TIGER

Journal Articles: 48 results
"Greening Up" the Suzuki Reaction  Evangelos Aktoudianakis, Elton Chan, Amanda R. Edward, Isabel Jarosz, Vicki Lee, Leo Mui, Sonya S. Thatipamala, and Andrew P. Dicks
This article describes the green synthesis of a biaryl compound via a Pd(0)-catalyzed Suzuki cross-coupling reaction in water. The methodology exposes students to purely aqueous microscale organic reactivity and showcases topical research regarding an industrial process.
Aktoudianakis, Evangelos; Chan, Elton; Edward, Amanda R.; Jarosz, Isabel; Lee, Vicki; Mui, Leo; Thatipamala, Sonya S.; Dicks, Andrew P. J. Chem. Educ. 2008, 85, 555.
Aromatic Compounds |
Catalysis |
Green Chemistry |
Microscale Lab |
Phenols |
Water / Water Chemistry
Synthesis of Diapocynin  Mina S. Dasari, Kristy M. Richards, Mikaela L. Alt, Clark F. P. Crawford, Amanda Schleiden, Jai Ingram, Abdel Aziz Amadou Hamidou, Angela Williams, Patricia A. Chernovitz, Rensheng Luo, Grace Y. Sun, Ron Luchtefeld, and Robert E. Smith
Diapocynin is synthesized by the oxidative coupling of apocynin and analyzed by FTIR, 1H NMR, and negative ion atmospheric pressure chemical ionization LCMS.
Dasari, Mina S.; Richards, Kristy M.; Alt, Mikaela L.; Crawford, Clark F. P.; Schleiden, Amanda; Ingram, Jai; Hamidou, Abdel Aziz Amadou; Williams, Angela; Chernovitz, Patricia A.; Luo, Rensheng; Sun, Grace Y.; Luchtefeld, Ron; Smith, Robert E. J. Chem. Educ. 2008, 85, 411.
Drugs / Pharmaceuticals |
HPLC |
Mass Spectrometry |
Phenols |
Synthesis
A Bioanalytical Chemistry Experiment for Undergraduate Students: Biosensors Based on Metal Nanoparticles  John Njagi, John Warner, and Silvana Andreescu
Describes a laboratory experiment on the development of a biosensor in which students apply electrochemical methods to deposit gold nanoparticles onto electrode surfaces, immobilize an enzyme using glutaraldehyde chemistry, and perform quantitative analysis of phenol using a biosensor with amperometric detection.
Njagi, John; Warner, John; Andreescu, Silvana. J. Chem. Educ. 2007, 84, 1180.
Bioanalytical Chemistry |
Electrochemistry |
Enzymes |
Oxidation / Reduction |
Phenols
Enthalpy of Vaporization and Vapor Pressures: An Inexpensive Apparatus  Rubin Battino, David A. Dolson, Michael R. Hall, and Trevor M. Letcher
Describes an inexpensive apparatus for the determination of the vapor pressure of a liquid as a function of temperature for the purpose of calculating enthalpy changes of vaporization. Also described are a simple air thermostat and an inexpensive temperature controller based on an integrated temperature sensor.
Battino, Rubin; Dolson, David A.; Hall, Michael R.; Letcher, Trevor M. J. Chem. Educ. 2007, 84, 822.
Gases |
Laboratory Equipment / Apparatus |
Lipids |
Phenols |
Physical Properties |
Thermodynamics |
Liquids |
Phases / Phase Transitions / Diagrams
Phenol  Jay A. Young
Safety precautions for handling phenol are discussed.
Young, Jay A. J. Chem. Educ. 2007, 84, 759.
Phenols |
Laboratory Management
Comparative Methylation of 1,8-Dihydroxy-9,10-anthraquinone: Chemoselectivity in the Organic Chemistry Laboratory  Grigoriy A. Sereda
Describes a laboratory experiment that gives organic chemistry students an example of an environmentally friendly pyrolytic procedure of organic synthesis. Another synthesis with the same reactants teaches the students that appropriate reaction conditions may allow the chemist to perform an organic reaction with high chemoselectivity.
Sereda, Grigoriy A. J. Chem. Educ. 2005, 82, 1839.
Reactions |
Ethers |
Green Chemistry |
Phenols |
Synthesis |
Thin Layer Chromatography |
UV-Vis Spectroscopy
The Base-Induced Reaction of Salicylaldehyde with 1-Bromobutane in Acetone: Two Related Examples of Chemical Problem Solving  Holly D. Bendorf and Chriss E. McDonald
Each student performs his or her own experimental work, running one of the two reactions, and acquiring the proton and carbon NMR, IR, and mass spectra. The students work in groups to propose structures for the products and mechanisms for their formation. The students are also asked to address why the reactions take different courses.
