TIGER

Journal Articles: 691 results
Synthesis of Albendazole Metabolite: Characterization and HPLC Determination  Graciela Mahler, Danilo Davyt, Sandra Gordon, Marcelo Incerti, Ivana Núñez, Horacio Pezaroglo, Laura Scarone, Gloria Serra, Mauricio Silvera, and Eduardo Manta
In this laboratory activity, students are introduced to the synthesis of an albendazole metabolite obtained by a sulfide oxidation reaction. Albendazole as well as its metabolite, albendazole sulfoxide, are used as anthelmintic drugs. The oxidation reagent is H2O2 in acetic acid. The reaction is environmental friendly, fast, and proceeds with high yield. The crude reaction is analyzed by HPLC chromatography to determine purity. The simplicity of the experiment allows students to study chiral concepts, physicochemical and spectroscopic properties of the compounds, and HPLC determinations.
Mahler, Graciela; Davyt, Danilo; Gordon, Sandra; Incerti, Marcelo; Núñez, Ivana; Pezaroglo, Horacio; Scarone, Laura; Serra, Gloria; Silvera, Mauricio; Manta, Eduardo. J. Chem. Educ. 2008, 85, 1652.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
HPLC |
Medicinal Chemistry |
Organosulfur Compounds |
Oxidation / Reduction |
Synthesis
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
The Synthesis of a Cockroach Pheromone  Patty L. Feist
This paper describes the synthesis of gentisyl quinone isovalerate or blattellaquinone, a sex pheromone of the German cockroach and a compound with real-world applications. The experiment also affords students practice in extraction as well as IR and NMR spectroscopy.
Feist, Patty L. J. Chem. Educ. 2008, 85, 1548.
Esters |
IR Spectroscopy |
Natural Products |
NMR Spectroscopy |
Oxidation / Reduction |
Synthesis
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
The Baeyer–Villiger Oxidation with Trifluoroacetic Acid and Household Sodium Percarbonate  Richard A. Kjonaas and Anthony E. Clemons
Reports a method for carrying out the BaeyerVilliger oxidation of cyclopentanone to d-valerolactone in a large-section introductory organic chemistry laboratory course.
Kjonaas, Richard A.; Clemons, Anthony E. J. Chem. Educ. 2008, 85, 827.
Aldehydes / Ketones |
Esters |
NMR Spectroscopy |
Oxidation / Reduction |
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
The Role of Water Chemistry in Marine Aquarium Design: A Model System for a General Chemistry Class  Jeffrey J. Keaffaber, Ramiro Palma, and Kathryn R. Williams
Water chemistry is central to aquarium design, and it provides many potential applications for discussion in undergraduate chemistry and engineering courses. This article uses a hypothetical tank to house ocean sunfish as a model to show students the calculations and other considerations that are needed when designing a marine aquarium.
Keaffaber, Jeffrey J.; Palma, Ramiro; Williams, Kathryn R. J. Chem. Educ. 2008, 85, 225.
Acids / Bases |
Aqueous Solution Chemistry |
Consumer Chemistry |
Oxidation / Reduction |
Stoichiometry |
Water / Water Chemistry
Using Ozone in Organic Chemistry Lab: The Ozonolysis of Eugenol  Bruce M. Branan, Joshua T. Butcher, and Lawrence R. Olsen
This organic laboratory involves the ozonolysis of eugenol (clove oil) followed by a reductive workup that generates an aldehyde easily identified by its NMR and IR spectra.
Branan, Bruce M.; Butcher, Joshua T.; Olsen, Lawrence R. J. Chem. Educ. 2007, 84, 1979.
Aldehydes / Ketones |
Gases |
IR Spectroscopy |
Laboratory Equipment / Apparatus |
Natural Products |
NMR Spectroscopy |
Synthesis |
Oxidation / Reduction
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
A Guided-Inquiry Approach to the Sodium Borohydride Reduction and Grignard Reaction of Carbonyl Compounds  Robert E. Rosenberg
Students teams identify unknowns and their reaction products and use their data to deduce that esters are less electrophilic than the other carbonyl compounds present, that Grignard reagents are more nucleophilic than sodium borohydride, and that carboxylic acid derivatives do not undergo the nucleophilic addition reactions that are characteristic of aldehydes and ketones.
Rosenberg, Robert E. J. Chem. Educ. 2007, 84, 1474.
Addition Reactions |
Aldehydes / Ketones |
Esters |
Grignard Reagents |
IR Spectroscopy |
Oxidation / Reduction |
Reactions |
Student-Centered Learning
Mercury Beating Heart: Modifications to the Classical Demonstration  Metodija Najdoski, Valentin Mirceski, Vladimir M. Petruševski, and Sani Demiri
The classic mercury beating heart demonstration is modified with various electrolytes.
Najdoski, Metodija; Mirceski, Valentin; Petruševski, Vladimir M.; Demiri, Sani. J. Chem. Educ. 2007, 84, 1292.
Electrochemistry |
Oxidation / Reduction |
Surface Science
Demonstration of the Fenton Reaction  Dean C. Luehrs and Alex E. Roher
Presents a lecture demonstration of the Fenton reaction with applications to medicine and environmental engineering.
Luehrs, Dean C.; Roher, Alex E. J. Chem. Educ. 2007, 84, 1290.
Applications of Chemistry |
Dyes / Pigments |
Oxidation / Reduction |
Reactive Intermediates
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
A Bioanalytical Chemistry Experiment for Undergraduate Students: Biosensors Based on Metal Nanoparticles  John Njagi, John Warner, and Silvana Andreescu
Describes a laboratory experiment on the development of a biosensor in which students apply electrochemical methods to deposit gold nanoparticles onto electrode surfaces, immobilize an enzyme using glutaraldehyde chemistry, and perform quantitative analysis of phenol using a biosensor with amperometric detection.
Njagi, John; Warner, John; Andreescu, Silvana. J. Chem. Educ. 2007, 84, 1180.
Bioanalytical Chemistry |
Electrochemistry |
Enzymes |
Oxidation / Reduction |
Phenols
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
Exploring Faraday's Law of Electrolysis Using Zinc–Air Batteries with Current Regulative Diodes  Masahiro Kamata and Miei Paku
Describes a new educational experiment using low-cost zincair batteries and current regulative diode arrays to quickly confirm Faraday's law of electrolysis.
Kamata, Masahiro; Paku, Miei. J. Chem. Educ. 2007, 84, 674.
Electrochemistry |
Electrolytic / Galvanic Cells / Potentials |
Laboratory Equipment / Apparatus |
Oxidation / Reduction
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
A Pollutant Transformation Laboratory Exercise for Environmental Chemistry: The Reduction of Nitrobenzenes by Anaerobic Solutions of Humic Acid  Frank M. Dunnivant and Mark-Cody Reynolds
Presents a laboratory for advanced undergraduate- or graduate-level environmental chemistry in which students study the reduction of substituted nitrobenzenes by natural organic matter under anaerobic conditions. The exercise involves solution preparation, pH and EH buffers, organic reaction mechanisms, reaction kinetics, and instrumental analysis.
Dunnivant, Frank M.; Reynolds, Mark-Cody. J. Chem. Educ. 2007, 84, 315.
Instrumental Methods |
pH |
Solutions / Solvents |
Mechanisms of Reactions |
Kinetics |
Oxidation / Reduction
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
Entropy and the Shelf Model: A Quantum Physical Approach to a Physical Property  Arnd H. Jungermann
A quantum physical approach relying on energy quantization leads to three simple rules which are the key to understanding the physical property described by molar entropy values.
Jungermann, Arnd H. J. Chem. Educ. 2006, 83, 1686.
Alcohols |
Alkanes / Cycloalkanes |
Carboxylic Acids |
Covalent Bonding |
Ionic Bonding |
Physical Properties |
Quantum Chemistry |
Thermodynamics
Using a Simulated Industrial Setting for the Development of an Improved Solvent System for the Recrystallization of Benzoic Acid: A Student-Centered Project  Timothy R. Hightower and Jay D. Heeren
Presents a peer-led, problem-solving organic laboratory exercise that provide students with an opportunity to produce a more efficient recrystallization solvent in an industrial environment.
Hightower, Timothy R.; Heeren, Jay D. J. Chem. Educ. 2006, 83, 1663.
Carboxylic Acids |
Industrial Chemistry |
Separation Science |
Solutions / Solvents
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
Developing Critical Thinking Skills: The "Sabotaged" Synthesis of Methyl p-Bromobenzoate  Eric J. Mahan and Mary Alice Nading
Before beginning an experiment, students are told that someone might have sabotaged their experiment to produce other-than-expected results. The objective is to perform the experiment, determine if any sabotage has occurred, and, if so, identify the changes that were made to the reagents as well as the person responsible.
Mahan, Eric J.; Nading, Mary Alice. J. Chem. Educ. 2006, 83, 1652.
Alcohols |
Carboxylic Acids |
Esters |
IR Spectroscopy |
NMR Spectroscopy |
Mass Spectrometry |
Synthesis
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
Enantioselective Reduction by Crude Plant Parts: Reduction of Benzofuran-2-yl Methyl Ketone with Carrot (Daucus carota) Bits  Silvana Ravía, Daniela Gamenara, Valeria Schapiro, Ana Bellomo, Jorge Adum, Gustavo Seoane, and David Gonzalez
Presents the enantioselective reduction of a ketone by crude plant parts, using carrot (Daucus carota) as the reducing agent.
Ravía, Silvana; Gamenara, Daniela; Schapiro, Valeria; Bellomo, Ana; Adum, Jorge; Seoane, Gustavo; Gonzalez, David. J. Chem. Educ. 2006, 83, 1049.
Aldehydes / Ketones |
Biotechnology |
Catalysis |
Chromatography |
Green Chemistry |
Oxidation / Reduction |
Stereochemistry |
Separation Science
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
Reductive Amination: A Remarkable Experiment for the Organic Laboratory  Kim M. Touchette
The synthesis of N-(2-hydroxy-3-methoxybenzyl)-N-p-tolylacetamide is a fast, simple three-step sequence that serves as a useful example of the reductive amination reaction for the organic chemistry laboratory.
Touchette, Kim M. J. Chem. Educ. 2006, 83, 929.
Aldehydes / Ketones |
Amines / Ammonium Compounds |
Green Chemistry |
Instrumental Methods |
IR Spectroscopy |
NMR Spectroscopy |
Oxidation / Reduction |
Solids
A Simple Combinatorial Experiment Based on Fischer Esterification. An Experiment Suitable for the First-Semester Organic Chemistry Lab  Peter A. Wade, Susan A. Rutkowsky, and Daniel B. King
Describes a combinatorial experiment for the synthesis of esters by Fischer esterification in which a total of eight esters are prepared as six mixtures.
Wade, Peter A.; Rutkowsky, Susan A.; King, Daniel B. J. Chem. Educ. 2006, 83, 927.
Alcohols |
Carboxylic Acids |
Combinatorial Chemistry |
Equilibrium |
Esters |
Gas Chromatography |
Synthesis
Iodolactonization of 4-Pentenoic Acid   R. David Crouch, Alexander Tucker-Schwartz, and Kathryn Barker
Describes an experiment in which 4-pentenoic acid is converted into a lactone via iodolactonization.
Crouch, R. David; Tucker-Schwartz, Alexander; Barker, Kathryn. J. Chem. Educ. 2006, 83, 921.
Alkenes |
Carboxylic Acids |
IR Spectroscopy |
Mechanisms of Reactions |
NMR Spectroscopy |
Reactions |
Synthesis
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
Ozonolysis Problems That Promote Student Reasoning  Ray A. Gross Jr.
The structural features inherent in acyclic monoterpenes that follow the isoprene rule often lead to unique sets of ozonolysis products from which their structures, excluding stereochemistry, can be determined from molecular formulas only. This article shows how students may elucidate the structures of these compounds by analysis of the oxidative and reductive workup products.
Gross, Ray A., Jr. J. Chem. Educ. 2006, 83, 604.
Aldehydes / Ketones |
Alkenes |
Alkynes |
Carboxylic Acids |
Oxidation / Reduction |
Student-Centered Learning
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
Synthesis of Methyl Diantilis, a Commercially Important Fragrance  William H. Miles and Katelyn B. Connell
Describes the synthesis of a family of fragrances, including the commercially important Methyl Diantilis, and provides an excellent introduction to intellectual property laws.
Miles, William H.; Connell, Katelyn B. J. Chem. Educ. 2006, 83, 285.
Alcohols |
Food Science |
Catalysis |
Ethers |
Industrial Chemistry |
IR Spectroscopy |
Lewis Acids / Bases |
NMR Spectroscopy |
Oxidation / Reduction |
Synthesis
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
Environmentally Responsible Redox Chemistry: An Example of Convenient Oxidation Methodology without Chromium Waste  Robyn L. Crumbie
This article describes a simple experiment that uses recyclable Magtrieve as the oxidant in a simple reaction sequence emphasizing the reciprocity of oxidation and reduction processes in organic synthesis.
Crumbie, Robyn L. J. Chem. Educ. 2006, 83, 268.
Chromatography |
Green Chemistry |
IR Spectroscopy |
Oxidation / Reduction |
Synthesis
A Solvent-Free Baeyer–Villiger Lactonization for the Undergraduate Organic Laboratory: Synthesis of γ-t-Butyl-ε-caprolactone  John J. Esteb, J. Nathan Hohman, Diana E. Schlamadinger, and Anne M. Wilson
The BaeyerVilliger reaction provides an efficient method to convert ketones to esters or lactones. In this experiment, m-chloroperoxybenzoic acid and 4-tert-butylcyclohexanone are mixed together for under solvent-free conditions to produce ?-t-butyl-e-caprolactone.
Esteb, John J.; Hohman, J. Nathan; Schlamadinger, Diana E.; Wilson, Anne M. J. Chem. Educ. 2005, 82, 1837.
Green Chemistry |
Synthesis |
Esters |
Oxidation / Reduction
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 Discovery-Oriented Approach to Organic Chemistry. 6. Selective Reduction in Organic Chemistry: Reduction of Aldehydes in the Presence of Esters Using Sodium Borohydride  Ashvin R. Baru and Ram S. Mohan
Describes two discovery oriented lab experiments involving the chemoselective reduction of vanillin acetate and methyl 4-formylbenzoate in the presence of esters using sodium borohydride, followed by product identification using 1H and 13C NMR spectroscopy.
Baru, Ashvin R.; Mohan, Ram S. J. Chem. Educ. 2005, 82, 1674.
NMR Spectroscopy |
Alcohols |
Aldehydes / Ketones |
Esters |
Oxidation / Reduction |
Thin Layer Chromatography |
Synthesis
Laboratory Experiments on the Electrochemical Remediation of the Environment. Part 8. Microscale Simultaneous Photocatalysis  Jorge G. Ibanez, Rodrigo Mena-Brito, and Arturo Fregoso-Infante
In this article we describe a microscale experiment in which the simultaneous oxidation of an organic compound (citric acid) and the reduction of a metal ion (Cu2+) are photocatalytically performed in an aqueous slurry containing TiO2 irradiated with UV light. This produces electrons (capable of reducing the metal ions) and holes (capable of oxidizing the organic molecule) that can be used for environmental clean up. The experiment allows students to have a better comprehension of the different phenomena involved in a typical photocatalytic process.
Ibanez, Jorge G.; Mena-Brito, Rodrigo; Fregoso-Infante, Arturo. J. Chem. Educ. 2005, 82, 1549.
Aqueous Solution Chemistry |
Electrochemistry |
Microscale Lab |
Oxidation / Reduction |
Reactions |
Photochemistry |
Semiconductors |
UV-Vis Spectroscopy
Laboratory Experiments on the Electrochemical Remediation of the Environment. Part 7: Microscale Production of Ozone  Jorge G. Ibanez, Rodrigo Mayen-Mondragon, M. T. Moran-Moran, Alejandro Alatorre-Ordaz, Bruce Mattson, and Scot Eskestrand
Ozone, a powerful oxidizing and disinfecting agent, is produced electrochemically in the undergraduate laboratory with simple equipment and under very mild conditions. Tests are given to characterize it, to observe its action in simulated environmental applications, and to measure its rate of production.
Ibanez, Jorge G.; Mayen-Mondragon, Rodrigo; Moran-Moran, M. T.; Alatorre-Ordaz, Alejandro; Mattson, Bruce; Eskestrand, Scot. J. Chem. Educ. 2005, 82, 1546.
Aqueous Solution Chemistry |
Descriptive Chemistry |
Electrochemistry |
Electrolytic / Galvanic Cells / Potentials |
Laboratory Equipment / Apparatus |
Microscale Lab |
Oxidation / Reduction |
Reactions
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
The Entrance and Exit Effects in Small Electrochemical Filter-Press Reactors Used in the Laboratory  Angel Frías-Ferrer, José González-García, Verónica Sáez, Eduardo Expósito, Carlos M. ánchez-Sánchez, Vicente Montiel, Antonio Aldaz, and Frank C. Walsh
An experiment has been designed to aid chemical engineering students in understanding the importance of size in small reactors in order to get suitable data for subsequent extrapolations to larger reactors and, therefore, for the scaleup of small systems. The experimental arrangement and procedures are described, and the theory needed to interpret the experimental results is discussed. Reactor geometry and size and experimental procedure are highlighted as key parameters in the study.
Frías-Ferrer, Angel; González-García, José; Sáez, Verónica; Expósito, Eduardo; ánchez-Sánchez, Carlos M.; Montiel, Vicente; Aldaz, Antonio; Walsh, Frank C. J. Chem. Educ. 2005, 82, 1395.
Electrochemistry |
Industrial Chemistry |
Oxidation / Reduction |
Transport Properties
Application of ChemDraw NMR Tool: Correlation of Program-Generated 13C Chemical Shifts and pKa Values of para-Substituted Benzoic Acids  Hongyi Wang
An application of ChemDraw NMR Tool was demonstrated by correlation of program-generated 13C NMR chemical shifts and pKa values of para-substituted benzoic acids. Experimental 13C NMR chemical shifts were analyzed in the same way for comparison. The project can be used as an assignment at the end of the first-year organic chemistry course to review topics or explore new techniques: Hammett equation, acidbase equilibrium theory, electronic nature of functional groups, inductive and resonance effects, structurereactivity relationship, NMR spectroscopy, literature search, database search, and ChemDraw software.
Wang, Hongyi. J. Chem. Educ. 2005, 82, 1340.
Acids / Bases |
Equilibrium |
NMR Spectroscopy |
Aqueous Solution Chemistry |
Carboxylic Acids
A Microwave-Assisted Reduction of Cyclohexanone Using Solid-State-Supported Sodium Borohydride  Lori L. White and Kevin W. Kittredge
We report a microwave-assisted reduction of cyclohexanone by sodium borohydride that is supported on SiO2. The reaction was completed in less than 3 minutes. Workup and analysis by GCMS, IR, and 1H NMR was possible in a two and half-hour laboratory session. This reduction was used successfully in a second-year organic chemistry laboratory. Students were exposed to a green chemistry reaction using solid-state-supported reactants in the absence of solvent.
White, Lori L.; Kittredge, Kevin W. J. Chem. Educ. 2005, 82, 1055.
Oxidation / Reduction |
Solid State Chemistry |
Green Chemistry |
Alcohols |
Aldehydes / Ketones
Circular Dichroism Investigation of Dess–Martin Periodinane Oxidation in the Organic Chemistry Laboratory  Nicole A. Reed, Robert D. Rapp, Christian S. Hamann, and Pamela G. Artz
Using circular dichroism, organic laboratory students investigated the change in absolute stereochemistry upon oxidation of menthol to menthone. In the first laboratory period, the oxidation was performed with DessMartin periodinane, which is a facile and less toxic oxidizing agent. Half the laboratory group performed the oxidation with ()-menthol and the other half used (+)-menthol to produce ()-menthone and (+)-menthone, respectively. The products were analyzed in the second laboratory period using infrared spectroscopy and gas chromatography/mass spectrometry to determine the fraction of starting alcohol converted to ketone. Comparison was made between CD spectra both for the menthol reactant and menthone product and for the (+)- and ()-menthone enantiomers.
Reed, Nicole A.; Rapp, Robert D.; Hamann, Christian S.; Artz, Pamela G. J. Chem. Educ. 2005, 82, 1053.
Instrumental Methods |
Molecular Properties / Structure |
Oxidation / Reduction |
Reactions |
Enantiomers
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
Single-Molecule Electronic Measurements with Metal Electrodes  Stuart Lindsay
The process of transferring electrons from one metal electrode to another via an intervening molecule differs from electrochemically or optically-induced electron transfer in important ways. The simplest process of ballistic electron transport with no charge localization on the molecule (tunneling) should be easy to understand quantitatively, yet experimental reports and theoretical calculations can differ by orders of magnitude. Here, we show how many of the discrepancies are resolved with measurements carefully constructed to provide data on single molecules connected to electrodes in well-defined ways.
