TIGER

Journal Articles: 252 results
Experimental Design and Optimization: Application to a Grignard Reaction  Naoual Bouzidi and Christel Gozzi
This 5-week project, which systematically investigates optimizing the synthesis of benzyl-1-cyclopentan-1-ol, constitutes an initiation into research methodology and experimental design to prepare the student-engineer for an industry internship. Other pedagogical goals include experience in synthetic techniques, obtaining reproducible yields, and using quantitative analysis methods.
Bouzidi, Naoual; Gozzi, Christel. J. Chem. Educ. 2008, 85, 1544.
Addition Reactions |
Alcohols |
Aldehydes / Ketones |
Chemometrics |
Gas Chromatography |
Organometallics |
Synthesis
Quantitative Analysis of Nail Polish Remover Using Nuclear Magnetic Resonance Spectroscopy Revisited  Markus M. Hoffmann, Joshua T. Caccamis, Mark P. Heitz, and Kenneth D. Schlecht
Substantial modifications intended for a second- or third-year laboratory course in analytical chemistry are presented for a previously described procedure using NMR spectroscopy to quantitatively determine analytes in commercial nail polish remover. The revised experiment introduces student collaboration to critically interpret a relatively large set of data.
Hoffmann, Markus M.; Caccamis, Joshua T.; Heitz, Mark P.; Schlecht, Kenneth D. J. Chem. Educ. 2008, 85, 1421.
Alcohols |
Aldehydes / Ketones |
Consumer Chemistry |
Instrumental Methods |
Laboratory Equipment / Apparatus |
NMR Spectroscopy |
Quantitative Analysis
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
2-Propanol  Jay A. Young
Safe handling and laboratory use of 2-propanol are discussed.
Young, Jay A. J. Chem. Educ. 2008, 85, 1186.
Alcohols |
Laboratory Management
Polymer-Supported Reagents and 1H–19F NMR Couplings: The Synthesis of 2-Fluoroacetophenone  Nicola Pohl and Kimberly Schwarz
Describes an experiment in which 2-bromoacetophenone is converted to 2-fluoroacetophenone using a solid-phase nucleophilic fluorine source. The experiment introduces students to the utility of solid-phase reagents in organic synthesis, to NMR-active nuclei other than 1H without the requirement of a special NMR probe, and to the unique uses of fluorine in molecular design.
Pohl, Nicola; Schwarz, Kimberly. J. Chem. Educ. 2008, 85, 834.
Aldehydes / Ketones |
NMR Spectroscopy |
Nucleophilic Substitution |
Synthesis
Converting Municipal Waste into Automobile Fuel: Ethanol from Newspaper  Mark Mascal and Richard Scown
In this experiment, waste newspaper is pulped with acid and its cellulose hydrolyzed to produce glucose syrup that is fermented and distilled to yield ethanol. In doing so, students are introduced to carbohydrate chemistry and the use of fermentation in organic synthesis.
Mascal, Mark; Scown, Richard. J. Chem. Educ. 2008, 85, 546.
Acids / Bases |
Alcohols |
Applications of Chemistry |
Biotechnology |
Carbohydrates |
Qualitative Analysis |
Synthesis |
Thin Layer Chromatography
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
Regioselectivity in Organic Synthesis: Preparation of the Bromohydrin of α-Methylstyrene  Brad Andersh, Kathryn N. Kilby, Meghan E. Turnis, and Drew L. Murphy
In the described experiment, the regiochemical outcome of the addition of "HOBr" to a-methylstyrene is investigated. Although both "classic" qualitative analysis and instrumental techniques are described, the emphasis of this experiment is on the utilization 13C and DEPT-135 NMR spectroscopy to determine the regiochemical outcome of the addition.
Andersh, Brad; Kilby, Kathryn N.; Turnis, Meghan E.; Murphy, Drew L. J. Chem. Educ. 2008, 85, 102.
Addition Reactions |
Alcohols |
Alkenes |
Constitutional Isomers |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Synthesis
A Discovery-Based Experiment Involving Rearrangement in the Conversion of Alcohols to Alkyl Halides  Richard A. Kjonaas and Ryand J. F. Tucker
This article reports a discovery-based experiment in which students convert three alcohols to alkyl halides under acidic conditions and record the 13C NMR spectrum in each case. By comparing the number of resonances observed with the number of resonances predicted for each possible product, students draw several conclusions about the resulting rearrangement.
Kjonaas, Richard A.; Tucker, Ryand J. F. J. Chem. Educ. 2008, 85, 100.
Alcohols |
Carbocations |
Gas Chromatography |
NMR Spectroscopy |
Nucleophilic Substitution
tert-Amyl Alcohol  Jay A. Young
Safe handling of tert-amyl alcohol are discussed.
Young, Jay A. J. Chem. Educ. 2008, 85, 43.
Alcohols |
Laboratory Management
n-Amyl Alcohol  Jay A. Young
Safe handling of n-amyl alcohol are discussed.
Young, Jay A. J. Chem. Educ. 2008, 85, 42.
Alcohols |
Laboratory Management
Determination of the Rotational Barrier for Kinetically Stable Conformational Isomers via NMR and 2D TLC  Gregory T. Rushton, William G. Burns, Judi M. Lavin, Yong S. Chong, Perry Pellechia, and Ken D. Shimizu
After the synthesis of a N,N'-diaryl naphthalene diimide, students estimate the rotational barrier about a CarylNimidesingle bond by studying the reequilibration of the two resulting isomers using two-dimensional thin-layer chromatography, followed by a more accurate determination through a 1H NMR time study.
Rushton, Gregory T.; Burns, William G.; Lavin, Judi M.; Chong, Yong S.; Pellechia, Perry; Shimizu, Ken D. J. Chem. Educ. 2007, 84, 1499.
Alcohols |
Chromatography |
Conformational Analysis |
Equilibrium |
Kinetics |
NMR Spectroscopy |
Physical Properties |
Rate Law |
Thin Layer Chromatography
The Quartz-Crystal Microbalance in an Undergraduate Laboratory Experiment  Vladimir Tsionsky
Describes a typical student experiment on the determination of the viscosity of liquids using a quartz-crystal microbalance.
Tsionsky, Vladimir. J. Chem. Educ. 2007, 84, 1337.
Alcohols |
Alkanes / Cycloalkanes |
Laboratory Equipment / Apparatus |
Liquids |
Physical Properties |
Solutions / Solvents
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
pHantastic Fluorescence  Mark Muyskens
Students easily extract a fluorescent substance from shavings of a wood called narra. The fluorescence is dramatically pH dependent and can be turned on and off repeatedly using commonly available acid and base solutions.
Muyskens, Mark. J. Chem. Educ. 2006, 83, 768A.
Fluorescence Spectroscopy |
Natural Products |
Nucleophilic Substitution |
pH |
Solutions / Solvents |
UV-Vis Spectroscopy
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
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
The Finkelstein Reaction: Quantitative Reaction Kinetics of an SN2 Reaction Using Nonaqueous Conductivity  R. David Pace and Yagya Regmi
Presents a quantitative kinetics laboratory exercise featuring the Finkelstein reaction (SN2) for use in the first-semester organic chemistry course that utilizes nonaqueous conductivity as the method by which relevant structuretemperaturesolvent effects are examined.
Pace, R. David; Regmi, Yagya. J. Chem. Educ. 2006, 83, 1344.
Calibration |
Kinetics |
Nucleophilic Substitution |
Rate Law |
Reactions |
Solutions / Solvents
Methanol  Jay A. Young
The hazards of methanol are discussed.
Young, Jay A. J. Chem. Educ. 2006, 83, 1131.
Alcohols |
Laboratory Management
Semiempirical and DFT Investigations of the Dissociation of Alkyl Halides  Jack R. Waas
Enthalpy changes corresponding to the gas phase heats of dissociation of 12 organic halides were calculated using two semiempirical methods, the HartreeFock method, and two DFT methods. All five methods agreed generally with the expected empirically known trends in the dissociation of alkyl halides.
Waas, Jack R. J. Chem. Educ. 2006, 83, 1017.
Alkanes / Cycloalkanes |
Computational Chemistry |
Mechanisms of Reactions |
Molecular Modeling |
Reactions |
Reactive Intermediates |
Thermodynamics |
Elimination Reactions |
Nucleophilic Substitution
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
n-Butyl Alcohol  Jay A. Young
The hazards of n-butyl alcohol are discussed.
Young, Jay A. J. Chem. Educ. 2006, 83, 840.
Alcohols |
Laboratory Management
Synthesis of Unsymmetrical Alkynes via the Alkylation of Sodium Acetylides. An Introduction to Synthetic Design for Organic Chemistry Students  Jennifer N. Shepherd and Jason R. Stenzel
Teams of students design a microscale synthesis of an unsymmetrical alkyne using commercially available terminal alkynes and alkyl halides and characterize the resulting products using TLC, IR, and 1H NMR spectroscopy. Depending on the chosen reactants, students observe both substitution and elimination products, or in some cases, no reaction at all.
Shepherd, Jennifer N.; Stenzel, Jason R. J. Chem. Educ. 2006, 83, 425.
Alkylation |
Alkynes |
Elimination Reactions |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Nucleophilic Substitution |
Synthesis
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
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
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
Menthol Stereoisomers  William F. Coleman
The JCE Featured Molecules for July come from the paper by Edward M. Treadwell and T. Howard Black on the use of commercially available stereoisomers of menthol to illustrate properties of enantiomers and diastereomers. The paper describes the use of four of the eight possible stereoisomers. Structures of all eight stereoisomers are included in this months molecule collection, labeled by the chirality of the three chiral atoms. In addition to the exercises described in the paper, students can be asked to match the appropriate structures to those shown in the paper, or to generate structures for the isomers that are not discussed.
Coleman, William F. J. Chem. Educ. 2005, 82, 1048.
Molecular Properties / Structure |
Molecular Modeling |
Alcohols
Catechol  Jay A. Young
The hazards of catechol are discussed.
Young, Jay A. J. Chem. Educ. 2005, 82, 31.
Alcohols |
Laboratory Management |
Laboratory Equipment / Apparatus
Ethyl Alcohol  Jay A. Young
The hazards of ethyl alcohol are described.
Young, Jay A. J. Chem. Educ. 2004, 81, 1414.
Laboratory Management |
Alcohols |
Laboratory Equipment / Apparatus
Cautionary Comments  John J. Esteb and Anne M. Wilson
We never claimed that our procedure would work as written for any alcohol other than the three that we have included.