Bendorf, Holly D.; McDonald, Chriss E. J. Chem. Educ. 2003, 80, 1185.
Chromatography |
Mass Spectrometry |
NMR Spectroscopy |
Aromatic Compounds |
Aldehydes / Ketones |
Ethers |
Phenols |
IR Spectroscopy
The 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
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
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
The Pechmann Reaction  Michael S. Holden and R. David Crouch
A solid acid-catalyzed version of the Pechmann reaction for the synthesis of coumarins is described. The Pechmann reaction is a multiple-transformation process which is not a part of the normal organic chemistry curriculum.
Holden, Michael S.; Crouch, R. David. J. Chem. Educ. 1998, 75, 1631.
Catalysis |
Mechanisms of Reactions |
Microscale Lab |
Synthesis |
Reactions |
Phenols
The Use of MO Calculations to Teach Students Some Concepts of Aromatic Substitution Reactions  Petrus Zeegers
The experiments described here are an attempt to help students unify the theoretical and practical aspects of their studies in organic chemistry. Simple aromatic compounds (4-X-phenols) have been used to illustrate the relationship between theoretical molecular orbital calculations and an industrially useful multi step organic synthesis.
Zeegers, Petrus. J. Chem. Educ. 1997, 74, 299.
MO Theory |
Aromatic Compounds |
Phenols
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
Nitration of phenols: A two-phase system  Zeegers, Petrus J.
Nitration of phenols is often overlooked in undergraduate organic chemistry courses.
Zeegers, Petrus J. J. Chem. Educ. 1993, 70, 1036.
Phenols |
Aromatic Compounds |
Reactions |
Quantitative Analysis |
Mechanisms of Reactions |
Chromatography |
NMR Spectroscopy
Microscale reactions of vanillin   Fowler, Rosemary G.
In this paper five microscale experiments which allow first-year organic student sot study the properties and reactions of vanillin are presented.
Fowler, Rosemary G. J. Chem. Educ. 1992, 69, A43.
Aldehydes / Ketones |
Aromatic Compounds |
Phenols |
Microscale Lab |
IR Spectroscopy |
NMR Spectroscopy
Microscale synthesis of 2,6-bis(morpholinomethyl)-p-cresol: A phenolic Mannich base   Payne, Edward W.
This paper outlines a microscale laboratory preparation that is an extension of the basic Mannich reaction.
Payne, Edward W. J. Chem. Educ. 1992, 69, A40.
Microscale Lab |
Phenols |
Synthesis
Cautionary note regarding the phenol color test by ferric chloride in acidic solution  Hasegawa, Tadashi; Usui, Toyokazu
Effect of acids on the phenol color test by ferric chloride.
Hasegawa, Tadashi; Usui, Toyokazu J. Chem. Educ. 1992, 69, 840.
Phenols |
Qualitative Analysis |
Acids / Bases
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
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
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
Synthesis of a phenol-formaldehyde thermosetting polymer  Bedard, Y.; Riedl, B.
Procedure that allows for the synthesis of a 50% aqueous solution of a prepolymer that, with the proper application of heat and pressure, can be used to bind together wood or other materials.
Bedard, Y.; Riedl, B. J. Chem. Educ. 1990, 67, 977.
Synthesis |
Aldehydes / Ketones |
Phenols |
Polymerization
Beauty or the beast: Nitration of phenol  McCullough, Thomas, CSC; Kubena, Kassia
Eliminating the black, sticky goo produced when nitrating phenols with dilute aqueous nitric acid.
McCullough, Thomas, CSC; Kubena, Kassia J. Chem. Educ. 1990, 67, 801.
Phenols |
Laboratory Management
Industrial chemistry in the organic laboratory: C4 alkylations  Teegarden, David M.; Varco-Shea, Theresa C.; Conklin, Karen T.; Markle, Cynthia A.; Anderson, Scott D.
A set of experiments to illustrate reactions of the tertiary-butyl group; the products are all compounds that occur in consumer products and have received considerable attention in the popular press (BHT, BHA, TBHQ, and MTBE).
Teegarden, David M.; Varco-Shea, Theresa C.; Conklin, Karen T.; Markle, Cynthia A.; Anderson, Scott D. J. Chem. Educ. 1990, 67, 619.
