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Journal Articles: 29 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
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
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
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
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
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
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, 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
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
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
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
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 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
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
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
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
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
Relative rates of electrophilic aromatic substitution  Casanova, Joseph, Jr.
An experiment involving the bromination of various aromatic substrates that covers several aspects of kinetic phenomena.
Casanova, Joseph, Jr. J. Chem. Educ. 1964, 41, 341.
Aromatic Compounds |
Electrophilic Substitution |
Rate Law |
Kinetics
The 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
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