Esteb, John J.; Wilson, Anne M. J. Chem. Educ. 2004, 81, 641.
Alcohols |
IR Spectroscopy
Cautionary Comments   R. G. Landolt
Im concerned about a safety factor in the paper, A Solvent-Free Oxidation of Alcohols in an Organic Laboratory".
Landolt, R. G. J. Chem. Educ. 2004, 81, 641.
Alcohols |
Synthesis
The Tragedy of Hamlet, Son of an Organic Chemist of Denmark  Ronald G. Brisbois
Herein, Hamlet (the son of an organic chemist of Denmark) is the surrogate of any and every student as he uses a thoroughly Shakespearean approach to sorting out some of the key distinguishing features of SN2 versus SN1 reactions.
Brisbois, Ronald G. J. Chem. Educ. 2004, 81, 502.
Kinetics |
Mechanisms of Reactions |
Stereochemistry |
Nucleophilic Substitution
The Substitution–Elimination Mechanistic Disc Method  Paul T. Buonora and Yu Jin Lim
In this manuscript a mnemonic device designed to facilitate presentation of the competing SN1, SN2, E1, and E2 mechanisms is presented.
Buonora, Paul T.; Lim, Yu Jin. J. Chem. Educ. 2004, 81, 368.
Mechanisms of Reactions |
Elimination Reactions |
Nucleophilic Substitution
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
Using Conductivity Devices in Nonaqueous Solutions II: Demonstrating the SN2 Mechanism  Thomas A. Newton and Beth Ann Hill
The use of a conductivity apparatus in nonaqueous solutions to demonstrate structurereactivity correlations and solvent effects in the SN2 reaction is described.
Newton, Thomas A.; Hill, Beth Ann. J. Chem. Educ. 2004, 81, 61.
Conductivity |
Nucleophilic Substitution |
Mechanisms of Reactions
Using Conductivity Devices in Nonaqueous Solutions I: Demonstrating the SN1 Mechanism  Thomas A. Newton and Beth Ann Hill
The use of a conductivity apparatus in nonaqueous solutions to demonstrate structurereactivity correlations and solvent effects in the SN1 reaction is described.
Newton, Thomas A.; Hill, Beth Ann. J. Chem. Educ. 2004, 81, 58.
Conductivity |
Nucleophilic Substitution |
Mechanisms of Reactions
Triethanolamine  Jay A. Young
Properties, hazards, and storage requirements for triethanolamine.
Young, Jay A. J. Chem. Educ. 2004, 81, 24.
Laboratory Equipment / Apparatus |
Laboratory Management |
Amines / Ammonium Compounds |
Physical Properties |
Alcohols
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
Measuring Breath Alcohol Concentrations with an FTIR Spectrometer  Adam Kneisel and Michael K. Bellamy
Students use aqueous ethanol solutions to make a calibration curve that relates absorbance signals of breath samples with blood alcohol concentrations. Students use their calibration curve to determine the time needed for their calculated blood alcohol levels to drop below the legal limit following use of a commercial mouthwash.
Kneisel, Adam; Bellamy, Michael K. J. Chem. Educ. 2003, 80, 1448.
Forensic Chemistry |
Instrumental Methods |
IR Spectroscopy |
Fourier Transform Techniques |
Alcohols
Spiral Puzzle for Organic Chemistry Students  Ender Erdik
Puzzle to review organic reactions and their reagents.
Erdik, Ender. J. Chem. Educ. 2003, 80, 428.
Synthesis |
Learning Theories |
Enrichment / Review Materials |
Addition Reactions |
Alkylation |
Electrophilic Substitution |
Elimination Reactions |
Reactions |
Nucleophilic Substitution |
Mechanisms of Reactions |
Grignard Reagents
Organic Functional Group Playing Card Deck  Michael J. Welsh
Organic functional group playing card deck used for review of the name and structure of organic functional groups that can be used to play any game that a normal deck of cards is used for.
Welsh, Michael J. J. Chem. Educ. 2003, 80, 426.
Nomenclature / Units / Symbols |
Nonmajor Courses |
Enrichment / Review Materials |
Alcohols |
Aldehydes / Ketones |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes |
Amides |
Amines / Ammonium Compounds |
Aromatic Compounds |
Carboxylic Acids |
Esters |
Ethers |
Mechanisms of Reactions |
Synthesis
The Flawed Nature of the Calibration Factor in Breath-Alcohol Analysis  Dominick A. Labianca
Analysis of factors that influence breath-alcohol tests.
Labianca, Dominick A. J. Chem. Educ. 2002, 79, 1237.
Drugs / Pharmaceuticals |
Forensic Chemistry |
Calibration |
Alcohols |
Gases |
Chemometrics |
Applications of Chemistry
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
DeLorenzo's Four Interesting Mysteries Verified  Josefina Ma. Ferriols-Pavico
Results of experiments testing why women become intoxicated more easily than men, why alcohol consumption might enhance cigarettes' carcinogenic effects, why latex condoms with oil-based lubricants work better than latex condoms with water-based lubricants, and why red meat goes better with red wine and white meat with white wine?
Ferriols-Pavico, Josefina Ma. J. Chem. Educ. 2002, 79, 1217.
Lipids |
Learning Theories |
Alcohols |
Applications of Chemistry
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
Of Magnets and Mechanisms  Edward G. Neeland
Using magnets to demonstrate the electron flow (mechanism) of nucleophilic substitution reactions.
Neeland, Edward G. J. Chem. Educ. 2002, 79, 186.
Magnetic Properties |
Mechanisms of Reactions |
Learning Theories |
Nucleophilic Substitution
Was the Driver Drunk? An Instrumental Methods Experiment for the Determination of Blood Alcohol Content  Jennifer L. Zabzdyr and Sheri J. Lillard
Forensic-based experiment to motivate correct analytical procedures and careful interpretation of data by using gas chromatography with flame ionization detection.
Zabzdyr, Jennifer L.; Lillard, Sheri J. J. Chem. Educ. 2001, 78, 1225.
Chromatography |
Instrumental Methods |
Applications of Chemistry |
Forensic Chemistry |
Quantitative Analysis |
Qualitative Analysis |
Alcohols |
Gas Chromatography
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
Intermediates, Transition States, Butterflies, and Frogs  Trevor M. Kitson
The changes that occur in typical simple SN1 and SN2 reactions are compared to the metamorphoses undergone by caterpillars and tadpoles, respectively.
Kitson, Trevor M. J. Chem. Educ. 2001, 78, 504.
Mechanisms of Reactions |
Reactive Intermediates |
Nucleophilic Substitution
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
It Says in the Books That Ethanol Burns with a Cool Flame  Jay A. Young
An alcohol lab fire with fatal results.
Young, Jay A. J. Chem. Educ. 2000, 77, 1488.
Alcohols
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
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
Computational Investigations for Undergraduate Organic Chemistry: Modeling Markovnikov and anti-Markovnikov Reactions for the Formation of Alkyl Halides and Alcohols  Rita K. Hessley
This paper describes how the early introduction of molecular modeling for the study of reaction mechanisms leading to alcohols from alkenes can increase students' involvement in their own learning and can effectively challenge their misapprehension about memorization.
Hessley, Rita K. J. Chem. Educ. 2000, 77, 794.
Computational Chemistry |
Alcohols |
Molecular Modeling |
Mechanisms of Reactions
Molecular Orbital Animations for Organic Chemistry  Steven A. Fleming, Greg R. Hart, and Paul B. Savage
Introduces the application of highest occupied and lowest unoccupied molecular orbitals (HOMOs and LUMOs) in animated form.
Fleming, Steven A.; Hart, Greg R.; Savage, Paul B. J. Chem. Educ. 2000, 77, 790.
MO Theory |
Molecular Modeling |
Mathematics / Symbolic Mathematics |
Mechanisms of Reactions |
Electrophilic Substitution |
Nucleophilic Substitution
The 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
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
"New" Compounds from Old Plastics: Recycling PET Plastics via Depolymerization. An Activity for the Undergraduate Organic Lab  Don Kaufman, Geoff Wright, Ryan Kroemer, and Josh Engel
This paper describes work done to develop a meaningful undergraduate organic lab activity that illustrates chemistry of the real world while utilizing reactions typically included in the organic lecture and lab. We show how a common plastic can be converted into several compounds using ester hydrolysis and SN2 reactions.
Kaufman, Don; Wright, Geoff; Kroemer, Ryan; Engel, Josh. J. Chem. Educ. 1999, 76, 1525.
Consumer Chemistry |
Synthesis |
Esters |
Nucleophilic Substitution
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
A Puzzling Alcohol Dehydration Reaction Solved by GC–MS Analysis  Michael W. Pelter and Rebecca M. Macudzinski
The reaction of 2-methyl-2-propanol with ~50% sulfuric acid at 100 C yields isobutylene, which reacts further by a "puzzling" reaction. By coupling the GC/MS analysis of the product mixture with their knowledge of the mechanism of alcohol dehydration and alkene reactivity, students are able to identify the major products of this reaction.
Pelter, Michael W.; Macudzinski, Rebecca M. J. Chem. Educ. 1999, 76, 826.
Synthesis |
Microscale Lab |
Mass Spectrometry |
Gas Chromatography |
Alcohols |
Alkenes
Reduction of 2,6-Dimethylcyclohexanone with Sodium Borohydride Revisited: A Correction on the Structural Assignments of the Products, and the Discovery of a Solvent Effect  Bruce A. Hathaway
Changing the solvent from methanol to ethanol produced a different ratio of cis-cis to trans-trans than was reported in the original work. Therefore, a short series of solvents was investigated to determine if there was a solvent effect. The results indicate that as the size and bulk of the solvent increase, the proportion of the trans alcohol product increases.
Hathaway, Bruce A. J. Chem. Educ. 1998, 75, 1623.
Stereochemistry |
NMR Spectroscopy |
Aldehydes / Ketones |
Alcohols
How To Learn and Have Fun with Poly(Vinyl Alcohol) and White Glue  V. de Zea Bermudez, P. Passos de Almeida, and J. Féria Seita
The general behavior of Newtonian, shear-thinning, shear-thickening, thixotropic, negative thixotropic, and viscoelastic fluids is characterized and briefly discussed in terms of existing theoretical models. Whenever possible, examples of these types of fluids taken from everyday life are given for better understanding.
de Zea Bermudez, Verónica; de Almeida, P. Passos; Seita, J. Féria. J. Chem. Educ. 1998, 75, 1410.