Industrial Chemistry |
Aromatic Compounds |
Phenols |
Synthesis |
Mechanisms of Reactions
Antioxidants in plastic: An instrumental analysis project  Chan, Wing Hong; Lam, King Sum; Yu, Wai Keung
The authors have devised the following project in their instrumental analysis laboratory to investigate the antioxidant content in polypropylene products.
Chan, Wing Hong; Lam, King Sum; Yu, Wai Keung J. Chem. Educ. 1989, 66, 172.
Phenols |
Instrumental Methods |
Gas Chromatography |
UV-Vis Spectroscopy
Photochemistry of phenyl alkyl ketones: The "Norrish type II" photoreaction: An organic photochemistry experiment   Marciniak, Bronislaw
In this paper a student laboratory experiment is described aimed to study the "Norrish type II" reception of valerophenone. The advantage of this experiment is that it can be performed with a simple irradiation system and with a gas chromatograph and it brings students into contact with some problems of organic photochemistry.
Marciniak, Bronislaw J. Chem. Educ. 1988, 65, 832.
Aldehydes / Ketones |
Photochemistry |
Phenols |
Chromatography
The preparation of 4-hydroxy-2,3,4,5-tetraphenyl-2-cyclopenten-1-one and its base catalyzed conversion into 2,3,4,5-tetraphenycyclopentadienone: An organic laboratory experiment   Harrison, Ernest A., Jr.
An organic laboratory experiment that permits direct observation of a pedagogically interesting transformation.
Harrison, Ernest A., Jr. J. Chem. Educ. 1988, 65, 828.
Aldehydes / Ketones |
Phenols |
Alkanes / Cycloalkanes |
IR Spectroscopy |
Synthesis
A safe, convenient method of generating bromine for qualitative analysis  Slayden, Suzauee W.; Do, Thuy H.; Smiley, Kimberly Y.; Nelson, Donna J.
A safe, convenient method of generating bromine used as a qualitative test for unsaturation, active methylene groups, phenols, and amines.
Slayden, Suzauee W.; Do, Thuy H.; Smiley, Kimberly Y.; Nelson, Donna J. J. Chem. Educ. 1987, 64, 368.
Qualitative Analysis |
Alkenes |
Phenols |
Amines / Ammonium Compounds |
Laboratory Management
Hydrogen bonding and retention on silica: A concept illustrated by TLC chromatography of nitrophenols  Feigenbaum, A.
The TLC experiments presented in this paper illustrate several important features regarding retention, elution, and selectivity on silica through the study of the chromatographic behavior of nitrophenols.
Feigenbaum, A. J. Chem. Educ. 1986, 63, 815.
Heterocycles |
Thin Layer Chromatography |
Acids / Bases |
Phenols |
Hydrogen Bonding
Thin-layer chromatographic separation of phenols  Kurth, Mark J.
The structural complexity of typical TLC experiments precludes meaningful discussions of important aspects of TLC.
Kurth, Mark J. J. Chem. Educ. 1986, 63, 360.
Thin Layer Chromatography |
Phenols
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
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
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
Phenyl acetate preparation from phenol and acetic acid: Reassessment of a common textbook misconception  Hocking, M. B.
The determination of the approximate equilibrium concentration for the phenol and acetic acid system, together with an effective method for the direct preparation of phenyl acetate.
Hocking, M. B. J. Chem. Educ. 1980, 57, 527.
Phenols
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
Oxidative coupling of phenols. A biomimetic undergraduate organic laboratory experiment  Hart, Harold; Reilly, James L.
It is the purpose of this paper to describe a laboratory experiment suitable for undergraduates which illustrates the oxidative coupling of phenols. To place the experiment in proper context, the authors briefly review general features of the reaction.
Hart, Harold; Reilly, James L. J. Chem. Educ. 1978, 55, 120.
Phenols |
Oxidation / Reduction
Imidazole - Versatile today, prominent tomorrow  Matuszak, C. A.; Matuszak, A. J.
Imidazole chemistry has pedagogical utility for all the organic chemistry students pursing careers in the life sciences.
Matuszak, C. A.; Matuszak, A. J. J. Chem. Educ. 1976, 53, 280.
Grignard Reagents |
Aromatic Compounds |
Heterocycles |
Phenols |
Acids / Bases |
Catalysis |
Coordination Compounds |
Hydrogen Bonding
A series of related organic experiments with optional structure determinations  Fairless, Billy J.; Ragsdale, Gary; Kerby, Claudia
The authors wish to report three related experiments that have been received with enthusiasm by organic students.
