TIGER

Journal Articles: 104 results
Representing Fractional Distributions in Chemistry  Addison Ault
The purpose of this paper is to present a common approach to the representation of all forms of fractional distributions. Using a common approach is simple, easy to understand, and can reveal otherwise hidden relationships between phenomena.
Ault, Addison. J. Chem. Educ. 2008, 85, 1432.
Acids / Bases |
Amino Acids |
Carboxylic Acids |
Enzymes |
Kinetics |
Reactions
Oxidation of Aromatic Aldehydes Using Oxone  Rajani Gandhari, Padma P. Maddukuri, and Thottumkara K. Vinod
Describes an eco-friendly procedure for the oxidation of aldehydes to carboxylic acids in water or a water-ethanol mixture using Oxone as the oxidant. The use of eco-friendly solvents, a non-toxic reagent, and the elimination of extraction solvents in the procedure demonstrate important green chemistry themes to students.
Gandhari, Rajani; Maddukuri, Padma P.; Vinod, Thottumkara K. J. Chem. Educ. 2007, 84, 852.
Aldehydes / Ketones |
Aromatic Compounds |
Aqueous Solution Chemistry |
Carboxylic Acids |
Green Chemistry |
Mechanisms of Reactions |
NMR Spectroscopy |
Oxidation / Reduction
Entropy and the Shelf Model: A Quantum Physical Approach to a Physical Property  Arnd H. Jungermann
A quantum physical approach relying on energy quantization leads to three simple rules which are the key to understanding the physical property described by molar entropy values.
Jungermann, Arnd H. J. Chem. Educ. 2006, 83, 1686.
Alcohols |
Alkanes / Cycloalkanes |
Carboxylic Acids |
Covalent Bonding |
Ionic Bonding |
Physical Properties |
Quantum Chemistry |
Thermodynamics
Using a Simulated Industrial Setting for the Development of an Improved Solvent System for the Recrystallization of Benzoic Acid: A Student-Centered Project  Timothy R. Hightower and Jay D. Heeren
Presents a peer-led, problem-solving organic laboratory exercise that provide students with an opportunity to produce a more efficient recrystallization solvent in an industrial environment.
Hightower, Timothy R.; Heeren, Jay D. J. Chem. Educ. 2006, 83, 1663.
Carboxylic Acids |
Industrial Chemistry |
Separation Science |
Solutions / Solvents
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
Weak Acid pKa Determination Using Capillary Zone Electrophoresis  Mike Solow
In this experiment, students use capillary zone electrophoresis to determine the effective mobility of benzoic acid at two different hydrogen ion concentrations. A plot of these data yields the pKa of benzoic acid.
Solow, Mike. J. Chem. Educ. 2006, 83, 1194.
Acids / Bases |
Aqueous Solution Chemistry |
Carboxylic Acids |
Electrophoresis |
Instrumental Methods
Borodin  E. J. Behrman
Borodin made the first synthetic organic fluorine compound by reacting potassium hydrogen fluoride with benzoyl chloride to form benzoyl fluoride, a process known generally today as the Hunsdiecker reaction.
Behrman, E. J. J. Chem. Educ. 2006, 83, 1138.
Carboxylic Acids |
Acids / Bases |
Reactions |
Nutrition
The Synthesis of Copper(II) Carboxylates Revisited  Kevin Kushner, Robert E. Spangler, Ralph A. Salazar, Jr., and J. J. Lagowski
Describes an electrochemical synthesis of copper(II) carboxylates for use in the general chemistry laboratory course for chemistry majors.
Kushner, Kevin; Spangler, Robert E.; Salazar, Ralph A., Jr.; Lagowski, J. J. J. Chem. Educ. 2006, 83, 1042.
Carboxylic Acids |
Coordination Compounds |
Electrochemistry |
Metals |
Solutions / Solvents |
Transition Elements |
Undergraduate Research |
Synthesis
An Exploration of a Photochemical Pericyclic Reaction Using NMR Data  Sara M. Hein
This inexpensive, small-scale experiment for advanced organic students describes the unambiguous identification of a photochemical dimerization product from eleven possible candidates.
Hein, Sara M. J. Chem. Educ. 2006, 83, 940.
Addition Reactions |
Alkanes / Cycloalkanes |
Alkenes |
Carboxylic Acids |
Conformational Analysis |
NMR Spectroscopy |
Photochemistry |
Synthesis
A Simple Combinatorial Experiment Based on Fischer Esterification. An Experiment Suitable for the First-Semester Organic Chemistry Lab  Peter A. Wade, Susan A. Rutkowsky, and Daniel B. King
Describes a combinatorial experiment for the synthesis of esters by Fischer esterification in which a total of eight esters are prepared as six mixtures.
Wade, Peter A.; Rutkowsky, Susan A.; King, Daniel B. J. Chem. Educ. 2006, 83, 927.
Alcohols |
Carboxylic Acids |
Combinatorial Chemistry |
Equilibrium |
Esters |
Gas Chromatography |
Synthesis
Iodolactonization of 4-Pentenoic Acid   R. David Crouch, Alexander Tucker-Schwartz, and Kathryn Barker
Describes an experiment in which 4-pentenoic acid is converted into a lactone via iodolactonization.
Crouch, R. David; Tucker-Schwartz, Alexander; Barker, Kathryn. J. Chem. Educ. 2006, 83, 921.
Alkenes |
Carboxylic Acids |
IR Spectroscopy |
Mechanisms of Reactions |
NMR Spectroscopy |
Reactions |
Synthesis
Ozonolysis Problems That Promote Student Reasoning  Ray A. Gross Jr.