Alcohols |
Liquids
Why Do Alcoholic Beverages Have "Legs"?  Todd P. Silverstein
After a sip of wine, "legs" of liquid typically run up and down the inside of the glass for many minutes. This phenomenon stems from the dipole-dipole intermolecular forces that are so important in understanding the physical behavior of aqueous solutions.
Silverstein, Todd P. J. Chem. Educ. 1998, 75, 723.
Noncovalent Interactions |
Aqueous Solution Chemistry |
Learning Theories |
Alcohols |
Hydrogen Bonding
Demonstration Explosion  Lee, Charles "Skip"
A glass carboy containing methanol explodes.
Lee, Charles "Skip" J. Chem. Educ. 1998, 75, 543.
Alcohols
Demonstration Explosion  Charles "Skip" Lee
A glass carboy containing methanol explodes.
Lee, Charles "Skip". J. Chem. Educ. 1998, 75, 543.
Alcohols
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
Mechanism Templates: Lecture Aids for Effective Presentation of Mechanism in Introductory Organic Chemistry  Brian J. McNelis
To promote active student learning of mechanism in introductory organic chemistry, hand-outs have been developed with incomplete structures for reaction processes depicted, which are called mechanism templates. The key to these lecture aids is to provide only enough detail in the diagram to facilitate notetaking, ensuring that these templates are dynamic learning tools that must be utilized by an engaged and alert student.
Brian J. McNelis. J. Chem. Educ. 1998, 75, 479.
Learning Theories |
Mechanisms of Reactions |
Reactions |
Addition Reactions |
Acids / Bases |
Electrophilic Substitution |
Nucleophilic Substitution
Nucleophilic Addition vs. Substituion: A Puzzle for the Organic Laboratory  Ernest F. Silversmith
The chemistry of beta-carbonyl compounds is studied. Beta-carbonyl compounds react with hydrazines to give products with a 5-membered ring containing two nitrogens. The experiment makes students determine whether ethyl 2-acetyl-3-oxobutanoate reacts like a beta-diketone or like a beta-keto ester.
Silversmith, Ernest F. J. Chem. Educ. 1998, 75, 221.
Learning Theories |
Nucleophilic Substitution |
Aldehydes / Ketones |
Esters |
Mechanisms of Reactions
Grignard Synthesis of Various Tertiary Alcohols  T. Stephen Everett
A general Grignard procedure is presented for the synthesis of aliphatic, tertiary alcohols containing six to nine carbons. Without revealing the specific starting materials, students are challenged to identify their unknown products from physical (boiling points, refractive indices) and spectral (infrared O-H, C-H and fingerprint regions) data.
Everett, T. Stephen. J. Chem. Educ. 1998, 75, 86.
IR Spectroscopy |
Alcohols |
Mechanisms of Reactions |
Synthesis
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
The Diels-Alder Reaction of 2,4-Hexadien-1-ol with Maleic Anhydride: A Novel Preparation for the Undergraduate Organic Chemistry Laboratory Course  Keith F. McDaniel and R. Matthew Weekly
The reaction of 2,4-hexadien-1-ol with maleic anhydride provides an excellent exercise for undergraduate laboratory courses. In addition to the expected Diels-Alder reaction, which takes place readily in refluxing toluene, subsequent intramolecular cleavage of the resulting bicyclic anhydride by the pendant hydroxy group generates a lactone. Thus, two important organic reactions can be carried out in a single laboratory session.
McDaniel, Keith F.; Weekley, R. Matthew. J. Chem. Educ. 1997, 74, 1465.
Synthesis |
NMR Spectroscopy |
Molecular Properties / Structure |
Alcohols
Microscale Dehydration of Cyclohexanol Using a Macroreticular Cation Exchange Resin as Catalyst  Harriet P. Moeur, Sharon A. Swatik, and Robert P. Pinnell
In this experiment, cyclohexanol is dehydrated to cyclohexene using Amberlyst 15 macroreticular resin as an acid catalyst. The procedure is carried out with partners, one student using phosphoric acid-sulfuric acid catalyst, the other student using the resin. Yields and ease of manipulation between the two options are compared.
Moeur, Harriet P.; Swatik, Sharon A. ; Pinnell, Robert P. J. Chem. Educ. 1997, 74, 833.
Microscale Lab |
Alcohols |
Catalysis
Old MacDonald Named a Compound: Branched Enynenynols  Dennis Ryan
An imaginary teacher of organic chemistry thinks up some whimsical compounds for his students to name using IUPAC nomenclature rules.
Ryan, Dennis. J. Chem. Educ. 1997, 74, 782.
Learning Theories |
Nomenclature / Units / Symbols |
Alcohols |
Alkenes |
Alkynes |
Molecular Properties / Structure
Catalytic Transfer Hydogenation Reactions for Undergraduate Practical Programs  R. W. Hanson
A brief review of catalytic transfer hydrogenation (CTH) reactions is given. Attention is drawn, particularly, to the utility of ammonium formate as the hydrogen donor in this type of reaction.
Hanson, R. W. J. Chem. Educ. 1997, 74, 430.
Catalysis |
Aldehydes / Ketones |
Alcohols |
Amines / Ammonium Compounds |
Mechanisms of Reactions
Identification of Primary, Secondary, and Tertiary Alcohols: An Experiment in Spectrophotometry, Organic Chemistry, and Analytical Chemistry  I. A. Leenson
A simple method is presented that enables students to distinguish in a few minutes between primary, secondary and tertiary alkyl alcohols. This method is based on peculiarities of absorption spectra in the near-UV region of alkyl nitrites, the products of alcohol nitrosation.
Leenson, I. A. J. Chem. Educ. 1997, 74, 424.
Alcohols |
Molecular Properties / Structure |
Spectroscopy |
UV-Vis Spectroscopy
The TCICA Test for Distinguishing Primary and Secondary Alcohols  Gene A. Hiegel and Afshin K. Chaharmohal
Simple primary and secondary alcohols can easily be distinguished by their rate of oxidation with trichloroisocyanuric acid (TCICA). The TCICA test is conducted by adding the unknown to a solution of TCICA in acetonitrile containing hydrochloric acid and measuring the time for a precipitate to form. Primary alcohols react slowly and secondary alcohols react rapidly.
Hiegel, Gene A.; Chaharmohal, Afshin K. J. Chem. Educ. 1997, 74, 423.
Alcohols |
Molecular Properties / Structure
The Acid Catalyzed Dehydration of an Isomeric 2-Methylcyclohexanol Mixture: A Kinetic and Regiochemical Study of the Evelyn Effect  John J. Cawley and Patrick E. Linder
This paper details an experiment which serves as an introduction to organic laboratory research. The reaction is the dehydration of a cis, trans mixture of 2-methylcyclohexanols. At intervals of times the reactant mixture is sampled for the cis and trans reactants. At those same intervals of times the receiver flasks of product cyclohexanes being collected are changed, such that sequential fractions of material are obtained.
Cawley, John J.; Linder, Patrick E. J. Chem. Educ. 1997, 74, 102.
Catalysis |
Kinetics |
Alcohols |
Stereochemistry
Visualizing the SN2 Inversion  Rosan, Alan M.
Slight modification to the construction of the model presented.
Rosan, Alan M. J. Chem. Educ. 1996, 73, A228.
Nucleophilic Substitution |
Mechanisms of Reactions
Following Microscale Organic Reactions Using FT-IR  Janice Ems-Wilson
This article describes an experiment that encourages discussion of carbohydrate chemistry in terms of reaction mechanisms, conformational analysis, and spectroscopy. The specific experiment involves the preparation of the bis(acetonide) of D-(+)-mannose.
Ems-Wilson, Janice. J. Chem. Educ. 1996, 73, A170.
Microscale Lab |
Carbohydrates |
Mechanisms of Reactions |
Conformational Analysis |
Spectroscopy |
Synthesis |
Aldehydes / Ketones |
Alcohols
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 Mnemonic for the Inositols   Terence J. Painter
The mnemonic derives from the mythical tale of Scylla and Charybdis in Homer's Odyssey. It takes the form of an imaginary headline in a newspaper: SCYLLA MEETS CHARYBDIS - EPIC NEWS MUCH ALARMS SICILY.
Painter, Terence J. J. Chem. Educ. 1996, 73, 949.
Alcohols
The Neglected Element in Sophomore Organic Chemistry  Kelly L. Bieda and Suzzane T. Purrington
There are many aspects of organic chemistry that would benefit from the inclusion of organofluorine chemistry. The properties of fluorine help in the clarification of many topics such as bond strength, leaving groups, substitution reactions, radical reactions, polymers, pharmaceuticals, and enzymes.
Bieda, Kelly L.; Purrington, Suzanne T. J. Chem. Educ. 1996, 73, 754.
Drugs / Pharmaceuticals |
Enzymes |
Polymerization |
Nucleophilic Substitution
The Esterification of Trifluoroacetic Acid: A Variable Temperature NMR Kinetics Study  Thomas N. Gallaher, David A. Gaul, and Serge Schreiner
This paper describes an addition to a previously published experiment in which NMR is used to follow the kinetics of the reaction of trifluoroacetic acid with alcohols. A variable temperature accessory is used to determine the energy of activation and reaction order with respect to the alcohol concentration.
Gallaher, Thomas N.; Gaul, David A.; Schreiner, Serge. J. Chem. Educ. 1996, 73, 465.
Kinetics |
NMR Spectroscopy |
Alcohols |
Esters
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
Enzymatic Resolution of (+/-)-Menthol Using Transesterification with Methyl (2R)-(+)-2-Chloropropanoate: A Biocatalyzed Reaction Studied by NMR Spectroscopy and Polarimetry for an Advanced Undergraduate Project in Modern Organic Chemistry  C. Poiré, C. Rabiller, C. Chon, and P. Hudhomme
Lipase from Candida rugosa is used as an efficient biocatalyst for the kinetic resolution of (+/-)-Menthol. Methyl (2R)-(+)-2-chloropropanoate is chosen as an acyl donor for the transesterification reaction of menthol.
Poiré, C.; Rabiller, C.; Chon, C.; Hudhomme, P. J. Chem. Educ. 1996, 73, 93.
Bioorganic Chemistry |
Alcohols |
Catalysis |
Enzymes |
NMR Spectroscopy
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
A Ternary Phase Diagram for a Less Hazardous System  Barbara A. Udale and John D. Wells
Using a n-propanol-n-heptane-water system to generate data for construction of a ternary phase diagram.
Udale, Barbara A.; Wells, John D. J. Chem. Educ. 1995, 72, 1106.