Lindsay, Stuart. J. Chem. Educ. 2005, 82, 727.
Electrochemistry |
Nanotechnology |
Oxidation / Reduction
Procedure for Decomposing a Redox Reaction into Half-Reactions  Ilie Fishtik and Ladislav H. Berka
The principle of stoichiometric uniqueness provides a simple algorithm to check whether a simple redox reaction may be uniquely decomposed into half-reactions in a single way. For complex redox reactions the approach permits a complete enumeration of a finite and unique number of ways a redox reaction may be decomposed into half-reactions. Several examples are given.
Fishtik, Ilie; Berka, Ladislav H. J. Chem. Educ. 2005, 82, 553.
Stoichiometry |
Equilibrium |
Electrochemistry |
Oxidation / Reduction |
Reactions |
Thermodynamics
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
Analysis of Gold Ores by Fire Assay  Kristy M. Blyth, David N. Phillips, and Wilhelm van Bronswijk
This article describes a laboratory exercise for the analysis of gold using the fire-assay technique. This method of analysis not only provides students with an introduction to the technique of fire assay, but also covers some very interesting acidbase and redox chemistry. The gold is collected in a lead button while the remainder of the constituents find their way into a slag. The gold is recovered from the lead by absorption in a boneash cupel.
Blyth, Kristy M.; Phillips, David N.; van Bronswijk, Wilhelm. J. Chem. Educ. 2004, 81, 1780.
Acids / Bases |
Industrial Chemistry |
Metals |
Quantitative Analysis |
Oxidation / Reduction
Volatile Organic Sulfur Compounds of Environmental Interest: Dimethyl Sulfide and Methanethiol. An Introductory Overview  Thomas G. Chasteen and Ronald Bentley
Volatile organic sulfur compounds and their degradation products play important environmental roles in global warming, acid precipitation, and cloud formation. Two important members of this group, dimethyl sulfide, DMS, and methanethiol, MT, are formed by living organisms as well as by abiotic processes. The chemical reactions responsible for the biosynthesis of DMS and MT are emphasized here, as well as means for their degradation. Since sulfur compounds are often ignored in normal course work, this article provides a basic foundation for an understanding of these interesting and environmentally significant compounds.
Chasteen, Thomas G.; Bentley, Ronald. J. Chem. Educ. 2004, 81, 1524.
Atmospheric Chemistry |
Bioorganic Chemistry |
Gases |
Oxidation / Reduction
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
Studying Current–Potential Curves Using Bipotentiometric Iodometric Back-Titration for the Determination of Ascorbic Acid in Fruits and Vegetables  Roxana A. Verdini and Claudia M. Lagier
A method for the determination of the ascorbic acid content in fruits and vegetables was used to introduce the principles of voltammetry. The procedure combines an iodometric back-titration with voltammetric (bipotentiometric) end point detection, which minimizes the risk of ascorbic acid oxidation, allowing for a rapid and efficient quantification of vitamin C in fruits and vegetables. A better understanding of the titration curve is achieved by analyzing the schematic currentpotential curves of the anodic and cathodic half-cell reactions during the titration.
Verdini, Roxana A.; Lagier, Claudia M. J. Chem. Educ. 2004, 81, 1482.
Constitutional Isomers |
Electrochemistry |
Food Science |
Instrumental Methods |
Oxidation / Reduction |
Titration / Volumetric Analysis |
Vitamins |
Consumer Chemistry
The Conversion of Carboxylic Acids to Ketones: A Repeated Discovery  John W. Nicholson and Alan Wilson
This article describes the history of the reaction converting carboxylic acids to ketones. The reaction has been rediscovered several times, yet has actually been known for centuries.
Nicholson, John W.; Wilson, Alan. J. Chem. Educ. 2004, 81, 1362.
Synthesis |
Carboxylic Acids |
Aldehydes / Ketones
Catalytic Hydrogenation of Organic Compounds without H2 Supply: An Electrochemical System  Daniela Maria do Amaral Ferraz Navarro and Marcelo Navarro
A system for hydrogenation of organic compounds without a hydrogen gas supply is described. The process involves an electrochemical apparatus for the generation of hydrogen in situ. The simplicity of the experiment allows students to carry out easy experiments in the laboratory and the instructors to introduce the following concepts: electrochemical principles and catalytic and hydrogenation reactions. A sacrificial anode of nickel is used in the electrochemical system with a double function: to permit the use of an undivided cell and activate the cathode surface.
Navarro, Daniela Maria do Amaral Ferraz; Navarro, Marcelo. J. Chem. Educ. 2004, 81, 1350.
Catalysis |
Chromatography |
Electrochemistry |
Oxidation / Reduction
Simple Epoxide Formation for the Organic Laboratory Using Oxone  William C. Broshears, John J. Esteb, Jeremy Richter, and Anne M. Wilson
This experiment demonstrates a simple synthesis of an epoxide and formation of a secondary oxidizing agent.
Broshears, William C.; Esteb, John J.; Richter, Jeremy; Wilson, Anne M. J. Chem. Educ. 2004, 81, 1018.
Oxidation / Reduction |
Synthesis
A Reliable Homemade Electrode Based on Glassy Polymeric Carbon  André L. Santos, Regina M. Takeuchi, Herenilton P. Oliveira, Marcello G. Rodrigues, and Robert L. Zimmerman
The production of glassy polymeric carbon (GPC) through the thermal treatment of a phenolic resin is described.
Santos, André L.; Takeuchi, Regina M.; Oliveira, Herenilton P.; Rodrigues, Marcello G.; Zimmerman, Robert L. J. Chem. Educ. 2004, 81, 842.
Electrochemistry |
Crystals / Crystallography |
IR Spectroscopy |
Oxidation / Reduction
Chlor–Alkali Industry: A Laboratory Scale Approach  C. M. Sánchez-Sánchez, E. Expósito, A. Frías-Ferrer, J. González-García, V. Montiel, and A. Aldaz
An experiment is described that approximates the industrial chloralkali process using a membrane cell.
Sánchez-Sánchez, C. M.; Expósito, E.; Frías-Ferrer, A.; González-García, J.; Montiel, V.; Aldaz, A. J. Chem. Educ. 2004, 81, 698.
Electrochemistry |
Industrial Chemistry |
Oxidation / Reduction
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
Variability of the Cell Potential of a Given Chemical Reaction  Ladislav H. Berka and Ilie Fishtik
It is demonstrated in this article that while the value of the free energy change for any chemical reaction is independent of path (a state function), the value of the standard cell potential of a reaction is dependent on the half-cell reactions used to carry out that reaction.
Berka, Ladislav H.; Fishtik, Ilie. J. Chem. Educ. 2004, 81, 584.
Electrochemistry |
Oxidation / Reduction |
Thermodynamics |
Physical Properties |
Electrolytic / Galvanic Cells / Potentials
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
Laboratory Experiments on the Electrochemical Remediation of the Environment. Part 6: Microscale Production of Ferrate  Jorge G. Ibanez, Monica Tellez-Giron, Diana Alvarez, and Elizabeth Garcia-Pintor
Ferrate, a powerful oxidizing and disinfecting agent, is synthesized chemically and electrochemically in the undergraduate laboratory with simple equipment and under very mild conditions. Tests are given to characterize it and to observe its action in simulated environmental applications.
Ibanez, Jorge G.; Tellez-Giron, Monica; Alvarez, Diana; Garcia-Pintor, Elizabeth. J. Chem. Educ. 2004, 81, 251.
Aqueous Solution Chemistry |
Electrochemistry |
Green Chemistry |
Microscale Lab |
Oxidation / Reduction
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
Well Wishes. A Case on Septic Systems and Well Water Requiring In-Depth Analysis and Including Optional Laboratory Experiments  Mary M. Walczak and Juliette M. Lantz
This paper describes the use of a case study to teach introductory chemistry students the chemical principles of solution concentration (especially ppm) and dilution, aqueous redox reactions, and stoichiometric conversions between different solution species.
Walczak, Mary M.; Lantz, Juliette M. J. Chem. Educ. 2004, 81, 218.
Consumer Chemistry |
Water / Water Chemistry |
Solutions / Solvents |
Oxidation / Reduction |
Stoichiometry
Comment on the Hazards of Peroxide Decomposition  J. C. Jones
The issue under discussionthe presence in ether of peroxides and their explosive decompositionis an important one, and the correspondence referred to is focused on laboratory safety. I believe however that an interesting point of pedagogic value can be gleaned from it.
Jones, J. C. J. Chem. Educ. 2004, 81, 193.
Ethers |
Oxidation / Reduction
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
A Spectrophotometric Study of the Permanganate–Oxalate Reaction: An Analytical Laboratory Experiment  Gene E. Kalbus, Van T. Lieu, and Lee H. Kalbus
The experiment is divided into two parts. Part I involves the determination of an unknown oxalate. Part II of the experiment involves examination of the effect of sulfuric acid concentration and the effect of manganous ion concentration on the rate of and outcome of the permanganateoxalate reaction.
Kalbus, Gene E.; Lieu, Van T.; Kalbus, Lee H. J. Chem. Educ. 2004, 81, 100.
Oxidation / Reduction |
Stoichiometry |
UV-Vis Spectroscopy
Acid–Base and Precipitation Equilibria in Wine  Miguel Palma and Carmelo G. Barroso
A simple but effective experiment demonstrates the interactions between simultaneous equilibria involving hydrogen tartrate and helps students realize the importance of multiple equilibria in real-world systems.
Palma, Miguel; Barroso, Carmelo G. J. Chem. Educ. 2004, 81, 94.
Acids / Bases |
Aqueous Solution Chemistry |
Consumer Chemistry |
Food Science |
Alcohols |
Carboxylic Acids
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
Stearic Acid  Jay A. Young
Properties, hazards, and storage requirements for stearic acid.
Young, Jay A. J. Chem. Educ. 2004, 81, 25.
Laboratory Equipment / Apparatus |
Laboratory Management |
Carboxylic Acids |
Acids / Bases |
Physical Properties
Photogalvanic Cells for Classroom Investigations: A Contribution for Ongoing Curriculum Modernization  Claudia Bohrmann-Linde and Michael W. Tausch
Laboratory experiments examining the fundamental processes in the conversion of light into electrical energy using photogalvanic cells have been developed. These simple cells are suitable for classroom investigations examining the operating principles of photogalvanic cells and the influence of different parameters on their efficiency.
Bohrmann-Linde, Claudia; Tausch, Michael W. J. Chem. Educ. 2003, 80, 1471.
Electrochemistry |
Atomic Properties / Structure |
Photochemistry |
Oxidation / Reduction |
Electrolytic / Galvanic Cells / Potentials
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
The Relative Explosive Power of Some Explosives  Marten J. ten Hoor
The efficiency of an explosive is measured by its relative explosive power, REP. This quantity is defined as REP = QVg/m2, where Q is the energy released in the explosion, Vg is the total volume (at STP) of gas produced, and m is the mass of the explosive that has reacted. These three quantities can be determined from the explosion equation of the explosive.
ten Hoor, Marten J. J. Chem. Educ. 2003, 80, 1397.
Gases |
Oxidation / Reduction
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
Photocatalytic Hydrogen Production by Direct Sunlight: A Laboratory Experiment  Atif Koca and Musa Sahin
The experiment can be used to introduce students to the concept of a renewable and sustainable hydrogen energy system of the future, as well as its production techniques, and to demonstrate the use of a CdS/ZnS photocatalyst system for photocatalytic hydrogen production from direct sunlight.
Koca, Atif; Sahin, Musa. J. Chem. Educ. 2003, 80, 1314.
Catalysis |
Atomic Properties / Structure |
Photochemistry |
Oxidation / Reduction
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
Demonstrating Corrosion Using Galvanic Cells (J. Chem. Educ. 1998, 75, 747-748)   Algirdas Sulcius
Comments on and suggestions for improving the original experimental procedure.
Sulcius, Algirdas. J. Chem. Educ. 2003, 80, 1138.
Microscale Lab |
Electrochemistry |
Oxidation / Reduction |
Electrolytic / Galvanic Cells / Potentials
A Graphical Presentation of the Born–Haber Cycle for Estimating the Electrode Potentials of Metals  Michael Laing
The traditional BornHaber cycle for estimating E for Mn+/M is represented visually by plotting step-by-step the values of ?Hat, IEi, and ?Hhyd for the metal.
Laing, Michael. J. Chem. Educ. 2003, 80, 1057.
Electrochemistry |
Metals |
Oxidation / Reduction
Reproportionation of Copper(I)  Jan Malyszko and Maria Kaczor
Cu(I) is an example of an intermediate oxidation state that can undergo disproportionation or reproportionation reactions depending on the solvent and background electrolyte. A simple experiment to demonstrate the reproportionation of copper(I) from the reaction between copper metal and copper(II) in acidic aqueous solution containing an excess of chlorides is presented.
Malyszko, Jan; Kaczor, Maria. J. Chem. Educ. 2003, 80, 1048.
Electrochemistry |
Oxidation / Reduction |
Oxidation State
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
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
"Chiral Acetate": The Preparation, Analysis, and Applications of Chiral Acetic Acid  Addison Ault
Production of chiral acetic acid using deuterium and tritium and its application to understanding stereochemistry and the specificity of enzymatic reactions.
Ault, Addison. J. Chem. Educ. 2003, 80, 333.
Chirality / Optical Activity |
Enzymes |
Isotopes |
Synthesis |
Stereochemistry |
Enrichment / Review Materials |
Carboxylic Acids |
Enantiomers |
Reactions |
Mechanisms of Reactions
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
Environmental Redox Potential and Redox Capacity Concepts Using a Simple Polarographic Experiment  Alejandro Pidello
Laboratory designed to enable students to distinguish clearly between redox potential and redox capacity concepts through results obtained in a complex natural system (soil).
Pidello, Alejandro. J. Chem. Educ. 2003, 80, 68.
Agricultural Chemistry |
Electrochemistry |
Oxidation / Reduction |
Potentiometry
Microscale Quantitative Analysis of Hard Water Samples Using an Indirect Potassium Permanganate Redox Titration  John N. Richardson, Mark T. Stauffer, and Jennifer L. Henry
A procedure for a microscale quantitative analysis of hard water samples using an indirect potassium permanganate redox titration.
Richardson, John N.; Stauffer, Mark T.; Henry, Jennifer L. J. Chem. Educ. 2003, 80, 65.
Microscale Lab |
Quantitative Analysis |
Oxidation / Reduction |
Titration / Volumetric Analysis |
Water / Water Chemistry
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
CLIP: Acetic Anhydride  Jay A. Young
Boric acid is a mild oxidizing agent.
Young, Jay A. J. Chem. Educ. 2002, 79, 1202.
Oxidation / Reduction
CLIP: Acetic Anhydride  Charlie A. Crutchfield
Boric acid is not an oxidizing agent.
Crutchfield, Charlie A. J. Chem. Educ. 2002, 79, 1202.
Oxidation / Reduction
CLIP: Acetic Anhydride  Charlie A. Crutchfield
Boric acid is not an oxidizing agent.
Crutchfield, Charlie A. J. Chem. Educ. 2002, 79, 1202.
Oxidation / Reduction
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
Determining Oxidation–Reduction on a Simple Number Line  Amy L. Cox and James R. Cox
Using a simple number line to analyze oxidation-reduction reactions encountered in introductory/general chemistry, organic chemistry, and biochemistry.
Cox, Amy L.; Cox, James R. J. Chem. Educ. 2002, 79, 965.
Oxidation / Reduction
Chiral Compounds and Green Chemistry in Undergraduate Organic Laboratories: Reduction of a Ketone by Sodium Borohydride and Baker's Yeast  Nicola Pohl, Allen Clague, and Kimberly Schwarz
Students compare biological and chemical means of introducing chirality into a molecule by investigating the reduction of a ketoester with two different reducing agents.
Pohl, Nicola; Clague, Allen; Schwarz, Kimberly. J. Chem. Educ. 2002, 79, 727.
Chirality / Optical Activity |
Oxidation / Reduction |
Synthesis |
Green 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
Redox Redux: Recommendations for Improving Textbook and IUPAC Definitions  Ed Vitz
Defining oxidation / reduction reactions as those in which oxidation states of the reactant(s) change.
Vitz, Ed. J. Chem. Educ. 2002, 79, 397.
Electrochemistry |
Mechanisms of Reactions |
Oxidation / Reduction |
Oxidation State
A Simple Student Experiment for Teaching Surface Electrochemistry: Adsorption of Polyoxometalate on Graphite Electrodes  David Martel, Neso Sojic, and Alexander Kuhn
Experiment that illustrates the electrochemical behavior of a surface-adsorbed redox species through cyclic voltametry.
Martel, David; Sojic, Neso; Kuhn, Alexander. J. Chem. Educ. 2002, 79, 349.
Catalysis |
Electrochemistry |
Surface Science |
Oxidation / Reduction
Integrating HPLC and Electrochemistry: A LabVIEW-Based Pulsed Amperometric Detection System  Mark B. Jensen
Using the voltametry of glucose to develop a method for the pulsed amperometric detection of carbohydrates (glucose, fructose, and sucrose) following their separation by liquid chromatography.
Jensen, Mark B. J. Chem. Educ. 2002, 79, 345.
Chromatography |
Electrochemistry |
Instrumental Methods |
HPLC |
Carbohydrates |
Separation Science |
Oxidation / Reduction
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
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
Formic Acid  Jay A. Young
Properties, hazards, and storage requirements for formic acid.
Young, Jay A. J. Chem. Educ. 2002, 79, 157.
Acids / Bases |
Physical Properties |
Laboratory Management |
Carboxylic Acids
Microscale Determination of Vitamin C by Weight Titrimetry  Gaston A. East and Erica C. Nascimento
Electroanalytical method for the microscale determination of vitamin C using a nontraditional oxidimetric titrant.
East, Gaston A.; Nascimento, Erica C. J. Chem. Educ. 2002, 79, 100.
Electrochemistry |
Instrumental Methods |
Microscale Lab |
Quantitative Analysis |
Vitamins |
Titration / Volumetric Analysis |
Oxidation / Reduction
Soap from Nutmeg: An Integrated Introductory Organic Chemistry Laboratory Experiment  Marcio C. S. de Mattos and David E. Nicodem
A sequence of experiments in which trimyristin is extracted, isolated, and purified from nutmeg, then converted to a soap (sodium myristate) and acidified to produce myristic acid.
de Mattos, Marcio C. S.; Nicodem, David E. J. Chem. Educ. 2002, 79, 94.
Natural Products |
Carboxylic Acids |
Consumer Chemistry |
Fatty Acids
An Efficient Composition for Bengal Lights  M. Comet, L. Schreyeck, and H. Fuzellier
Producing bengal lights (colored flames) using different mixtures of colorants to introduce the solid-phase redox theory in inorganic chemistry.
Comet, M.; Schreyeck, L.; Fuzellier, H. J. Chem. Educ. 2002, 79, 70.
Metals |
Oxidation / Reduction |
Solid State Chemistry
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
pH of Sodium Acetate Solutions  Guy Schmitz
Example of buffering power in deviations of the pH of sodium acetate from calculated values.
Schmitz, Guy. J. Chem. Educ. 2002, 79, 29.
Acids / Bases |
Carboxylic Acids |
pH
Response to Potential-Energy-Only Models (re J. Chem. Educ. 2000, 77, 155-156)  Frank Rioux and Roger L. DeKock
Example of buffering power in deviations of the pH of sodium acetate from calculated values.
Rioux, Frank; DeKock, Roger L. J. Chem. Educ. 2002, 79, 29.
Acids / Bases |
Carboxylic Acids |
pH |
Atomic Properties / Structure |
Quantum Chemistry |
Theoretical Chemistry
Determination of Free Lime in Clinker and Cement by Iodometry. An Undergraduate Experiment in Redox Titrimetry  Oi-Wah Lau, Shiu-Fai Luk, Nina L. N. Cheng, and Hoi-Yin Woo
Experiment to determine the free lime in cement and clinker through iodometry.
Lau, Oi-Wah; Luk, Shiu-Fai; Cheng, Nina L. N.; Woo, Hoi-Yin. J. Chem. Educ. 2001, 78, 1671.
Acids / Bases |
Industrial Chemistry |
Quantitative Analysis |
Oxidation / Reduction |
Titration / Volumetric Analysis |
Separation Science
Demonstrations with Nitrocellulose: Possible Further Pedagogic Value (re J. Chem. Educ. 2000, 77, 1449)  Edward G. Senkbeil
Characteristic of explosives to have fuel and oxidizer in the same structure.
