerns
In this study, students in an open-ended, project-based organic chemistry laboratory were compared with others in a more conventional, "cookbook" laboratory. Those in the experimental sections were more likely to view the lab as a place to experiment and make mistakes, while those in the conventional sections were more likely to adopt a passive role.
Cooper, Melanie M.; Kerns, Timothy S. J. Chem. Educ. 2006, 83, 1356.
Electrophilic Substitution |
Learning Theories |
Student-Centered Learning
More on the Nature of Resonance  Robert C. Kerber
The author continues to find the use of delocalization preferable to resonance.
Kerber, Robert C. . J. Chem. Educ. 2006, 83, 1291.
Aromatic Compounds |
Covalent Bonding |
Molecular Properties / Structure |
Resonance Theory |
Nomenclature / Units / Symbols
More on the Nature of Resonance  William B. Jensen
Supplements a recent article on the interpretation of resonance theory with three additional observationsone historical and two conceptual.
Jensen, William B. J. Chem. Educ. 2006, 83, 1290.
Aromatic Compounds |
Covalent Bonding |
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Resonance Theory
If It's Resonance, What Is Resonating?  Robert C. Kerber
This article reviews the origin of the terminology associated with the use of more than one Lewis-type structure to describe delocalized bonding in molecules and how the original usage has evolved to reduce confusion
Kerber, Robert C. . J. Chem. Educ. 2006, 83, 223.
Aromatic Compounds |
Covalent Bonding |
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Resonance Theory
A Green Starting Material for Electrophilic Aromatic Substitution for the Undergraduate Organic Laboratory  T. Michelle Jones-Wilson and Elizabeth A. Burtch
Traditional experiments in the undergraduate organic chemistry laboratory involve the use of hazardous organic materials. Substitution of alternative green procedures wherever possible reduces organic waste and allows students to consider the need for environmentally sound chemistry. A green electrophilic aromatic substitution reaction (EAS), nitration of tyrosine, has been developed for use in the undergraduate laboratory. This reaction allows students to consider the varied aspects of EAS including activating and deactivating groups and o, p, m directors in a green environment.
Jones-Wilson, T. Michelle; Burtch, Elizabeth A. J. Chem. Educ. 2005, 82, 616.
Amino Acids |
Aromatic Compounds |
Green Chemistry |
Synthesis |
Electrophilic Substitution
"You're Repulsive!"Teaching VSEPR in a Not-So-Elegant Way  Robert S. H. Liu
Valence shell electron pair repulsive (VSEPR) interaction is an important concept particularly in discussing structural properties of molecules. In this article we showed five organic examples not commonly associated with VSEPR but yet all involving repulsive interactions of valence electrons, which provides ready explanations for altered chemical reactivity and spectroscopic properties of organic compounds. The ready catchy phrase Youre Repulsive! is the common thread used throughout these five examples.
Liu, Robert S. H. J. Chem. Educ. 2005, 82, 558.
Mechanisms of Reactions |
UV-Vis Spectroscopy |
Reactions |
Addition Reactions |
Electrophilic Substitution
Comments on Purser's Article: "Lewis Structures are Models for Predicting Molecular Structure, Not Electronic Structure"   Gordon H. Purser
Weinhold makes four major criticisms of my article. I shall address each of these criticisms.
Purser, Gordon H. J. Chem. Educ. 2005, 82, 528.
Molecular Properties / Structure |
Lewis Structures |
Resonance Theory |
MO Theory
Comments on Purser's Article: "Lewis Structures are Models for Predicting Molecular Structure, Not Electronic Structure"  Frank Weinhold
Some time ago in this Journal, Purser expressed strong views on the proper teaching of Lewis structures, as summarized in the quoted title. Because his criticisms are based on substantial factual misrepresentations and errors, it seemed desirable to call attention to a few of the conspicuous misstatements in order that readers may judge the opinions and conclusions from a more informed perspective.
Weinhold, Frank. J. Chem. Educ. 2005, 82, 527.