The structural features inherent in acyclic monoterpenes that follow the isoprene rule often lead to unique sets of ozonolysis products from which their structures, excluding stereochemistry, can be determined from molecular formulas only. This article shows how students may elucidate the structures of these compounds by analysis of the oxidative and reductive workup products.
Gross, Ray A., Jr. J. Chem. Educ. 2006, 83, 604.
Aldehydes / Ketones |
Alkenes |
Alkynes |
Carboxylic Acids |
Oxidation / Reduction |
Student-Centered Learning
Application of ChemDraw NMR Tool: Correlation of Program-Generated 13C Chemical Shifts and pKa Values of para-Substituted Benzoic Acids  Hongyi Wang
An application of ChemDraw NMR Tool was demonstrated by correlation of program-generated 13C NMR chemical shifts and pKa values of para-substituted benzoic acids. Experimental 13C NMR chemical shifts were analyzed in the same way for comparison. The project can be used as an assignment at the end of the first-year organic chemistry course to review topics or explore new techniques: Hammett equation, acidbase equilibrium theory, electronic nature of functional groups, inductive and resonance effects, structurereactivity relationship, NMR spectroscopy, literature search, database search, and ChemDraw software.
Wang, Hongyi. J. Chem. Educ. 2005, 82, 1340.
Acids / Bases |
Equilibrium |
NMR Spectroscopy |
Aqueous Solution Chemistry |
Carboxylic Acids
Formation of α-Tetralone by Intramolecular Friedel–Crafts Acylation  Michael S. Holden, R. David Crouch, and Kathryn A. Barker
A microscale procedure is described for the formation of the industrially-important compound alpha-tetralone. This is an example of an intramolecular FriedelCrafts acylation, utilizing 4-phenylbutanoic acid and a proton source. The title reaction demonstrates the concept of ring-forming reactions and highlights the use of carboxylic acids as an electrophile precursor in electrophilic aromatic substitution reactions.
Holden, Michael S.; Crouch, R. David; Barker, Kathryn A. J. Chem. Educ. 2005, 82, 934.
Aromatic Compounds |
Microscale Lab |
Synthesis |
Carboxylic Acids |
IR Spectroscopy |
NMR Spectroscopy
The Conversion of Carboxylic Acids to Ketones: A Repeated Discovery  John W. Nicholson and Alan Wilson
This article describes the history of the reaction converting carboxylic acids to ketones. The reaction has been rediscovered several times, yet has actually been known for centuries.
Nicholson, John W.; Wilson, Alan. J. Chem. Educ. 2004, 81, 1362.
Synthesis |
Carboxylic Acids |
Aldehydes / Ketones
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
Stearic Acid  Jay A. Young
Properties, hazards, and storage requirements for stearic acid.
Young, Jay A. J. Chem. Educ. 2004, 81, 25.
Laboratory Equipment / Apparatus |
Laboratory Management |
Carboxylic Acids |
Acids / Bases |
Physical Properties
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
Featured Molecules: Ascorbic Acid and Methylene Blue  William F. Coleman and Randall J. Wildman
Fully manipulable Chime versions of ascorbic acid and methylene blue, for the articles "Arsenic: Not So Evil After All?"; "Out of the Blue"; "Greening the Blue Bottle"; and "Sailing on the 'C': A Vitamin Titration with a Twist"
Coleman, William F.; Wildman, Randall J. J. Chem. Educ. 2003, 80, 584.
Molecular Modeling |
Molecular Properties / Structure |
Carboxylic Acids
Organic Functional Group Playing Card Deck  Michael J. Welsh
Organic functional group playing card deck used for review of the name and structure of organic functional groups that can be used to play any game that a normal deck of cards is used for.
Welsh, Michael J. J. Chem. Educ. 2003, 80, 426.
Nomenclature / Units / Symbols |
Nonmajor Courses |
Enrichment / Review Materials |
Alcohols |
Aldehydes / Ketones |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes |
Amides |
Amines / Ammonium Compounds |
Aromatic Compounds |
Carboxylic Acids |
Esters |
Ethers |
Mechanisms of Reactions |
Synthesis
"Chiral Acetate": The Preparation, Analysis, and Applications of Chiral Acetic Acid  Addison Ault
Production of chiral acetic acid using deuterium and tritium and its application to understanding stereochemistry and the specificity of enzymatic reactions.
Ault, Addison. J. Chem. Educ. 2003, 80, 333.
Chirality / Optical Activity |
Enzymes |
Isotopes |
Synthesis |
Stereochemistry |
Enrichment / Review Materials |
Carboxylic Acids |
Enantiomers |
Reactions |
Mechanisms of Reactions
C–H and C–D Bonds: An Experimental Approach to the Identity of C–H Bonds by Their Conversion to C–D Bonds  Alex T. Rowland
Three experiments that allow students to determine the relative reactivity of C-H bonds that are aliphatic, alpha, benzylic, or aromatic by the ease of substitution of deuterium for oxygen.
Rowland, Alex T. J. Chem. Educ. 2003, 80, 311.
Acids / Bases |
IR Spectroscopy |
Isotopes |
NMR Spectroscopy |
Undergraduate Research |
Alkanes / Cycloalkanes |
Aromatic Compounds |
Carboxylic Acids
The Cis-Trans Equilibrium of N-Acetyl-L-Proline. An Experiment for the Biophysical Chemistry Laboratory  Kathryn R. Williams, Bhavin Adhyaru, Igor German, and Eric Alvarez
A cis-trans equilibrium system that demonstrates the effect of solvent polarity and aqueous pH.