Phases / Phase Transitions / Diagrams |
Aqueous Solution Chemistry |
Alcohols |
Alkanes / Cycloalkanes |
Solutions / Solvents
Animation of Imaginary Frequencies at the Transition State  Higgins, Robert H.
176. Computer simulations of reactions mechanisms using HyperChem and ChemPlus software.
Higgins, Robert H. J. Chem. Educ. 1995, 72, 703.
Mechanisms of Reactions |
Molecular Properties / Structure |
Reactive Intermediates |
Computational Chemistry |
Nucleophilic Substitution
"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
Propylene Oxide Addition to Hydrochloric Acid: A Textbook Error  Rebecca E. Phillips and Robert L. Soulen
Procedure illustrating organic synthesis involving propylene oxide, a major industrial chemical, and important features of the SN1 and SN2 mechanisms (there are some differences on how this reaction is described in several organic textbooks).
Phillips, Rebecca E.; Soulen, Robert L. J. Chem. Educ. 1995, 72, 624.
Synthesis |
Mechanisms of Reactions |
Nucleophilic Substitution
A Model To Show the SN2 Inversion  Sands, Richard D.; Dressman, Devin C.; Wyatt, Shawn R.
Paper model illustrating the SN2 inversion.
Sands, Richard D.; Dressman, Devin C.; Wyatt, Shawn R. J. Chem. Educ. 1995, 72, 428.
Mechanisms of Reactions |
Nucleophilic Substitution |
Molecular Modeling
Hydrogen-Bonding Equilibrium in Phenol Analyzed by NMR Spectroscopy  Lessinger, Leslie
Experimental procedure for determining the equilibrium constant for the hydrogen-bonding equilibrium of phenol in carbon tetrachloride solution; data and analysis included.
Lessinger, Leslie J. Chem. Educ. 1995, 72, 85.
Equilibrium |
Noncovalent Interactions |
NMR Spectroscopy |
Hydrogen Bonding |
Aromatic Compounds |
Alcohols
Chart for Deciding Mechanism for Reaction of Alkyl Halide with Nucleophile/Base  McClelland, Bruce W.
The decision chart offered here is based upon the well-known and accepted characteristics of the reaction system mechanisms described in typical introductory organic chemistry textbooks.
McClelland, Bruce W. J. Chem. Educ. 1994, 71, 1047.
Mechanisms of Reactions |
Nucleophilic Substitution
Chemical Magic: Polymers from a Nonexistent Monomer  Seymour, Raymond B.; Kauffman, George B.
Synthesis, properties, and applications of polyvinyl alcohol and related polymers.
Seymour, Raymond B.; Kauffman, George B. J. Chem. Educ. 1994, 71, 582.
Polymerization |
Alcohols
The Hydration of 1-Hexene and 1-Hexyne  Touchette, Kim M.; Weiss, Hilton M.; Rozenberg, Daniel
The sulfuric acid-catalyzed hydration of 1-hexene and 1-hexyne.
Touchette, Kim M.; Weiss, Hilton M.; Rozenberg, Daniel J. Chem. Educ. 1994, 71, 534.
Alkynes |
Alkenes |
Alcohols |
Catalysis |
Synthesis
The Dehydration of 2-Methylcyclohexanol Revisited: The Evelyn Effect  Todd, David
Modification to an earlier procedure that allows students to observe the results of a hydride shift mechanism.
Todd, David J. Chem. Educ. 1994, 71, 440.
Alcohols |
Mechanisms of Reactions |
Gas Chromatography |
Alkenes |
Elimination Reactions
A New Approach To Teaching Organic Chemical Mechanisms  Wentland, Stephen H.
Describing the mechanisms of organic reactions using five simple steps or operations.
Wentland, Stephen H. J. Chem. Educ. 1994, 71, 3.
Mechanisms of Reactions |
Addition Reactions |
Nucleophilic Substitution |
Electrophilic Substitution |
Elimination Reactions |
Resonance Theory |
Molecular Properties / Structure
Separation of methylene blue and fluorescein: A microscale undergraduate experiment in column chromatography   Svoronos, Paris; Sarlo, Edward
A simple microscale column chromatography experiment that offers a student-friendly introduction to the procedure.
Svoronos, Paris; Sarlo, Edward J. Chem. Educ. 1993, 70, A158.
Chromatography |
Alcohols |
Microscale Lab
Microscale yeast mediated enantiospecific reduction of vanillin, and the absolute configuration of (-)-(R)-[alpha]-deuteriovanillyl alcohol: A bioorganic chemistry experiment   Lee, Moses
An experiment is introduced to a sophomore chemistry course that demonstrates the effeciency and enantiospecificity of microbial/enzyme-mediated reactions and the use of NMR methods in determining the optical activity and absolute configuration of chiral alcohols.
Lee, Moses J. Chem. Educ. 1993, 70, A155.
Enantiomers |
Alcohols |
Bioorganic Chemistry |
Chirality / Optical Activity |
NMR Spectroscopy |
Microscale Lab
GC/MS experiments for the organic chemistry laboratory: I. E2 elimination of 2-bromo-2-methyloctane   Novak, Michael; Heinrich, Julie; Martin, Kristy A.; Green, John; Lytle, Scott
Two capillary GC/MS experiments that were designed for and tested in a sophomore organic laboratory course.
Novak, Michael; Heinrich, Julie; Martin, Kristy A.; Green, John; Lytle, Scott J. Chem. Educ. 1993, 70, A103.
Gas Chromatography |
Alkenes |
Alkanes / Cycloalkanes |
Alcohols |
Elimination Reactions |
Synthesis
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
The aromatic substitution game  Zanger, Murray; Gennaro, Alfonso R.; McKee, James R.
This paper describes a game used to bring attention to the need for students to reconsider substitution theories learned in earlier chapters.
Zanger, Murray; Gennaro, Alfonso R.; McKee, James R. J. Chem. Educ. 1993, 70, 985.
Nucleophilic Substitution |
Synthesis
Liquid chromatographic determination of malic and lactic acids in wine following malolactic fermentation  Brogley, John; Mullick, Joydip; Quigley, Michael N.
This lab takes advantage of wine's unique position in society to invite students to participate in an engaging actvity.
Brogley, John; Mullick, Joydip; Quigley, Michael N. J. Chem. Educ. 1993, 70, 507.
Consumer Chemistry |
Food Science |
Acids / Bases |
Chromatography |
Quantitative Analysis |
Alcohols |
Applications of Chemistry
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
Microscale elimination reactions: Experiments for organic chemistry using the small scale approach  Gilow, Helmuth M.
Procedure illustrating E1 and E2 reactions.
Gilow, Helmuth M. J. Chem. Educ. 1992, 69, A265.
Microscale Lab |
Reactions |
Elimination Reactions |
Alcohols |
Alkenes |
Catalysis
Solubility of alcohols  Corkern, Walter H.; Munchausen, Linda L.
A very visible demonstration of a gradual progression of a range of solubility, using an alcohol, a dye, and water in a petri dish.
Corkern, Walter H.; Munchausen, Linda L. J. Chem. Educ. 1992, 69, 928.
Alcohols |
Precipitation / Solubility
Pinacol rearrangement of cyclopentylcyclohexane-1,1'-diol revisited.  Sands, Richard D.
Two cyclic diols are treated with ice-cold boron trifluoride etherate to make rearrangement instead of diene formation the major product.
Sands, Richard D. J. Chem. Educ. 1992, 69, 667.
Mechanisms of Reactions |
Alcohols |
Aldehydes / Ketones
Estimation of blood-alcohol concentration.  Labianca, Dominick A.
This article focuses on the answers to questions regarding blood alcohol levels, including estimates of % BAC, effects of beverage type and food consumption, and biochemical considerations.
Labianca, Dominick A. J. Chem. Educ. 1992, 69, 628.
Alcohols |
Applications of Chemistry
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
A source of isomer-drawing assignments  Kjonaas, Richard A.
A comprehensive source from which instructors can choose a wide variety of good isomer drawing examples to use as homework assignments and exam questions.
Kjonaas, Richard A. J. Chem. Educ. 1992, 69, 452.
Stereochemistry |
Alcohols |
Alkanes / Cycloalkanes |
Alkenes |
Aldehydes / Ketones |
Ethers |
Esters |
Alkynes
Enhancing interest in organic chemistry. Part I. Relating redolence in organic chemistry class.  Smith, Terrill D.
The author supplies a list of compounds that can be passed around in class for students to guess their origin from an odor.
Smith, Terrill D. J. Chem. Educ. 1992, 69, 233.
Esters |
Aldehydes / Ketones |
Alcohols |
Phenols
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
The water solubility of 2-butanol: A widespread error  Alger, Donald B.
There seems to be widespread misreporting of the solubility of 2-butanol. This misreporting is an example of the importance of consulting original sources.
Alger, Donald B. J. Chem. Educ. 1991, 68, 939.
Alcohols |
Aldehydes / Ketones |
Precipitation / Solubility
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
A study of the Lucas test  Kjonaas, Richard A.; Riedford, Bernie A.
These authors performed the Lucas test on a number of alcohols and discuss the problems associated with the Lucas test's detection of secondary alcohols.
Kjonaas, Richard A.; Riedford, Bernie A. J. Chem. Educ. 1991, 68, 704.
Alcohols |
Qualitative Analysis
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
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
A convenient synthesis of 3,4-pentadien-1-ol from 3-butyn-1-ol: Spectral analysis and unusual durability of the allene moiety  Price, William A.; Patten, Timothy E.
Description of a convenient synthesis of 3,4-pentadien-1-ol from 3-butyn-1-ol: Spectral analysis and unusual durability of the allene moiety.
Price, William A.; Patten, Timothy E. J. Chem. Educ. 1991, 68, 256.
Synthesis |
Alcohols |
Alkenes |
NMR Spectroscopy
Organic Nomenclature (Lampman, Gary)  Damey, Richard F.
An interactive tutorial / drill for naming organic compounds.
Damey, Richard F. J. Chem. Educ. 1990, 67, A220.
Nomenclature / Units / Symbols |
Enrichment / Review Materials |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes |
Ethers |
Alcohols |
Amines / Ammonium Compounds |
Phenols
An operationally simple hydroboration-oxidation experiment  Kabalka, George W.; Wadgaonkar, Prakash P.; Chatla, Narayana
The reactions involve the use of in situ generated diborane as the hydroborating reagent and sodium perborate as the oxidizing agent to convert cyclopentene to cyclopentanol.
Kabalka, George W.; Wadgaonkar, Prakash P.; Chatla, Narayana J. Chem. Educ. 1990, 67, 975.