Senkbeil, Edward G. J. Chem. Educ. 2001, 78, 1596.
Descriptive Chemistry |
Oxidation / Reduction |
Calorimetry / Thermochemistry |
Rate Law
Demonstrations with Nitrocellulose: Possible Further Pedagogic Value (re J. Chem. Educ. 2000, 77, 1449)  J. C. Jones
Characteristic of explosives to have fuel and oxidizer in the same structure.
Jones, J. C. J. Chem. Educ. 2001, 78, 1596.
Descriptive Chemistry |
Oxidation / Reduction |
Calorimetry / Thermochemistry |
Rate Law
Moisture Analysis in Lotion by Karl Fischer Coulometry. An Experiment for Introductory Analytical Chemistry  Patricia Ann Mabrouk and Kristine Castriotta
Measuring moisture content in hand and body lotions using Karl Fischer coulometry.
Mabrouk, Patricia Ann; Castriotta, Kristine. J. Chem. Educ. 2001, 78, 1385.
Consumer Chemistry |
Electrochemistry |
Quantitative Analysis |
Oxidation / Reduction |
Titration / Volumetric Analysis
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
The Joy of Color in Ceramic Glazes with the Help of Redox Chemistry  Allen A. Denio
The chemistry of pottery, ceramic glazes, and the firing process.
Denio, Allen A. J. Chem. Educ. 2001, 78, 1298.
Oxidation / Reduction |
Geochemistry |
Applications of Chemistry |
Dyes / Pigments |
Metals
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
Ethanol Metabolism and the Transition from Organic Chemistry to Biochemistry  Richard D. Feinman
Introducing alcohol dehydrogenase and aldehyde dehydrogenase reactions in organic chemistry to ease transition to biochemistry.
Feinman, Richard D. J. Chem. Educ. 2001, 78, 1215.
Metabolism |
Oxidation / Reduction |
Reactions |
Mechanisms of Reactions |
Alcohols |
Carbohydrates
Oxidation of Benzoin to Benzil Using Alumina-Supported Active MnO2  R. David Crouch, Michael S. Holden, and Jennifer S. Burger
Oxidation of benzoin to benzil using alumina-supported active MnO2; purification of the products using column chromatography.
Crouch, R. David; Holden, Michael S.; Burger, Jennifer S. J. Chem. Educ. 2001, 78, 951.
Chromatography |
Microscale Lab |
Synthesis |
Oxidation / Reduction
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
Combustion of White Phosphorus  Richard L. Keiter and Chaminda P. Gamage
The combustion of white phosphorus.
Keiter, Richard L.; Gamage, Chaminda P. J. Chem. Educ. 2001, 78, 908.
Descriptive Chemistry |
Photochemistry |
Main-Group Elements |
Oxidation / Reduction
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
Laboratory Experiments on Electrochemical Remediation of the Environment. Part 5: Indirect H2S Remediation  J. G. Ibanez
Experiment to introduce students in general chemistry, environmental chemistry, or electrochemistry to the concept of indirect electrolysis, its application in environmental remediation schemes, the role of a mediator, and the application of redox chemistry concepts.
Ibanez, J. G. J. Chem. Educ. 2001, 78, 778.
Electrochemistry |
Gases |
Microscale Lab |
Oxidation / Reduction |
Applications of Chemistry
Chemical Laboratory Information Profile: Acetic Acid (glacial)  Jay A. Young
Properties, hazards, and storage requirements for acetic acid (glacial).
Young, Jay A. J. Chem. Educ. 2001, 78, 721.
Acids / Bases |
Laboratory Management |
Physical Properties |
Carboxylic Acids
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
The Household Chemistry of Cleaning Pennies  Laurence D. Rosenhein
Although it is well known that solutions of vinegar and table salt are effective in removing tarnish from pennies, chemical explanations of this behavior are not included in sources of this "household chemistry" and erroneous explanations have crept into popular literature on this subject; this article provides some relevant empirical information on the system.
Rosenhein, Laurence D. J. Chem. Educ. 2001, 78, 513.
Consumer Chemistry |
Coordination Compounds |
Oxidation / Reduction
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
Organic-Solvent-Free Phase-Transfer Oxidation of Alcohols Using Hydrogen Peroxide  Martin Hulce and David W. Marks
Six representative alcohols are oxidized to the corresponding aldehyde or ketone, integrating the various techniques of extraction, drying, filtration, column chromatography, gas chromatography, NMR and IR spectroscopy, and reaction kinetics.
Hulce, Martin; Marks, David W. J. Chem. Educ. 2001, 78, 66.
Catalysis |
Oxidation / Reduction |
Reactions |
Kinetics |
Chromatography |
Gas Chromatography |
Separation Science |
NMR Spectroscopy |
IR Spectroscopy |
Alcohols |
Phenols
Dog with Ball Joins Flying Bird
(re J. Chem. Educ. 1999, 76, 1656)  Richard S. Treptow
Comparing structural models to simple figures.
Treptow, Richard S. J. Chem. Educ. 2001, 78, 31.
Molecular Properties / Structure |
Carboxylic Acids |
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
A Microscale Oxidation Puzzle  Michael W. Pelter, Rebecca M. Macudzinski, and Mary Ellen Passarelli
We have adapted oxidation of an alcohol with sodium hypochlorite solution to a "puzzle" approach by using a diol as the substrate for oxidation. The diols under investigation have both a primary and a secondary hydroxyl group. The assignment is to perform the reaction and determine the structure of the product through interpretation of the IR spectrum.
Pelter, Michael W.; Macudzinski, Rebecca M.; Passarelli, Mary Ellen. J. Chem. Educ. 2000, 77, 1481.
IR Spectroscopy |
Microscale Lab |
Alcohols |
Oxidation / Reduction |
Molecular Properties / Structure
Combustion Demonstration Using Updated Flame Tornado  Edward G. Senkbeil
This demonstration uses the combustion of different forms of cellulose and an updated version of the "flame tornado" as an ignition source to illustrate the factors affecting the combustion process. The objectives of the experiment are to illustrate the factors affecting the rate of a combustion reaction and to demonstrate the factors affecting the production of a flame by using the flame tornado.
Senkbeil, Edward G. J. Chem. Educ. 2000, 77, 1449.
Descriptive Chemistry |
Oxidation / Reduction |
Reactions |
Rate Law
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
Kinetic Isotope Effect in the Chromic Acid Oxidation of Secondary Alcohols  Charles E. Harding, Christopher W. Mitchell, and Jozsef Devenyi
The kinetic isotope effect is an invaluable tool in studying certain organic reaction mechanisms. Two activities involving the technique that are suitable for introductory organic laboratory students are described. A simple competition experiment utilizing the benzhydrol?benzhydrol-d1 system and chromic acid oxidation is used to demonstrate qualitatively that there is a kinetic isotope effect involved in this process.
Harding, Charles E.; Mitchell, Christopher W.; Devenyi, Jozsef. J. Chem. Educ. 2000, 77, 1042.
Isotopes |
Kinetics |
Mechanisms of Reactions |
Alcohols |
Oxidation / Reduction
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
Elucidation of Molecular Structure Using NMR Long-Range Coupling: Determination of the Single Isomer Formed in a Regiospecific Reaction  Samuel Delagrange and Françoise Nepveu
The experiment presented in this article introduces students to the main concepts of two essential NMR techniques for investigating molecular structure. Heteronuclear multiple bond connectivity (HMBC) and proton-coupled 13C NMR are used to determine which isomer, from a possible two, is formed by a regiospecific reaction. The demonstration, based on long-range coupling between quaternary carbons and protons on neighboring carbons, is presented step by step.
Delagrange, Samuel; Nepveu, Françoise. J. Chem. Educ. 2000, 77, 895.
Molecular Properties / Structure |
NMR Spectroscopy |
Synthesis |
Carboxylic Acids |
Reactions |
Diastereomers
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
Letters  
Points out that solid NaHSO3 does not exist.
Tudela, David. J. Chem. Educ. 2000, 77, 830.
Gases |
Oxidation / Reduction |
Carbohydrates
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
The Oxidation of Primary Alcohols to Esters: Three Related Investigative Experiments  Chriss E. McDonald

McDonald, Chriss E. J. Chem. Educ. 2000, 77, 750.
Oxidation / Reduction |
Alcohols |
Esters |
Synthesis |
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
The Thermodynamics and Kinetics of "HeaterMeals": An Exercise in Undergraduate Inorganic Chemistry  William B. Jensen
The author traces his steps in unraveling the chemistry behind an innovative new commercial product called HeaterMeals, which makes use of an "inorganic oven" composed of magnesium metal, iron metal, and salt water as a way of heating prepackaged meals. The thermodynamic, kinetic, and structural roles played by each component are analyzed and correlated with various topics taught in a typical introductory inorganic course.
Jensen, William B. J. Chem. Educ. 2000, 77, 713.
Electrochemistry |
Consumer Chemistry |
Thermodynamics |
Applications of Chemistry |
Calorimetry / Thermochemistry |
Oxidation / Reduction
A Comparative Study of Microscale and Standard Burets  Mono M. Singh, Cynthia B. McGowan, Zvi Szafran, and R. M. Pike
This paper describes a comparative study of the performance of microscale titrations using 2-mL microscale burets with those using Beral pipets and normal 50- and 10-mL burets. The usefulness of a microburet in general and analytical chemistry is demonstrated by presenting results from acid-base, oxidation-reduction, precipitation, complexometric, and pH titrations.
Singh, Mono M.; McGowan, Cynthia B.; Szafran, Zvi; Pike, Ronald M. J. Chem. Educ. 2000, 77, 625.
Acids / Bases |
Aqueous Solution Chemistry |
Laboratory Equipment / Apparatus |
Microscale Lab |
Quantitative Analysis |
Oxidation / Reduction |
Titration / Volumetric Analysis |
pH |
Precipitation / Solubility
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
Catalytic Oxidation of Ammonia: A Sparkling Experiment  Vladimir A. Volkovich and Trevor R. Griffiths
A lecture demonstration experiment on the catalytic oxidation of ammonia using chromium(III) oxide as a catalyst is described.
Volkovich, Vladimir A.; Griffiths, Trevor R. J. Chem. Educ. 2000, 77, 177.
Catalysis |
Oxidation / Reduction |
Reactions
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
A Simple and Efficient Ozone Generator  Debra J. Sponholtz, Michael A. Walters, Jimmy Tung, and Joseph J. BelBruno
We report on the construction of an inexpensive, efficient, and compact ozonolysis apparatus, suitable for use in oxidation chemistry, which is a convenient alternative to the more expensive generators currently on the market. The details, operating parameters, and application of the ozone generator to the oxidation of methylallyl oxazolidione are also presented.
Sponholtz, Debra J.; Walters, Michael A.; Tung, Jimmy; BelBruno, Joseph J. J. Chem. Educ. 1999, 76, 1712.
Laboratory Equipment / Apparatus |
Reactive Intermediates |
Synthesis |
Oxidation / Reduction
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
Ascorbic Acid as a Standard for Iodometric Titrations: An Analytical Experiment for General Chemistry  Cesar R. Silva, Jose A. Simoni, Carol H. Collins, and Pedro L. O. Volpe
Ascorbic acid is suggested as the weighable compound for the standardization of iodine solutions in an analytical experiment in general chemistry. The experiment involves an iodometric titration in which iodine reacts with ascorbic acid, oxidizing it to dehydroascorbic acid.
Silva, Cesar R.; Simoni, Jose A.; Collins, Carol H.; Volpe, Pedro L. O. J. Chem. Educ. 1999, 76, 1421.
Oxidation / Reduction |
Quantitative Analysis |
Titration / Volumetric Analysis |
Acids / Bases
Chemistry Comes Alive! Vol. 3: Abstract of Special Issue 23 on CD-ROM  Jerrold J. Jacobsen and John W. Moore
Volume 3 contains several related topics generally included in an introductory chemistry course. The general areas are Enthalpy and Thermodynamics, Oxidation-Reduction, and Electrochemistry.
Jacobsen, Jerrold J.; Moore, John W. J. Chem. Educ. 1999, 76, 1311.
Calorimetry / Thermochemistry |
Thermodynamics |
Oxidation / Reduction |
Electrochemistry
Lemon Cells Revisited  Radhakrishnamurty, P.
Analysis of the reactions and nature of the electrodes in the lemon cell.
Radhakrishnamurty, P. J. Chem. Educ. 1999, 76, 1190.
Electrochemistry |
Electrolytic / Galvanic Cells / Potentials |
Oxidation / Reduction
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
The Discovery-Oriented Approach to Organic Chemistry 2. Selectivity in Alcohol Oxidation: An Exercise in 1H NMR Spectroscopy for Sophomore Organic Laboratories  Steven R. Shadwick and Ram S. Mohan
A simple oxidation experiment that presents the student with a puzzle and is a good exercise in 1H NMR spectroscopy. The experiment, which illustrates the important concept of selectivity in organic synthesis, involves selective oxidation of a mixture of 1-heptanol and 2-heptanol using commercial swimming pool chlorine.
Shadwick, Steven R.; Mohan, Ram S. J. Chem. Educ. 1999, 76, 1121.
NMR Spectroscopy |
Alcohols |
Oxidation / Reduction |
Synthesis
In Search of a Deep Understanding of Cu2+/0 and Zn2+/0 E° Values  Steven H. Strauss
This paper presents an example of an interesting way to introduce periodic trends in undergraduate inorganic chemistry courses. The student, guided by the instructor, "investigates" the significantly different M2+/0 E values for two adjacent period 4 elements, copper and zinc, as though the investigation were a research project.
Strauss, Steven H. J. Chem. Educ. 1999, 76, 1095.
Periodicity / Periodic Table |
Transition Elements |
Descriptive Chemistry |
Oxidation / Reduction
A Spectrophotometric Method for Quantitative Determination of Bromine Using Tris(2-carboxyethyl)phosphine  Joan Han, Troy Story, and Grace Han
A simple spectrophotometric method for quantitative determination of bromine is described.
Han, Joan; Story, Troy; Han, Grace. J. Chem. Educ. 1999, 76, 976.
Quantitative Analysis |
Oxidation / Reduction |
Stoichiometry |
UV-Vis Spectroscopy
A Further Demonstration of Sulfite-Induced Redox Cycling of Metal Ions Initiated by Shaking  Horacio D. Moya, Eduardo Almeida Neves, and Nina Coichev
Details of a fascinating laboratory demonstration of the sulfite-induced redox cycling of Ni(II)/Ni(III), which is initiated by shaking the solution in the presence of air, are reported. The balance between the sulfite and oxygen concentration controls the direction of the overall reaction.
Moya, Horacio D.; Neves, Eduardo Almeida; Coichev, Nina. J. Chem. Educ. 1999, 76, 930.
Oxidation / Reduction |
Metals |
Catalysis
An Analysis of College Chemistry Textbooks As Sources of Misconceptions and Errors in Electrochemistry  Michael J. Sanger and Thomas J. Greenbowe
The oxidation-reduction and electrochemistry chapters of 10 introductory college chemistry textbooks were reviewed for misleading or erroneous statements, using a list of student misconceptions. As a result of this analysis, we provide suggestions for chemistry instructors and textbook authors.
Sanger, Michael J.; Greenbowe, Thomas J. J. Chem. Educ. 1999, 76, 853.
Electrochemistry |
Oxidation / Reduction |
Learning Theories
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
Redox Buffer Strength  Robert de Levie
The proper functioning of enzymes in bodily fluids requires that the pH be maintained within rather narrow limits. The first line of defense against large pH fluctuations in such fluids is the passive control provided by the presence of pH buffers. It is equally important for many enzymes that the redox potential is kept within a narrow range. In that case, stability of the potential is most readily achieved with a redox buffer. In this communication the redox buffer strength is defined by analogy with acid-base buffer strength.
de Levie, Robert. J. Chem. Educ. 1999, 76, 574.
Aqueous Solution Chemistry |
Electrochemistry |
Oxidation / Reduction |
Acids / Bases |
Enzymes
A Simple, Safe Way To Prepare Halogens and Study Their Visual Properties at a Technical Secondary School  Domingo A. Liprandi, Orlando R. Reinheimer, José F. Paredes, and Pablo C. L'Argentière
In this paper we propose an easy-to-build apparatus to obtain chlorine, bromine, and iodine. The experiment was developed considering not only theoretical and safety conditions but simplicity and clarity as well.
Liprandi, Domingo A.; Reinheimer, Orlando R.; Paredes, José F.; L'Argentière, Pablo C. J. Chem. Educ. 1999, 76, 532.
Oxidation / Reduction |
Aqueous Solution Chemistry
Oxidation Numbers  Gion Calzaferri
Assigning oxidation numbers to organic compounds and Jrgensen's axioms.
Calzaferri, Gion. J. Chem. Educ. 1999, 76, 362.
Oxidation / Reduction |
Stoichiometry |
Molecular Properties / Structure |
Oxidation State
Is It Real Gold?  Harold H. Harris
The oxidation-reduction couples involved in the corrosion of gold alloys and the dissolution of "noble" metals are related to an inquiry to the newspaper columnist, Ann Landers. the origin of several contemporary phrases (touch stone, acid test, Hallmark) are found in the chemistry of gold.
Harris, Harold H. J. Chem. Educ. 1999, 76, 198.
Acids / Bases |
Oxidation / Reduction |
Qualitative Analysis |
Applications of Chemistry
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
Lead Globules  Francisco J. Arnáiz and Maria R. Pedrosa
Reaction of plumbate solutions with aluminum. A variety of lead films can be formed depending on the conditions. The method we describe permits obtaining a large lead globule in less than 1 minute.
Arnáiz, Francisco J.; Pedrosa, Maria R. J. Chem. Educ. 1998, 75, 1431.
Qualitative Analysis |
Oxidation / Reduction
A Simple, Transparent Fume Hood  John Fredericks
An inexpensive transparent fume hood can be constructed from a clear-plastic two-liter soft drink bottle that is cut just above the base. A length of vacuum tubing is secured to the opening of the bottle using black electrical tape. The tubing is then connected to a water aspirator.
Fredericks, John. J. Chem. Educ. 1998, 75, 1299.
Gases |
Laboratory Equipment / Apparatus |
Oxidation / Reduction |
Laboratory Management
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
Let's Dot Our I's and Cross Our T's  Leenson, Ilya A.

Leenson, Ilya A. J. Chem. Educ. 1998, 75, 1088.
Stoichiometry |
Oxidation / Reduction
Laboratory Experiments on Electrochemical Remediation of the Environment. Part 4: Color Removal of Simulated Wastewater by Electrocoagulation-Electroflotation  Jorge G. Ibanez, M. M. Singh, and Z. Szafran
Due to the large production of aqueous waste streams from textile mills and dye production plants, several processes have been under intense study. Electrochemical processes offer some distinctive advantages, including effects due to: 1) the production of electrolysis gases, and 2) the production of polyvalent cations from the oxidation of corrodible anodes (like Fe and Al).
Ibanez, Jorge G.; Singh, Mono M.; Szafran, Zvi. J. Chem. Educ. 1998, 75, 1040.
Microscale Lab |
Electrochemistry |
Water / Water Chemistry |
Oxidation / Reduction |
Microscale Lab
Balancing Organic Reactions  Woolf, A.A.
Assigning oxidation numbers to atoms that change in the redox process.
Woolf, A.A. J. Chem. Educ. 1998, 75, 938.
Stoichiometry |
Oxidation / Reduction
The Clemmensen Reduction  Palacios, Juan C.; Cintas, Pedro
Clemmensen reduction does not involve the formation of alcohols.
Palacios, Juan C.; Cintas, Pedro J. Chem. Educ. 1998, 75, 938.
Oxidation / Reduction
Letters  
Clemmensen reduction does not involve the formation of alcohols.
J. Chem. Educ. 1998, 75, 938.
Oxidation / Reduction
Slide Projector Corrosion Cell  Silvia Tejada, Estela Guevara, and Esperanza Olivares
The process of corrosion can be demonstrated in a slide projector, since the cell is in the shape of a slide, or on the stage of an overhead projector by setting up a simple galvanic cell. Corrosion occurs as the result of a galvanic cell reaction, in which the corroding metal acts as the anode. Several simple demonstrations relating to corrosion are described here.
Tejada, Silvia; Guevara, Estela; Olivares, Esperanza. J. Chem. Educ. 1998, 75, 747.
Electrochemistry |
Microscale Lab |
Oxidation / Reduction |
Reactions |
Electrolytic / Galvanic Cells / Potentials |
Applications of Chemistry
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
The Chemical Adventures of Sherlock Holmes: The Baker Street Burning  Thomas G. Waddell and Thomas R. Rybolt
A chemical mystery featuring Sherlock Holmes and Dr. Watson.