Molecular Properties / Structure |
Lewis Structures |
Resonance Theory |
MO Theory
Writing Electron Dot Structures   Kenneth R. Magnell
Drill with feedback for students learning to write electron dot structures.
Magnell, Kenneth R. J. Chem. Educ. 2003, 80, 711.
Covalent Bonding |
Lewis Structures |
Resonance Theory |
Enrichment / Review Materials
The Anomalous Reactivity of Fluorobenzene in Electrophilic Aromatic Substitution and Related Phenomena  Joel Rosenthal and David I. Schuster
Extensive analysis of the reactivity of fluorobenzene (electrophilic substitution); includes resonance and other inductive effects, acidities of fluorinated aromatic compounds, and properties of other organofluorine compounds.
Rosenthal, Joel; Schuster, David I. J. Chem. Educ. 2003, 80, 679.
Aromatic Compounds |
Mechanisms of Reactions |
Synthesis |
Electrophilic Substitution |
Enrichment / Review Materials |
Resonance Theory
Spiral Puzzle for Organic Chemistry Students  Ender Erdik
Puzzle to review organic reactions and their reagents.
Erdik, Ender. J. Chem. Educ. 2003, 80, 428.
Synthesis |
Learning Theories |
Enrichment / Review Materials |
Addition Reactions |
Alkylation |
Electrophilic Substitution |
Elimination Reactions |
Reactions |
Nucleophilic Substitution |
Mechanisms of Reactions |
Grignard Reagents
Keto-Enol Tautomers in a Carbonyl Phosphonium Salt  David E. Berry and G. W. Patenaude
Observations of keto-enol tautomers of a phosphonium ion.
Berry, David E.; Patenaude, G. W. J. Chem. Educ. 2002, 79, 498.
Synthesis |
NMR Spectroscopy |
Organometallics |
Resonance Theory
The Electrophilic Bromination of Toluene: Determination of the Ortho, Meta, and Para Ratios by Quantitative FTIR Spectrometry  Ross E. Smith IV, James R. McKee, and Murray Zanger
Determining the ratio of ortho:meta:para bromotoluenes when an electrophilic aromatic substitution is carried out on a monosubstituted benzene.
Smith, Ross E., IV; McKee, James R.; Zanger, Murray. J. Chem. Educ. 2002, 79, 227.
Instrumental Methods |
IR Spectroscopy |
Microscale Lab |
Synthesis |
Quantitative Analysis |
Electrophilic Substitution |
Aromatic Compounds
The Mechanism of Aqueous Hydrolysis of Nitro Derivatives of Phenyl Phenylmethanesulfonate. An Organic Laboratory Experiment  S. D. Mulder, B. E. Hoogenboom, and A. G. Splittgerber
Synthesis, purification, and characterization of three esters.
Mulder, S. D.; Hoogenboom, B. E.; Splittgerber, A. G. J. Chem. Educ. 2002, 79, 218.
Mechanisms of Reactions |
Molecular Properties / Structure |
Resonance Theory |
Reactive Intermediates |
Equilibrium |
Esters |
Aromatic Compounds |
Brønsted-Lowry Acids / Bases
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
Electrophilic Substitution in Naphthalene: Kinetic vs Thermodynamic Control  Leslie D. Field, Sever Sternhell, and Howard V. Wilton
Deuterium-protium exchange in naphthalene effected by trifluoroacetic acid and aluminium tris-trifluoroacetate was followed by proton NMR spectroscopy. These results are a potential "textbook" example of kinetic versus thermodynamic control, which is much clearer than the usually quoted reversible sulfonation of naphthalene.
Field, Leslie D.; Sternhell, Sever; Wilton, Howard V. J. Chem. Educ. 1999, 76, 1246.