Synthesis |
Mechanisms of Reactions |
Alkenes |
Alcohols
Cobaloximes as vehicles for college teaching  Brown, T. M.; Dronsfield, A. T.; Cooksey, C. J.; Crich, D.
Cobaloximes are probably the most accessible and "least nasty" of all organometallic compounds, are highly colored, exhibit unusual oxidation states, demonstrate a vivid nucleophilic attack, and lend themselves to chromatographic investigation without the need for UV light.
Brown, T. M.; Dronsfield, A. T.; Cooksey, C. J.; Crich, D. J. Chem. Educ. 1990, 67, 973.
Coordination Compounds |
Organometallics |
Nucleophilic Substitution
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
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
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
From cyclohexanol to diethyl hexanedioate (diethyl adipate): A two-step synthetic sequence for microscale organic laboratory   Wintner, Claude E.; Gray, Christina A.
The authors have developed a two-step microscale sequence from cyclohexanol through adipic acid to diethyl adipate that has proved to be successful in the first year organic laboratory.
Wintner, Claude E.; Gray, Christina A. J. Chem. Educ. 1990, 67, 341.
Microscale Lab |
Synthesis |
Alcohols
Steric course of lactonization in the deamination of glutamic acid: An organic mechanism experiment  Markgraf, J. Hodge; Davis, Howard A.
The stereochemical consequences of a reaction at a chiral center offer a unique way to distinguish among mechanistic hypothesis.
Markgraf, J. Hodge; Davis, Howard A. J. Chem. Educ. 1990, 67, 173.
Mechanisms of Reactions |
Stereochemistry |
Alcohols
Drying ethanol by azeotropic distillation  Mattson, Guy; Hertel, George R.
The commercial process for producing absolute ethanol can be used as a basis for an unusual homework or take-home exam problem.
Mattson, Guy; Hertel, George R. J. Chem. Educ. 1990, 67, 46.
Separation Science |
Alcohols
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
Getting away from the cookbook in the organic laboratory  Potter, Neil H.; McGrath, Thomas F.
An organic laboratory program in which students perform traditional experiments during the first semester followed by intensive independent work the second semester.
Potter, Neil H.; McGrath, Thomas F. J. Chem. Educ. 1989, 66, 666.
Synthesis |
Alcohols
Safety Warning: Uncontrolled Reaction  Smith, David H.
An experimental procedure published recently led to a potentially serious accident.
Smith, David H. J. Chem. Educ. 1989, 66, 359.
Atomic Spectroscopy |
Alcohols
A series of synthetic organic experiments demonstrating physical organic principles  Sayed, Yousry; Ahlmark, Chris A.; Martin, Ned H.
The sequence of reactions described here incorporates several common synthetic organic transformations involving alkenes, alcohols, alkyl halides, and ketones that demonstrate some important principles of physical organic chemistry.
Sayed, Yousry; Ahlmark, Chris A.; Martin, Ned H. J. Chem. Educ. 1989, 66, 174.
Synthesis |
Alkenes |
Alcohols |
Aldehydes / Ketones |
Reactions
Trifluoroacetylation of unknown alcohols: An integrated microscale organic experiment using spectroscopic methods  Piers, Kenneth; Hsung, Richard
The authors have found that trifluoroacetylation of unknown alcohols is a fast, clean, easily performed microscale experiment that integrates a number of aspects of laboratory work, viz. synthesis, isolation, characterization, spectroscopic measurement, and interpretation, and unknown identification.
Piers, Kenneth; Hsung, Richard J. Chem. Educ. 1989, 66, 90.
Alcohols |
Microscale Lab |
Qualitative Analysis |
NMR Spectroscopy |
IR Spectroscopy
A conversion of methyl ketones into acetylenes: A project for a problem oriented or microscale organic chemistry course  Silveira, Augustine, Jr.; Orlando, Steven C.
The authors present their adaptation of an open-ended project on the conversion of methyl ketones into acetylenes for the microscale lab and describe its pedagogic utility.
Silveira, Augustine, Jr.; Orlando, Steven C. J. Chem. Educ. 1988, 65, 630.
Microscale Lab |
Aldehydes / Ketones |
Synthesis |
Nucleophilic Substitution |
Gas Chromatography
Undergraduate experiments with a long-lived radical (Fremy's salt): Synthesis of 1,4-benzoquinones by degradative oxidation of p-hydroxybenzyl alcohols  Morey, J.
The long-lived, stable radical described in this article can be prepared and stored for several months and therefore is an excellent basis for a series of experiments that the author designed for his class.
Morey, J. J. Chem. Educ. 1988, 65, 627.
Aqueous Solution Chemistry |
Free Radicals |
Alcohols |
Aromatic Compounds
The SHOP process: An example of industrial creativity  Reuben, Bryan; Wittcoff, Harold
The Shell Higher Olefins Process is probably the most remarkable industrial chemical process to have been developed in the past decade; this article highlights the process.
Reuben, Bryan; Wittcoff, Harold J. Chem. Educ. 1988, 65, 605.
Industrial Chemistry |
Surface Science |
Alcohols |
Polymerization |
Applications of Chemistry |
Fatty Acids
The biochemistry of brewing   Bering, Charles L.
There are few topics that hold the attention of students as much as the one presented in this paper.
Bering, Charles L. J. Chem. Educ. 1988, 65, 519.
Biological Cells |
Carbohydrates |
Applications of Chemistry |
Alcohols |
Metabolism |
Enzymes |
Biotechnology |
Molecular Biology |
Consumer Chemistry
Incorporation of consumer products in the teaching of analytical chemistry   Lieu, Van T.; Kalbus, Gene E.
A development and selection of a number of experiments involving the use of common consumer products for incorporation into quantitative and instrumental analysis laboratories.
Lieu, Van T.; Kalbus, Gene E. J. Chem. Educ. 1988, 65, 207.
Applications of Chemistry |
Alcohols |
Acids / Bases |
Food Science |
Consumer Chemistry |
Quantitative Analysis |
Instrumental Methods
Organic lecture demonstrations  Silversmith, Ernest F.
Organic chemistry may not be known for its spectacular, attention getting chemical reactions. Nevertheless, this author describes a few organic chemistry reactions that put points across and generate interest. This article provides a convenient sources of demonstrations and urges others to add to the collection. Demonstrations concerning: carbohydrates, spectroscopy, proteins, amines, carbohydrates, carboxylic acids, and much more.
Silversmith, Ernest F. J. Chem. Educ. 1988, 65, 70.
Molecular Properties / Structure |
Nucleophilic Substitution |
Acids / Bases |
Physical Properties |
Alkenes |
Stereochemistry |
Enantiomers |
Chirality / Optical Activity |
Aldehydes / Ketones |
Alcohols
Determination of methanol in gasoline by gas chromatography: A laboratory experiment  Tackett, Stanford L.
Determining the methanol in gasoline by gas chromatography without pretreating the samples.
Tackett, Stanford L. J. Chem. Educ. 1987, 64, 1059.
Quantitative Analysis |
Alcohols |
Gas Chromatography
Two working models for the SN2 mechanism  Anderson, Martin M.
Design of an articulated physical model demonstrating the mechanism of the SN2 reaction.
Anderson, Martin M. J. Chem. Educ. 1987, 64, 1023.
Nucleophilic Substitution |
Mechanisms of Reactions |
Molecular Modeling
A problem involving organic qualitative analysis  Silvert, D. J.
Five different organic compounds are to be identified from the result of three simple qualitative tests on each unknown (dichromate, DNPH, and iodoform tests).
Silvert, D. J. J. Chem. Educ. 1987, 64, 971.
Qualitative Analysis |
Alcohols |
Aldehydes / Ketones
Characterizing a tetrahedral intermediate in an acyl transfer reaction: An undergraduate 1H NMR demonstration  Rzepa, Henry S.; Lobo, Ana M.; Marques, M. Matilde; Prabhakar, Sundaresan
A simple experiment involving the detection by 1H NMR spectroscopy of a stable intermediate formed by nucleophilic attack and its characterization as a chiral species.
Rzepa, Henry S.; Lobo, Ana M.; Marques, M. Matilde; Prabhakar, Sundaresan J. Chem. Educ. 1987, 64, 725.
NMR Spectroscopy |
Nucleophilic Substitution |
Chirality / Optical Activity
Molecular structure: Property relationships  Seybold, Paul G.; May, Michael; Bagal, Ujjvala A.
How molecular structure can be represented mathematically and how this can lead to a better understanding of the connection between molecular structures and properties.
Seybold, Paul G.; May, Michael; Bagal, Ujjvala A. J. Chem. Educ. 1987, 64, 575.
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Alcohols
The reactivity selectivity principle: Should it ever be used?  Buncel, Erwin; Wilson, Harold
Applications and failures of the reactivity selectivity principle; quantitative aspects of the reactivity selectivity principle; and rationalization of reactivity selectivity principle failures.
Buncel, Erwin; Wilson, Harold J. Chem. Educ. 1987, 64, 475.
Mechanisms of Reactions |
Free Radicals |
Carbocations |
Nucleophilic Substitution
Spectroscopic analysis using the near-infrared region of the electromagnetic spectrum  Crandall, Elbert W.
Review of the use of near-IR to study simple compounds (amines, hydroxyl, and carbonyl compounds) and polymers.
Crandall, Elbert W. J. Chem. Educ. 1987, 64, 466.
Spectroscopy |
IR Spectroscopy |
Amines / Ammonium Compounds |
Alcohols |
Molecular Properties / Structure
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
Concerning dehydration of 2-methycyclohexanol  Feigenbaum, A.
One half of class dehydrates 2-methycyclohexanol, the other half dehydrates 1-methycyclohexanol; gas chromatography retention times are then compared for the two product mixtures.
Feigenbaum, A. J. Chem. Educ. 1987, 64, 273.
Alcohols |
Alkenes |
Stereochemistry |
Constitutional Isomers |
Gas Chromatography
The energy relationships of corn production and alcohol fermentation  Van Koevering, Thomas E.; Morgan, Michael D.; Younk, Thomas J.
The production of alcohol from corn lends itself well to illustrating the practical applications of scientific principles that deal with energy transformations and inefficiencies.
Van Koevering, Thomas E.; Morgan, Michael D.; Younk, Thomas J. J. Chem. Educ. 1987, 64, 11.
Natural Products |
Applications of Chemistry |
Plant Chemistry |
Green Chemistry |
Alcohols |
Calorimetry / Thermochemistry |
Photosynthesis
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
An experiment in forensic chemistry: The Breathalyzer  Timmer, William C.
