TIGER

Journal Articles: 386 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
Frank Westheimer's Early Demonstration of Enzymatic Specificity  Addison Ault
Reviews one of the most significant accomplishments of one of the most respected chemists of the 20th centurya series of stereospecific enzymatic oxidation and reduction experiments that led chemists to recognize enantiotopic and diastereotopic relationships of atoms, or groups of atoms, within molecules.
Ault, Addison. J. Chem. Educ. 2008, 85, 1246.
Asymmetric Synthesis |
Bioorganic Chemistry |
Catalysis |
Chirality / Optical Activity |
Enantiomers |
Enzymes |
Isotopes |
Nucleophilic Substitution |
Oxidation / Reduction |
Stereochemistry
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
Polymer-Supported Reagents and 1H–19F NMR Couplings: The Synthesis of 2-Fluoroacetophenone  Nicola Pohl and Kimberly Schwarz
Describes an experiment in which 2-bromoacetophenone is converted to 2-fluoroacetophenone using a solid-phase nucleophilic fluorine source. The experiment introduces students to the utility of solid-phase reagents in organic synthesis, to NMR-active nuclei other than 1H without the requirement of a special NMR probe, and to the unique uses of fluorine in molecular design.
Pohl, Nicola; Schwarz, Kimberly. J. Chem. Educ. 2008, 85, 834.
Aldehydes / Ketones |
NMR Spectroscopy |
Nucleophilic Substitution |
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
A Discovery-Based Experiment Involving Rearrangement in the Conversion of Alcohols to Alkyl Halides  Richard A. Kjonaas and Ryand J. F. Tucker
This article reports a discovery-based experiment in which students convert three alcohols to alkyl halides under acidic conditions and record the 13C NMR spectrum in each case. By comparing the number of resonances observed with the number of resonances predicted for each possible product, students draw several conclusions about the resulting rearrangement.
Kjonaas, Richard A.; Tucker, Ryand J. F. J. Chem. Educ. 2008, 85, 100.
Alcohols |
Carbocations |
Gas Chromatography |
NMR Spectroscopy |
Nucleophilic Substitution
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
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
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
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
pHantastic Fluorescence  Mark Muyskens
Students easily extract a fluorescent substance from shavings of a wood called narra. The fluorescence is dramatically pH dependent and can be turned on and off repeatedly using commonly available acid and base solutions.
Muyskens, Mark. J. Chem. Educ. 2006, 83, 768A.
Fluorescence Spectroscopy |
Natural Products |
Nucleophilic Substitution |
pH |
Solutions / Solvents |
UV-Vis Spectroscopy
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
The Finkelstein Reaction: Quantitative Reaction Kinetics of an SN2 Reaction Using Nonaqueous Conductivity  R. David Pace and Yagya Regmi
Presents a quantitative kinetics laboratory exercise featuring the Finkelstein reaction (SN2) for use in the first-semester organic chemistry course that utilizes nonaqueous conductivity as the method by which relevant structuretemperaturesolvent effects are examined.
Pace, R. David; Regmi, Yagya. J. Chem. Educ. 2006, 83, 1344.
Calibration |
Kinetics |
Nucleophilic Substitution |
Rate Law |
Reactions |
Solutions / Solvents
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
Semiempirical and DFT Investigations of the Dissociation of Alkyl Halides  Jack R. Waas
Enthalpy changes corresponding to the gas phase heats of dissociation of 12 organic halides were calculated using two semiempirical methods, the HartreeFock method, and two DFT methods. All five methods agreed generally with the expected empirically known trends in the dissociation of alkyl halides.
Waas, Jack R. J. Chem. Educ. 2006, 83, 1017.
Alkanes / Cycloalkanes |
Computational Chemistry |
Mechanisms of Reactions |
Molecular Modeling |
Reactions |
Reactive Intermediates |
Thermodynamics |
Elimination Reactions |
Nucleophilic Substitution
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
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
Synthesis of Unsymmetrical Alkynes via the Alkylation of Sodium Acetylides. An Introduction to Synthetic Design for Organic Chemistry Students  Jennifer N. Shepherd and Jason R. Stenzel
Teams of students design a microscale synthesis of an unsymmetrical alkyne using commercially available terminal alkynes and alkyl halides and characterize the resulting products using TLC, IR, and 1H NMR spectroscopy. Depending on the chosen reactants, students observe both substitution and elimination products, or in some cases, no reaction at all.