Thomas G. Waddell and Thomas R. Rybolt. J. Chem. Educ. 1998, 75, 484.
Enrichment / Review Materials |
Forensic Chemistry |
Qualitative Analysis |
Oxidation / Reduction |
Alcohols |
Dyes / Pigments
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
Kinetics of p-Nitrophenol Degradation by Pseudomonas sp.: An Experiment Illustrating Bioremediation  Michelle H. Duong, Samuel L. Penrod, and Stanley B. Grant
This paper describes a simple experiment illustrating bioremediation which is well suited for undergraduate classes in environmental chemistry, microbiology, or engineering.
Duong, Michelle H.; Penrod, Samuel L.; Grant, Stanley B. J. Chem. Educ. 1997, 74, 1451.
Biotechnology |
Kinetics |
Oxidation / Reduction |
Applications of Chemistry
Laboratory Experiments on Electrochemical Remediation of the Environment. Part 2: Microscale Indirect Electrolytic Destruction of Organic Wastes  Jorge G. Ibanez, M. M. Singh, R. M. Pike, and Z. Szafran
The objective of this experiment is to destroy, at the microscale level, a sample of surrogate organic waste by generating a powerful oxidizer at the anode of an electrochemical cell. This generated species oxidizes the waste to harmless products. The oxidizer can then be regenerated and recycled.
Ibanez, Jorge G.; Singh M. M.; Pike, R. M.; Szafran, Z. J. Chem. Educ. 1997, 74, 1449.
Electrochemistry |
Oxidation / Reduction |
Microscale Lab |
Electrolytic / Galvanic Cells / Potentials |
Applications of Chemistry
Acid Rain Demonstration: The Formation of Nitrogen Oxides as a By-Product of High-Temperature Flames in Connection with Internal Combustion Engines  Jerry A. Driscoll
This demonstration illustrates the formation of nitrogen oxides resulting from a high temperature flame.
Driscoll, Jerry A. J. Chem. Educ. 1997, 74, 1424.
Equilibrium |
Learning Theories |
Water / Water Chemistry |
Oxidation / Reduction
Using Mathematica and Maple To Obtain Chemical Equations  William R. Smith and Ronald W. Missen
A straightforward stepwise procedure is described for each of Mathematica and Maple, applicable to systems of any complexity. The procedures are illustrated by two examples, one for a "difficult" redox system, and the other for a multi-equation inorganic system.
Smith, William R.; Missen, Ronald W. J. Chem. Educ. 1997, 74, 1369.
Stoichiometry |
Learning Theories |
Electrochemistry |
Oxidation / Reduction |
Mathematics / Symbolic Mathematics
Redox Balancing without Puzzling  Marten J. ten Hoor
Once it has been established by experiment that the given reactants can indeed be converted into the given products, chemistry has done its job. Balancing the equation of the reaction is a matter of mathematics only.
ten Hoor, Marten J. J. Chem. Educ. 1997, 74, 1367.
Stoichiometry |
Oxidation / Reduction
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
Letter to the Editor about Letter to the Editor "Redox Challenges" from David M. Hart and Response from Roland Stout (J. Chem. Educ. 1996, 73, A226-7)  Andrzej Sobkowiak
Examples of a variety of redox equations.
Sobkowiak, Andrzej. J. Chem. Educ. 1997, 74, 1256.
Stoichiometry |
Reactions |
Oxidation / Reduction
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
Free Radical Reactions in Aqueous Solutions: Examples from Advanced Oxidation Processes for Wastewater from the Chemistry in Airborne Water Droplets  N. Colin Baird
A common free radical reaction in aqueous solution is electron transfer, especially to the hydroxyl radical and to ozone. Hydrogen peroxide and free radicals related to it act as weak acids, so both their neutral and deprotonated forms must be considered in reactions. Free radical reactions also play an important role in the chemistry of water droplets suspended in air in clouds and fogs.
Baird, N. Colin. J. Chem. Educ. 1997, 74, 817.
Aqueous Solution Chemistry |
Free Radicals |
Reactive Intermediates |
Atmospheric Chemistry |
Acids / Bases |
Oxidation / Reduction
Double Redox Reactions
The authors reply:  Claudio Giomini, Giancarlo Marrosu, and Mario E. Cardinali
Balancing redox equations.
Giomini, Claudio; Marrosu, Giancarlo; Cardinali, Mario E. J. Chem. Educ. 1997, 74, 744.
Oxidation / Reduction |
Stoichiometry
Double Redox Reactions  Zoltán Tóth
Balancing redox equations.
Tóth, Zoltán. J. Chem. Educ. 1997, 74, 744.
Oxidation / Reduction |
Stoichiometry
An Analysis of the Algebraic Method for Balancing Chemical Reactions  John A. Olson
A new aspect of this treatment is the mathematical formulation of a third condition involving a balance between oxidation and reduction. The treatment begins with the three general conditions that a balanced chemical reaction must satisfy. These conditions are then expressed in mathematical form that enables the stoichiometric coefficients to be determined.
Olson, John A. . J. Chem. Educ. 1997, 74, 538.
Oxidation / Reduction |
Stoichiometry
Correction  
Correction in equation 1.
J. Chem. Educ. 1997, 74, 480.
Aromatic Compounds |
Molecular Properties / Structure
Valency  Peter G. Nelson
The concept of valency is refined and developed. Three types of valency are distinguished : primary or classical, coordinate, and nonclassical. The first relates to simple compounds and to the components of multiple ones, the second to coordination compounds, and the third to transition-metal carbonyls and similar species. Each type is defined, evaluated, and applied to the prediction of the atomic composition of compounds.
Nelson, Peter G. J. Chem. Educ. 1997, 74, 465.
Valence Bond Theory |
Coordination Compounds |
Oxidation / Reduction
Microburger Biochemistry: Extraction and Spectral Characterization of Myoglyobin from Hamburger  Sheri A. Bylkas and Laura A. Andersson
The protocol combines protein extraction, oxidation and reduction, and simple spectroscopic analysis, as well as gel filtration chromatography and generation/analysis of spectral scans. Mammalian myoglobin (Mb) is easily extracted from steak, to illustrate and address why fresh meat is red and aged meat is brown; the protein has unique spectral properties that are diagnostic for characterization of sample identity.
Bylkas, Sheri A.; Andersson, Laura A. J. Chem. Educ. 1997, 74, 426.
Laboratory Equipment / Apparatus |
Proteins / Peptides |
Oxidation / Reduction |
UV-Vis Spectroscopy |
Chromatography
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
Understanding Oxidation - Reduction in Organic Chemistry  Jean-Pierre Anselme
Explanation of oxidation and reduction as applied to organic chemistry.
Anselme, Jean-Pierre. J. Chem. Educ. 1997, 74, 69.
Oxidation / Reduction
Following Microscale Organic Reactions Using FT-IR  Ems-Wilson, Janice
The progress of two microscale reactions, the reduction of cyclohexanone with sodium borohydride and the photochemical formation of benzopinacol, was monitored, qualitatively, using FT-IR.
Ems-Wilson, Janice J. Chem. Educ. 1996, 73, A171.
Microscale Lab |
Aldehydes / Ketones |
Photochemistry |
Oxidation / Reduction |
IR Spectroscopy
An Organoleptic Laboratory Experiment  John M. Risley
Compounds in ten different classes of organic molecules that are used in the fragrance and food industry are provided to students. Students whiff the vapors of each compound and describe the organoleptic properties using a set of terms utilized in the fragrance and food industry. A set of questions guides students to an understanding of the relationship between structure of molecules and smell.
Risley, John M. J. Chem. Educ. 1996, 73, 1181.
Molecular Properties / Structure |
Consumer Chemistry |
Physical Properties |
Nonmajor Courses |
Alcohols |
Aldehydes / Ketones |
Amines / Ammonium Compounds |
Carboxylic Acids |
Esters |
Ethers |
Phenols
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
A Student-Designed Potentiometric Titration: Quantitative Determination of Iron(II) by Caro's Acid Titration  Joyce R. Powell, Sheryl A. Tucker, William E. Acree Jr., Jennifer A. Sees, Lindsey H. Hall
A laboratory experiment involving the feasibility of using Caro's acid, H2SO5, as a titrant in the potentiometric determination of iron(II) is presented.
Powell, Joyce R.; Tucker, Sheryl A.; Acree Jr., William E.; Sees, Jennifer A.; Hall, Lindsey H. J. Chem. Educ. 1996, 73, 984.
Potentiometry |
Titration / Volumetric Analysis |
Oxidation / Reduction |
Quantitative Analysis
A Simple Method for Determining the Temperature Coefficient of Voltaic Cell Voltage  Alfred E. Saieed, Keith M. Davies
This article describes a relatively simple method for preparing voltaic cells, and through their temperature coefficient, ?E/?T, it explores relationships between ?G, ?H,and ?S for the cell reactions involved.
Saieed, Alfred E.; Davies, Keith M. J. Chem. Educ. 1996, 73, 959.
Electrochemistry |
Calorimetry / Thermochemistry |
Thermodynamics |
Electrolytic / Galvanic Cells / Potentials |
Laboratory Equipment / Apparatus |
Laboratory Management |
Oxidation / Reduction
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
Improved End Point Detection in the Redox Titration of Vitamin C in Green Peppers  S. Todd Deal and Sandi R. Pope
We have used E. R. Johnson's "infamous pepper lab" (titrimetric determination of vitamin C content in raw and cooked green peppers) in our introductory biochemistry course for years with varying success. Our solution to the problem discussed in this article has proven to be remarkably simple.
Deal, S. Todd; Pope, Sandi R. J. Chem. Educ. 1996, 73, 547.
Titration / Volumetric Analysis |
Oxidation / Reduction |
Food Science
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
Bacterial Toxicity Assessment Using Resazurin Reduction Kinetics: An Undergraduate Toxicity Experiment for the Chemistry-Biology Major  S. Helliwell and T. J. Harden
An undergraduate toxicity experiment is described using the redox indicator resazurin as an indicator of dehydrogenase activity. Two types of bacteria are utilized, the Gram positive Streptococcus cremoris and a Gram negative bacterium, Escherichia coli, to demonstrate the potentially different toxicological responses to the same chemical.
Helliwell, S.; Harden, T. J. J. Chem. Educ. 1996, 73, 368.
Toxicology |
Oxidation / Reduction |
Kinetics
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
The Mechanism of NaBH4 Addition to Aldehydes: A Labeling Experiment  Rolland K. Robinson and Karl De Jesus
In order to determine the sources of hydrogens in NaBH4 reductions of aldehydes, a series of reductions were carried out using differentially deuterated reagents and solvents.
Robinson, Rolland K.; De Jesus, Karl. J. Chem. Educ. 1996, 73, 264.
Aldehydes / Ketones |
Oxidation / Reduction
Fundamental Issues of Thermodynamics Illuminated by Conspicuous Inorganic Chemistry: Oxidation of [Co(H2O)6]2+ to [Co(H2O)6]3+ by Hydrogen Peroxide: A Nonspontaneous Redox Reaction Made Feasible by Thermodynamic Coupling  Susan Cline Schäffer and Claus E. Schäffer
The thermodynamic properties of hydrogen peroxide as an oxidizing agent do not allow it to oxidize [Co(OH2)6]2+ to [Co(OH2)6]3+. However, if [Co(OH2)6]3+ is formed in two steps, hydrogen peroxide is able to do it.
Schäffer, Susan Cline; Schäffer, Claus E. J. Chem. Educ. 1996, 73, 180.
Thermodynamics |
Oxidation / Reduction
A Commercial Device Involving the Breathalyzer Test Reaction  Kathleen J. Dombrink
The breathalyzer test, formerly used by law-enforcement agencies to determine the percentage blood alcohol in suspected DUI cases, is still used in the device FINAL CALL, which is available commercially. The reaction involves the reduction of chromuim(VI) in the orange dichromate ion, Cr2O72- to the green chromium(III) ion, Cr3+ by ethyl alcohol.
Dombrink, Kathleen J. J. Chem. Educ. 1996, 73, 135.
Applications of Chemistry |
Oxidation / Reduction
Phase Transfer Catalysis Applied to Oxidation  Claude Amsterdamsky
Benzhydrol and cycloheptanol have been oxidized to ketones using commercial bleach as oxidizer and tetrabutylammonium hydrogen sulfate as a phase transfer catalyst.
Amsterdamsky, Claude. J. Chem. Educ. 1996, 73, 92.
Alcohols |
Oxidation / Reduction |
Aldehydes / Ketones |
Catalysis
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
Monitoring Oxidation of Bromocresol Green with a Diode Laser: A General Chemistry IBM Personal Science Laboratory (PSL) Experiment  Zimmer, John; Reeves, James; Jones, Rebecca; Cizerle, Kirk; Ward, Dick
Procedure for monitoring the oxidation of bromocresol green using a diode laser and a radiometric probe; includes data and analysis.
Zimmer, John; Reeves, James; Jones, Rebecca; Cizerle, Kirk; Ward, Dick J. Chem. Educ. 1995, 72, A118.
Oxidation / Reduction |
Spectroscopy |
Kinetics |
Lasers
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
Baeyer-Villiger Oxidation of Indane-1-ones: Monitoring of the Reaction by VPC and IR Spectroscopy  Elie Stephan
Procedure for the Baeyer-Villiger oxidation of indane-1-ones.
Stephan, Elie. J. Chem. Educ. 1995, 72, 1142.
IR Spectroscopy |
Synthesis |
Mechanisms of Reactions |
Oxidation / Reduction |
Aldehydes / Ketones
Redox Challenges: Good Times for Puzzle Fanatics  Roland Stout
Three difficult to balance redox equations.
Stout, Roland. J. Chem. Educ. 1995, 72, 1125.
Reactions |
Stoichiometry |
Oxidation / Reduction |
Enrichment / Review Materials
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
"Double Unknown " Microscale Preparation and COSY Analysis of an Unknown Ester:
An Introductory 2D-NMR Experiment   Stephen E. Branz, Robert G. Miele, Roy K. Okuda, and Daniel A. Straus
Proton NMR activity designed to highlight the power of the technique to analyze structures and not merely confirm the identity of known substances.
Branz, Stephen E.; Miele, Robert G.; Okuda, Roy K.; Straus, Daniel A. J. Chem. Educ. 1995, 72, 659.
NMR Spectroscopy |
Stereochemistry |
Alcohols |
Carboxylic Acids |
Esters
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
Resistance Measurement as a Tool for Corrosion Studies  Singh, N. P.; Gupta, S. C.; Sood, B. R.
Procedure for determining the rate of corrosion by measuring changes in the resistance of a thin wire or strip of metal; sample data and analysis included.
Singh, N. P.; Gupta, S. C.; Sood, B. R. J. Chem. Educ. 1995, 72, 465.
Oxidation / Reduction |
Metals |
Rate Law |
Reactions |
Electrochemistry
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
Corrosion Inhibitors for Aluminum: Student Experiments  Muller, Bodo
Investigation of the effect different chelating agents have on inhibiting the corrosion of aluminum flakes in paint (metallic basecoats).
Muller, Bodo J. Chem. Educ. 1995, 72, 350.
Electrochemistry |
Metals |
Oxidation / Reduction |
Industrial Chemistry |
Coordination Compounds
Baker's Yeast Reduction of alpha-Diketones: A Four-Hour Experiment for Undergraduate Students  Besse, Pascale; Bolte, Jean; Veschambre, Henri
Procedure for quickly and efficiently reducing alpha-diketones using bakers' yeast.
Besse, Pascale; Bolte, Jean; Veschambre, Henri J. Chem. Educ. 1995, 72, 277.
Oxidation / Reduction |
Synthesis |
Aldehydes / Ketones
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
Small Scale Determination of the pKa Values for Organic Acids  Flash, Patrick
Determination and interpretation of the pKa values for a series of organic acids as a concrete example of the effect of structure on acid strength.
Flash, Patrick J. Chem. Educ. 1994, 71, A6.
Acids / Bases |
Molecular Properties / Structure |
Carboxylic Acids
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
A Simple and Safe Catalytic Hydrogenation of 4-Vinylbenzoic Acid  De, Shantanu; Gambhir, Geetu; Krishnamurty, H. G.
An alternative procedure to catalytic hydrogenation is catalytic transfer hydrogenation. In this technique, the reduction of an organic compound is achieved with the aid of a donor substance in the presence of a catalyst.
De, Shantanu; Gambhir, Geetu; Krishnamurty, H. G. J. Chem. Educ. 1994, 71, 992.
Catalysis |
Oxidation / Reduction |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes
A Fascinating Demonstration of Sulfite Induced Redox Cycling of Metal Ions Initiated by Shaking  Coichev, Nina; van Eldik, Rudi
A complete redox cycle with the net oxidation of sulfite and reduction of oxygen.
Coichev, Nina; van Eldik, Rudi J. Chem. Educ. 1994, 71, 767.
Metals |
Oxidation / Reduction
Vanadium Ions as Visible Electron Carriers in a Redox System  Bare, William D.; Resto, Wilfredo
Demonstration using a column to display the four, differently colored, oxidation states of vanadium simultaneously.
Bare, William D.; Resto, Wilfredo J. Chem. Educ. 1994, 71, 692.
Oxidation / Reduction |
Transition Elements |
Metals |
Oxidation State
Acid-Base Titration Curves in Disproportionating Redox Systems  Michalowski, Tadeusz; Lesiak, Andrzej
Titrations for disproportioning systems with two bromine compounds (Br2 and HBrO) and iodine (I2) as examples.
Michalowski, Tadeusz; Lesiak, Andrzej J. Chem. Educ. 1994, 71, 632.
Acids / Bases |
Titration / Volumetric Analysis |
Oxidation / Reduction |
Quantitative Analysis
Photometric Determination of the Rate Expression for MnO4- Mediated Organic Oxidations  Crouch, R. David
Photometric procedure for studying the kinetics of the MnO4- mediated oxidation of mandelic acid in KOH.
Crouch, R. David J. Chem. Educ. 1994, 71, 597.
Rate Law |
Oxidation / Reduction |
Photochemistry |
Kinetics
Calculation of pH and Potential E for Bromine Aqueous Solution  Michalowski, Tadeusz
The electron prebalance concept applied to the pH calculation of an aqueous solution of Br2 (bromine water) as an example.
Michalowski, Tadeusz J. Chem. Educ. 1994, 71, 560.
pH |
Aqueous Solution Chemistry |
Oxidation / Reduction
Electrophilic Aromatic Substitution, Promoted by Bentonitic Clay  Angeles, Enrique; Ramirez, Alberto; Martinez, Ignacio; Moreno, Enrique
Experiment that uses bentonitic clay as a catalyst instead of the conventional Lewis acid in the chlorination and bromination of benzene and dimerization of toluene.
Angeles, Enrique; Ramirez, Alberto; Martinez, Ignacio; Moreno, Enrique J. Chem. Educ. 1994, 71, 533.
Aromatic Compounds |
Electrophilic Substitution |
Catalysis
A Warning for Frost Diagrams Users  Martinez de llarduya, Jesus M.; Villafane, Fernando
How the use of the correct diagram prevents wrong conclusions, and how some predictions depend on the use of each type of basic-solution diagram.
Martinez de llarduya, Jesus M.; Villafane, Fernando J. Chem. Educ. 1994, 71, 480.
Oxidation / Reduction |
Aqueous Solution Chemistry
A Handy Reagent for Testing the Reducing Power of Sugars  Sandell, Arvid
Using the reduction of copper(II) as a semi-quantitative test for reducing sugars.
Sandell, Arvid J. Chem. Educ. 1994, 71, 346.
Carbohydrates |
Oxidation / Reduction |
Coordination Compounds
Pyrotechnic Reactions Without Oxygen  Wright, Stephen W.
Reaction of K3FeF6 with Al and poly(tetrafluoroethylene) with Mg.
Wright, Stephen W. J. Chem. Educ. 1994, 71, 251.
Oxidation / Reduction |
Reactions
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
Classroom Demonstration of Chromium(VI)/Chromium(III) in the Breathalyzer Test Reaction  Jones, Rebecca B.; Dreisbach, Joseph H.
Demonstrating the breathalyzer reaction.
Jones, Rebecca B.; Dreisbach, Joseph H. J. Chem. Educ. 1994, 71, 158.
Nonmajor Courses |
Oxidation State |
Oxidation / Reduction
Conversion Reactions in Inorganic Chemistry  Habashi, Fathi.
Liberation of metals from their sulfides through reaction with oxygen.
Habashi, Fathi. J. Chem. Educ. 1994, 71, 130.
Reactions |
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
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
A convenient method of esterification of fatty acids: An undergraduate organic laboratory experiment  Di Raddo, Pasquale
A convenient method of esterification of fatty acids for undergraduate organic chemistry lab.