Williams, Kathryn R.; Adhyaru, Bhavin; German, Igor; Alvarez, Eric. J. Chem. Educ. 2002, 79, 372.
Amino Acids |
Biophysical Chemistry |
NMR Spectroscopy |
Proteins / Peptides |
NMR Spectroscopy |
Amines / Ammonium Compounds |
Carboxylic Acids |
Equilibrium |
Stereochemistry |
Diastereomers
Formic Acid  Jay A. Young
Properties, hazards, and storage requirements for formic acid.
Young, Jay A. J. Chem. Educ. 2002, 79, 157.
Acids / Bases |
Physical Properties |
Laboratory Management |
Carboxylic Acids
Soap from Nutmeg: An Integrated Introductory Organic Chemistry Laboratory Experiment  Marcio C. S. de Mattos and David E. Nicodem
A sequence of experiments in which trimyristin is extracted, isolated, and purified from nutmeg, then converted to a soap (sodium myristate) and acidified to produce myristic acid.
de Mattos, Marcio C. S.; Nicodem, David E. J. Chem. Educ. 2002, 79, 94.
Natural Products |
Carboxylic Acids |
Consumer Chemistry |
Fatty Acids
The Vitamin C Clock Reaction  Stephen W. Wright
Clock reaction using supermarket materials (vitamin C, hydrogen peroxide, tincture of iodine, and starch).
Wright, Stephen W. J. Chem. Educ. 2002, 79, 41.
Consumer Chemistry |
Oxidation / Reduction |
Vitamins |
Carboxylic Acids
pH of Sodium Acetate Solutions  Guy Schmitz
Example of buffering power in deviations of the pH of sodium acetate from calculated values.
Schmitz, Guy. J. Chem. Educ. 2002, 79, 29.
Acids / Bases |
Carboxylic Acids |
pH
Response to Potential-Energy-Only Models (re J. Chem. Educ. 2000, 77, 155-156)  Frank Rioux and Roger L. DeKock
Example of buffering power in deviations of the pH of sodium acetate from calculated values.
Rioux, Frank; DeKock, Roger L. J. Chem. Educ. 2002, 79, 29.
Acids / Bases |
Carboxylic Acids |
pH |
Atomic Properties / Structure |
Quantum Chemistry |
Theoretical Chemistry
The Combined Effects of pH and Percent Methanol on the HPLC Separation of Benzoic Acid and Phenol  Seema M. Joseph and John A. Palasota
Investigating the combined effects of pH and percent methanol on the HPLC separation of benzoic acid and phenol.
Joseph, Seema M.; Palasota, John A. J. Chem. Educ. 2001, 78, 1381.
Chromatography |
Instrumental Methods |
Separation Science |
Carboxylic Acids |
Aromatic Compounds |
Phenols
Chemical Laboratory Information Profile: Acetic Acid (glacial)  Jay A. Young
Properties, hazards, and storage requirements for acetic acid (glacial).
Young, Jay A. J. Chem. Educ. 2001, 78, 721.
Acids / Bases |
Laboratory Management |
Physical Properties |
Carboxylic Acids
Simulating How a Virus Spreads through a Population: An Introduction to Acid-Base Chemistry in the Organic Chemistry Laboratory  Ronald M. Jarret
The traditional lab exercise that achieves separation of a mixture of 4-aminoacetophenone and benzoic acid by chemically active extraction has been expanded to include an exercise that uses materials from the extraction experiment to simulate how a virus spreads through a population.
Jarret, Ronald M. J. Chem. Educ. 2001, 78, 525.
Acids / Bases |
Separation Science |
Solutions / Solvents |
Aromatic Compounds |
Carboxylic Acids
Dog with Ball Joins Flying Bird
(re
J. Chem. Educ. 1999, 76, 1656)  Richard S. Treptow
Comparing structural models to simple figures.
Treptow, Richard S. J. Chem. Educ. 2001, 78, 31.
Molecular Properties / Structure |
Carboxylic Acids |
Molecular Modeling
Organic Acids without a Carboxylic Acid Functional Group  G. V. Perez and Alice L. Perez
This paper presents several organic molecules that have been labeled as acids but do not contain a carboxylic acid functional group. Various chemical principles such as pKa, tautomerization, aromaticity, conformation, resonance, and induction are explored.
Perez, G. V.; Perez, Alice L. J. Chem. Educ. 2000, 77, 910.
Acids / Bases |
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Phenols |
Carboxylic Acids |
Aromatic Compounds
Elucidation of Molecular Structure Using NMR Long-Range Coupling: Determination of the Single Isomer Formed in a Regiospecific Reaction  Samuel Delagrange and Françoise Nepveu
The experiment presented in this article introduces students to the main concepts of two essential NMR techniques for investigating molecular structure. Heteronuclear multiple bond connectivity (HMBC) and proton-coupled 13C NMR are used to determine which isomer, from a possible two, is formed by a regiospecific reaction. The demonstration, based on long-range coupling between quaternary carbons and protons on neighboring carbons, is presented step by step.
Delagrange, Samuel; Nepveu, Françoise. J. Chem. Educ. 2000, 77, 895.
Molecular Properties / Structure |
NMR Spectroscopy |
Synthesis |
Carboxylic Acids |
Reactions |
Diastereomers
Amino Acids, Aromatic Compounds, and Carboxylic Acids: How Did They Get Their Common Names?  Sam H. Leung
This article provides a brief survey of the origins of the common names of some amino acids, aromatic compounds, and carboxylic acids.