Shepherd, Jennifer N.; Stenzel, Jason R. J. Chem. Educ. 2006, 83, 425.
Alkylation |
Alkynes |
Elimination Reactions |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Nucleophilic Substitution |
Synthesis
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
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 Tragedy of Hamlet, Son of an Organic Chemist of Denmark  Ronald G. Brisbois
Herein, Hamlet (the son of an organic chemist of Denmark) is the surrogate of any and every student as he uses a thoroughly Shakespearean approach to sorting out some of the key distinguishing features of SN2 versus SN1 reactions.
Brisbois, Ronald G. J. Chem. Educ. 2004, 81, 502.
Kinetics |
Mechanisms of Reactions |
Stereochemistry |
Nucleophilic Substitution
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
The Substitution–Elimination Mechanistic Disc Method  Paul T. Buonora and Yu Jin Lim
In this manuscript a mnemonic device designed to facilitate presentation of the competing SN1, SN2, E1, and E2 mechanisms is presented.
Buonora, Paul T.; Lim, Yu Jin. J. Chem. Educ. 2004, 81, 368.
Mechanisms of Reactions |
Elimination Reactions |
Nucleophilic Substitution
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
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
Using Conductivity Devices in Nonaqueous Solutions II: Demonstrating the SN2 Mechanism  Thomas A. Newton and Beth Ann Hill
The use of a conductivity apparatus in nonaqueous solutions to demonstrate structurereactivity correlations and solvent effects in the SN2 reaction is described.
Newton, Thomas A.; Hill, Beth Ann. J. Chem. Educ. 2004, 81, 61.
Conductivity |
Nucleophilic Substitution |
Mechanisms of Reactions
Using Conductivity Devices in Nonaqueous Solutions I: Demonstrating the SN1 Mechanism  Thomas A. Newton and Beth Ann Hill
The use of a conductivity apparatus in nonaqueous solutions to demonstrate structurereactivity correlations and solvent effects in the SN1 reaction is described.
Newton, Thomas A.; Hill, Beth Ann. J. Chem. Educ. 2004, 81, 58.
Conductivity |
Nucleophilic Substitution |
Mechanisms of Reactions
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
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
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
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
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 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
Of Magnets and Mechanisms  Edward G. Neeland
Using magnets to demonstrate the electron flow (mechanism) of nucleophilic substitution reactions.
Neeland, Edward G. J. Chem. Educ. 2002, 79, 186.
Magnetic Properties |
Mechanisms of Reactions |
Learning Theories |
Nucleophilic Substitution
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
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
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
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
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
Intermediates, Transition States, Butterflies, and Frogs  Trevor M. Kitson
The changes that occur in typical simple SN1 and SN2 reactions are compared to the metamorphoses undergone by caterpillars and tadpoles, respectively.
Kitson, Trevor M. J. Chem. Educ. 2001, 78, 504.
Mechanisms of Reactions |
Reactive Intermediates |
Nucleophilic Substitution
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
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
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
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
"New" Compounds from Old Plastics: Recycling PET Plastics via Depolymerization. An Activity for the Undergraduate Organic Lab  Don Kaufman, Geoff Wright, Ryan Kroemer, and Josh Engel
This paper describes work done to develop a meaningful undergraduate organic lab activity that illustrates chemistry of the real world while utilizing reactions typically included in the organic lecture and lab. We show how a common plastic can be converted into several compounds using ester hydrolysis and SN2 reactions.
Kaufman, Don; Wright, Geoff; Kroemer, Ryan; Engel, Josh. J. Chem. Educ. 1999, 76, 1525.
Consumer Chemistry |
Synthesis |
Esters |
Nucleophilic Substitution
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
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
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
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
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
Nucleophilic Addition vs. Substituion: A Puzzle for the Organic Laboratory  Ernest F. Silversmith
The chemistry of beta-carbonyl compounds is studied. Beta-carbonyl compounds react with hydrazines to give products with a 5-membered ring containing two nitrogens. The experiment makes students determine whether ethyl 2-acetyl-3-oxobutanoate reacts like a beta-diketone or like a beta-keto ester.