Di Raddo, Pasquale J. Chem. Educ. 1993, 70, 1034.
Carboxylic Acids |
Esters |
Gas Chromatography |
NMR Spectroscopy |
Fatty Acids
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
Climbing a potential ladder to understanding concepts in electrochemistry  Runo, James R.; Peters, Dennis G.
An introduction of a unified approach that makes use of a potential latter in order to assist students in overcoming and clarifying the problems encountered when learning electrochemistry.
Runo, James R.; Peters, Dennis G. J. Chem. Educ. 1993, 70, 708.
Electrochemistry |
Oxidation / Reduction
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
Is This Reaction a Substitution, Oxidation-Reduction, or Transfer?  Imyanitov, Naum S.
Author argues that separation of chemical reaction types based on convention do not always follow objective and consistent rules. This leads to confusion among students and artificial borders within the various sub-disciplines in chemistry.
Imyanitov, Naum S. J. Chem. Educ. 1993, 70, 14.
Reactions |
Oxidation / Reduction
Quantitative analysis by FTIR: Thin films of copolymers of ethylene and vinyl acetate.  Mathias, Lon J.; Hankins, Marie G.; Bertolucci, Craig M.; Grubb, Tina L.; Muthiah, Jeno.
Quantitation of coploymers of ethylene and vinyl acetate using FTIR.
Mathias, Lon J.; Hankins, Marie G.; Bertolucci, Craig M.; Grubb, Tina L.; Muthiah, Jeno. J. Chem. Educ. 1992, 69, A217.
IR Spectroscopy |
Fourier Transform Techniques |
Quantitative Analysis |
Alkenes |
Carboxylic Acids
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
Synthesis of a heteropolytungstate and its use in outer-sphere redox kinetics  Walmsley, Frank
An inorganic chemistry experiment has been developed combining two topics usually included in inorganic chemistry: heteropoly ions and mechanisms of oxidation-reduction reactions of transition metal ions.
Walmsley, Frank J. Chem. Educ. 1992, 69, 936.
Oxidation / Reduction |
Kinetics |
Synthesis |
Coordination Compounds
A more environmentally acceptable determination of iron in an ore  Byars, Jeffrey; McCreary, Terry W.
The method for titrimetric determination of iron in which zinc is used as the reactant in situ rather that as a Jones reductor, has several advantages over conventional determination of iron.
Byars, Jeffrey; McCreary, Terry W. J. Chem. Educ. 1992, 69, 935.
Oxidation / Reduction |
Quantitative Analysis
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
Frost diagrams: A tool for predicting redox reactions.  Birk, James P.; Hocker, Heidi.
A HyperCard stack that provides an easily used format for making redox reaction predictions for one or two elements by comparing slopes of the lines connecting two oxidation states.
Birk, James P.; Hocker, Heidi. J. Chem. Educ. 1992, 69, 509.
Oxidation / Reduction |
Oxidation State
The chemical logic of life and the earth's biosphere: A simple, one-diagram outline  Ochiai, Ei-Ichiro
This diagram is intended to give a compact overall picture of the chemical logic of life and of the earth's biosphere.
Ochiai, Ei-Ichiro J. Chem. Educ. 1992, 69, 356.
Acids / Bases |
Oxidation / Reduction
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
Algorithm for plotting titration curves (author response).  Rodrigues de Moura, Daniel.
Our model, contrary to Jackman's statement, can be applied to redox systems that are pH-dependant.
Rodrigues de Moura, Daniel. J. Chem. Educ. 1992, 69, 257.
pH |
Oxidation / Reduction |
Titration / Volumetric Analysis
Algorithm for plotting titration curves.  Jackman, Donald C.
de Moura's algorithm for plotting redox titration curves seems to be good for systems that are not dependent on pH or product concentration, but is not applicable to those situations that is student is more likely to encounter.
Jackman, Donald C. J. Chem. Educ. 1992, 69, 257.
Oxidation / Reduction |
Titration / Volumetric Analysis |
pH
Electrochemistry of proton-coupled redox reactions: Role of the electrode surface.  Thorp, H. Holden.
In this article examples of the effects of the surface properties on a working electrode are explored.
Thorp, H. Holden. J. Chem. Educ. 1992, 69, 250.
Electrochemistry |
Oxidation / Reduction |
pH
When the barking dog bites the hand that feeds it: A safety caution.  Worley, John D.
Plastic gloves should not be used at any point during the barking dog demonstration.
Worley, John D. J. Chem. Educ. 1992, 69, 241.
Oxidation / Reduction
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
Redox equations with an infinite number of balanced solutions  Riley, Jeremy; Richmond, Thomas G. R.
Some mathematically minded students prefer to use various algebraic methods to solve oxidation/reduction problems instead of the half-reaction method. This can lead to redox reactions in which the reactants actually yield a family of balanced equations rather than a unique solution.
Riley, Jeremy; Richmond, Thomas G. R. J. Chem. Educ. 1992, 69, 114.
Oxidation / Reduction
The bird-scarer (combustion) demo   Battino, Rubin; Arehart, James D.; Foot, Neville W.; Stott, James B.
This is a demonstration version of a device used to scare birds with loud noises occurring at regular intervals.
Battino, Rubin; Arehart, James D.; Foot, Neville W.; Stott, James B. J. Chem. Educ. 1992, 69, 64.
Reactions |
Oxidation / Reduction
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 mild and convenient oxidation of alcohols: Benzoin to benzil and borneol to camphor  Straub, Thomas S.
A traditional organic chemistry laboratory poses threat to both student safety and the environment: this author provides an alternative procedure.
Straub, Thomas S. J. Chem. Educ. 1991, 68, 1048.
Heterocycles |
Oxidation / Reduction |
Alcohols
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
Hydroboration-oxidation of (1R)-(+)-alpha-pinene to isopinocampheol: A microscale experiment that displays regio- and stereochemistry using NMR spectroscopy and molecular mechanics calculations  Blankespoor, Ronald L.; Piers, Kenneth
The hydroboration-oxidation of alkenes is an important route to alcohols and therefore receives considerable treatment in standard organic textbooks. These authors present their findings of an example (an alkene that undergoes the hydroboration oxidation process) that displays both regiochemistry and stereochemistry.
Blankespoor, Ronald L.; Piers, Kenneth J. Chem. Educ. 1991, 68, 693.
Alkenes |
Oxidation / Reduction |
NMR Spectroscopy |
Alcohols
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
Recovery of silver from and some uses for waste silver chloride  Murphy, J. A.; Ackerman, A. H.; Heeren, J. K.
Procedures for conversion to silver nitrate, using waste AgCl as an oxidizing agent, and electrodepositon experiments.
Murphy, J. A.; Ackerman, A. H.; Heeren, J. K. J. Chem. Educ. 1991, 68, 602.
Reactions |
Oxidation / Reduction |
Electrochemistry
An internal comparison of the intermolecular forces of common organic functional groups: A thin-layer chromatography experiment  Beauvais, Robert; Holman, R. W.
Due to the latest trends in organic chemistry textbook content sequences, it has become desirable to develop an experiment that is rapid, simple, and general, that would compare and contrast the various functional group classes of organic molecules in terms of their relative polarities, dipole moments, and intermolecular forces of attraction.
Beauvais, Robert; Holman, R. W. J. Chem. Educ. 1991, 68, 428.
Alkanes / Cycloalkanes |
Alkenes |
Alcohols |
Carboxylic Acids |
Aldehydes / Ketones |
Esters |
Qualitative Analysis |
Thin Layer Chromatography |
Noncovalent Interactions |
Molecular Properties / Structure
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
Experimental demonstration of corrosion phenomena: Part II. corrosion phenomena of steel in aqueous media  Arce, Elsa M.; Ramirez, Roman; Cortes, Felipe; Ibanez, Jorge G.
A description of an experiment that uses a sample of carbon steel to show the effect of aggressive ions and inhibiting ions upon it corrosion behavior.
Arce, Elsa M.; Ramirez, Roman; Cortes, Felipe; Ibanez, Jorge G. J. Chem. Educ. 1991, 68, 351.
Metals |
Aqueous Solution Chemistry |
Oxidation / Reduction
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
Redox demonstrations and descriptive chemistry: Part 3. Copper (I)-copper(II) equilibria   Ophardt, Charles E.
The unusual redox properties of copper (I) and copper (II) ions explained and illustrated.
Ophardt, Charles E. J. Chem. Educ. 1991, 68, 248.
Descriptive Chemistry |
Oxidation State |
Oxidation / Reduction
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
Superoxide dismutase and the Briggs-Rauscher reaction  Franz, David A.
Oxygen-derived species provide chemistry teachers with excellent examples for discussion of molecular-orbital theory, bond order and reactivity, redox potentials, radical reactivity, disproportionation, and enzyme activity.
Franz, David A. J. Chem. Educ. 1991, 68, 57.
Enzymes |
Biophysical Chemistry |
MO Theory |
Oxidation / Reduction |
Covalent Bonding
Design of corrosion inhibitors: Use of the hard and soft acid-base (HSAB) theory  Walters, Frederick H.
Using hard and soft acid-base theory to understand corrosion.
Walters, Frederick H. J. Chem. Educ. 1991, 68, 29.
Acids / Bases |
Oxidation / Reduction |
Metals |
Electrochemistry |
Periodicity / Periodic Table
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 iodohexane via hydroboration-iodination: A microscale organic laboratory experiment involving air-sensitive compounds  Gooch, E. Eugene
Use of ICl and organoborane intermediates to prepare iodohexane that parallels similar methods that introduce iodine radionuclides into fatty acids for use as heart imaging agents via positron emission tomography.
Gooch, E. Eugene J. Chem. Educ. 1990, 67, A232.
Synthesis |
Microscale Lab |
Carboxylic Acids |
Medicinal Chemistry
Versed and reversed: A meter for mobile equilibrium  Vemulapalli, G. K.
The principle of mobile equilibrium in verse.
Vemulapalli, G. K. J. Chem. Educ. 1990, 67, 1003.
Equilibrium |
Oxidation / Reduction
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
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
Redox ion exchanger fuel cell  Rawat, Jagdish Prasad; Ansari, Abdul Aziz
Study of the usefulness of a redox reaction between Fe 3+ and Zn on an ion-exchanger bed for the preparation of a fuel cell.
Rawat, Jagdish Prasad; Ansari, Abdul Aziz J. Chem. Educ. 1990, 67, 808.
Oxidation / Reduction |
Ion Exchange |
Electrochemistry |
Electrolytic / Galvanic Cells / Potentials
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
Calculation of equilibrium constant in esterification reactions  Sarlo, Edward; Svoronos, Paris; Kulas, Patricia
Procedure for measuring the equilibrium constant in esterification reactions.
Sarlo, Edward; Svoronos, Paris; Kulas, Patricia J. Chem. Educ. 1990, 67, 796.
Esters |
Alcohols |
Carboxylic Acids |
Equilibrium
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 bromate clock reaction: The formation of purple tris(diphosphato)manganate(III)  Rich, Ronald L.; Noyes, Richard M.
Bromate is used to oxidize nearly colorless Mn(II) to a deep purple complex of Mn(III).
Rich, Ronald L.; Noyes, Richard M. J. Chem. Educ. 1990, 67, 606.
Reactions |
Oxidation / Reduction |
Kinetics
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
A syllabus for a two-semester chemistry course for health professions (author response)  Daly, John M.; Sarquis, Jerry L.
While oxidation-reduction is not given a major heading, it is included in several different places in the syllabus.
Daly, John M.; Sarquis, Jerry L. J. Chem. Educ. 1990, 67, 540.
Nonmajor Courses |
Oxidation / Reduction
A syllabus for a two-semester chemistry course for health professions   Bosch, E.; Prat, M. D.
The author believes that the main criticism of the proposed program is the lack of a redox section.
Bosch, E.; Prat, M. D. J. Chem. Educ. 1990, 67, 539.
Oxidation / Reduction |
Nonmajor Courses
Hydroboration for the large organic laboratory  Pickering, Miles
This paper reports an experiment in hydroboration without large hood space requirements, without special glassware requirements, and without inert atmospheric precautions.
Pickering, Miles J. Chem. Educ. 1990, 67, 436.
Oxidation / Reduction |
Alkenes |
Alcohols |
Qualitative Analysis
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
The palladium-catalyzed oxidation of 2-vinylnaphthalene: A microscale organic synthesis experiment   Byers, Jeffrey H.; Ashfaq, Aalla; Morse, Wendy R.
The Wacker oxidation experiment as described is cost-efficient due to the small scale employed, and is a valuable addition to the undergraduate organic curriculum.
Byers, Jeffrey H.; Ashfaq, Aalla; Morse, Wendy R. J. Chem. Educ. 1990, 67, 340.
Microscale Lab |
Synthesis |
Alkynes |
Aldehydes / Ketones |
Oxidation / Reduction
The subjection of glutaraldehyde to the Tollens test  Hill, William D., Jr.
Redox equations have been established for the Tollens test with respect to compounds containing two aldehyde groups such as glutaraldehyde.
Hill, William D., Jr. J. Chem. Educ. 1990, 67, 329.
Aldehydes / Ketones |
Oxidation / Reduction
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
Oxidation of cysteine to cystine using hydrogen peroxide  Hill, John W.; Coy, Robert B.; Lewandowski, Peter E.
This synthesis has several advantages as an undergraduate laboratory exercise.
Hill, John W.; Coy, Robert B.; Lewandowski, Peter E. J. Chem. Educ. 1990, 67, 172.
Amino Acids |
Oxidation / Reduction
In praise of thiosulfate  Tykodi, R. J.
The reactions of thiosulfate make impressive lecture demonstrations and worthwhile laboratory experiments.
Tykodi, R. J. J. Chem. Educ. 1990, 67, 146.
Acids / Bases |
Precipitation / Solubility |
Oxidation / Reduction |
Aqueous Solution Chemistry |
Stoichiometry
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
Chemical Reactions, Reactions in Aqueous Solution, and Oxidation Reduction Reactions, Review II (Weyh, J. A.; Crook, J. R.; Hauge, L. N.)  Coleman, William F.
Programs intended to provide students with drill and practice in equation writing (including formula writing), equation balancing, and reaction predicting.
Coleman, William F. J. Chem. Educ. 1989, 66, A172.
Reactions |
Aqueous Solution Chemistry |
Oxidation / Reduction |
Enrichment / Review Materials
Chemical Reactions, Reactions in Aqueous Solution, and Oxidation Reduction Reactions, Review I (Weyh, J. A.; Crook, J. R.; Hauge, L. N.)  Balahura, Robert J.
Programs intended to provide students with drill and practice in equation writing (including formula writing), equation balancing, and reaction predicting.
Balahura, Robert J. J. Chem. Educ. 1989, 66, A172.
Reactions |
Aqueous Solution Chemistry |
Oxidation / Reduction |
Enrichment / Review Materials
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
Illustrating the inductive effect on acid strength of carboxylic acids  Kolb, Kenneth E.; Kolb, Doris
The effect of various substituents on acid strength can be easily demonstrated using aqueous solutions of various carboxylic acids containing a suitable indicator.
Kolb, Kenneth E.; Kolb, Doris J. Chem. Educ. 1989, 66, 1034.
Acids / Bases |
Carboxylic Acids
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
Oxidation of cyclohexanol - An amoebalike reaction  Kolb, Kenneth E.; Kolb, Doris
Cyclohexanol is oxidized to cyclohexanone.
Kolb, Kenneth E.; Kolb, Doris J. Chem. Educ. 1989, 66, 955.
Oxidation / Reduction |
Alcohols |
Reactions
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
The corrosion inhibition of a metal: Student corrosion experiment III  Onuchukwu, A. I.
Presents the principles and an investigation of the corrosion inhibition of a metal.
Onuchukwu, A. I. J. Chem. Educ. 1989, 66, 681.
Oxidation / Reduction |
Metals
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
A laboratory procedure for the reduction of chromium(VI) to chromium(III)  Lunn, George; Sansone, Eric B.
The authors describe work aimed at reducing the hazards associated with the disposal of Cr(VI) compounds.
Lunn, George; Sansone, Eric B. J. Chem. Educ. 1989, 66, 443.
Oxidation / Reduction |
Laboratory Management
Interaction between scientific research and chemical education: Development of a corrosion experiment  Higa, Claudio O.; da Costa, Sylvia L. F. A.; Agostinho, Silvia M. L.
This work presents the results of an investigation of the effect of the corrosion inhibitor benzotriazole on copper corrosion through weight-loss experiments.
Higa, Claudio O.; da Costa, Sylvia L. F. A.; Agostinho, Silvia M. L. J. Chem. Educ. 1989, 66, 441.
Oxidation / Reduction
Reduction of Indigo: Sodium Hydrosulfite as a Reducing Agent  Williamson, Kenneth L.
The confusion between sodium hydrogen sulfite, sodium bisulfite, and sodium hydrosulfite is a common one.
Williamson, Kenneth L. J. Chem. Educ. 1989, 66, 359.
Oxidation / Reduction |
Laboratory Management
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
Chemically induced pulsations of interfaces: The mercury beating heart  Avnir, David
When an iron needle just touches a mercury drop submerged in a pool of an acidic solution of an oxidizer, it pulsates rapidly in a mode that resembles a beating heart.
Avnir, David J. Chem. Educ. 1989, 66, 211.
Oxidation / Reduction
Ion association, solubilities, and reduction potentials in aqueous solution  Russo, Steven O.; Hanania, George I. H.
It is the author's belief that a combined approach to ionic activity and ion association presents to the student a realistic and more quantitative view of electrolyte solutions than is otherwise possible.
Russo, Steven O.; Hanania, George I. H. J. Chem. Educ. 1989, 66, 148.
Aqueous Solution Chemistry |
Electrolytic / Galvanic Cells / Potentials |
Ionic Bonding |
Oxidation / Reduction
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
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
Oxidation numbers and their limitations  Woolf, A. A.
An in-depth look at oxidation numbers of various elements in a number of different compounds.
Woolf, A. A. J. Chem. Educ. 1988, 65, 45.
Organometallics |
Oxidation State |
Oxidation / Reduction
Stable organic oxidants: Paradox or possibility  Bretherick, Leslie
Thermal instability of organic oxidant salts and the possibility of producing safer analogs.
Bretherick, Leslie J. Chem. Educ. 1987, 64, A43.
Oxidation / Reduction
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
The kinetic rate law for autocatalytic reactions  Mata-Perez, Fernando; Perez-Benito, Joaquin F.
A method for obtaining accurate rate constants for autocatalytic reactions.
Mata-Perez, Fernando; Perez-Benito, Joaquin F. J. Chem. Educ. 1987, 64, 925.
Kinetics |
Rate Law |
Catalysis |
Oxidation / Reduction
Preparation of lead compounds: An exercise in applied chemistry  Laing, Michael; Williams-Wynn, David; Suhramoney, Saroj
Uses and synthesis of Pb(NO3)2, PbO2, PbCrO4, PbS, PbO, lead carbonate, lead acetate, and lead metal itself.
Laing, Michael; Williams-Wynn, David; Suhramoney, Saroj J. Chem. Educ. 1987, 64, 811.
Synthesis |
Metals |
Oxidation / Reduction |
Oxidation State |
Reactions |
Descriptive Chemistry
Redox demonstrations and descriptive chemistry: Part 2. Halogens  Ophardt, Charles E.
Oxidation states of bromine and iodine.
Ophardt, Charles E. J. Chem. Educ. 1987, 64, 807.
Oxidation / Reduction |
Descriptive Chemistry |
Oxidation State
The stepwise reduction of permanganate in alkaline conditions: A lecture demonstration  Ruoff, Peter
Demonstrates the +VII, +VI, +V, and +IV oxidation states of manganese and their characteristic colors.
Ruoff, Peter J. Chem. Educ. 1987, 64, 624.
Oxidation / Reduction |
Oxidation State
Recent advances in the concept of hard and soft acids and bases  Pearson, Ralph G.
The hard / soft acids / bases principle has been justifiably criticized because of the lack of a precise definition of hardness and the inability to quantify this property; recent developments have overcome these objections, however.
Pearson, Ralph G. J. Chem. Educ. 1987, 64, 561.
Acids / Bases |
Coordination Compounds |
MO Theory |
Oxidation / Reduction
Passivation of copper in acid medium  Alonso, C.; Ocon, P.
Determining and explaining the polarization curve of copper in a 70% solution of phosphoric acid.
Alonso, C.; Ocon, P. J. Chem. Educ. 1987, 64, 459.
Acids / Bases |
Oxidation / Reduction |
Electrochemistry
The induction by iron(II) of the oxidation of iodide by dichromate  Jolly, William L.