Leung, Sam H. J. Chem. Educ. 2000, 77, 48.
Amino Acids |
Aromatic Compounds |
Nomenclature / Units / Symbols |
Carboxylic Acids
Preparation and Identification of Benzoic Acids and Benzamides: An Organic "Unknown" Lab  Douglass F. Taber, Jade D. Nelson, and John P. Northrop
The reaction of an unknown substituted benzene derivative with oxalyl chloride and aluminum chloride gives the acid chloride. Hydrolysis of the acid chloride gives the acid, and reaction of the acid with concentrated aqueous ammonia gives the benzamide. The equivalent weight of the acid can be determined by titration; given this information and the melting points of the acid and the benzamide, it is possible to deduce the structure of the initial unknown.
Taber, Douglass F.; Nelson, Jade D.; Northrop, John P. J. Chem. Educ. 1999, 76, 828.
Qualitative Analysis |
Aromatic Compounds |
Carboxylic Acids
A Modified Synthesis of the Insect Repellent DEET  Peter H. Knoess and Edward G. Neeland
In the preparation of the insect repellent DEET, lab procedures prepare the intermediate m-toluoyl chloride by heating m-toluic acid with thionyl chloride for times ranging from 15 to 45 minutes. The acid chloride is then worked up under Schotten-Baumann conditions to yield DEET.
Knoess, Peter H.; Neeland, Edward G. J. Chem. Educ. 1998, 75, 1267.
Synthesis |
Aromatic Compounds |
Carboxylic Acids
Synthesis of Aspirin: A General Chemistry Experiment  John A. Olmsted III
An experiment is described that is suitable for the early portion of the laboratory in a general chemistry course and integrates organic examples. It is the two-step synthesis of aspirin starting from oil of wintergreen. The mechanism for this synthesis provides examples of three major classes of chemical reactions: hydrolysis, condensation, and proton transfer.
Olmsted, John A., III. J. Chem. Educ. 1998, 75, 1261.
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Mechanisms of Reactions |
Aromatic Compounds |
Carboxylic Acids |
Aldehydes / Ketones
Synthesis of Exotic Soaps in the Chemistry Laboratory  Otto Phanstiel IV, Eric Dueno, and Queenie Xianghong Wang
A variety of different triglyceride sources ranging from Vietnamese garlic oil to a local restaurant's grill sludge were saponified to generate a series of exotic soaps. Students did not quantify their results, but described their products in terms of color, texture and odor.
Phanstiel, Otto, IV; Dueno, Eric; Wang, Queenie Xianghong. J. Chem. Educ. 1998, 75, 612.
Qualitative Analysis |
Carboxylic Acids |
Lipids |
Consumer Chemistry |
Applications of Chemistry |
Fatty Acids
Does Copper Metal React with Acetic Acid?  Stephen DeMeo
Starting with a discrepant event and led through a series of experiments, students of an introductory chemistry course investigate if copper metal reacts with acetic acid. Finding that oxygen from the air plays an important role in the reaction of these substances, students ultimately realize that the conditions under which two reactants interact are important in determining the type of products that are made.
DeMeo, Stephen. J. Chem. Educ. 1997, 74, 844.
Acids / Bases |
Aqueous Solution Chemistry |
Carboxylic Acids
Determination of the Enantiomeric Purity of Naproxen: An Organic Chemistry Laboratory Experiment  Thomas D. Walsh and Curtis S. Koontz
Recent availability of and publicity surrounding the antiinflammatory drug naproxen presents an opportunity for an organic chemistry laboratory experiment of great up-to-the-minute interest.
Walsh, Thomas D.; Koontz, Curtis S. . J. Chem. Educ. 1997, 74, 585.
Stereochemistry |
Drugs / Pharmaceuticals |
Molecular Properties / Structure |
Aromatic Compounds |
Carboxylic Acids
Reduction of Carboxylic Acids with Sodium Borohydride and an Electrophile  Jan William Simek, Thad Tuck, and Kelly Courter Bush
Integration of new reduction conditions into a procedure applicable to the first-year organic chemistry laboratory, where reduction of the carboxylic acid group has remained an obstacle, notwithstanding the use of borane or LiAlH4 (2) on the microscale. The NaBH4 method with either electrophile can be modified to any scale; in our hands, the use of I2 as the electrophile performed better at the semimicro scale than the H2SO4 method.
Simek, Jan William; Tuck, Thad; Bush, Kelly Courter . J. Chem. Educ. 1997, 74, 107.
Carboxylic Acids |
Aromatic Compounds |
Oxidation / Reduction
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
Synthesis of Ethyl Salicylate Using Household Chemicals  Sally Solomon, Chinhyu Hur, Alan Lee, and Kurt Smith
Ethyl salicylate is synthesized, isolated, and characterized in a three-step process using simple equipment and household chemicals.
Solomon, Sally; Hur, Chinyu; Lee, Alan; Smith, Kurt. J. Chem. Educ. 1996, 73, 173.
Synthesis |
Aromatic Compounds |
Carboxylic Acids
"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
Small Scale Determination of the pKa Values for Organic Acids  Flash, Patrick
Determination and interpretation of the pKa values for a series of organic acids as a concrete example of the effect of structure on acid strength.
Flash, Patrick J. Chem. Educ. 1994, 71, A6.
Acids / Bases |
Molecular Properties / Structure |
Carboxylic Acids
A convenient method of esterification of fatty acids: An undergraduate organic laboratory experiment  Di Raddo, Pasquale
A convenient method of esterification of fatty acids for undergraduate organic chemistry lab.