Silversmith, Ernest F. J. Chem. Educ. 1998, 75, 221.
Learning Theories |
Nucleophilic Substitution |
Aldehydes / Ketones |
Esters |
Mechanisms of Reactions
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
Visualizing the SN2 Inversion  Rosan, Alan M.
Slight modification to the construction of the model presented.
Rosan, Alan M. J. Chem. Educ. 1996, 73, A228.
Nucleophilic Substitution |
Mechanisms of Reactions
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 Neglected Element in Sophomore Organic Chemistry  Kelly L. Bieda and Suzzane T. Purrington
There are many aspects of organic chemistry that would benefit from the inclusion of organofluorine chemistry. The properties of fluorine help in the clarification of many topics such as bond strength, leaving groups, substitution reactions, radical reactions, polymers, pharmaceuticals, and enzymes.
Bieda, Kelly L.; Purrington, Suzanne T. J. Chem. Educ. 1996, 73, 754.
Drugs / Pharmaceuticals |
Enzymes |
Polymerization |
Nucleophilic Substitution
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
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
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
Animation of Imaginary Frequencies at the Transition State  Higgins, Robert H.
176. Computer simulations of reactions mechanisms using HyperChem and ChemPlus software.
Higgins, Robert H. J. Chem. Educ. 1995, 72, 703.
Mechanisms of Reactions |
Molecular Properties / Structure |
Reactive Intermediates |
Computational Chemistry |
Nucleophilic Substitution
Propylene Oxide Addition to Hydrochloric Acid: A Textbook Error  Rebecca E. Phillips and Robert L. Soulen
Procedure illustrating organic synthesis involving propylene oxide, a major industrial chemical, and important features of the SN1 and SN2 mechanisms (there are some differences on how this reaction is described in several organic textbooks).
Phillips, Rebecca E.; Soulen, Robert L. J. Chem. Educ. 1995, 72, 624.
Synthesis |
Mechanisms of Reactions |
Nucleophilic Substitution
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
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
A Model To Show the SN2 Inversion  Sands, Richard D.; Dressman, Devin C.; Wyatt, Shawn R.
Paper model illustrating the SN2 inversion.
Sands, Richard D.; Dressman, Devin C.; Wyatt, Shawn R. J. Chem. Educ. 1995, 72, 428.
Mechanisms of Reactions |
Nucleophilic Substitution |
Molecular Modeling
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
Chart for Deciding Mechanism for Reaction of Alkyl Halide with Nucleophile/Base  McClelland, Bruce W.
The decision chart offered here is based upon the well-known and accepted characteristics of the reaction system mechanisms described in typical introductory organic chemistry textbooks.
McClelland, Bruce W. J. Chem. Educ. 1994, 71, 1047.
Mechanisms of Reactions |
Nucleophilic 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
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
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
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
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
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
The aromatic substitution game  Zanger, Murray; Gennaro, Alfonso R.; McKee, James R.
This paper describes a game used to bring attention to the need for students to reconsider substitution theories learned in earlier chapters.
Zanger, Murray; Gennaro, Alfonso R.; McKee, James R. J. Chem. Educ. 1993, 70, 985.
Nucleophilic Substitution |
Synthesis
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
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
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
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
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
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
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
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
Cobaloximes as vehicles for college teaching  Brown, T. M.; Dronsfield, A. T.; Cooksey, C. J.; Crich, D.
Cobaloximes are probably the most accessible and "least nasty" of all organometallic compounds, are highly colored, exhibit unusual oxidation states, demonstrate a vivid nucleophilic attack, and lend themselves to chromatographic investigation without the need for UV light.
Brown, T. M.; Dronsfield, A. T.; Cooksey, C. J.; Crich, D. J. Chem. Educ. 1990, 67, 973.
Coordination Compounds |
Organometallics |
Nucleophilic Substitution
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
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
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
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
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
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
A conversion of methyl ketones into acetylenes: A project for a problem oriented or microscale organic chemistry course  Silveira, Augustine, Jr.; Orlando, Steven C.