Kinetics |
Thermodynamics |
Mechanisms of Reactions |
NMR Spectroscopy |
Electrophilic Substitution
The "Big Dog-Puppy Dog" Analogy for Resonance  Todd P. Silverstein
In this analogy, puppy dogs are restricted to a specific dog run; they represent s-bond electron pairs. Big dogs are allowed to roam freely over several consecutive dog runs; they represent delocalized p-bond electron pairs. By adding a bunny rabbit who is chased by the big dog, the analogy can be expanded to account for delocalized formal charge in a resonance hybrid.
Silverstein, Todd P. J. Chem. Educ. 1999, 76, 206.
Covalent Bonding |
Learning Theories |
Resonance Theory |
Molecular Properties / Structure
Mechanism Templates: Lecture Aids for Effective Presentation of Mechanism in Introductory Organic Chemistry  Brian J. McNelis
To promote active student learning of mechanism in introductory organic chemistry, hand-outs have been developed with incomplete structures for reaction processes depicted, which are called mechanism templates. The key to these lecture aids is to provide only enough detail in the diagram to facilitate notetaking, ensuring that these templates are dynamic learning tools that must be utilized by an engaged and alert student.
Brian J. McNelis. J. Chem. Educ. 1998, 75, 479.
Learning Theories |
Mechanisms of Reactions |
Reactions |
Addition Reactions |
Acids / Bases |
Electrophilic Substitution |
Nucleophilic Substitution
Regioselective Hydrochlorination: An Experiment for the Undergraduate Laboratory  Philip Boudjouk, Beon-Kyu Kim, and Byung-Hee Han
A simple and convenient procedure for the addition of hydrogen chloride to a variety of olefins is described. Conventional glassware is used and product isolation is straightforward using distillation techniques.
Boudjouk, Philip; Kim, Beon-Kyu; Han, Byung-Hee. J. Chem. Educ. 1997, 74, 1223.
Learning Theories |
NMR Spectroscopy |
Synthesis |
Electrophilic Substitution
Making Organic Concepts Visible  Robert S. H. Liu and Alfred E. Asato
Graphic illustrations, with a Hawaiian flavor, have been introduced to clarify the following concepts encountered in introductory organic chemistry: functional groups, resonance structures, polarizability, ionization in mass spectroscopy and difference in reactivities between alkyl and vinyl halides
Liu, Robert S. H.; Asato, Alfred E. J. Chem. Educ. 1997, 74, 783.
Mechanisms of Reactions |
Resonance Theory
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
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
Electrophilic Aromatic Substitution Discovery Lab  Jarret, Ronald M.; New, Jamie; Patraitis, Cynthia
An organic chemistry lab for introductory chemistry in which students must determine the reaction mechanism of an organic synthesis; includes sample data and analysis.
Jarret, Ronald M.; New, Jamie; Patraitis, Cynthia J. Chem. Educ. 1995, 72, 457.
Synthesis |
Mechanisms of Reactions |
Electrophilic Substitution
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
A New Approach To Teaching Organic Chemical Mechanisms  Wentland, Stephen H.
Describing the mechanisms of organic reactions using five simple steps or operations.
Wentland, Stephen H. J. Chem. Educ. 1994, 71, 3.
Mechanisms of Reactions |
Addition Reactions |
Nucleophilic Substitution |
Electrophilic Substitution |
Elimination Reactions |
Resonance Theory |
Molecular Properties / Structure
Do our students really understand the Hammett equation?   Schwan, Adrian L.
In this author's experience, many students can proceed through text questions dealing with the Hammett equation without having a full understanding of the Hammett analysis. He offers a question that enables students to gain a better appreciation of this concept.
Schwan, Adrian L. J. Chem. Educ. 1993, 70, 1001.
Chemometrics |
Resonance Theory |
Constitutional Isomers
Davidsoniana Jones and the cult of the curved arrow  Brisbois, Ronald G.
Puzzles to help students understand valence bond theory, resonance, and tautomerism.
Brisbois, Ronald G. J. Chem. Educ. 1992, 69, 971.
Resonance Theory
Spontaneous detonation of a mixture of two odd electron gases   Briggs, Thomas S.
Instructions for safe detonation of ClO2 and NO (the fastest known reaction between two stable molecules at room temperature).