This note describes a simple experiment, suitable for a quantitative analysis course, that illustrates the chemistry of the breath alcohol test.
Timmer, William C. J. Chem. Educ. 1986, 63, 897.
Forensic Chemistry |
Alcohols |
Applications of Chemistry
Michael addition and aldol condensation: A simple teaching model for organic laboratory  Garcia-Raso, A.; Garcia-Raso, J.; Sinisterra, J. V.; Mestres, R.
Three experiments are presented in this paper: Michael addition; Michael addition followed by aldol addition; and Michael addition followed by aldol condensation.
Garcia-Raso, A.; Garcia-Raso, J.; Sinisterra, J. V.; Mestres, R. J. Chem. Educ. 1986, 63, 443.
Addition Reactions |
Aldehydes / Ketones |
Alcohols
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
Optical projection experiments to demonstrate new curricula contents   Perina, Ivo
Demonstration of experiments by optical projection compared with classic demonstration of experiments has a number of advantages.
Perina, Ivo J. Chem. Educ. 1986, 63, 344.
Alcohols |
Enzymes |
Atmospheric Chemistry
Reduction of cyclohexanone with sodium borohydride in aqueous alkaline solution: a beginning organic chemistry experiment  Hudak, Norman J.; Sholes, Anne H.
A beginning organic chemistry experiment that involves the reduction of cyclohexanone with sodium borohydride in aqueous alkaline solution.
Hudak, Norman J.; Sholes, Anne H. J. Chem. Educ. 1986, 63, 161.
Alkanes / Cycloalkanes |
Aqueous Solution Chemistry |
Acids / Bases |
Alcohols
Acetylation of an unknown alcohol: An introductory 1H-NMR experiment  Branz, Stephen E.
Students use NMR analysis to identify the acetylation product of an unknown alcohol.
Branz, Stephen E. J. Chem. Educ. 1985, 62, 899.
Alcohols |
NMR Spectroscopy
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
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
Explosive isopropanol  Bonafede, Julio Dante
Relates an explosion due to the formation of peroxides.
Bonafede, Julio Dante J. Chem. Educ. 1984, 61, 652.
Alcohols
Butanol safety hazard  Sharpless, T. W.
Distillation of an aged sample of 2-butanol led to an explosion resulting from the presence of hydroperoxide.
Sharpless, T. W. J. Chem. Educ. 1984, 61, 476.
Alcohols
Analysis of alcohols  McCullough, Brother Thomas
Identifying unknown alcohols using boiling point and viscosity measurements.
McCullough, Brother Thomas J. Chem. Educ. 1984, 61, 68.
Alcohols |
Physical Properties |
Qualitative Analysis
The determination of the stereochemistry of erythro-1,2-diphenyl-1,2-ethanediol: an undergraduate organic experiment  Rowland, Alex T.
The author describes a successful experiment that has been conducted by first-year organic chemistry students which illustrates the power of H NMR spectroscopy in a configuration determination.
Rowland, Alex T. J. Chem. Educ. 1983, 60, 1084.
Phenols |
Alcohols |
NMR Spectroscopy |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
The determination of 1-octanol/water partition ratios: an organic chemistry laboratory experiment  Umland, Jean B.
An organic chemistry laboratory experiment in the determination of 1-octanol/water partition ratios.
Umland, Jean B. J. Chem. Educ. 1983, 60, 1081.
Alcohols
Aromatic substitution reactions: when you've said ortho, meta, and para you haven't said it all  Traynham, James G.
The author presents a range of examples for nucleophilic, electrophilic, and free-radical reactions where the ipso is an important, predominant, or even exclusive site of reaction.
Traynham, James G. J. Chem. Educ. 1983, 60, 937.
Nucleophilic Substitution |
Electrophilic Substitution |
Free Radicals |
Diastereomers |
Stereochemistry |
Reactions
Ethanol from corn: one route to gasohol  Maslowsky, Edward, Jr.
The experiment in this article illustrates the preparation of ethanol through the action of enzymes and yeast in whole kernel corn. The purpose is to illustrate as closely as practical the method used either industrially or on the farm to convert corn into ethanol, while a second is to illustrate distillation.
Maslowsky, Edward, Jr. J. Chem. Educ. 1983, 60, 752.
Applications of Chemistry |
Green Chemistry |
Alcohols |
Separation Science
A quantitative gas chromatographic ethanol determination: a contemporary analytical experiment  Leary, James J.
This note describes a gas chromatographic experiment for the quantitative determination of volume percent ethanol in water ethanol solutions.
Leary, James J. J. Chem. Educ. 1983, 60, 675.
Gas Chromatography |
Quantitative Analysis |
Water / Water Chemistry |
Alcohols
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
A chemistry laboratory project to develop thinking and writing skills  Goodman, W. Daniel; Bean, John C.
The "Ester Project" requires students to carry out an independent investigation of the synthesis of one or more alphatic esters and to present their research in the form of professional papers. The students, as a group, judge each paper for the quality of research and the quality of writing according to criteria and methods devised jointly by the students and the instructor.
Goodman, W. Daniel; Bean, John C. J. Chem. Educ. 1983, 60, 483.
Alcohols |
Esters
A reinvestigation of the synthesis of 4-methyl-3-heptanol  Hoffman, Robert V.; Alexander, M. D.; Buntain, Gregory; Hardenstein, Richard; Mattox, Cynthia; McLaughlin, Susan; McMinn, Denise; Spray, Scott; White, Steven
A previously reported laboratory may have reported gas chromatographic separation of the 4-methyl-3-heptanol diastereomiers in error. The side reactions in the Grignard reaction account for the observed results.
Hoffman, Robert V.; Alexander, M. D.; Buntain, Gregory; Hardenstein, Richard; Mattox, Cynthia; McLaughlin, Susan; McMinn, Denise; Spray, Scott; White, Steven J. Chem. Educ. 1983, 60, 78.
Hormones |
Alcohols |
Grignard Reagents |
IR Spectroscopy |
NMR Spectroscopy |
Aldehydes / Ketones |
Gas Chromatography |
Synthesis |
Natural Products
A modification of the copper catalysis demonstration apparatus  Olsen, Edwin S.; Ashmore, R. E.
A modification to an earlier device for illustrating the oxidation of alcohols to carbonyl compounds over a copper catalyst.
Olsen, Edwin S.; Ashmore, R. E. J. Chem. Educ. 1982, 59, 1042.
Catalysis |
Alcohols |
Laboratory Equipment / Apparatus
Ketone synthesis using household bleach  Perkins, Robert A.; Chau, Felix
Household bleach is used to synthesize several different ketones from alcohols.
Perkins, Robert A.; Chau, Felix J. Chem. Educ. 1982, 59, 981.
Synthesis |
Aldehydes / Ketones |
Alcohols
Student preparation of alkanols from alkenes  McKee, J. R.; Kauffman, J. M.
The hydration of 1-hexene to form 2-hexanol demonstrates Markovnikov addition, produces a higher yield of alcohol, and starts with a less expensive alkene than cyclohexene hydrations.
McKee, J. R.; Kauffman, J. M. J. Chem. Educ. 1982, 59, 695.
Alcohols |
Alkenes |
Mechanisms of Reactions |
Addition Reactions
Organic lecture demonstrations of common-ion effect, ionizing power of solvents, and first-order reaction kinetics  Danen, Wayne C.; Blecha, Sr. M. Therese
The hydrolysis of tert-butyl chloride is the basis of three demonstrations which each illustrate an important principle of organic chemistry: the common-ion or mass law effect, the effect of changing the ionizing power of a solvent on a solvolysis reaction, and the collecting and plotting of data to illustrate a first-order reaction.
Danen, Wayne C.; Blecha, Sr. M. Therese J. Chem. Educ. 1982, 59, 659.
Aqueous Solution Chemistry |
Solutions / Solvents |
Nucleophilic Substitution |
Kinetics |
Rate Law
An 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
Preparation of solid derivatives by differential scanning calorimetry  Crandall, E. W.; Pennington, Maxine
Derivatives of alcohols, amines, phenols, aldehydes, ketones, and haloalkanes are prepared and their phase transitions observed using a differential scanning calorimeter.
Crandall, E. W.; Pennington, Maxine J. Chem. Educ. 1980, 57, 824.
Phases / Phase Transitions / Diagrams |
Aldehydes / Ketones |
Alcohols |
Amines / Ammonium Compounds |
Phenols |
Physical Properties |
Calorimetry / Thermochemistry
Nucleophilic substitution reactions: Modifications and an extension  Newton, T. A.; Warren, H. W.
Modifications to a procedure comparing the reaction of n-butyl and t-butyl alcohol with equimolar amounts of HCl and HBr.
Newton, T. A.; Warren, H. W. J. Chem. Educ. 1980, 57, 747.
Nucleophilic Substitution |
Reactions
Gas chromatographic determination of methyl salicylate in rubbing alcohol: An experiment employing standard addition  Van Atta, Robert E.; Van Atta, R. Lewis
Provides an exercise in standard addition as applied to the gas chromatographic analysis of the methyl salicylate in wintergreen rubbing alcohol.
Van Atta, Robert E.; Van Atta, R. Lewis J. Chem. Educ. 1980, 57, 230.
Alcohols |
Gas Chromatography |
Instrumental Methods
Allyl alcohol plant stream analysis: Relating industrial chemistry to the undergraduate laboratory  Bard, James R.; Sandoval, Antonio A.
Exercise that seeks to familiarize students with an industrial chemical process using a reaction not normally found in undergraduate textbooks and to broaden appreciation of NMR spectroscopy to include its analytical capabilities and limitations by showing how NMR could be used for analysis of a typical plant stream.
Bard, James R.; Sandoval, Antonio A. J. Chem. Educ. 1980, 57, 218.
Alcohols |
Industrial Chemistry |
Applications of Chemistry |
NMR Spectroscopy
Drugs in the chemistry laboratory: The conversion of acetaminophen into phenacetin  Volker, Eugene J.; Pride, Ernest; Hough, Charles
The phenolic alcohol group of acetaminophen is alkylated with ethyl iodide using the basic catalyst K2CO3.
Volker, Eugene J.; Pride, Ernest; Hough, Charles J. Chem. Educ. 1979, 56, 831.
Nonmajor Courses |
Applications of Chemistry |
Medicinal Chemistry |
Drugs / Pharmaceuticals |
Synthesis |
Catalysis |
Phenols |
Alcohols
A dynamic carbon model capable of showing changes in hybridization  Fountain, K. R.