The authors present their adaptation of an open-ended project on the conversion of methyl ketones into acetylenes for the microscale lab and describe its pedagogic utility.
Silveira, Augustine, Jr.; Orlando, Steven C. J. Chem. Educ. 1988, 65, 630.
Microscale Lab |
Aldehydes / Ketones |
Synthesis |
Nucleophilic Substitution |
Gas Chromatography
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
Organic lecture demonstrations  Silversmith, Ernest F.
Organic chemistry may not be known for its spectacular, attention getting chemical reactions. Nevertheless, this author describes a few organic chemistry reactions that put points across and generate interest. This article provides a convenient sources of demonstrations and urges others to add to the collection. Demonstrations concerning: carbohydrates, spectroscopy, proteins, amines, carbohydrates, carboxylic acids, and much more.
Silversmith, Ernest F. J. Chem. Educ. 1988, 65, 70.
Molecular Properties / Structure |
Nucleophilic Substitution |
Acids / Bases |
Physical Properties |
Alkenes |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity |
Aldehydes / Ketones |
Alcohols
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
Two working models for the SN2 mechanism  Anderson, Martin M.
Design of an articulated physical model demonstrating the mechanism of the SN2 reaction.
Anderson, Martin M. J. Chem. Educ. 1987, 64, 1023.
Nucleophilic Substitution |
Mechanisms of Reactions |
Molecular Modeling
Characterizing a tetrahedral intermediate in an acyl transfer reaction: An undergraduate 1H NMR demonstration  Rzepa, Henry S.; Lobo, Ana M.; Marques, M. Matilde; Prabhakar, Sundaresan
A simple experiment involving the detection by 1H NMR spectroscopy of a stable intermediate formed by nucleophilic attack and its characterization as a chiral species.
Rzepa, Henry S.; Lobo, Ana M.; Marques, M. Matilde; Prabhakar, Sundaresan J. Chem. Educ. 1987, 64, 725.
NMR Spectroscopy |
Nucleophilic Substitution |
Chirality / Optical Activity
The reactivity selectivity principle: Should it ever be used?  Buncel, Erwin; Wilson, Harold
Applications and failures of the reactivity selectivity principle; quantitative aspects of the reactivity selectivity principle; and rationalization of reactivity selectivity principle failures.
Buncel, Erwin; Wilson, Harold J. Chem. Educ. 1987, 64, 475.
Mechanisms of Reactions |
Free Radicals |
Carbocations |
Nucleophilic Substitution
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
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
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
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
Organic lecture demonstrations of common-ion effect, ionizing power of solvents, and first-order reaction kinetics  Danen, Wayne C.; Blecha, Sr. M. Therese
The hydrolysis of tert-butyl chloride is the basis of three demonstrations which each illustrate an important principle of organic chemistry: the common-ion or mass law effect, the effect of changing the ionizing power of a solvent on a solvolysis reaction, and the collecting and plotting of data to illustrate a first-order reaction.
Danen, Wayne C.; Blecha, Sr. M. Therese J. Chem. Educ. 1982, 59, 659.
Aqueous Solution Chemistry |
Solutions / Solvents |
Nucleophilic Substitution |
Kinetics |
Rate Law
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
Nucleophilic substitution reactions: Modifications and an extension  Newton, T. A.; Warren, H. W.
Modifications to a procedure comparing the reaction of n-butyl and t-butyl alcohol with equimolar amounts of HCl and HBr.
Newton, T. A.; Warren, H. W. J. Chem. Educ. 1980, 57, 747.
Nucleophilic Substitution |
Reactions
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
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
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
A dynamic carbon model capable of showing changes in hybridization  Fountain, K. R.
It is possible to construct a simple dynamic model of a carbon atom that demonstrates the Walden inversion, the SN1 reaction, and when joined with another units like itself demonstrates the full spectrum of elimination reactions.
Fountain, K. R. J. Chem. Educ. 1979, 56, 379.