Di Raddo, Pasquale J. Chem. Educ. 1993, 70, 1034.
Carboxylic Acids |
Esters |
Gas Chromatography |
NMR Spectroscopy |
Fatty Acids
Quantitative analysis by FTIR: Thin films of copolymers of ethylene and vinyl acetate.  Mathias, Lon J.; Hankins, Marie G.; Bertolucci, Craig M.; Grubb, Tina L.; Muthiah, Jeno.
Quantitation of coploymers of ethylene and vinyl acetate using FTIR.
Mathias, Lon J.; Hankins, Marie G.; Bertolucci, Craig M.; Grubb, Tina L.; Muthiah, Jeno. J. Chem. Educ. 1992, 69, A217.
IR Spectroscopy |
Fourier Transform Techniques |
Quantitative Analysis |
Alkenes |
Carboxylic Acids
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 One-Step Synthesis of Cinnamic Acids Using Malonic Acid: The Verley-Doebner Modification of the Knoevenagel Condensation  Kolb, Kenneth E.; Field, Kurt W.; Schatz, Paul F.
With this procedure malonic acid itself, rather than its diester, can be effectively condensed with benzaldehyde to produce trans-cinnamic acid.
Kolb, Kenneth E.; Field, Kurt W.; Schatz, Paul F. J. Chem. Educ. 1990, 67, A304.
Microscale Lab |
Synthesis |
Acids / Bases |
Aromatic Compounds |
Aldehydes / Ketones |
Carboxylic Acids
Synthesis of iodohexane via hydroboration-iodination: A microscale organic laboratory experiment involving air-sensitive compounds  Gooch, E. Eugene
Use of ICl and organoborane intermediates to prepare iodohexane that parallels similar methods that introduce iodine radionuclides into fatty acids for use as heart imaging agents via positron emission tomography.
Gooch, E. Eugene J. Chem. Educ. 1990, 67, A232.
Synthesis |
Microscale Lab |
Carboxylic Acids |
Medicinal Chemistry
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
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
Polarized light and rates of chemical reactions  Weir, John J.
This experiment provides the opportunity to introduce the principles of reaction kinetics, polarized light, and the chemistry of optically active compounds; the rate of the acid-catalyzed hydrolysis of sucrose to glucose and fructose is determined.
Weir, John J. J. Chem. Educ. 1989, 66, 1035.
Rate Law |
Kinetics |
Chirality / Optical Activity |
Carboxylic Acids
Illustrating the inductive effect on acid strength of carboxylic acids  Kolb, Kenneth E.; Kolb, Doris
The effect of various substituents on acid strength can be easily demonstrated using aqueous solutions of various carboxylic acids containing a suitable indicator.
Kolb, Kenneth E.; Kolb, Doris J. Chem. Educ. 1989, 66, 1034.
Acids / Bases |
Carboxylic Acids
Reactions of borohydride in carboxylic acid media: A summary  Nutaitis, Charles F.
Sodium borohydride / carboxylic acid systems represent a paradox of reactivity; depending on the substrate being transformed and the method sued to mix the reagents, this methodology can lead to reaction media that are either more or less reactive than sodium borohydride itself.
Nutaitis, Charles F. J. Chem. Educ. 1989, 66, 673.
Carboxylic Acids |
Mechanisms of Reactions
The proton NMR spectrum of ascorbic acid: A relevant example of deceptively simple second-order behavior  Reid, R. Stephen
To dispel student misconceptions, the use of the proton NMR spectrum of asorbic acid in D20 as an example has proven very effective.
Reid, R. Stephen J. Chem. Educ. 1989, 66, 344.
NMR Spectroscopy |
Rate Law |
Carboxylic Acids |
Vitamins
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
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
Catalysis of the carbonylation of alcohols to carboxylic acids including acetic acid synthesis from methanol  Forster, Denis; Dekleva, Thomas W.
These authors outline the fundamental aspects of the acetic acid process and suggest ways of extending the sythesis to higher carboxylic acids.
Forster, Denis; Dekleva, Thomas W. J. Chem. Educ. 1986, 63, 204.
Acids / Bases |
Alcohols |
Carboxylic Acids |
Alcohols |
Industrial Chemistry
Buffer capacity of various acetic acid-sodium acetate systems: A lecture experiment  Donahue, Craig J.; Panek, Mary G.
Uses indicators to illustrate the response of two buffers with the same initial pH value but differing buffer capacities.
Donahue, Craig J.; Panek, Mary G. J. Chem. Educ. 1985, 62, 337.
Acids / Bases |
pH |
Dyes / Pigments |
Aqueous Solution Chemistry |
Carboxylic Acids
A problem on formulas  Browne, Elaine J.
A problem suitable as an indicator of abstract thought and as an aid in selecting students for admission to honors or advanced placement courses.
Browne, Elaine J. J. Chem. Educ. 1985, 62, 242.
Carboxylic Acids
A short set of 13C-NMR correlation tables  Brown, D. W.
The object of these tables is to enable a student to calculate rapidly approximate d values for 13C nuclei in as wide a variety of compounds as possible.
Brown, D. W. J. Chem. Educ. 1985, 62, 209.
NMR Spectroscopy |
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes |
Aromatic Compounds |
Amides |
Carboxylic Acids |
Esters
Synthesis of benzoic acid using household bleach  Perkins, Robert
Conversion of acetophenone to benzoic acid (the haloform reaction) using household bleach.