A surprising mechanism for an inorganic reaction in aqueous solution.
Jolly, William L. J. Chem. Educ. 1987, 64, 444.
Oxidation / Reduction |
Aqueous Solution Chemistry |
Reactions |
Mechanisms of Reactions |
Catalysis
On a common graphical flaw in the carboxylic acid/alcohol relative acidity argument  McClard, Ronald W.
Why are carboxylic acids so much more acidic than aliphatic alcohols?
McClard, Ronald W. J. Chem. Educ. 1987, 64, 416.
Carboxylic Acids |
Alcohols |
Acids / Bases
Thioxanthone sulfone radical anion: A relatively stable ketyl  Castrillon, Jose
Thioxanthone sulfone is induced to produce a deep blue color upon standing that disappears on shaking.
Castrillon, Jose J. Chem. Educ. 1987, 64, 352.
Free Radicals |
Oxidation / Reduction
Introduction to overhead projector demonstrations  Kolb, Doris
General suggestions for using the overhead projector and 21 demonstrations. [Debut]
Kolb, Doris J. Chem. Educ. 1987, 64, 348.
Rate Law |
Reactions |
Catalysis |
Equilibrium |
Transition Elements |
Metals |
Oxidation / Reduction |
Acids / Bases
A cyclic voltammetry experiment using a mercury electrode  Brillas, Enrique; Garrido, Jose A.; Rodriquez, Rosa M.; Domenech, Javier
An easy and inexpensive experiment designed to illustrate cyclic voltammetry in the study of a simple reversible reaction.
Brillas, Enrique; Garrido, Jose A.; Rodriquez, Rosa M.; Domenech, Javier J. Chem. Educ. 1987, 64, 189.
Electrochemistry |
Oxidation / Reduction
Kinetics of oxidation of bromcresol green  Pickering, Miles; Heiler, David
Study of the bleaching of bromcresol green by hypochlorite.
Pickering, Miles; Heiler, David J. Chem. Educ. 1987, 64, 81.
Kinetics |
Oxidation / Reduction |
Dyes / Pigments |
Acids / Bases |
Mechanisms of Reactions
Comparison of chemical oxidation of alkanes, alkenes, and alcohols on the overhead projector  Kolb, Kenneth E.
This overhead projector demonstration utilizes two classical oxidants, permanganates and dichromate, to distinguish between alkanes, alkenes, and primary, secondary, and tertiary alcohols.
Kolb, Kenneth E. J. Chem. Educ. 1986, 63, 977.
Alcohols |
Alkanes / Cycloalkanes |
Alkenes |
Oxidation / Reduction |
Qualitative Analysis
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
Electrochemical cell conventions in general chemistry   West, Allen C.
This author argues that conventions make electrochemistry harder for students to learn and much harder to remember. For this reason, instructors must connect our presentation of galvanic cells more closely with the physical world of galvanic cells than "conventional" electrochemistry does.
West, Allen C. J. Chem. Educ. 1986, 63, 609.
Electrochemistry |
Electrolytic / Galvanic Cells / Potentials |
Oxidation / Reduction
Determination of reaction stoichiometries by flow injection analysis: A laboratory exercise  Rios, Angel; Castro, Dolores Luqne de; Valcarcel, Miguel
These authors took advantage of the features of Flow Injection Analysis and developed an easy and simple photometric method intended for calculation of complex-formation and redox reaction stoichiometries.
Rios, Angel; Castro, Dolores Luqne de; Valcarcel, Miguel J. Chem. Educ. 1986, 63, 552.
Oxidation / Reduction |
Instrumental Methods |
Photochemistry |
Stoichiometry |
Kinetics |
Rate Law |
Coordination Compounds
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
Selective oxidation in the presence of a heterocycle  Bowles, K. Dean; Quincy, David A.; McKenna, John I.; Natale, N. R.
The process of weighing the advantages and disadvantages of various oxidation methods are presented in this paper.
Bowles, K. Dean; Quincy, David A.; McKenna, John I.; Natale, N. R. J. Chem. Educ. 1986, 63, 358.
Alcohols |
Aldehydes / Ketones |
Heterocycles |
Oxidation / Reduction |
Carboxylic Acids
Number of oxidations relative to methylene: A convenient method of recognizing and quantifying organic oxidation-reduction  Kjonaas, Richard A.
This paper describes the use of a type of molecular oxidation number called "Number of oxidations relative to methylene".
Kjonaas, Richard A. J. Chem. Educ. 1986, 63, 311.
Oxidation / Reduction |
Qualitative Analysis |
Alkenes
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
Molten salt techniques for students: Attacking hematite with pyrosulfate  Atkinson, George F.
This experiment teaches students molten salt techniques.
Atkinson, George F. J. Chem. Educ. 1986, 63, 88.
Oxidation / Reduction |
Titration / Volumetric Analysis
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
New stoichiometry for copper dissolution in nitric acid  El-Cheikh, F. M.; Khalil, S. A.; El-Manguch, M. A.; Omar, Hadi A.
NO2 does not appear to be a primary product in the oxidation of copper metal by nitric acid.
El-Cheikh, F. M.; Khalil, S. A.; El-Manguch, M. A.; Omar, Hadi A. J. Chem. Educ. 1985, 62, 761.
Reactions |
Stoichiometry |
Oxidation / Reduction
The design of laboratory experiments in the 1980's: A case study on the oxidation of alcohols with household bleach  Mohrig, Jerry R.; Nienhuis, David M.; Linck, Catherine F.; Van Zoeren, Carol; Fox, Brian G.; Mahaffy, Peter G.
Improved safety by replacing chromium(VI) with bleach in the oxidation of an alcohol.
Mohrig, Jerry R.; Nienhuis, David M.; Linck, Catherine F.; Van Zoeren, Carol; Fox, Brian G.; Mahaffy, Peter G. J. Chem. Educ. 1985, 62, 519.
Oxidation / Reduction |
Alcohols |
Mechanisms of Reactions
Estimating the one electron reduction potential for vanadium (V) by chemical techniques: An experiment for general chemistry  Wentworth, R. A. D.
Procedure requires no electrochemical equipment because the method depends solely upon observations of the spontaneity of the reactions of V(V) with a series of potential reducing agents and V(IV) with a series of potential oxidizing agents.
Wentworth, R. A. D. J. Chem. Educ. 1985, 62, 440.
Oxidation State |
Oxidation / Reduction |
Electrochemistry
Buffer capacity of various acetic acid-sodium acetate systems: A lecture experiment  Donahue, Craig J.; Panek, Mary G.
Uses indicators to illustrate the response of two buffers with the same initial pH value but differing buffer capacities.
Donahue, Craig J.; Panek, Mary G. J. Chem. Educ. 1985, 62, 337.
Acids / Bases |
pH |
Dyes / Pigments |
Aqueous Solution Chemistry |
Carboxylic Acids
Drug stabilization against oxidative degradation  Akers, Michael J.
Describes the process of oxidation and ways in which pharmaceutical preparations can be protected from oxidative degredation.
Akers, Michael J. J. Chem. Educ. 1985, 62, 325.
Drugs / Pharmaceuticals |
Oxidation / Reduction |
Medicinal Chemistry |
Nonmajor Courses
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
Methemoglobinemia: An illness caused by the ferric state  Senozan, N. M.
Hemoglobin's ability to carry oxygen depends on the iron being in the +2 state; methemoglobinemia involves the oxidation of hemoglobin iron to the +3 state.
Senozan, N. M. J. Chem. Educ. 1985, 62, 181.
Proteins / Peptides |
Enzymes |
Medicinal Chemistry |
Oxidation / Reduction |
Oxidation State
Oxidation of alcohols using calcium hypochlorite and solid/liquid phase-transfer catalysis  Hill, John W.; Jenson, Jeffrey A.; Henke, Charles F.; Yaritz, Joseph G.; Pedersen, Richard L.
Includes synthesis of an aldehyde from a primary alcohol as well as several ketones from secondary alcohols.
Hill, John W.; Jenson, Jeffrey A.; Henke, Charles F.; Yaritz, Joseph G.; Pedersen, Richard L. J. Chem. Educ. 1984, 61, 1118.
Alcohols |
Oxidation / Reduction |
Catalysis |
Aldehydes / Ketones |
Synthesis
Preparation and analysis of potassium tris(oxalato)ferrate(III)trihydrate: A general chemistry experiment  Olmsted, John, III
The analysis of this compound combines gravimetric and titrimeric methods and includes a unique and colorful photoredox reaction.
Olmsted, John, III J. Chem. Educ. 1984, 61, 1098.
Synthesis |
Photochemistry |
Oxidation / Reduction |
Gravimetric Analysis |
Titration / Volumetric Analysis
The Fe(II)-Cr(VI) reaction without using mercury  Klett, Lee D.; Black, Arthur H.; Parker, Gordon A.
Procedure that employs titanium rather than mercury in the oxidation-reduction titration of iron(II) with chromium(VI).
Klett, Lee D.; Black, Arthur H.; Parker, Gordon A. J. Chem. Educ. 1984, 61, 1020.
Reactions |
Oxidation State |
Oxidation / Reduction |
Metals
How to get the most from the dichromate volcano demonstration: Aluminothermy  Trogler, William C.
Reducing the green ash produced by the dichromate volcano (Cr2O3) with aluminum in a thermite-like display.
Trogler, William C. J. Chem. Educ. 1984, 61, 908.
Reactions |
Oxidation / Reduction
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
The extraction of gold and its simulation with copper  Bradley, J. D.; Brand, M.; Louli, J. A. M.
The simulation of the extraction of gold by the use of its analog, copper, makes it possible to capitalize on the glamor of gold without sacrificing any chemical principles.
Bradley, J. D.; Brand, M.; Louli, J. A. M. J. Chem. Educ. 1984, 61, 634.
Separation Science |
Metallurgy |
Industrial Chemistry |
Applications of Chemistry |
Oxidation / Reduction |
Metals
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
A new method for the preparation of derivatives of carboxylic acids  Brindle, Ian D.; Chassie, Susan
Preparation technique using potassium fluoride. From the "State-of-the-Art Symposium for Chemical Educators: Chemistry of the Food Cycle".
Brindle, Ian D.; Chassie, Susan J. Chem. Educ. 1984, 61, 347.
Synthesis |
Carboxylic Acids
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
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
Electrochemistry of the Hall-Heroult process for aluminum smelting  Haupin, W. E.
A discussion of aluminum holds great pedagogical value on many fronts: discussion of the Bayer process, electrolysis of alumina, electrolyte chemistry, dissolution of alumina, electrode reactions, current efficiency, cell voltage, and other topics for advanced graduate study. From State-of-the-Art Symposium: Electrochemistry, ACS meeting, Kansas City, 1982.
Haupin, W. E. J. Chem. Educ. 1983, 60, 279.
Electrochemistry |
Electrolytic / Galvanic Cells / Potentials |
Applications of Chemistry |
Industrial Chemistry |
Oxidation / Reduction
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
3-Ketoesters by malonic synthesis  Pollet, Patrick L.
This essay reviews a synthesis strategy.
Pollet, Patrick L. J. Chem. Educ. 1983, 60, 244.
Synthesis |
Carboxylic Acids |
Aldehydes / Ketones |
Alkylation
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
On the Nernst equations of mercury-mercuric oxide half-cell electrodes  Kam, T. T.
The purpose of this paper is to present the derivation of the Nernst equation and the standard potential of the mercury-mercuric oxide electrodes, together with the comparison between the experimentally measured electrode potentials and the theoretical values obtained by the Nernst equations.
Kam, T. T. J. Chem. Educ. 1983, 60, 133.
Electrochemistry |
Electrolytic / Galvanic Cells / Potentials |
Oxidation / Reduction
Oxidation by Mn207: An impressive demonstration of the powerful oxidizing property of dimanganeseheptoxide  Koch, Klaus R.
Demonstrates the formation of Mn2O7 and its powerful oxidation of simple alcohols.
Koch, Klaus R. J. Chem. Educ. 1982, 59, 973.
Oxidation / Reduction |
Oxidation State
Reduction potentials and hydrogen overvoltage: An overhead projector demonstration  Ramette, Richard W.
Relates the scale of standard reduction potentials to the observed behavior of metals in their reactions with hydrogen ion to produce hydrogen gas.
Ramette, Richard W. J. Chem. Educ. 1982, 59, 866.
Electrochemistry |
Metals |
Oxidation / Reduction
How students reconcile discordant data: A study of lab report discussions  Pickering, Miles; Monts, David L.
A study conducted to determine how students deal with experimental results that seem to violate chemical laws.
Pickering, Miles; Monts, David L. J. Chem. Educ. 1982, 59, 794.
Chemometrics |
Oxidation / Reduction |
Stoichiometry
Spontaneous combustion of familiar substances in chlorine  Briggs, Thomas S.
Reacting chlorine generated from liquid bleach with red phosphorus (from a match book) and iron from steel wool.
Briggs, Thomas S. J. Chem. Educ. 1982, 59, 788.
Reactions |
Oxidation / Reduction
Some tungsten oxidation-reduction chemistry: A paint pot titration  Pickering, Miles; Monts, David L.
Mild reducing agents reduce WO3 to a nonstoichiometric blue oxide, "mineral blue," whose approximate formula is WO2.2-3.0.
Pickering, Miles; Monts, David L. J. Chem. Educ. 1982, 59, 693.
Titration / Volumetric Analysis |
Oxidation / Reduction |
Stoichiometry
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
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
Demonstration of electrochemical cell properties by a simple, colorful oxidation-reduction experiment  Hendricks, Lloyd J.; Williams, John T.
The color of a solution close to an electrode is changed from that of the bulk solution to either of two contrasting colors, depending on whether the electrode reaction is a reduction or oxidation.
Hendricks, Lloyd J.; Williams, John T. J. Chem. Educ. 1982, 59, 586.
Electrochemistry |
Oxidation / Reduction
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
The direct electrochemical synthesis of [(C6H5)3Ph]2[CoCl4]: An example of the use of anodic oxidation in the preparation of metal ion complexes  Oldham, Colin; Tuck, Dennis G.
Uses a 6 V lantern battery and a simple voltmeter / ammeter.
Oldham, Colin; Tuck, Dennis G. J. Chem. Educ. 1982, 59, 420.
Electrochemistry |
Synthesis |
Coordination Compounds |
Oxidation / Reduction
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
Conjugate and nonconjugate reduction with LiAlH4 and NaBH4  Meyer, G. Richard
Most organic textbooks present a limited consideration of the action of lithium aluminum hydride and sodium borohydride. This paper explores the topic in greater depth.
Meyer, G. Richard J. Chem. Educ. 1981, 58, 628.
Oxidation / Reduction |
Reactions
Structure-resonance theory for pericyclic transition states  Herndon, William C.
The purpose of this article is to show that structure-resonance theory can be used to understand the effects of structure or substituents on the rates of thermal pericyclic reactions.
Herndon, William C. J. Chem. Educ. 1981, 58, 371.
Aromatic Compounds |
Resonance Theory |
Molecular Properties / Structure
Benzene, a familiar hazard?  Smith, Roger M.
Reviews the hazards of benzene.
Smith, Roger M. J. Chem. Educ. 1980, 57, A85.
Aromatic Compounds |
Toxicology
Stoichiometry of redox reactions  Parker, Gordon A.
A question involving an amplification reaction sequence and the balancing of oxidation-reduction reactions.
Parker, Gordon A. J. Chem. Educ. 1980, 57, 721.
Stoichiometry |
Oxidation / Reduction
Ion exchange separation of the oxidation states of vanadium  Cornelius, Richard
An experiment designed to emphasize the discrete nature of the different oxidation states of vanadium by giving students an opportunity to separate the four species by ion exchange chromatography.
Cornelius, Richard J. Chem. Educ. 1980, 57, 316.
Ion Exchange |
Separation Science |
Oxidation State |
Transition Elements |
Metals |
Oxidation / Reduction
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
Steam distillation of essential oils - Anethole from anise followed by permanganate oxidation to anisic acid  Garin, David L.
Provides the procedure for the oxidation step to this experiment.
Garin, David L. J. Chem. Educ. 1980, 57, 138.
Separation Science |
Oxidation / Reduction
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
Oxidation-reduction: An example of chemical sophistry  Sisler, Harry H.; VanderWerf, Calvin A.
Examines the common definition for oxidation - reduction found in most introductory textbooks and specific examples of oxidation - reduction reactions.
Sisler, Harry H.; VanderWerf, Calvin A. J. Chem. Educ. 1980, 57, 42.
Oxidation / Reduction
The second year course in inorganic chemistry at the free university of Amsterdam  Bolster, M. W. G.
Includes an outline of the experiments used in the course.
Bolster, M. W. G. J. Chem. Educ. 1979, 56, 734.
Coordination Compounds |
Crystal Field / Ligand Field Theory |
IR Spectroscopy |
Magnetic Properties |
Kinetics |
Oxidation / Reduction |
Mechanisms of Reactions |
Catalysis
The thermite lecture demonstration  Bozzelli, Joseph W.; Barat, Robert B.
Glycerine plus KMnO4 are used to ignite the thermite in a clay flower pot.
Bozzelli, Joseph W.; Barat, Robert B. J. Chem. Educ. 1979, 56, 675.
Reactions |
Oxidation / Reduction
An improved method in the redox titration of oxalic acid by permanganate  Datta, M.; Ameta, Suresh C.; Pande, P. N.; Gupta, H. L.; Bokadia, M. M.
To avoid heating, the authors have introduced this reaction with ascorbic acid.
Datta, M.; Ameta, Suresh C.; Pande, P. N.; Gupta, H. L.; Bokadia, M. M. J. Chem. Educ. 1979, 56, 659.
Oxidation / Reduction |
Titration / Volumetric Analysis |
Stoichiometry
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
The precipitation of ferrous hydroxide: A lecture demonstration  Lau, O. W.
This demonstration can illustrate such topics as the solubility of ionic compounds, electrode potentials of transition elements and their modification by formation of either an insoluble compound of a complex ion, and mixed valence compounds.
Lau, O. W. J. Chem. Educ. 1979, 56, 474.
Precipitation / Solubility |
Solutions / Solvents |
Aqueous Solution Chemistry |
Transition Elements |
Metals |
Oxidation / Reduction |
Oxidation State
Excretion of ingested ascorbic acid: An easy, interesting undergraduate experiment  Sirota, G. R.; MacInnis, W. K.; Rasmussen, P. W.
The student ingests ascorbic acid and then measures the amount excreted in his urine using a microfluorometric procedure.
Sirota, G. R.; MacInnis, W. K.; Rasmussen, P. W. J. Chem. Educ. 1979, 56, 421.
Carboxylic Acids |
Vitamins |
Quantitative Analysis
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
Compact Compacts  Huebner, Jay S.; Shiflett, R. B.; Blanck, Harvey F.
A collection of three suggestions regarding demonstrating the oxidation of hydrocarbons and the primary, secondary, and tertiary structure of proteins and the first law of thermodynamics as applied to air conditioning.
Huebner, Jay S.; Shiflett, R. B.; Blanck, Harvey F. J. Chem. Educ. 1979, 56, 389.
Oxidation / Reduction |
Alkanes / Cycloalkanes |
Molecular Properties / Structure |
Proteins / Peptides |
Thermodynamics
Purification by sub-zero temperature washing  Chu, Samuel S.-T.
Separating an ester from the carboxylic acid from which it was synthesized.
Chu, Samuel S.-T. J. Chem. Educ. 1979, 56, 384.
Synthesis |
Esters |
Carboxylic Acids |
Laboratory Management
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
Acid-base half-reactions - A useful formalism for review lessons  Atkinson, G. F.
An effective way to draw analogies between acid-base and redox effects while reviewing both.
Atkinson, G. F. J. Chem. Educ. 1979, 56, 238.
Oxidation / Reduction |
Reactions |
Acids / Bases |
Enrichment / Review Materials
Aqueous chromic acid oxidation of secondary alcohols in diethyl ether: A convenient undergraduate organic chemistry experiment  Thompson, Kerry L.; Krishnamurthy, S.; Nylund, Thomas; Ravindranathan, M.
A two-phase procedure for the oxidation of secondary alcohols to ketones that is applicable to a wide variety of substrates.
Thompson, Kerry L.; Krishnamurthy, S.; Nylund, Thomas; Ravindranathan, M. J. Chem. Educ. 1979, 56, 203.
Aqueous Solution Chemistry |
Oxidation / Reduction |
Alcohols |
Ethers |
Synthesis |
Aldehydes / Ketones
A chemiluminescence demonstration - Oxalyl chloride oxidation  Bramwell, Fitzgerald B.; Goodman, Sidney; Chandross, Edwin A.; Kaplan, Martin
An effective chemiluminescence demonstration requiring minimal preparation based on the oxidation of oxalyl chloride by hydrogen peroxide.