Molecular Modeling |
Nucleophilic Substitution |
Elimination Reactions
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
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
Nucleophilic substitution by phase transfer catalysis  Reeves, W. Preston; White, Mitchell R.; Bier, Deana
The preparation of alkyl thiocyanates to be an excellent and versatile experiment for first year organic students.
Reeves, W. Preston; White, Mitchell R.; Bier, Deana J. Chem. Educ. 1978, 55, 56.
Nucleophilic Substitution |
Catalysis
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
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
A molecular model for SN2 reactions  Newman, Melvin S.
Plan for a homemade mechanical model designed to demonstrate many of the features of SN2 reactions.
Newman, Melvin S. J. Chem. Educ. 1975, 52, 462.
Molecular Mechanics / Dynamics |
Molecular Modeling |
Molecular Properties / Structure |
Nucleophilic Substitution |
Mechanisms of Reactions |
Reactions
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
The remarkable reactivity of aryl halides with nucleophiles   Bunnett, Joseph F.
Nucleophilic attack on carbon; nucleophilic attack on hydrogen; aryl formation by halide ion loss from o-halophenyl anions; nucleophilic attack on halogen; acceptance of an electron, and its consequences.
Bunnett, Joseph F. J. Chem. Educ. 1974, 51, 312.
Nucleophilic Substitution |
Reactions
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
SN1 and SN2 reactions: Paper marionette for demonstration  Sone, Yachiyo; Sone, Kozo
Describes the construction of a paper marionette for demonstrating SN1 and SN2 reactions.
Sone, Yachiyo; Sone, Kozo J. Chem. Educ. 1973, 50, 615.
Nucleophilic Substitution |
Mechanisms of Reactions |
Reactions |
Molecular Modeling
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
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
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
Nucleophilic substitution reactions at secondary carbon atoms. A modification of accepted views  Raber, Douglas J.; Harris, J. Milton
Considers reaction mechanisms that are intermediate between SN1 and SN2 and the possible role of ion pairs.
Raber, Douglas J.; Harris, J. Milton J. Chem. Educ. 1972, 49, 60.
Nucleophilic Substitution |
Mechanisms of Reactions
Reaction mechanisms in organic chemistry. Concerted reactions  Caserio, Marjorie C.
Examines displacement and elimination, cyclization, and rearrangement reactions, as well as theoretical considerations and generalized selection rules.
Caserio, Marjorie C. J. Chem. Educ. 1971, 48, 782.
Mechanisms of Reactions |
Reactions |
Nucleophilic Substitution |
Elimination Reactions
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
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
Free-radical bromination of p-toluic acid. An experiment in organic chemistry  Tuleen, D. L.; Hess, B. A., Jr.
This paper describes the synthesis of a-bromo-p-toluic acid (II) and the subsequent displacement of bromide ion by three nucleophiles.
Tuleen, D. L.; Hess, B. A., Jr. J. Chem. Educ. 1971, 48, 476.
Free Radicals |
Nucleophilic Substitution
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
Donor-acceptor interactions in organic chemistry  Sunderwirth, S. G.
The purpose of this article is to aid teachers in making even more effective use of theoretical considerations in teaching organic chemistry; the primary objective is to emphasize the underlying principles that are common to the following four basic types of reactions: substitution, addition, elimination, and rearrangement.
Sunderwirth, S. G. J. Chem. Educ. 1970, 47, 728.
Reactions |
Mechanisms of Reactions |
Addition Reactions |
Elimination Reactions |
Nucleophilic Substitution
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
Nucleophilic reactivities of the halide anions  Puar, Mohindar S.
Ranks the nucleophilic reactivities of free halide ions in various solvents.
Puar, Mohindar S. J. Chem. Educ. 1970, 47, 473.
Nucleophilic Substitution
A model to demonstrate the Walden inversion  Hamon, D. P. G.
Presents the design of a model capable of illustrating the Walden inversion.
Hamon, D. P. G. J. Chem. Educ. 1970, 47, 398.
Molecular Modeling |
Molecular Properties / Structure |
Nucleophilic Substitution |
Reactions
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
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
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
Resolution and stereochemistry of asymmetric silicon, germanium, tin, and lead compounds  Belloli, Robert
It is the purpose of this review to summarize the results of stereochemical studies on compounds containing an asymmetric group IVA atom.