Perkins, Robert J. Chem. Educ. 1984, 61, 551.
Synthesis |
Carboxylic Acids |
Aromatic Compounds
A new method for the preparation of derivatives of carboxylic acids  Brindle, Ian D.; Chassie, Susan
Preparation technique using potassium fluoride. From the "State-of-the-Art Symposium for Chemical Educators: Chemistry of the Food Cycle".
Brindle, Ian D.; Chassie, Susan J. Chem. Educ. 1984, 61, 347.
Synthesis |
Carboxylic Acids
Application of aromatic solvent induced shifts in organic chemistry  Kalyanam, Nagabushanam
This article illustrates the predictability of the movement of proton signals in the case of carbonyl compounds when the solvent is changed from a standard aliphatic solvent to an aromatic solvent.
Kalyanam, Nagabushanam J. Chem. Educ. 1983, 60, 635.
Aromatic Compounds |
Carboxylic Acids |
NMR Spectroscopy |
Solutions / Solvents
A quick and simple conversion of carboxylic acids into their anilides of heating with phenyl isothiocyanate  Ram, Ram N.; Kumar, Pradeep; Mukerjee, Arya K.
In this article, the authors report a quick and easy procedure using phenyl isothiocyanate, which is ideally suited to students.
Ram, Ram N.; Kumar, Pradeep; Mukerjee, Arya K. J. Chem. Educ. 1983, 60, 508.
Carboxylic Acids |
Aromatic Compounds |
Phenols |
Reactions
3-Ketoesters by malonic synthesis  Pollet, Patrick L.
This essay reviews a synthesis strategy.
Pollet, Patrick L. J. Chem. Educ. 1983, 60, 244.
Synthesis |
Carboxylic Acids |
Aldehydes / Ketones |
Alkylation
Richard Anschutz (1852-1937), Kekule's forgotten successor Part II: The work  Kauffman, George B.
In his mistaken attempt to prove that maleic and fumaric acids are structural rather than geometric isomers, Anschutz carried out much useful work not only on these compounds but also on many polybasic acids and their derivatives.
Kauffman, George B. J. Chem. Educ. 1982, 59, 745.
Carboxylic Acids |
Stereochemistry |
Diastereomers |
Acids / Bases |
Molecular Properties / Structure
The oxidation of terminal alkenes by permanganate: A practical demonstration of the use of phase transfer agents  Brown, Keith C.; Chang, Victor S.; Dar, Fazal H.; Lamb, Shannon E.; Lee, Donald G.
An oxidative cleavage of a terminal alkene to give the corresponding carboxylic acid with one less carbon atom.
Brown, Keith C.; Chang, Victor S.; Dar, Fazal H.; Lamb, Shannon E.; Lee, Donald G. J. Chem. Educ. 1982, 59, 696.
Alkenes |
Oxidation / Reduction |
Carboxylic Acids
Entropy and equilibria: A reassessment of ionization data for substituted acetic acids  Edward, John T.
Investigating the effect of various substituents on the proton-transfer reaction of substituted acetic acids in the gas phase and in water.
Edward, John T. J. Chem. Educ. 1982, 59, 354.
Thermodynamics |
Carboxylic Acids |
Acids / Bases |
Aqueous Solution Chemistry |
Equilibrium |
Gases
Excretion of ingested ascorbic acid: An easy, interesting undergraduate experiment  Sirota, G. R.; MacInnis, W. K.; Rasmussen, P. W.
The student ingests ascorbic acid and then measures the amount excreted in his urine using a microfluorometric procedure.
Sirota, G. R.; MacInnis, W. K.; Rasmussen, P. W. J. Chem. Educ. 1979, 56, 421.
Carboxylic Acids |
Vitamins |
Quantitative Analysis
A more convenient method of preparation of amide derivatives of carboxylic acids  Long, Karen P.
An adaptation of this method was devised for use in a qualitative organic analysis program.
Long, Karen P. J. Chem. Educ. 1979, 56, 420.
Synthesis |
Amides |
Carboxylic Acids |
Qualitative Analysis |
Catalysis
Purification by sub-zero temperature washing  Chu, Samuel S.-T.
Separating an ester from the carboxylic acid from which it was synthesized.
Chu, Samuel S.-T. J. Chem. Educ. 1979, 56, 384.
Synthesis |
Esters |
Carboxylic Acids |
Laboratory Management
An nmr protonation study of metal diethylenetriaminepentaacetic acid complexes: An integrated senior chemistry experiment  Letkeman, Peter
A protonation study of an aminocarboxylic acid and its metal complexes that can be expanded to cover topics from instrumental techniques to a study of the kinetics of metal-ligand bond formation.
Letkeman, Peter J. Chem. Educ. 1979, 56, 348.
NMR Spectroscopy |
Carboxylic Acids |
Amino Acids |
Coordination Compounds |
Instrumental Methods |
Kinetics |
Crystal Field / Ligand Field Theory
Amides and hydrazides from amine and hydrazine hydrochlorides  Shama, Sami A.; Tran, Thuran L.
The Schotten-Baumann procedure is extensively used for the preparation of carboxylic acid derivatives in the undergraduate chemistry laboratory.
Shama, Sami A.; Tran, Thuran L. J. Chem. Educ. 1978, 55, 816.
Amines / Ammonium Compounds |
Carboxylic Acids |
Synthesis
A synthesis of o-chlorocinnamic acid utilizing a Meerwein reaction. An undergraduate organic experiment  Cleland, George H.
The authors share an experimental procedure that converts an o-chloroaniline to o-chlorocinnamic acid.