Briggs, Thomas S. J. Chem. Educ. 1991, 68, 938.
Reactions |
Resonance Theory
Explaining resonance - a colorful approach  Abel, Kenton B.; Hemmerlin, William M.
An analogy using color to help students understand that a resonance molecule does not shift back and forth between Lewis Structures, but is in fact a hybrid of the two structures.
Abel, Kenton B.; Hemmerlin, William M. J. Chem. Educ. 1991, 68, 834.
Resonance Theory |
Lewis Structures |
Molecular Properties / Structure
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
NMR analysis of product mixtures in electrophilic aromatic substitution  Clark, Mary Ann; Duns, Glenn; Golberg, Danny; Karwowska, Anna; Turgeon, Andree; Turley, Jolanda
Use of mole fraction analysis permits precise quantitative product mixture analysis, a large improvement over qualitative and semiquantitative techniques.
Clark, Mary Ann; Duns, Glenn; Golberg, Danny; Karwowska, Anna; Turgeon, Andree; Turley, Jolanda J. Chem. Educ. 1990, 67, 802.
NMR Spectroscopy |
Electrophilic Substitution |
Aromatic Compounds |
Quantitative Analysis
A new approach to the generation of sigma complex structures  Young, Joseph G.
An alternative to the electron pushing approach for determining intermediate resonance structures for electrophilic aromatic substitutions.
Young, Joseph G. J. Chem. Educ. 1990, 67, 550.
Aromatic Compounds |
Electrophilic Substitution |
Resonance Theory |
Mechanisms of Reactions
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
A visual aid for teaching the resonance concept  Delvigne, Francis
Using "dot clouds" to represent electron densities and resonance in structures such as benzene.
Delvigne, Francis J. Chem. Educ. 1989, 66, 461.
Resonance Theory |
Aromatic Compounds
Teaching the concept of resonance with transparent overlays  Richardson, W. S.
The overlap method can be useful in the development of the concept of a partial charge on the atoms of an ion.
Richardson, W. S. J. Chem. Educ. 1986, 63, 518.
Resonance Theory |
Molecular Properties / Structure
The arithmetic of aromaticity  Glidewell, Christopher; Lloyd, Douglas
In this article, the authors explore an aspect of conjugated systems that have received little attention, namely polycyclic hydrocarbons.
Glidewell, Christopher; Lloyd, Douglas J. Chem. Educ. 1986, 63, 306.
Alkanes / Cycloalkanes |
Resonance Theory |
Aromatic Compounds
Aromatic substitution reactions: when you've said ortho, meta, and para you haven't said it all  Traynham, James G.
The author presents a range of examples for nucleophilic, electrophilic, and free-radical reactions where the ipso is an important, predominant, or even exclusive site of reaction.
Traynham, James G. J. Chem. Educ. 1983, 60, 937.
Nucleophilic Substitution |
Electrophilic Substitution |
Free Radicals |
Diastereomers |
Stereochemistry |
Reactions
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
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
Acylation of ferrocene: Effect of temperature on reactivity as measured by reverse phase high performance liquid chromatography  McKone, Harold T.
A reverse-phase separation of the products of the Friedel-Crafts acylation of ferrocene.
McKone, Harold T. J. Chem. Educ. 1980, 57, 380.
HPLC |
Chromatography |
Aromatic Compounds |
Electrophilic Substitution |
Separation Science
The aromatic ring  Kolb, Doris
Historic analysis and attempts to explain the structure of benzene, the concept of resonance, Huckel's rule, polycyclic aromatic compounds, non-classical aromatic compounds, and a definition for aromaticity.
Kolb, Doris J. Chem. Educ. 1979, 56, 334.
Aromatic Compounds |
Molecular Properties / Structure |
Resonance Theory
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
Apparent ionic charge in electrolyte and polyelectrolyte solutions  Magdelenat, H.; Turq, P.; Tivant, P.; Chemla, M.; Menez, R.; Drifford, M.