Belloli, Robert J. Chem. Educ. 1969, 46, 640.
Stereochemistry |
Organometallics |
Enantiomers |
Mechanisms of Reactions |
Nucleophilic Substitution
Preparation of p-anisole: An organic chemistry experiment  Smith, Richard F.; Bates, Alvin C.
In this experiment, p-anisaldehyde is converted to p-anisonitrile by a modification of the three-step aldehyde-nitrile synthesis of Smith and Walker.
Smith, Richard F.; Bates, Alvin C. J. Chem. Educ. 1969, 46, 174.
Synthesis |
Mechanisms of Reactions |
Addition Reactions |
Nucleophilic Substitution |
Elimination Reactions |
Catalysis
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
Bimolecular nucleophilic displacement reactions  Edwards, John O.
The bimolecular nucleophilic displacement reaction is important and should be included in any detailed discussion of kinetics and mechanism at an early undergraduate level.
Edwards, John O. J. Chem. Educ. 1968, 45, 386.
Reactions |
Nucleophilic Substitution |
Kinetics |
Mechanisms of Reactions
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
Substitution reactions in octahedral complexes  Banerjea, D.
Commentary on the cited article by one of the authors that article referenced.
Banerjea, D. J. Chem. Educ. 1967, 44, 485.
Coordination Compounds |
Nucleophilic Substitution
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
Substitution reactions in octahedral complexes  Jones, G. R. H.
Examines the possibility of direct substitution, in aqueous solution, of a ligand in an octahedral complex by a nucleophile other than water or OH-.
Jones, G. R. H. J. Chem. Educ. 1966, 43, 657.
Coordination Compounds |
Mechanisms of Reactions |
Aqueous Solution Chemistry |
Nucleophilic Substitution |
Transition Elements |
Metals
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
Reaction mechanisms in organic chemistry. I. The experimental approach  Caserio, Marjorie C.
Reviews a variety of method that may be employed to determine the mechanism of organic reactions.
Caserio, Marjorie C. J. Chem. Educ. 1965, 42, 570.
Reactions |
Mechanisms of Reactions |
Reactive Intermediates |
Kinetics |
Nucleophilic Substitution |
Addition Reactions |
Elimination 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
A simple model for the SN2 mechanism.  Nyquist, H. LeRoy
Presents a simple, physical model for the SN2 mechanism.
Nyquist, H. LeRoy J. Chem. Educ. 1965, 42, 103.
Molecular Modeling |
Reactions |
Nucleophilic Substitution |
Mechanisms of Reactions
Nucleophlic substitution at a saturated carbon atom; Elimination reactions (Bunton, C. A.; Banthorpe, D. V.)  Bunnett, Joseph F.

Bunnett, Joseph F. J. Chem. Educ. 1964, 41, 406.
Nucleophilic Substitution |
Elimination Reactions |
Mechanisms of Reactions
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
A second order kinetics experiment  Teerlink, Wilford J.; Asay, Jeanette; Sugihara, James M.
Investigates the nucleophilic displacement reaction of ethyl p-toluenesulfonate by iodide in acetone.
Teerlink, Wilford J.; Asay, Jeanette; Sugihara, James M. J. Chem. Educ. 1964, 41, 161.
Kinetics |
Nucleophilic Substitution
Nucleophilic reactions at trigonally bonded carbon  Cash, R. Vincent
Examines the mechanisms of nucleophilic displacement reactions, nucleophilic addition reactions, and nucleophilic addition with elimination, all at trigonally bonded carbon.
Cash, R. Vincent J. Chem. Educ. 1964, 41, 108.
Nucleophilic Substitution |
Reactions |
Mechanisms of Reactions |
Addition Reactions |
Elimination Reactions
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
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 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
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
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
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
Introducing stereoisomerism  Schreiber, Kurt C.
Criticizes the traditional presentation of stereochemistry in isolation and offers a more integrated approach.
Schreiber, Kurt C. J. Chem. Educ. 1955, 32, 83.
Stereochemistry |
Molecular Properties / Structure |
Nucleophilic Substitution
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