Cleland, George H. J. Chem. Educ. 1978, 55, 814.
Carboxylic Acids |
Synthesis
p-Carboxystyrene. A Wittig procedure in aqueous medium  Broos, Rene; Tavernier, Dirk; Anteunis, Marc
In this paper, the authors present a student preparation of p-carboxyl group, as it makes the reaction product soluble in alkaline and insoluble in acid medium, provides for an easy way of separation.
Broos, Rene; Tavernier, Dirk; Anteunis, Marc J. Chem. Educ. 1978, 55, 813.
Aqueous Solution Chemistry |
Acids / Bases |
Carboxylic Acids |
Separation Science
Favorskii rearrangement in bridged polycyclic compounds  Chenier, Philip J.
Favorskii rearrangement in bridged polycyclic compounds: This can be classified as an intramolecular rearrangement from carbon to carbon, involving a migrating group Z moving without its electrons from migrating origin A to an electron-rich terminus B.
Chenier, Philip J. J. Chem. Educ. 1978, 55, 286.
Mechanisms of Reactions |
Carboxylic Acids |
Aldehydes / Ketones |
Aromatic Compounds
Selective reduction of functionalized carboxylic acids with borane-methyl sulfide: A convenient undergraduate organic experiment  Krishnamurthy, S.; Thompson, Kerry L.
Introduces a new selective reducing agent, borane-methyl sulfide.
Krishnamurthy, S.; Thompson, Kerry L. J. Chem. Educ. 1977, 54, 778.
Carboxylic Acids |
Oxidation / Reduction |
Mechanisms of Reactions
Organic derivatives of oxo acids II. Acids, salts, and esters of Groups IIIA-IVA elements  Fernelius, W. C.; Loening, Kurt; Adams, Roy
Considers the nomenclature of acids, salts, and esters of groups IIIA-VA elements.
Fernelius, W. C.; Loening, Kurt; Adams, Roy J. Chem. Educ. 1977, 54, 509.
Nomenclature / Units / Symbols |
Acids / Bases |
Carboxylic Acids |
Esters
Reactions of organocopper intermediates. An undergraduate laboratory experiment  Schambach, Robert A.
This paper describes an undergraduate organo-metallic laboratory experiment which investigates the reactivity of organo-copper intermediates generated during the copper-quinoline decarboxylation of o-nitrobenzoic acid.
Schambach, Robert A. J. Chem. Educ. 1976, 53, 735.
Organometallics |
Carboxylic Acids |
Reactions
The determination of a mechanism of isomerization of maleic acid to fumaric acid  Meek, John S.
Procedure in which students attempt to determine the mechanism for the isomerization of maleic acid to fumaric acid by heating with hydrochloric acid.
Meek, John S. J. Chem. Educ. 1975, 52, 541.
Mechanisms of Reactions |
Molecular Properties / Structure |
Stereochemistry |
Carboxylic Acids
Benzylthiuronium bicarbonate for the derivatization of carboxylic acids  Reddy, J. V. Krishna; Bopari, K. S.
Preparing benzylithiuronium carboxylates with benzylithiuronium bicarbonate.
Reddy, J. V. Krishna; Bopari, K. S. J. Chem. Educ. 1975, 52, 324.
Carboxylic Acids |
Synthesis
Probing chemical reactivity with the diphenyldiazomethane reaction  Dack, Michael R. J.
Examines uses of the reaction between diphenyldiazomethane and carboxylic acids to study the effects of temperature, pressure, solvent, and other variables.
Dack, Michael R. J. J. Chem. Educ. 1972, 49, 600.
Reactions |
Rate Law |
Kinetics |
Carboxylic Acids
The origin of the inductive effect  Stock, Leon M.
The results obtained in the investigation of the dissociation constants of carboxylic acids of known geometry and free from the complicating features of pi electron interactions and steric effects have established that the magnitude of the polar effect does not depend on either the number or the nature of the atoms between the substituent and the reaction site, nor do such substituent contributions depend on the number of paths available for their propagation.
Stock, Leon M. J. Chem. Educ. 1972, 49, 400.
Molecular Properties / Structure |
Carboxylic Acids
Actual effects controlling the acidity of carboxylic acids  Calder, G. V.; Barton, T. J.
The authors discuss the inaccurate treatment of the actual effects controlling the acidity of carboxylic acids found in many textbooks.
Calder, G. V.; Barton, T. J. J. Chem. Educ. 1971, 48, 338.
Acids / Bases |
Carboxylic Acids |
Reactions
Measurement of acidic catalysis. A physical-organic laboratory experiment  Berndt, Donald C.
This article describes an experiment for undergraduate laboratory courses which illustrate the acidic catalysis of many reactions of carbonyl and carboxyl functions.
Berndt, Donald C. J. Chem. Educ. 1971, 48, 200.
Carboxylic Acids |
Acids / Bases |
Reactions
Benzoic acid tree  Chen, Philip S.
Benzaldehyde undergoes autoxidation to benzoic acid by air, particularly upon exposure to light; the white benzoic acid is caused to form a crystalline tree on twisted pipe cleaners.
Chen, Philip S. J. Chem. Educ. 1970, 47, A119.
Carboxylic Acids |
Acids / Bases |
Crystals / Crystallography |
Oxidation / Reduction |
Aldehydes / Ketones
Detection of carboxylic acids by formation of ferric hydroxamates  Cleland, George H.; Knight, Duane W.
Offers an improved method for the detection of carboxylic acids through the formation of ferric hydroxamates.