Bramwell, Fitzgerald B.; Goodman, Sidney; Chandross, Edwin A.; Kaplan, Martin J. Chem. Educ. 1979, 56, 111.
Photochemistry |
Oxidation / Reduction
Double scales for equilibria  Chaston, S. H. H.
The acid / base, oxidant / reductant, and solid / solute scales described here can be used as visual representations of equilibria expressions.
Chaston, S. H. H. J. Chem. Educ. 1979, 56, 24.
Equilibrium |
Acids / Bases |
Oxidation / Reduction |
Solutions / Solvents |
Titration / Volumetric Analysis
Amides and hydrazides from amine and hydrazine hydrochlorides  Shama, Sami A.; Tran, Thuran L.
The Schotten-Baumann procedure is extensively used for the preparation of carboxylic acid derivatives in the undergraduate chemistry laboratory.
Shama, Sami A.; Tran, Thuran L. J. Chem. Educ. 1978, 55, 816.
Amines / Ammonium Compounds |
Carboxylic Acids |
Synthesis
A synthesis of o-chlorocinnamic acid utilizing a Meerwein reaction. An undergraduate organic experiment  Cleland, George H.
The authors share an experimental procedure that converts an o-chloroaniline to o-chlorocinnamic acid.
Cleland, George H. J. Chem. Educ. 1978, 55, 814.
Carboxylic Acids |
Synthesis
p-Carboxystyrene. A Wittig procedure in aqueous medium  Broos, Rene; Tavernier, Dirk; Anteunis, Marc
In this paper, the authors present a student preparation of p-carboxyl group, as it makes the reaction product soluble in alkaline and insoluble in acid medium, provides for an easy way of separation.
Broos, Rene; Tavernier, Dirk; Anteunis, Marc J. Chem. Educ. 1978, 55, 813.
Aqueous Solution Chemistry |
Acids / Bases |
Carboxylic Acids |
Separation Science
Dealkylation-isomerization of p-di-t-butylbenzene  Hawbecker, Byron L.; Kurtz, David W.; Elliott, Howard A.
The experiment described here can be conveniently used to explore several important facets of electrophilic aromatic substitution often ignored in typical laboratory programs.
Hawbecker, Byron L.; Kurtz, David W.; Elliott, Howard A. J. Chem. Educ. 1978, 55, 777.
Aromatic Compounds |
Electrophilic Substitution
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
Why green? More chemistry in the student synthesis of tris(ethylenediamine) cobalt(III) chloride  Krause, Ronald A.
What began as a "failure" in this laboratory exercise turned into a great opportunity for inquiry.
Krause, Ronald A. J. Chem. Educ. 1978, 55, 453.
Coordination Compounds |
Alcohols |
Equilibrium |
Oxidation / Reduction
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
Oxidative coupling of phenols. A biomimetic undergraduate organic laboratory experiment  Hart, Harold; Reilly, James L.
It is the purpose of this paper to describe a laboratory experiment suitable for undergraduates which illustrates the oxidative coupling of phenols. To place the experiment in proper context, the authors briefly review general features of the reaction.
Hart, Harold; Reilly, James L. J. Chem. Educ. 1978, 55, 120.
Phenols |
Oxidation / Reduction
Stoichiometric calculations   Parker, Gordon A.
The question presented here is designed for a sophomore or junior level quantitative analysis course, illustrates, calculations based upon oxidation-reduction reactions as applied to a common environmental problem and requires cognitive skill at the application level.
Parker, Gordon A. J. Chem. Educ. 1978, 55, 102.
Oxidation / Reduction |
Quantitative Analysis
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
Industrial analytical procedure for undergraduate analytical chemistry  Hurtubise, Robert J.
A procedure for determining the amount of BHA in cooking oil.
Hurtubise, Robert J. J. Chem. Educ. 1977, 54, 651.
Industrial Chemistry |
Food Science |
Oxidation / Reduction |
Quantitative Analysis
Substituent effects in electrophilic aromatic substitution. A laboratory in organic chemistry  Gilow, Helmuth
The acid catalyzed bromination of aromatic substrates with hydrobromous acid.
Gilow, Helmuth J. Chem. Educ. 1977, 54, 450.
Molecular Properties / Structure |
Aromatic Compounds |
Electrophilic Substitution |
Mechanisms of Reactions |
Catalysis
Experiments with electrophilic aromatic substitution reactions  Cox, B.; Kubler, D. G.; Wilson, C. A.
Comparing the bromination and nitration of benzene.
Cox, B.; Kubler, D. G.; Wilson, C. A. J. Chem. Educ. 1977, 54, 379.
Reactions |
Aromatic Compounds |
Electrophilic Substitution |
Stereochemistry |
Diastereomers
A demonstration in solid state chemistry: The nonstoichiometry of nickel oxide, NiO  Perrino, Charles T.; Johnson, Robert
A simple experiment to demonstrate the nonstoichiometric synthesis of nickel oxide.
Perrino, Charles T.; Johnson, Robert J. Chem. Educ. 1977, 54, 367.
Stoichiometry |
Oxidation State |
Oxidation / Reduction |
Solid State Chemistry |
Metals
White to rose and return: A multipurpose demonstration  Olson, Edwin S.
This demonstration is useful for illustrations of reversible redox reactions and for relative reduction potentials.
Olson, Edwin S. J. Chem. Educ. 1977, 54, 366.
Oxidation / Reduction |
Dyes / Pigments
Lecture demonstration of the various oxidation states of manganese  Arora, C. L.
Showing the colors associated with seven different oxidation states of magnesium and methods for preparing each.
Arora, C. L. J. Chem. Educ. 1977, 54, 302.
Oxidation / Reduction |
Oxidation State |
Transition Elements |
Metals
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 hydroboration-oxidation of alkenes. A convenient anti-Markownikoff hydration experiment  Kabalka, George W.; Hedgecock, Herbert C., Jr.
A hydroboration-oxidation sequence that relies on the borane dimethylsulfide complex as the hydroborating agent and trimethylamine-N-oxide dihydrate as the oxidizing agent.
Kabalka, George W.; Hedgecock, Herbert C., Jr. J. Chem. Educ. 1975, 52, 745.
Alkenes |
Oxidation / Reduction |
Addition Reactions
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
Conversion of black and white prints to color in daylight. A demonstration lecture for general and organic courses  Wheeler, Thomas N.
A black and white print is converted to a full color print with the lights on; includes a detailed discussion of the chemical processes involved in the demonstration.
Wheeler, Thomas N. J. Chem. Educ. 1975, 52, 607.
Photochemistry |
Reactions |
Consumer Chemistry |
Dyes / Pigments |
Oxidation / Reduction
Microbial oxidation of alkenes. An integrated organic-biology experiment  Kumler, Philip L.; DeJong, Peter J.
The conversion of an appropriate terminal alkene to a 1,2-epoxyalkane by Pseudomonas oleovorans introduces students to the techniques used in carrying out chemical conversions employing microorganisms.
Kumler, Philip L.; DeJong, Peter J. J. Chem. Educ. 1975, 52, 475.
Oxidation / Reduction |
Alkenes |
Bioorganic Chemistry |
Biotechnology |
Natural Products
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
A new chemistry program for nursing and allied health students  Stanitski, Conrad L.; Sears, Curtis T., Jr.
Outlines and discusses the topics considered in a chemistry program for nursing and allied health students.
Stanitski, Conrad L.; Sears, Curtis T., Jr. J. Chem. Educ. 1975, 52, 226.
Nonmajor Courses |
Applications of Chemistry |
Medicinal Chemistry |
Oxidation / Reduction |
Catalysis |
Acids / Bases |
pH |
Metabolism |
Drugs / Pharmaceuticals
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
Synthesis of sulfuric acid by the contact process. A student laboratory experiment  Martin, J. A.; Baudot, P.; Monal, J. L.; Lejaille, M. F.
Experimental apparatus and details for the synthesis of sulfuric acid by the contact process.
Martin, J. A.; Baudot, P.; Monal, J. L.; Lejaille, M. F. J. Chem. Educ. 1975, 52, 188.
Synthesis |
Catalysis |
Oxidation / Reduction |
Industrial Chemistry
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
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
Some reactions of tungsten: A lecture demonstration  Nelson, D. L.; Reeves, R. R.; Richtol, H. H.
Several demonstrations involving reactions of tungsten.
Nelson, D. L.; Reeves, R. R.; Richtol, H. H. J. Chem. Educ. 1973, 50, 810.
Metals |
Reactions |
Oxidation / Reduction
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
Analysis of commercial vitamin C tablets by iodometric and coulometric titrimetry  Marsh, Daniel G.; Jacobs, Deborah L.; Veening, Hans
The ascorbic acid content of vitamin C tablets is determined iodometrically using a back titration with standard thiosulfate; ascorbic acid is then titrated coullometrically by direct oxidation to dehydroascorbic acid using electrolytically generated bromine.
Marsh, Daniel G.; Jacobs, Deborah L.; Veening, Hans J. Chem. Educ. 1973, 50, 626.
Vitamins |
Titration / Volumetric Analysis |
Oxidation / Reduction |
Electrochemistry
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
Molecular weight determination of aldehydes and ketones. A quantitative organic experiment  Steinhaus, Ralph K.
The reaction between semicarbazide and an unknown ketone is used to determine molecular weight.
Steinhaus, Ralph K. J. Chem. Educ. 1973, 50, 293.
Physical Properties |
Quantitative Analysis |
Aldehydes / Ketones |
Oxidation / Reduction
Commercial gas replaces hydrogen in general chemistry laboratory  Ehlert, Thomas C.
Methane can be used in place of hydrogen to reduce metal oxides.
Ehlert, Thomas C. J. Chem. Educ. 1973, 50, 162.
Oxidation / Reduction |
Laboratory Management |
Gases |
Metals
Use of a new chemical reducing agent in the undergraduate organic laboratory  Kushner, Arthur S.; Vaccariello, Terry
Using sodium bis(2-methoxy-ethoxy)aluminum hydride as a reducing agent in the undergraduate organic laboratory.
Kushner, Arthur S.; Vaccariello, Terry J. Chem. Educ. 1973, 50, 154.
Laboratory Management |
Oxidation / Reduction
The difference in oxidizing strength of dilute and concentrated nitric acid  Glasoe, Paul K.
H2S gas is bubbled through dilute and concentrated HNO3.
Glasoe, Paul K. J. Chem. Educ. 1972, 49, A644.
Acids / Bases |
Oxidation / Reduction
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
Durable chrome plating  Plumb, Robert C.; Saur, Roger L.
How chrome plating works to protect bumpers from corrosion.
Plumb, Robert C.; Saur, Roger L. J. Chem. Educ. 1972, 49, 626.
Electrochemistry |
Oxidation / Reduction |
Applications of Chemistry |
Kinetics
Durable chrome plating  Plumb, Robert C.; Saur, Roger L.
How chrome plating works to protect bumpers from corrosion.
Plumb, Robert C.; Saur, Roger L. J. Chem. Educ. 1972, 49, 626.
Electrochemistry |
Oxidation / Reduction |
Applications of Chemistry |
Kinetics
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
The presentation of electrode potentials using an energy level diagram  Pinfold, T. A.
The tabular form in which standard electrode potentials are usually presented often leads to confusion that can be diminished by representing the electrochemical series on an energy diagram like that provided.
Pinfold, T. A. J. Chem. Educ. 1972, 49, 506.
Electrochemistry |
Oxidation / Reduction |
Electrolytic / Galvanic Cells / Potentials
Computer evaluation of titrations by Gran's method. An analytical chemistry experiment  MacDonald, Timothy J.; Barker, Barbara J.; Caruso, Joseph A.
A computer program has been developed for the evaluation of potentiometric redox titration data by Gran's method.
MacDonald, Timothy J.; Barker, Barbara J.; Caruso, Joseph A. J. Chem. Educ. 1972, 49, 200.
Titration / Volumetric Analysis |
Quantitative Analysis |
Oxidation / Reduction |
Electrochemistry |
Acids / Bases
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
Questions [and] Answers  Campbell, J. A.
Six questions requiring an application of basic principles of chemistry. [Debut]
Campbell, J. A. J. Chem. Educ. 1972, 49, 5.
Enrichment / Review Materials |
Vitamins |
Alcohols |
Oxidation / Reduction
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
Oxymercuration-demercuration. An organic experiment involving the Markovnikov hydration of olefins  Gibbs, R.; Weber, William P.
While acid catalyzed hydration of olefins to yield alcohol's is important in organic chemistry, it is seldom performed by students for practical reasons. The authors contribute a laboratory that can be particularly performed by organic chemistry students.
Gibbs, R.; Weber, William P. J. Chem. Educ. 1971, 48, 477.
Oxidation / Reduction |
Lipids
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
A color indicating time reaction  Chen, Philip S.
Combining solutions of sodium thoisulfate and ferric chloride produces a dramatic color change.
Chen, Philip S. J. Chem. Educ. 1970, 47, A784.
Reactions |
Oxidation / Reduction |
Aqueous Solution Chemistry
Catalysis demonstrations with Cr2O3  Briggs, Thomas S.
Cr2O3 is used as a catalyst in the oxidation of nonflammable substances such as glycerine and glacial acetic acid.
Briggs, Thomas S. J. Chem. Educ. 1970, 47, A206.
Oxidation / Reduction |
Reactions |
Catalysis
Autoxidation of benzoin  Chen, Philip S.
Benzoin in its enediol form undergoes autoxidation in alkaline solution in the presence of air.
Chen, Philip S. J. Chem. Educ. 1970, 47, A67.
Oxidation / Reduction |
Reactions
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
Detection of carboxylic acids by formation of ferric hydroxamates  Cleland, George H.; Knight, Duane W.
Offers an improved method for the detection of carboxylic acids through the formation of ferric hydroxamates.
Cleland, George H.; Knight, Duane W. J. Chem. Educ. 1970, 47, 781.
Carboxylic Acids |
Qualitative Analysis
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
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
A chemiluminescence reaction  Slabaugh, W. H.
A dramatic demonstration of chemiluminescence can be made with the oxidation of the vat dye violanthrone.
Slabaugh, W. H. J. Chem. Educ. 1970, 47, 522.
Photochemistry |
Oxidation / Reduction |
Dyes / Pigments
Controlled potential electrolysis: An experiment for elementary quantitative analysis  Kennedy, John H; Adams, Frank
Iron(II), iodide, and arsenic(III) are oxidized and data recorded using the E-cell Data-Stor Unit, a small silver coulometer.
Kennedy, John H; Adams, Frank J. Chem. Educ. 1970, 47, 461.
Quantitative Analysis |
Electrochemistry |
Oxidation / Reduction |
Reactions
The equivalent weight of the iodate ion in oxidimetric titrations  Pantani, Francesco
Titrations with potassium iodate can not only solve many analytical problems but are also of educational importance, since iodate ions are involved in numerous redox systems; this paper explains the analysis of these types of titrations and the determination of equivalent weight.
Pantani, Francesco J. Chem. Educ. 1970, 47, 309.
Titration / Volumetric Analysis |
Quantitative Analysis |
Oxidation / Reduction
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
Equivalence point potential in redox titrations  Heyn, Arno H. A.
Many analytical chemistry textbooks ignore or mistake the effect of [H+] on the equivalence point potential.
Heyn, Arno H. A. J. Chem. Educ. 1970, 47, 240.
Electrochemistry |
Titration / Volumetric Analysis |
Aqueous Solution Chemistry |
Equilibrium |
Quantitative Analysis |
Oxidation / Reduction |
Acids / Bases |
Solutions / Solvents
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
A simple cell for preparation of electrolytes  Penzes, S.
Design of a simple electrolytic cell that can produce a high concentration of the anodically dissolved metal.
Penzes, S. J. Chem. Educ. 1970, 47, 138.
Laboratory Equipment / Apparatus |
Electrochemistry |
Aqueous Solution Chemistry |
Synthesis |
Oxidation / Reduction |
Metals
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
The oxidation of hydrazine by basic iodine solutions: A stoichiometric study  Cooper, J. N.; Ramette, R. W.
This experiment relies on an oxidation-reduction reaction for which a variety of products is energetically possible.
Cooper, J. N.; Ramette, R. W. J. Chem. Educ. 1969, 46, 872.
Stoichiometry |
Oxidation / Reduction |
Reactions
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
Identification of an unknown ester: An analytical-organic experiment  Grob, Robert L.; Husk, G. Ronald
It is the student's challenge to hydrolyze an ester, separate and purify the resultant alcohol and acid, determine several physical and chemical characteristics, and arrive at a logical choice for its identity.
Grob, Robert L.; Husk, G. Ronald J. Chem. Educ. 1969, 46, 769.
Quantitative Analysis |
Esters |
Alcohols |
Carboxylic Acids
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
The Hantzsch pyridine synthesis: A factorial design experiment for the introductory organic laboratory  Norcross, B. E.; Clement, G.; Weinstein, M.
Students carry out the two-step Hantzsch pyridine synthesis; students are required to select the oxidizing agent and conditions for the second reaction step.
Norcross, B. E.; Clement, G.; Weinstein, M. J. Chem. Educ. 1969, 46, 694.
Synthesis |
Oxidation / Reduction |
Heterocycles |
Mechanisms of Reactions
A simple amperostat for coulometric titration  Vincent, Colin A.; Ward, J. G.
Describes the circuit, assembly, and performance of a simple amperostat for coulometric titration.
Vincent, Colin A.; Ward, J. G. J. Chem. Educ. 1969, 46, 613.
Laboratory Equipment / Apparatus |
Titration / Volumetric Analysis |
Quantitative Analysis |
Oxidation / Reduction |
Electrochemistry
A simple method for the analysis of cobalt in Co(III) complexes  Hughes, R. Graham; Endicott, John F.; Hoffman, Morton Z.; House, D. A.
Presents two direct chemical methods for effecting the Co(III) to Co2+ reduction.
Hughes, R. Graham; Endicott, John F.; Hoffman, Morton Z.; House, D. A. J. Chem. Educ. 1969, 46, 440.
Coordination Compounds |
Oxidation / Reduction |
Laboratory Management
Identification of carboxylic acids: Use of N-methylpiperazine and N-phenylpiperazine  Duff, J. G.; Yung, D. K.; Brenner, R. J.; Wilson, B. J.; Racz, W. J.
Demonstrates that N-phenylpiperazine is a useful reagent for the identification of carboxylic acids.
Duff, J. G.; Yung, D. K.; Brenner, R. J.; Wilson, B. J.; Racz, W. J. J. Chem. Educ. 1969, 46, 388.
Carboxylic Acids |
Qualitative Analysis
Group VI. The Sulfur Family D. Sulfur Dioxide  Alyea, Hubert N.
Seven demonstrations involving sulfur dioxide.
Alyea, Hubert N. J. Chem. Educ. 1968, 45, A977.
Phases / Phase Transitions / Diagrams |
Reactions |
Precipitation / Solubility |
Oxidation / Reduction
Nitrogen chemistry. E. Nitrites and nitrates  Mancuso, Carl J.; Alyea, Hubert N.; Slabaugh, W. A.
Demonstrations include nitric acid + H2S, sodium nitrate + carbon, fire-writing with KNO3, nitrate ring test, nitrate versus nitrite, and micro-analysis for nitrogen compounds.
Mancuso, Carl J.; Alyea, Hubert N.; Slabaugh, W. A. J. Chem. Educ. 1968, 45, A607.
Qualitative Analysis |
Microscale Lab |
Oxidation / Reduction
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
The kinetics of oxidation-reduction reactions: An alternate derivation of Marcus' cross relation  Newton, T. W.
The purpose of this article is to show how Marcus' cross relation can be derived from a simple, essentially mechanical model.
Newton, T. W. J. Chem. Educ. 1968, 45, 571.
Kinetics |
Oxidation / Reduction |
Reactions
Acids as derivatives of aldehydes prepared with silver oxides  Thomason, Sandra C.; Kubler, Donald G.
Examines the use of silver(i) and silver(II) oxide to convert aldehydes into acid derivatives.
Thomason, Sandra C.; Kubler, Donald G. J. Chem. Educ. 1968, 45, 546.
Acids / Bases |
Aldehydes / Ketones |
Oxidation / Reduction |
Synthesis
Effect of complexing agents on oxidation potentials  Helsen, Jef
A short note on a simple experiment to demonstrate the effect of complexing agents on the oxidation-reduction properties of redox couples such as Fe3+/Fe2+.
Helsen, Jef J. Chem. Educ. 1968, 45, 518.
Coordination Compounds |
Oxidation / Reduction |
Aqueous Solution Chemistry |
Electrochemistry
Mechanisms of oxidation-reduction reactions  Taube, Henry
Examines the mechanisms of oxidation-reduction reactions.