The purpose of this paper is to show how the comparison of the experimental values of the average displacement of charged particles obtained under the action of thermal motion alone with those obtained by the action of an external electric field, leads to the concept of "apparent charge". This is a good approximation of their actual structural charge in a given electrolyte solution at finite concentration and thus reflects the complexity of their structure.
Magdelenat, H.; Turq, P.; Tivant, P.; Chemla, M.; Menez, R.; Drifford, M. J. Chem. Educ. 1978, 55, 12.
Aqueous Solution Chemistry |
Solutions / Solvents |
Electrophilic Substitution |
Chemometrics |
Metals
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
A direct calorimetric demonstration of resonance energy in the benzene nucleus  van Vugt, W. H.; Mosselman, C.
This calorimetric experiment is intended as a first contact in chemical education with the aromaticity concept.
van Vugt, W. H.; Mosselman, C. J. Chem. Educ. 1975, 52, 746.
Calorimetry / Thermochemistry |
Resonance Theory
An alternative procedure to writing Lewis structures  Imkampe, Karl
Using simple molecular orbital pictures to represent all the resonance structures of larger organic molecules.
Imkampe, Karl J. Chem. Educ. 1975, 52, 429.
Lewis Structures |
Molecular Properties / Structure |
Resonance Theory
A 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
Resonance theory and the enumeration of Kekule structures  Herndon, William C.
The formulation of resonance theory as it is practiced today is explicated in the well-known books by Pauling and Wheland. Study of these texts show that resonance theory are so drastic that many theoreticians are loathe to ascribe validity to the less rigorous method.
Herndon, William C. J. Chem. Educ. 1974, 51, 10.
Resonance Theory |
Theoretical Chemistry |
Aromatic Compounds |
Molecular Properties / Structure
The determination of the resonance energy of benzene. A physical chemistry laboratory experiment  Stevenson, Gerald R.
This procedure relies on calorimetry to measure the resonance energy of benzene, a useful way to relate the concepts of aromaticity and resonance energy to experimental thermodynamics.
Stevenson, Gerald R. J. Chem. Educ. 1972, 49, 781.
Aromatic Compounds |
Resonance Theory |
Molecular Properties / Structure |
Calorimetry / Thermochemistry |
Thermodynamics
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
Selective reduction of dinitrobenzenes. An organic laboratory experiment  Idoux, John P.; Plain, Wendell
Different students are assigned different reducing agents and asked to explain why their particular selective reduction occurs as their results indicate.
Idoux, John P.; Plain, Wendell J. Chem. Educ. 1972, 49, 133.
Aromatic Compounds |
Resonance Theory |
Oxidation / Reduction
Directive effects in electrophilic aromatic substitution. An organic chemistry experiment  Beishline, Robert R.
The student is given the procedure for the monobromination of acetanilide in glacial acetic acid, but is not told where on the ring the bromine will substitute; he is required to prove the structure of the product through an independent synthesis of the preparation of a known derivative.
Beishline, Robert R. J. Chem. Educ. 1972, 49, 128.
Aromatic Compounds |
Electrophilic Substitution |
Synthesis |
Alkylation
Guanidine, trimethylenemethane, and "Y-delocalization." Can acyclic compounds have "aromatic" stability?  Gund, Peter
It appears that the Y-shaped configuration of 6 pi electrons as found in guanidine derivatives is an exceptionally stable one.
Gund, Peter J. Chem. Educ. 1972, 49, 100.
Aromatic Compounds |
Molecular Properties / Structure |
Resonance Theory |
MO Theory
Evidence of d pi-acceptor resonance in halogen substituents  Abdulla, Riaz F.
The association of various structural and dynamic phenomena through the postulate of d pi resonance has potential additional predictive value.
Abdulla, Riaz F. J. Chem. Educ. 1972, 49, 64.
Resonance Theory |
Mechanisms of Reactions
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
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
Cross conjugation  Phelan, Nelson F.; Orchin, Milton
Although qualitative conclusions may be obtained by judicious use of simple resonance theory, even in simple systems the electron distribution and extent of conjugation between the nonconjugated centers in cross conjugation is most effectively illustrated by molecular orbital descriptions.