Cleland, George H.; Knight, Duane W. J. Chem. Educ. 1970, 47, 781.
Carboxylic Acids |
Qualitative Analysis
Stereochemistry of the citric acid cycle  Smith, W. Grady; York, J. Lyndal
A large percentage of biochemistry texts show the trans structure for aconitate but label it cis.
Smith, W. Grady; York, J. Lyndal J. Chem. Educ. 1970, 47, 588.
Stereochemistry |
Molecular Properties / Structure |
Diastereomers |
Carboxylic Acids
The acidities of ascorbic and sialic acids  Hurd, Charies D.
This note concerning the pKa's of ascorbic and sialic acids id presented since the compounds are of general interest to organic chemists and carbohydrate chemists as well as biochemists.
Hurd, Charies D. J. Chem. Educ. 1970, 47, 481.
Acids / Bases |
Vitamins |
Carboxylic Acids |
Molecular Properties / Structure
Linear free energy relationships in the furan and thiophene ring systems  Freeman, Fillmore
The authors have correlated, by multiple linear regression analysis, sets of data taken from the literature with the Hammett equation for the dissociation constants of furoic and thiophene carboxylic acid derivatives.
Freeman, Fillmore J. Chem. Educ. 1970, 47, 140.
Molecular Properties / Structure |
Carboxylic Acids |
Heterocycles
Conversion of sucrose into a carboxylic acid: An undergraduate experiment  Carman, R. M.; Evans, R. F.
A cascade series of experiments transforms cane sugar into a carboxylic acid.
Carman, R. M.; Evans, R. F. J. Chem. Educ. 1969, 46, 847.
Carbohydrates |
Carboxylic Acids |
Heterocycles
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
Identification of carboxylic acids: Use of N-methylpiperazine and N-phenylpiperazine  Duff, J. G.; Yung, D. K.; Brenner, R. J.; Wilson, B. J.; Racz, W. J.
Demonstrates that N-phenylpiperazine is a useful reagent for the identification of carboxylic acids.
Duff, J. G.; Yung, D. K.; Brenner, R. J.; Wilson, B. J.; Racz, W. J. J. Chem. Educ. 1969, 46, 388.
Carboxylic Acids |
Qualitative Analysis
The dissociation of acetic acid dimer in the gas phase  Barton, Donald; Ralph, Roy; Kane, Kevin
The dissociation of acetic acid dimer in the gas phase is used to determine the temperature dependence of equilibrium constants.
Barton, Donald; Ralph, Roy; Kane, Kevin J. Chem. Educ. 1968, 45, 440.
Acids / Bases |
Gases |
Equilibrium |
Carboxylic Acids
Kinetic study by NMR  Socrates, G.
This experiment uses NMR to examine the kinetics of the hydration of pyruvic acid.
Socrates, G. J. Chem. Educ. 1967, 44, 575.
NMR Spectroscopy |
Kinetics |
Carboxylic Acids |
Alcohols
Random and systematic errors in the determination of association constants  Pasternak, R. A.; Brady, A. P.
Examines random and systematic errors in the context of studying association equilibria in solution of carboxylic acids and amides.
Pasternak, R. A.; Brady, A. P. J. Chem. Educ. 1963, 40, 254.
Equilibrium |
Chemometrics |
Carboxylic Acids |
Amides
The decarboxylation of organic acid  March, Jerry
Simple aliphatic acids (except for acetic) do not give good yields of the corresponding alkanes through decarboxylation, although many organic chemistry textbooks cite this as a general method for the preparation of alkanes.
March, Jerry J. Chem. Educ. 1963, 40, 212.
Acids / Bases |
Reactions |
Synthesis |
Alkanes / Cycloalkanes |
Carboxylic Acids
Infrared spectra of silver salts to characterize carboxylic acids  Bonner, William A.; DeGraw, Joseph I., Jr.
Describes the use of infrared spectra of silver salts to characterize carboxylic acids.
Bonner, William A.; DeGraw, Joseph I., Jr. J. Chem. Educ. 1962, 39, 639.
Qualitative Analysis |
Carboxylic Acids |
IR Spectroscopy
Determination of saponification equivalents of phenolic esters  Tobey, Stephen W.; McGregor, S. D.; Cottrill, Sharon L.
The objective of this paper is to show that by making a few key changes in existing techniques, a procedure of saponification determination is evolved that is not only applicable to ordinary alkyl esters of carboxylic acids, but gives excellent results with a wide variety of esters of phenol and other aromatic hydroxyl compounds.
Tobey, Stephen W.; McGregor, S. D.; Cottrill, Sharon L. J. Chem. Educ. 1961, 38, 611.
Esters |
Carboxylic Acids |
Phenols |
Aromatic Compounds
Hydrogen bonding and physical properties of substances  Ferguson, Lloyd N.
Physical properties influenced by hydrogen bonding considered in this paper include transition temperatures, vapor pressure, water solubility, the ionization of carboxylic acids, stereoisomerism, adsorption, and infrared spectra.
Ferguson, Lloyd N. J. Chem. Educ. 1956, 33, 267.
Hydrogen Bonding |
Noncovalent Interactions |
Physical Properties |
Aqueous Solution Chemistry |
Carboxylic Acids |
Stereochemistry |
IR Spectroscopy
A mnemonic for dicarboxylic acids  Cox, Gerald J.
This short note provides a mnemonic for the names of the dicarboxylic acids.
Cox, Gerald J. J. Chem. Educ. 1955, 32, 363.
Acids / Bases |
Nomenclature / Units / Symbols |
Carboxylic Acids