It is possible to construct a simple dynamic model of a carbon atom that demonstrates the Walden inversion, the SN1 reaction, and when joined with another units like itself demonstrates the full spectrum of elimination reactions.
Fountain, K. R. J. Chem. Educ. 1979, 56, 379.
Molecular Modeling |
Nucleophilic Substitution |
Elimination Reactions
Chemical toxicology. Part I. Organic compounds  Carter, D. E.; Fernando, Quintus
General principles of toxicology, and particular consideration of aliphatics, aromatic, and halogenated hydrocarbons; alcohols, aldehydes, esters, ethers, and ketones; sulfides, mercaptans, and carbon disulfide; nitrogen-containing compounds; and carcinogens.
Carter, D. E.; Fernando, Quintus J. Chem. Educ. 1979, 56, 284.
Toxicology |
Alcohols |
Aldehydes / Ketones |
Esters |
Ethers |
Aromatic Compounds |
Amines / Ammonium Compounds |
Lipids
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 new synthesis of tertiary alkyl N-aryl-carbamates from isocyanates  Bailey, William J.; Griffith, James R.
A simple, convenient, and fast procedure has been developed for the synthesis of tertiary alkyl N-acrylcarbamate from phenyl and 1-naphthyl isocyanates as solid derivatives of tertiary alcohols by the use of lithium tertiary alkoxides as catalysts.
Bailey, William J.; Griffith, James R. J. Chem. Educ. 1978, 55, 809.
Catalysis |
Alcohols |
Synthesis
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
Oxidation of primary alcohols to aldehydes with pyridinium chlorochromate. An organic chemistry experiment  Glaros, George
This organic chemistry experiment addresses a common misconception about aldehyde reactions.
Glaros, George J. Chem. Educ. 1978, 55, 410.
Alcohols |
Aldehydes / Ketones |
Reactions
Balloon models for organic molecules  Niac, G.
A balloon model can be used to demonstrate properties of small, organic molecules.
Niac, G. J. Chem. Educ. 1978, 55, 303.
Molecular Properties / Structure |
Alcohols |
Alkenes |
VSEPR Theory
Nucleophilic substitution by phase transfer catalysis  Reeves, W. Preston; White, Mitchell R.; Bier, Deana
The preparation of alkyl thiocyanates to be an excellent and versatile experiment for first year organic students.
Reeves, W. Preston; White, Mitchell R.; Bier, Deana J. Chem. Educ. 1978, 55, 56.
Nucleophilic Substitution |
Catalysis
Low-cost methanol for HPLC in the educational laboratory  Wolfhagen, James L.; Soltes, Ed J.
Method for purifying methanol for use in HPLC.
Wolfhagen, James L.; Soltes, Ed J. J. Chem. Educ. 1977, 54, 619.
HPLC |
Chromatography |
Laboratory Management |
Alcohols
Questions [and] Answers  Campbell, J. A.
309-314. Six questions involving practical applications of chemistry.
Campbell, J. A. J. Chem. Educ. 1977, 54, 437.
Enrichment / Review Materials |
Toxicology |
Alcohols |
Gases |
Natural Products
Synthesis of 4-methyl-3-heptanol and 4-methyl-3-heptanone. Two easily synthesized insect pheromones  Einterz, Robert M.; Ponder, Jay W.; Lenox, Ronald S.
A two step reaction sequence involving the Grignard synthesis of an alcohol followed by oxidation of this alcohol to the corresponding ketone.
Einterz, Robert M.; Ponder, Jay W.; Lenox, Ronald S. J. Chem. Educ. 1977, 54, 382.
Natural Products |
Synthesis |
Applications of Chemistry |
Grignard Reagents |
Mechanisms of Reactions |
Stereochemistry |
Alcohols |
Aldehydes / Ketones
Winemaking in the chemistry laboratory  Horn, David E.
Outlines a short course on the chemistry of winemaking and provides a procedure for making red wine from grape juice,
Horn, David E. J. Chem. Educ. 1977, 54, 375.
Alcohols |
Applications of Chemistry |
Consumer Chemistry
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
A molecular model for SN2 reactions  Newman, Melvin S.
Plan for a homemade mechanical model designed to demonstrate many of the features of SN2 reactions.
Newman, Melvin S. J. Chem. Educ. 1975, 52, 462.
Molecular Mechanics / Dynamics |
Molecular Modeling |
Molecular Properties / Structure |
Nucleophilic Substitution |
Mechanisms of Reactions |
Reactions
The determination of alcohol content of beer: A general and analytical experiment with high student interest value  Lokken, D. A.
Procedure that uses gas chromatography to determine the alcohol content of beer.
Lokken, D. A. J. Chem. Educ. 1975, 52, 329.
Gas Chromatography |
Alcohols |
Quantitative Analysis
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
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 remarkable reactivity of aryl halides with nucleophiles   Bunnett, Joseph F.
Nucleophilic attack on carbon; nucleophilic attack on hydrogen; aryl formation by halide ion loss from o-halophenyl anions; nucleophilic attack on halogen; acceptance of an electron, and its consequences.
Bunnett, Joseph F. J. Chem. Educ. 1974, 51, 312.
Nucleophilic Substitution |
Reactions
A 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
SN1 and SN2 reactions: Paper marionette for demonstration  Sone, Yachiyo; Sone, Kozo
Describes the construction of a paper marionette for demonstrating SN1 and SN2 reactions.
Sone, Yachiyo; Sone, Kozo J. Chem. Educ. 1973, 50, 615.
Nucleophilic Substitution |
Mechanisms of Reactions |
Reactions |
Molecular Modeling
Saving a life with alcohol  Scala, A. A.
Using alcohol as a treatment for ethylene glycol poisoning.
Scala, A. A. J. Chem. Educ. 1973, 50, 365.
Alcohols |
Toxicology |
Metabolism |
Constitutional Isomers
Drinking too fast can cause sudden death  Plumb, Robert C.; Eskelson, C. D.
Examines the metabolism of alcohol.
Plumb, Robert C.; Eskelson, C. D. J. Chem. Educ. 1973, 50, 365.
Alcohols |
Consumer Chemistry |
Applications of Chemistry |
Metabolism
Drinking too fast can cause sudden death  Plumb, Robert C.; Eskelson, C. D.
Examines the metabolism of alcohol.
Plumb, Robert C.; Eskelson, C. D. J. Chem. Educ. 1973, 50, 365.
Alcohols |
Consumer Chemistry |
Applications of Chemistry |
Metabolism
Determination of the relative and absolute configurations of (-)menthol and (+)neomenthol. An introductory stereochemistry experiment  Barry, J.
This activity serves to familiarize students with stereochemistry and the conformational analysis of cyclohexane systems.
Barry, J. J. Chem. Educ. 1973, 50, 292.
Stereochemistry |
Molecular Properties / Structure |
Alcohols |
Conformational Analysis
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
Nucleophilic substitution reactions at secondary carbon atoms. A modification of accepted views  Raber, Douglas J.; Harris, J. Milton
Considers reaction mechanisms that are intermediate between SN1 and SN2 and the possible role of ion pairs.
Raber, Douglas J.; Harris, J. Milton J. Chem. Educ. 1972, 49, 60.
Nucleophilic Substitution |
Mechanisms of Reactions
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
Reaction mechanisms in organic chemistry. Concerted reactions  Caserio, Marjorie C.
Examines displacement and elimination, cyclization, and rearrangement reactions, as well as theoretical considerations and generalized selection rules.
Caserio, Marjorie C. J. Chem. Educ. 1971, 48, 782.
Mechanisms of Reactions |
Reactions |
Nucleophilic Substitution |
Elimination Reactions
Conversions from cyclohexanol. An undergraduate laboratory project  Hanna, Samir B.; Wrobleski, James T.; Bohanon, Joseph T.; Peace, Bab W.
A procedure for a laboratory in conversions from cyclohexanol.
Hanna, Samir B.; Wrobleski, James T.; Bohanon, Joseph T.; Peace, Bab W. J. Chem. Educ. 1971, 48, 556.
Alkanes / Cycloalkanes |
Alcohols
Free-radical bromination of p-toluic acid. An experiment in organic chemistry  Tuleen, D. L.; Hess, B. A., Jr.
This paper describes the synthesis of a-bromo-p-toluic acid (II) and the subsequent displacement of bromide ion by three nucleophiles.
Tuleen, D. L.; Hess, B. A., Jr. J. Chem. Educ. 1971, 48, 476.
Free Radicals |
Nucleophilic Substitution
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
Donor-acceptor interactions in organic chemistry  Sunderwirth, S. G.
The purpose of this article is to aid teachers in making even more effective use of theoretical considerations in teaching organic chemistry; the primary objective is to emphasize the underlying principles that are common to the following four basic types of reactions: substitution, addition, elimination, and rearrangement.
Sunderwirth, S. G. J. Chem. Educ. 1970, 47, 728.
Reactions |
Mechanisms of Reactions |
Addition Reactions |
Elimination Reactions |
Nucleophilic Substitution
Nucleophilic reactivities of the halide anions  Puar, Mohindar S.
Ranks the nucleophilic reactivities of free halide ions in various solvents.
Puar, Mohindar S. J. Chem. Educ. 1970, 47, 473.
Nucleophilic Substitution
Organic nomenclature, I  Liotta, Charles
It is the purpose of this article to call attention to errors and misconceptions in the application of IUPAC Rules of Organic Nomenclature.
Liotta, Charles J. Chem. Educ. 1970, 47, 471.
Nomenclature / Units / Symbols |
Alkanes / Cycloalkanes |
Alcohols |
Heterocycles
A model to demonstrate the Walden inversion  Hamon, D. P. G.
Presents the design of a model capable of illustrating the Walden inversion.
Hamon, D. P. G. J. Chem. Educ. 1970, 47, 398.
Molecular Modeling |
Molecular Properties / Structure |
Nucleophilic Substitution |
Reactions
Indene reactions: An organic chemistry laboratory problem  Garrison, James A.
Students are given a problem in which they are to determine which of two published accounts of reaction products involving derivatives of idene is correct.
Garrison, James A. J. Chem. Educ. 1970, 47, 300.
Alkenes |
Alcohols
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 dehydration of 3,3-dimethyl-2-butanol  Taber, Richard L.; Grantham, Gary D.; Champion, William C.
Presents an experiment that demonstrates the usefulness of gas chromatography as an analytical technique, emphasizes structural rearrangement, makes use of elementary thermodynamics, and gives the student some experience in the original literature.
