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Journal Articles: 17 results
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 UVĀ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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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