Phelan, Nelson F.; Orchin, Milton J. Chem. Educ. 1968, 45, 633.
Valence Bond Theory |
MO Theory |
Resonance Theory
The electron repulsion theory of the chemical bond. II. An alternative to resonance hybrids  Luder, W. F.
The author proposes the electron repulsion theory of the chemical bond as an alternative to resonance hybrids.
Luder, W. F. J. Chem. Educ. 1967, 44, 269.
Covalent Bonding |
Resonance Theory
Electrophilic substitution in benzenoid compounds (Norman, R. O. C.; Taylor, R.)  Bunnett, Joseph F.

Bunnett, Joseph F. J. Chem. Educ. 1966, 43, A358.
Electrophilic Substitution |
Aromatic Compounds
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
Electronic interactions between nonconjugated groups  Ferguson, Lloyd N.; Nnadi, John C.
The purpose of this paper is to discuss some of the different molecular systems in which electronic interactions between classically nonconjugated groups are explicable in terms of molecular orbital theory as well as nonclassical resonance theory.
Ferguson, Lloyd N.; Nnadi, John C. J. Chem. Educ. 1965, 42, 529.
MO Theory |
Resonance Theory |
Molecular Properties / Structure
Homolytic, cationotropic, and anionotropic reactions: A mechanistic approach to organic chemistry  Hoogenboom, Bernard E.
Examines examples of radical, cationotropic, and anionotropic reactions.
Hoogenboom, Bernard E. J. Chem. Educ. 1964, 41, 639.
Mechanisms of Reactions |
Free Radicals |
Reactions |
Electrophilic Substitution |
Nucleophilic Substitution
Relative rates of electrophilic aromatic substitution  Casanova, Joseph, Jr.
An experiment involving the bromination of various aromatic substrates that covers several aspects of kinetic phenomena.
Casanova, Joseph, Jr. J. Chem. Educ. 1964, 41, 341.
Aromatic Compounds |
Electrophilic Substitution |
Rate Law |
Kinetics
Rules for molecular orbital structures  Meislich, Herbert
In view of the fact that molecular orbital theory makes more correct predictions and avoids the misconceptions that arise in the minds of novice students when they are exposed to resonance theory, it would be better to use M.O. theory as much as possible in teaching organic chemistry.
Meislich, Herbert J. Chem. Educ. 1963, 40, 401.
MO Theory |
Resonance Theory
Multicenter and assisted mechanistic pathways in the reactions of organometallic compounds  Dessy, Raymond E.; Paulik, Frank
Examines a variety of nucleophilic and electrophilic, multicenter and assisted mechanistic pathways in the reactions of organometallic compounds.
Dessy, Raymond E.; Paulik, Frank J. Chem. Educ. 1963, 40, 185.
Organometallics |
Mechanisms of Reactions |
Nucleophilic Substitution |
Electrophilic Substitution
The electronic structures and stereochemistry of NO2+, NO2, and NO2-  Panckhurst, M. H.
A comparison of the electronic structures and stereochemistry of NO2+, NO2, and NO2-.
Panckhurst, M. H. J. Chem. Educ. 1962, 39, 270.
Stereochemistry |
Molecular Properties / Structure |
Resonance Theory
Substitution at elements other than carbon (Ingold, C. K.)  Reinheimer, John D.

Reinheimer, John D. J. Chem. Educ. 1961, 38, A434.
Nucleophilic Substitution |
Electrophilic Substitution |
Organometallics
Apparatus for the Friedel-Crafts reaction: For the undergraduate organic chemistry laboratory  Kremer, Chester B.; Wilen, Samuel H.
A simple and practical reaction apparatus has been designed that offers several advantages over earlier set-ups.
Kremer, Chester B.; Wilen, Samuel H. J. Chem. Educ. 1961, 38, 306.