Taber, Richard L.; Grantham, Gary D.; Champion, William C. J. Chem. Educ. 1969, 46, 849.
Alcohols |
Alkenes |
Gas Chromatography
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
A unique laboratory-lecture in organic chemistry  Nienhouse, Everett J.
The laboratory-lecture considered centers about the products obtained from the dehydration of 4-methyl-2-pentanol.
Nienhouse, Everett J. J. Chem. Educ. 1969, 46, 765.
Alcohols |
Alkenes
Resolution and stereochemistry of asymmetric silicon, germanium, tin, and lead compounds  Belloli, Robert
It is the purpose of this review to summarize the results of stereochemical studies on compounds containing an asymmetric group IVA atom.
Belloli, Robert J. Chem. Educ. 1969, 46, 640.
Stereochemistry |
Organometallics |
Enantiomers |
Mechanisms of Reactions |
Nucleophilic Substitution
Preparation of p-anisole: An organic chemistry experiment  Smith, Richard F.; Bates, Alvin C.
In this experiment, p-anisaldehyde is converted to p-anisonitrile by a modification of the three-step aldehyde-nitrile synthesis of Smith and Walker.
Smith, Richard F.; Bates, Alvin C. J. Chem. Educ. 1969, 46, 174.
Synthesis |
Mechanisms of Reactions |
Addition Reactions |
Nucleophilic Substitution |
Elimination Reactions |
Catalysis
Dermatometry for coeds  Adamson, Arthur W.; Kunichika, K.; Shirley, F.; Orem, M.
It is possible to estimate the alcohol content of a drink from the contact angle of a drop on human skin.
Adamson, Arthur W.; Kunichika, K.; Shirley, F.; Orem, M. J. Chem. Educ. 1968, 45, 702.
Applications of Chemistry |
Consumer Chemistry |
Alcohols
Bimolecular nucleophilic displacement reactions  Edwards, John O.
The bimolecular nucleophilic displacement reaction is important and should be included in any detailed discussion of kinetics and mechanism at an early undergraduate level.
Edwards, John O. J. Chem. Educ. 1968, 45, 386.
Reactions |
Nucleophilic Substitution |
Kinetics |
Mechanisms of Reactions
Chromic acid oxidation of alcohols: A simple experiment on reaction rates  Lanes, Rose M.; Lee, Donald G.
In this experiment, students determine the relative rates of oxidation by adding quantities of several different alcohols to a solution of chromium(VI) in dilute sulfuric acid and visually monitoring the course of the reaction.
Lanes, Rose M.; Lee, Donald G. J. Chem. Educ. 1968, 45, 269.
Rate Law |
Kinetics |
Acids / Bases |
Alcohols
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
Dehydration of 2-methylcyclohexanol  Taber, Richard L.; Champion, William C.
This short article describes a simple alcohol dehydration that illustrates the Saytzeff Rule.
Taber, Richard L.; Champion, William C. J. Chem. Educ. 1967, 44, 620.
Alcohols |
Gas Chromatography |
Alkenes
Substitution reactions in octahedral complexes  Banerjea, D.
Commentary on the cited article by one of the authors that article referenced.
Banerjea, D. J. Chem. Educ. 1967, 44, 485.
Coordination Compounds |
Nucleophilic Substitution
Alcohols to alkyl halides: A kinetics experiment for elementary chemistry courses  Cooley, J. H.; McCown, J. D.; Shill, R. M.
The rate measurement in this procedure is accomplished by direct observation of the change in length or volume of the insoluble layer of an alkyl bromide that is formed from a mixture of alcohol, hydrobromic acid, and sulfuric acid.
Cooley, J. H.; McCown, J. D.; Shill, R. M. J. Chem. Educ. 1967, 44, 280.
Alcohols |
Synthesis |
Kinetics |
Rate Law
The martini as an alcoholic solution  Kauffman, George B.
Addresses the question, "How many time stronger in alcohol content is a 'strong' martini than the standard variety?"
Kauffman, George B. J. Chem. Educ. 1967, 44, 199.
Alcohols |
Solutions / Solvents
Teaching aromatic substitution: A molecular orbital approach  Meislich, Herbert
This paper presents a way of teaching aromatic substitution using the concepts of alternate polarity and electron delocalization through extended pi-bonding.
Meislich, Herbert J. Chem. Educ. 1967, 44, 153.
Aromatic Compounds |
MO Theory |
Nucleophilic Substitution |
Covalent Bonding |
Molecular Properties / Structure
Substitution reactions in octahedral complexes  Jones, G. R. H.
Examines the possibility of direct substitution, in aqueous solution, of a ligand in an octahedral complex by a nucleophile other than water or OH-.
Jones, G. R. H. J. Chem. Educ. 1966, 43, 657.
Coordination Compounds |
Mechanisms of Reactions |
Aqueous Solution Chemistry |
Nucleophilic Substitution |
Transition Elements |
Metals
Hydration of an alkyne: Undergraduate organic chemistry experiment  Rose, Norman C.
The hydration of 2-methyl-3-butyn-2-ol to yield 3-hydroxy-3-methyl-2-butanone is a very suitable reaction for undergraduates who have had little prior experience in the organic laboratory.
Rose, Norman C. J. Chem. Educ. 1966, 43, 324.
Alkynes |
Aldehydes / Ketones |
Alcohols
Reaction mechanisms in organic chemistry. I. The experimental approach  Caserio, Marjorie C.
Reviews a variety of method that may be employed to determine the mechanism of organic reactions.
Caserio, Marjorie C. J. Chem. Educ. 1965, 42, 570.
Reactions |
Mechanisms of Reactions |
Reactive Intermediates |
Kinetics |
Nucleophilic Substitution |
Addition Reactions |
Elimination Reactions
A simple model for the SN2 mechanism.  Nyquist, H. LeRoy
Presents a simple, physical model for the SN2 mechanism.
Nyquist, H. LeRoy J. Chem. Educ. 1965, 42, 103.
Molecular Modeling |
Reactions |
Nucleophilic Substitution |
Mechanisms of Reactions
Effect of liquid NH3 on wood: A demonstration of the alcohol structure of cellulose  Hirsch, Phillis R.
A lecture demonstration of the plasticization of wood with liquid ammonia can be a very effective tool for teaching the alcohol structure of cellulose to any class studying basic organic chemistry.
Hirsch, Phillis R. J. Chem. Educ. 1964, 41, 605.
Carbohydrates |
Alcohols |
Molecular Properties / Structure
Nucleophlic substitution at a saturated carbon atom; Elimination reactions (Bunton, C. A.; Banthorpe, D. V.)  Bunnett, Joseph F.

Bunnett, Joseph F. J. Chem. Educ. 1964, 41, 406.
Nucleophilic Substitution |
Elimination Reactions |
Mechanisms of Reactions
The decolorization of Baeyer's reagent by primary and secondary alcohols  Swinehart, James A.
The results of testing a large number of primary and secondary alcohols with Baeyer's reagent .
Swinehart, James A. J. Chem. Educ. 1964, 41, 392.
Alcohols
A second order kinetics experiment  Teerlink, Wilford J.; Asay, Jeanette; Sugihara, James M.
Investigates the nucleophilic displacement reaction of ethyl p-toluenesulfonate by iodide in acetone.
Teerlink, Wilford J.; Asay, Jeanette; Sugihara, James M. J. Chem. Educ. 1964, 41, 161.
Kinetics |
Nucleophilic Substitution
Nucleophilic reactions at trigonally bonded carbon  Cash, R. Vincent
Examines the mechanisms of nucleophilic displacement reactions, nucleophilic addition reactions, and nucleophilic addition with elimination, all at trigonally bonded carbon.
Cash, R. Vincent J. Chem. Educ. 1964, 41, 108.
Nucleophilic Substitution |
Reactions |
Mechanisms of Reactions |
Addition Reactions |
Elimination Reactions
Multicenter and assisted mechanistic pathways in the reactions of organometallic compounds  Dessy, Raymond E.; Paulik, Frank
Examines a variety of nucleophilic and electrophilic, multicenter and assisted mechanistic pathways in the reactions of organometallic compounds.
Dessy, Raymond E.; Paulik, Frank J. Chem. Educ. 1963, 40, 185.
Organometallics |
Mechanisms of Reactions |
Nucleophilic Substitution |
Electrophilic Substitution
A rapid test to distinguish tertiary from primary or secondary alcohols  Bordwell, Frederick C.; Wellman, Keith M.
Describes a protocol for distinguishing tertiary from primary or secondary alcohols and its application to a specific problem.
Bordwell, Frederick C.; Wellman, Keith M. J. Chem. Educ. 1962, 39, 308.
Alcohols |
Qualitative Analysis
Periodate cleavage of glycols: A quantitative organic analysis experiment  Schenk, George H.
This reaction is much used by organic chemists and uses the familiar standard solutions of iodine and sodium arsenite, common buffers, and stable organic glycols, such as ethylene glycol and pinacol.
Schenk, George H. J. Chem. Educ. 1962, 39, 32.
Quantitative Analysis |
Alcohols |
Reactions
The glycol centenary  Farber, Eduard
Describes the original synthesis of glycol by Adolphe Wurtz in 1856 and traces its subsequent production.
Farber, Eduard J. Chem. Educ. 1956, 33, 117.
Synthesis |
Alcohols
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
A laboratory exercise in catalytic dehydrogenation  Allison, Elizabeth; Gorsich, Richard; Binder, L. O.
Presents an apparatus that uses a copper catalyst to prepare aldehydes and ketones from alcohols through catalytic dehydrogenation.
Allison, Elizabeth; Gorsich, Richard; Binder, L. O. J. Chem. Educ. 1955, 32, 209.
Catalysis |
Alcohols |
Aldehydes / Ketones |
Synthesis
Introducing stereoisomerism  Schreiber, Kurt C.
Criticizes the traditional presentation of stereochemistry in isolation and offers a more integrated approach.
Schreiber, Kurt C. J. Chem. Educ. 1955, 32, 83.
Stereochemistry |
Molecular Properties / Structure |
Nucleophilic Substitution
Differentiating between primary, secondary, and tertiary alcohols  Ritter, Frank O.
A primary or secondary aliphatic alcohol dissolved in pure glacial acetic acid decolorizes a water solution of KMnO4, while a tertiary alcohol fails to do so; a secondary alcohol will continue to react with KMnO4 solution if a little concentrated sulfuric acid is added, while a primary alcohol does not.
Ritter, Frank O. J. Chem. Educ. 1953, 30, 395.
Molecular Properties / Structure |
Alcohols |
Quantitative Analysis