| Journal Articles: 45 results |
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A More Challenging Interpretative Nitration Experiment Employing Substituted Benzoic Acids and Acetanilides Edward M. Treadwell and Tung-Yin Lin
An experiment is described involving the nitration of ortho or meta, monosubstituted benzoic acids and monochlorinated acetanilides with nitric acid to evaluate the regioselectivity of addition through computational methods and 1H NMR spectroscopy.
Treadwell, Edward M.; Lin, Tung-Yin. J. Chem. Educ. 2008, 85, 1541.
Aromatic Compounds |
Computational Chemistry |
Electrophilic Substitution |
Molecular Modeling |
NMR Spectroscopy |
Synthesis
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A Green, Guided-Inquiry Based Electrophilic Aromatic Substitution for the Organic Chemistry Laboratory Eric Eby and S. Todd Deal
This alternative, electrophilic aromatic substitutionan iodination reaction of salicylamide, a popular analgesicuses environmentally friendly reagents and serves as a guided-inquiry experiment in which students are asked to predict the orientation of the substitution reaction and determine the product's structure using FT-IR spectroscopy.
Eby, Eric; Deal, S. Todd. J. Chem. Educ. 2008, 85, 1426.
Aromatic Compounds |
Constitutional Isomers |
Electrophilic Substitution |
Green Chemistry |
IR Spectroscopy |
Synthesis
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Zeroing In on Electrophilic Aromatic Substitution David C. Forbes, Mohini Agarwal, Jordan L. Ciza, and Heather A. Landry
Presents a unique and novel illustration of reactivity trends in the formation of trisubstituted benzene derivatives from disubstituted systems using electrophilic aromatic substitution reactions.
Forbes, David C.; Agarwal, Mohini; Ciza, Jordan L.; Landry, Heather A. J. Chem. Educ. 2007, 84, 1878.
Aromatic Compounds |
Constitutional Isomers |
Electrophilic Substitution |
Reactions
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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 UVvis 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
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Discovering Electronic Effects of Substituents in Nitrations of Benzene Derivatives Using GC–MS Analysis Malgorzata M. Clennan and Edward L. Clennan
Describes an organic lab in which students pool mass spectral data to identify the distribution of isomer products generated by the nitration of six benzene derivatives whose substituents differ in their electronic effects. Students also determine which substituents direct nitration predominantly to the ortho- or para- and to the meta positions.
Clennan, Malgorzata M.; Clennan, Edward L. J. Chem. Educ. 2007, 84, 1679.
Aromatic Compounds |
Constitutional Isomers |
Electrophilic Substitution |
Gas Chromatography |
Mass Spectrometry
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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
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Competitive Nitration of Benzene–Fluorobenzene and Benzene–Toluene Mixtures: Orientation and Reactivity Studies Using HPLC Ronald L. Blankespoor, Stephanie Hogendoorn, and Andrea Pearson
In this experiment for the first-year organic laboratory, mixtures of benzenetoluene and benzenefluorobenzene are competitively nitrated to determine the reactivity and orientation effects of CH3 and F. HPLC is used to analyze the reaction mixtures.
Blankespoor, Ronald L.; Hogendoorn, Stephanie; Pearson, Andrea. J. Chem. Educ. 2007, 84, 697.
Aromatic Compounds |
Constitutional Isomers |
Electrophilic Substitution |
HPLC
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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
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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
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"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 Youre 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
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The Anomalous Reactivity of Fluorobenzene in Electrophilic Aromatic Substitution and Related Phenomena Joel Rosenthal and David I. Schuster
Extensive analysis of the reactivity of fluorobenzene (electrophilic substitution); includes resonance and other inductive effects, acidities of fluorinated aromatic compounds, and properties of other organofluorine compounds.
Rosenthal, Joel; Schuster, David I. J. Chem. Educ. 2003, 80, 679.
Aromatic Compounds |
Mechanisms of Reactions |
Synthesis |
Electrophilic Substitution |
Enrichment / Review Materials |
Resonance Theory
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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