Laboratory Equipment / Apparatus |
Electrophilic Substitution
The 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
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
Theoretical chemistry in Russia  Hunsberger, I. Moyer
Examines contributions to organic structural theory and Russian criticisms of resonance theory.
Hunsberger, I. Moyer J. Chem. Educ. 1954, 31, 504.
Resonance Theory
Kekule's theory of aromaticity  Gero, Alexander
Examines what Kekule really wrote in his famous paper on the structure of benzene.
Gero, Alexander J. Chem. Educ. 1954, 31, 201.
Aromatic Compounds |
Molecular Properties / Structure |
Resonance Theory
Predicting reactions of a resonance hybrid from minor canonical structures  Gero, Alexander
Little effort seems to have been made to set up any general rules on the relative contributions of the several structural formulas (canonical structures) used to represent a resonance hybrid to the reactions of the hybrid.
Gero, Alexander J. Chem. Educ. 1954, 31, 136.
Resonance Theory |
Mechanisms of Reactions
Letters to the editor  Ferguson, Lloyd N.
Points out an additional reference that should have been made in an earlier article.
Ferguson, Lloyd N. J. Chem. Educ. 1954, 31, 102.
Aromatic Compounds |
Electrophilic Substitution
Letters  Bent, Richard L.
Addresses issues raised regarding an earlier paper on isomerism and mesomerism.
Bent, Richard L. J. Chem. Educ. 1953, 30, 648.
Molecular Properties / Structure |
Resonance Theory |
Covalent Bonding
Letters  Ferreira, Ricardo Carvalho
Identifies some inconsistencies in an earlier paper on isomerism and mesomerism.
Ferreira, Ricardo Carvalho J. Chem. Educ. 1953, 30, 647.
Molecular Properties / Structure |
Resonance Theory |
Covalent Bonding
Letters  Wolfrom, Melville L.
The author encourages American chemists to familiarize themselves with the conventions of representing configurational formulas.
Wolfrom, Melville L. J. Chem. Educ. 1953, 30, 479.
Molecular Modeling |
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Resonance Theory
Aspects of isomerism and mesomerism. I. (a) Formulas and their meaning (b) Mesomerism  Bent, Richard L.
Examines molecular, empirical, structural, configurational, and projection formulas, as well as mesomerism (electronic isomers) and various types of resonance.
Bent, Richard L. J. Chem. Educ. 1953, 30, 220.
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Resonance Theory
Letters  Brescia, Frank
The author calls for someone to invent another term for the word resonance as applied to the field of molecular structure.
Brescia, Frank J. Chem. Educ. 1952, 29, 261.
Resonance Theory |
Nomenclature / Units / Symbols |
Molecular Properties / Structure
The concept of resonance energy in elementary organic chemistry  Gero, Alexander
The author describes an empirically-based presentation of resonance energy that is perfectly within reach of introductory organic students.
Gero, Alexander J. Chem. Educ. 1952, 29, 82.
Resonance Theory
About a machistic theory in chemistry and its propagandists  Tatevskii, V. M.; Shakhparanov, M. I.
Russian scientists attack the resonance theory and the use of resonance structures.
Tatevskii, V. M.; Shakhparanov, M. I. J. Chem. Educ. 1952, 29, 13.
Molecular Properties / Structure |
Resonance Theory
The present state of the chemical structural theory  Kursanov, D. N.; Gonikberg, M. G.; Dubinin, B. M.; Kabachnik, M. I.; Kaverzneva, E. D.; Prilezhaeva, E. N.; Sokolov, N. D.; Freidlina, R. Kh.
Several members of the Russian Academy of Sciences attack the resonance theory and resonance structures.
Kursanov, D. N.; Gonikberg, M. G.; Dubinin, B. M.; Kabachnik, M. I.; Kaverzneva, E. D.; Prilezhaeva, E. N.; Sokolov, N. D.; Freidlina, R. Kh. J. Chem. Educ. 1952, 29, 2.
Molecular Properties / Structure |
Resonance Theory