Taube, Henry J. Chem. Educ. 1968, 45, 452.
Mechanisms of Reactions |
Oxidation / Reduction |
Reactions |
Oxidation State |
Coordination Compounds
Why does methane burn?  Sanderson, R. T.
A thermodynamic explanation for why methane burns.
Sanderson, R. T. J. Chem. Educ. 1968, 45, 423.
Thermodynamics |
Reactions |
Oxidation / Reduction |
Calorimetry / Thermochemistry |
Covalent Bonding |
Ionic Bonding
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
Using TLC to follow the oxidation of a secondary alcohol to a ketone  Davis, Michael
A short note regarding a simple procedure involving the use of thin layer chromatography to follow the oxidation of a secondary alcohol to a ketone.
Davis, Michael J. Chem. Educ. 1968, 45, 192.
Chromatography |
Thin Layer Chromatography |
Oxidation / Reduction |
Alcohols |
Aldehydes / Ketones
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
Biological oxidations and energy conservation  Kirschbaum, Joel
Examines the oxidative steps leading to the synthesis of ATP in living organisms and their metabolic control.
Kirschbaum, Joel J. Chem. Educ. 1968, 45, 28.
Bioenergetics |
Oxidation / Reduction |
Thermodynamics |
Metabolism
Metallurgy C. Reducton of Ore  Rogers, Crosby U.
Demonstrations include the reduction of Cu2O with charcoal, heating zinc carbonate, and zinc sulfide heated in air.
Rogers, Crosby U. J. Chem. Educ. 1967, 44, A717.
Metallurgy |
Metals |
Oxidation / Reduction
Reaction rates and equilibria. D. Redox  Klug, Evangeline B.
Sugar + chlorate + acid produces an exothermic reaction using a violent oxidizing agent.
Klug, Evangeline B. J. Chem. Educ. 1967, 44, A545.
Oxidation / Reduction |
Equilibrium
Energy C. Electrical Energy  Soule, Dean; Hornbeck, Leroy G.; Jackson, Kenneth V.; Barnard, Robert; Noerdin, Isjrin
Demonstrations include aluminum flashed in oxygen; photo-bromination of cinnamic acid, hexane, tartaric acid, toluene; photochemical H2+Cl2 explosion and the slow photochemical H2+Cl2 into 2HCl.
Soule, Dean; Hornbeck, Leroy G.; Jackson, Kenneth V.; Barnard, Robert; Noerdin, Isjrin J. Chem. Educ. 1967, 44, A83.
Reactions |
Oxidation / Reduction |
Photochemistry
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
The stoichiometry of an oxidation-reduction reaction  Latimer, George W., Jr.
A short note on the titration of hydrazine sulfate with standard bromate in the presence of sodium molybdate that requires students to identify the products through the use of some elementary qualitative analysis.
Latimer, George W., Jr. J. Chem. Educ. 1967, 44, 537.
Stoichiometry |
Oxidation / Reduction |
Reactions |
Titration / Volumetric Analysis |
Qualitative Analysis
The photochemical oxidation of aqueous iodide solutions: An experiment demonstrating the competitive reactions of the hydrated electron  Ayscough, P. B.; Burchill, C. E.; Ivin, K. J; Logan, S. R.
Hydrated electrons are formed by the photochemical method referred to in the cited article.
Ayscough, P. B.; Burchill, C. E.; Ivin, K. J; Logan, S. R. J. Chem. Educ. 1967, 44, 349.
Photochemistry |
Oxidation / Reduction |
Aqueous Solution Chemistry
VII - Combustion and flame  Anderson, Robbin C.
Presents and describes an extensive bibliography on the study of combustion and flames.
Anderson, Robbin C. J. Chem. Educ. 1967, 44, 248.
Oxidation / Reduction |
Reactions |
Gases
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
Stereochemical correlations in the camphor series  Markgraf, J. Hodge
This paper presents a series of experiments that require the student to interpret the effect of structure on the steric course of an oxidation and a reduction in a bicyclic system.
Markgraf, J. Hodge J. Chem. Educ. 1967, 44, 36.
Stereochemistry |
Reactions |
Oxidation / Reduction |
Mechanisms of Reactions |
Molecular Properties / Structure
A simple potentiostat for controlled potential electrolysis  Tackett, Stanford L.; Knowles, John A.
Present a circuit diagram and describes typical applications of a simple potentiostat for controlled potential electrolysis.
Tackett, Stanford L.; Knowles, John A. J. Chem. Educ. 1966, 43, 428.
Electrochemistry |
Oxidation / Reduction |
Instrumental Methods
Use of KMnO4, to oxidize interfering organic anions in qualitative analysis  Poonia, N. S.; Bhagwat, W. V.
A simple procedure is presented here that is based upon the oxidation of organic material by permanganate ion in acidified medium.
Poonia, N. S.; Bhagwat, W. V. J. Chem. Educ. 1966, 43, 424.
Qualitative Analysis |
Oxidation / Reduction
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
The use of oxidation potentials in inorganic chemistry  Jolly, William L.
This paper attempts to show, using a minimum of thermodynamics, how oxidation potentials can be used to predict the products and driving forces of oxidation-reduction reactions.
Jolly, William L. J. Chem. Educ. 1966, 43, 198.
Oxidation / Reduction |
Reactions |
Thermodynamics
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
Combustion versus biological oxidation  Asenjo, Conrado F.
Describes a simple toy that can be used to illustrate the difference between combustion and biological oxidation.
Asenjo, Conrado F. J. Chem. Educ. 1965, 42, 558.
Oxidation / Reduction |
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
Kinetics of corrosion of metals  Habashi, Fathi
It is the purpose of this paper to report that all corrosion processes that produce no insoluble end products and evolve hydrogen follow a single kinetic law.
Habashi, Fathi J. Chem. Educ. 1965, 42, 318.
Metals |
Oxidation / Reduction |
Kinetics
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
Continuous process for catalytic oxidation of ammonia  Olmsted, Michael P.
A heated platinum coil catalyzes the oxidation of ammonia.
Olmsted, Michael P. J. Chem. Educ. 1964, 41, A973.
Catalysis |
Oxidation / Reduction |
Reactions
The oxidation of iodide ion by persulfate ion  Moews, P. C., Jr.; Petrucci, R. H.
Presents the oxidation of iodide ion by persulfate ion as an ideal reaction to study as part of an experiment on kinetics.
Moews, P. C., Jr.; Petrucci, R. H. J. Chem. Educ. 1964, 41, 549.
Oxidation / Reduction |
Reactions |
Kinetics |
Rate Law
Signs of tensions in electrochemistry  Van Rysselberghe, Pierre
Discusses conventions and definitions for electrochemical terms and relationships.
Van Rysselberghe, Pierre J. Chem. Educ. 1964, 41, 486.
Electrochemistry |
Nomenclature / Units / Symbols |
Oxidation / Reduction
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
Rocket propulsion: The chemical challenge  Dafler, James R.
Examines the chemistry of rocket fuels and engines.
Dafler, James R. J. Chem. Educ. 1964, 41, 58.
Reactions |
Applications of Chemistry |
Oxidation / Reduction
Demonstration notes: Chemiluminescence in electrolysis  Villarreal, Fidel; Garcia, Octavio
Suggests a modification to the usual chemiluminescence demonstration with luminol.
Villarreal, Fidel; Garcia, Octavio J. Chem. Educ. 1963, 40, A477.
Electrochemistry |
Oxidation / Reduction
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
Random and systematic errors in the determination of association constants  Pasternak, R. A.; Brady, A. P.
Examines random and systematic errors in the context of studying association equilibria in solution of carboxylic acids and amides.
Pasternak, R. A.; Brady, A. P. J. Chem. Educ. 1963, 40, 254.
Equilibrium |
Chemometrics |
Carboxylic Acids |
Amides
The decarboxylation of organic acid  March, Jerry
Simple aliphatic acids (except for acetic) do not give good yields of the corresponding alkanes through decarboxylation, although many organic chemistry textbooks cite this as a general method for the preparation of alkanes.
March, Jerry J. Chem. Educ. 1963, 40, 212.
Acids / Bases |
Reactions |
Synthesis |
Alkanes / Cycloalkanes |
Carboxylic Acids
The stereochemistry of (-) menthol: An organic laboratory experiment  Dunathan, H. C.
This experiment determines the relative configuration of (-) menthol in which students measure optical rotations, follows the rate of a mutarotation, evaluates rate constants, and carries out a reaction involving asymmetric induction.
Dunathan, H. C. J. Chem. Educ. 1963, 40, 205.
Stereochemistry |
Molecular Properties / Structure |
Oxidation / Reduction
Inorganic reaction mechanisms by volumetric analysis: Oxidation of iodide ion  Moody, G. J.; Thomas, J. D. R.
Uses the Andrews' method of titration as a simple means of exposing the two-step oxidation of the iodide ion to iodine in concentrated hydrochloric acid with a variety of oxidizing agents.
Moody, G. J.; Thomas, J. D. R. J. Chem. Educ. 1963, 40, 151.
Reactions |
Mechanisms of Reactions |
Titration / Volumetric Analysis |
Oxidation / Reduction
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
Demonstration notes: Spontaneous combustion of H2S  Thomas, P. M.
Hydrogen sulfide passed over lead(IV) oxide bursts into flame.
Thomas, P. M. J. Chem. Educ. 1962, 39, A839.
Oxidation / Reduction |
Reactions
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
Oxidation-reduction mechanisms  Duke, F. R.
Summarizes various types of oxidation-reduction mechanisms.
Duke, F. R. J. Chem. Educ. 1961, 38, 161.
Oxidation / Reduction |
Mechanisms of Reactions
The Corrosion and Oxidation of Metals: Scientific Principles and Practical Applications (Evans, Ulick R.)  Goldstein, Ernst M.

Goldstein, Ernst M. J. Chem. Educ. 1960, 37, 662.
Oxidation / Reduction |
Metals
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
Oxidation of hydrogen sulfide in inorganic qualitative analysis  Stock, John T.; Shinozuka, Fujiko
Presents the results of an investigation into the sulfate-forming tendencies of various oxidizing agents.
Stock, John T.; Shinozuka, Fujiko J. Chem. Educ. 1959, 36, 385.
Qualitative Analysis |
Oxidation / Reduction
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
Balancing organic redox equations  Burrell, Harold P. C.
This paper presents a method for balancing organic redox equations based on the study of structural formulas and an artificial device - the use of hypothetical free radicals.
Burrell, Harold P. C. J. Chem. Educ. 1959, 36, 77.
Stoichiometry |
Oxidation / Reduction |
Free Radicals
Explosive hazard of aluminum-liquid oxygen mixtures  Austin, Calvin M.; Rohrer, Charles S.; Seifert, Ralph L.
Details the serious explosive hazards and ignition properties of aluminum-liquid oxygen mixtures; this demonstration should NEVER be used for classroom or public viewing purposes.
Austin, Calvin M.; Rohrer, Charles S.; Seifert, Ralph L. J. Chem. Educ. 1959, 36, 54.
Oxidation / Reduction
EDTA and complex formation  Johnston, M. B.; Bernard, A. J., Jr.; Flaschka, H. A.
It is the purpose of this paper to fill the void in chemistry texts regarding EDTA and its application to titrations in analytical chemistry, and to present some integrated experiments designed to serve as a general introduction to water-soluble chelates.
Johnston, M. B.; Bernard, A. J., Jr.; Flaschka, H. A. J. Chem. Educ. 1958, 35, 601.
Coordination Compounds |
Titration / Volumetric Analysis |
Quantitative Analysis |
Metals |
Oxidation / Reduction |
Precipitation / Solubility
The stability of solutions for the iodine clock reaction  Kauffman, George B.; Hall, Charles R.
The results of attempts to stabilize solutions needed for the iodine clock reaction to allow long-term storage.
Kauffman, George B.; Hall, Charles R. J. Chem. Educ. 1958, 35, 577.
Reactions |
Kinetics |
Oxidation / Reduction |
Aqueous Solution Chemistry
Systematic detection of anions through their parent elements  Caldas, Alcides; Gentil, Vicente
Presents an analysis scheme that aims at the detection of the parent elements of the anions, no matter what their state of combination.
Caldas, Alcides; Gentil, Vicente J. Chem. Educ. 1958, 35, 545.
Qualitative Analysis |
Precipitation / Solubility |
Oxidation / Reduction |
Aqueous Solution Chemistry
The reduction of carbon dioxide  Hollander, Jerome; Spialter, Leonard
Examines the reduction of carbon through a variety of processes, including catalytic hydrogenation, reduction by metals and complex metal hydrides, electrochemical reduction, and reduction under the influence of radiation.
Hollander, Jerome; Spialter, Leonard J. Chem. Educ. 1958, 35, 446.
Reactions |
Oxidation / Reduction |
Catalysis |
Metals |
Electrochemistry |
Nuclear / Radiochemistry
The use of N-chlorosuccinimide for identification of bromide and iodide ions  Filler, Robert
Describes the use of N-chlorosuccinimide as an oxidizing agent in preference to "chlorine water" for the identification of bromide and iodide ions.
Filler, Robert J. Chem. Educ. 1958, 35, 407.
Qualitative Analysis |
Oxidation / Reduction |
Aqueous Solution Chemistry
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
Reduction with complex metal hydrides  Gaylord, Norman G.
Focusses on the use of lithium aluminum hydride, aluminum hydride, magnesium aluminum hydride, sodium aluminum hydride, sodium borohydride, potassium borohydride, lithium borohydride, and lithium gallium hydride as analytical reducing reagents.
Gaylord, Norman G. J. Chem. Educ. 1957, 34, 367.
Oxidation / Reduction |
Metals |
Reactions
Hydrogen bonding and physical properties of substances  Ferguson, Lloyd N.
Physical properties influenced by hydrogen bonding considered in this paper include transition temperatures, vapor pressure, water solubility, the ionization of carboxylic acids, stereoisomerism, adsorption, and infrared spectra.
Ferguson, Lloyd N. J. Chem. Educ. 1956, 33, 267.
Hydrogen Bonding |
Noncovalent Interactions |
Physical Properties |
Aqueous Solution Chemistry |
Carboxylic Acids |
Stereochemistry |
IR Spectroscopy
Textbook errors: V. The reaction of the Leclanche dry cell  Mysels, Karol J.
Most textbooks do not completely and accurately describe the chemistry of the Leclanche dry cell.
Mysels, Karol J. J. Chem. Educ. 1955, 32, 638.
Electrochemistry |
Electrolytic / Galvanic Cells / Potentials |
Reactions |
Oxidation / Reduction
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
A mnemonic for dicarboxylic acids  Cox, Gerald J.
This short note provides a mnemonic for the names of the dicarboxylic acids.
Cox, Gerald J. J. Chem. Educ. 1955, 32, 363.
Acids / Bases |
Nomenclature / Units / Symbols |
Carboxylic Acids
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
Lecture demonstrations of incendiaries. II  Antelman, Marvin
Demonstrations described involve gunpowder, the combustion of sulfur dioxide, zirconium, nitric acid, sodium peroxide, hot iron, ammonium nitrate, organic chlorates and nitrates, and zinc stearate.
Antelman, Marvin J. Chem. Educ. 1955, 32, 273.
Reactions |
Oxidation / Reduction
Letters to the editor  Hendricks, B. Clifford
Questions what happens to the cryolite needed in the reduction of aluminum from its ore.
Hendricks, B. Clifford J. Chem. Educ. 1955, 32, 52.
Industrial Chemistry |
Oxidation / Reduction
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
A cell for the preparation of small quantities of alkali metals  Baker, Philip S.; Wells, G. F.; Rathkamp, W. R.
The work described here deals with the development of a miniature cell designed for the preparation of alkali metals (particularly lithium) from small amounts of their salts.
Baker, Philip S.; Wells, G. F.; Rathkamp, W. R. J. Chem. Educ. 1954, 31, 515.
Electrochemistry |
Oxidation / Reduction
An oxidation-reduction diagram  Tarsey, Alexandre R.
Describes the construction and properties of a chart capable of providing a visual approach to correlating the various concepts pertaining to oxidation and reduction potentials.
Tarsey, Alexandre R. J. Chem. Educ. 1954, 31, 375.
Oxidation / Reduction |
Electrochemistry
Material balances and redox equations  Bennett, George W.
It is the purpose of this paper to remind teachers of a third method of balancing redox equations that does not depend on rule-of-thumb empiricism but relies on the conservation of matter.
Bennett, George W. J. Chem. Educ. 1954, 31, 324.
Stoichiometry |
Oxidation / Reduction |
Oxidation State
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
Investigation of complex metal ions by the polarographic method  Gayer, Karl H.; Demmler, Anita; Elkind, Michael J.
The purpose of this paper is to present in a simplified and readily understandable manner the outline of one of the instrumental methods that, in recent years, has become an increasingly prominent tool in the investigation of complex metal ions.
Gayer, Karl H.; Demmler, Anita; Elkind, Michael J. J. Chem. Educ. 1953, 30, 557.
Coordination Compounds |
Instrumental Methods |
Electrochemistry |
Oxidation / Reduction |
Acids / Bases |
Aqueous Solution Chemistry
Letters  Davidson, David
Responds to comments made in a related letter.
Davidson, David J. Chem. Educ. 1953, 30, 534.
Equilibrium |
Chemometrics |
Acids / Bases |
Aqueous Solution Chemistry |
Oxidation / Reduction
Letters  Ricci, John E.
Discusses the question of teaching students how to "solve" problems requiring more than one equilibrium constant.
Ricci, John E. J. Chem. Educ. 1953, 30, 532.
Equilibrium |
Chemometrics |
Acids / Bases |
Aqueous Solution Chemistry |
Oxidation / Reduction
Demonstration of the intermediate position of cobalt between iron and nickel  Goldstein, Ernst M.
The different oxidizability of ferrous, cobaltous, and nickelous hydroxides, together with increasing color deepness of the oxidation products, can be used to demonstrate that cobalt is intermediate in its properties between iron and nickel.
Goldstein, Ernst M. J. Chem. Educ. 1953, 30, 387.
Periodicity / Periodic Table |
Metals |
Oxidation / Reduction |
Atomic Properties / Structure |
Qualitative Analysis
Letters  Swinehart, D. F.
The author responds to questions raised regarding his earlier article on oxidation states.
Swinehart, D. F. J. Chem. Educ. 1953, 30, 265.
Oxidation / Reduction |
Oxidation State
Letters  Miranda, Bienvenido T.
Commmentary on two earlier Journal articles.
Miranda, Bienvenido T. J. Chem. Educ. 1953, 30, 264.
Oxidation State |
Oxidation / Reduction |
Reactions
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
The algebra of simultaneous equilibria  Davidson, David; Geller, Kenneth
Presents a series of rules for dealing with simultaneous equilibria using simple algebra.
Davidson, David; Geller, Kenneth J. Chem. Educ. 1953, 30, 238.
Equilibrium |
Chemometrics |
Acids / Bases |
Aqueous Solution Chemistry |
Oxidation / Reduction
Redox diagrams  Sillen, Lars Gunnar
Develops redox diagrams that portray redox equilibria for a variety of species.
Sillen, Lars Gunnar J. Chem. Educ. 1952, 29, 600.
Oxidation / Reduction |
Oxidation State |
Metals
Letters  Hackney, J. C.
The author elaborates on the source of a fallacy in the calculation of an overall redox potential by combination of two half-cell potentials.
Hackney, J. C. J. Chem. Educ. 1952, 29, 472.
Electrochemistry |
Electrolytic / Galvanic Cells / Potentials |
Aqueous Solution Chemistry |
Oxidation / Reduction
Letters  Angus, L. H.
Briefly describes the use of ferroxyl gels to demonstrate the oxidation of iron.
Angus, L. H. J. Chem. Educ. 1951, 28, 556.
Oxidation / Reduction
Letters  Hackney, J. C.
Discusses pitfalls in the construction of "objective" examinations.
Hackney, J. C. J. Chem. Educ. 1951, 28, 556.
Oxidation / Reduction
The effect of nitrous acid on the oxidizing power of nitric acid  Brasted, Robert C.
this demonstration illustrates that the oxidizing action of nitric acid may be considerably enhanced by small quantities of nitrous acid which are usually present.
Brasted, Robert C. J. Chem. Educ. 1951, 28, 442.
Acids / Bases |
Oxidation / Reduction |
Aqueous Solution Chemistry
The use of starch-iodate paper in qualitative analysis  Lundin, John A.
Describes the preparation of starch-iodate paper and its use in detecting sulfur dioxide and reducing anions.
Lundin, John A. J. Chem. Educ. 1951, 28, 122.
Qualitative Analysis |
Oxidation / Reduction