Fairless, Billy J.; Ragsdale, Gary; Kerby, Claudia J. Chem. Educ. 1974, 51, 61.
Phenols |
Alkenes |
NMR Spectroscopy
Identifying phenols using N-methylpiperazine and N-phenylpiperazine  Yung, David; Whitehouse, Larry; Lo, Edmund
The purpose of this work is to determine if N-methylpiperazine and N-phenylpiperazine salts can serve as useful derivatives in characterizing phenols; physical data is provided regarding 45 N-methylpiperazine and N-phenylpiperazine salts of some phenols.
Yung, David; Whitehouse, Larry; Lo, Edmund J. Chem. Educ. 1970, 47, 474.
Phenols
Basic organic laboratory techniques and problem solving: The nitration of 4-nitrophenol  Pearson, Robert E.
The experiment described requires application of melting point data and the technique of recrystallization to identify the product of a simple chemical reaction.
Pearson, Robert E. J. Chem. Educ. 1969, 46, 692.
Physical Properties |
Phases / Phase Transitions / Diagrams |
Qualitative Analysis |
Phenols
Stoichiometry of the reaction of bromine with phenols  Lockwood, Karl L.
The purpose of this investigation is to establish the stoichiometry for the reaction of a number of phenols with bromine, and to demonstrate the rapid and quantitative nature of the reaction of bromine with enols.
Lockwood, Karl L. J. Chem. Educ. 1965, 42, 482.
Stoichiometry |
Phenols
Aqueous bromination with bromine chloride: A simplified method for the preparation of 2,6-dibromo-4-nitrophenol  Obenland, C. O.
The classic preparation of 2,6-dibromo-4-nitrophenol can be shortened and simplified by using bromine chloride in aqueous solution.
Obenland, C. O. J. Chem. Educ. 1964, 41, 566.
Synthesis |
Phenols |
Aqueous Solution Chemistry
The direct esterification of phenols  Offenhauer, Robert D.
It is not true that phenols cannot be esterfied by the direct action of an organic acid; includes an experiment demonstrating the fallacy of this common textbook error.
Offenhauer, Robert D. J. Chem. Educ. 1964, 41, 39.
Phenols |
Esters |
Reactions
Determination of saponification equivalents of phenolic esters  Tobey, S. W.
Suggests several questions for exploration regarding the determination of saponification equivalents of phenolic esters.
Tobey, S. W. J. Chem. Educ. 1963, 40, A986.
Esters |
Phenols
TLC on microscope slides: An organic chemistry experiment  Naff, M. Benton; Naff, Anna S.
This experiment consists of three sections: separation of known and unknown dye mixtures; separation of known and unknown mixtures of phenols; separation of dyes and impurities.
Naff, M. Benton; Naff, Anna S. J. Chem. Educ. 1963, 40, 534.
Chromatography |
Thin Layer Chromatography |
Separation Science |
Dyes / Pigments |
Phenols
A separation and identification experiment for elementary organic chemistry laboratory  Laughton, Paul M.
The student selects a test tube containing two unknowns and is told only that they have been selected from two of three possible groups: a primary or tertiary amine, an aldehyde or ketone, and an acid or phenol. The components are to be separated, their physical properties determined, their categories assigned, and one specific derivative prepared for each.
Laughton, Paul M. J. Chem. Educ. 1960, 37, 133.
Separation Science |
Qualitative Analysis |
Amines / Ammonium Compounds |
Aldehydes / Ketones |
Acids / Bases |
Phenols |
Physical Properties |
Synthesis
Textbook errors: XX. Miscellanea No. 2  Mysels, Karol J.
Subjects considered include the meaning of "element," the solubility of phenol in carbonate solutions, and the change of vapor pressure with temperature.
Mysels, Karol J. J. Chem. Educ. 1958, 35, 568.
Precipitation / Solubility |
Phenols |
Gases |
Liquids
The preparation of 2,3,6-tri-t-butylphenol  Somers, Bruce G.; Cook, Clinton D.
This preparation has been conducted by second-semester, elementary organic chemistry students with good results.
Somers, Bruce G.; Cook, Clinton D. J. Chem. Educ. 1955, 32, 312.
Synthesis |
Phenols |
Mechanisms of Reactions
The identification of esters of phenols  Carbone, Gabriel
The present modification is designed to better characterize esters of phenols and is based on the observations that the potassium salts of phenols are soluble in absolute alcohol wile the potassium salts of organic acids are relatively insoluble in absolute methanol.
Carbone, Gabriel J. Chem. Educ. 1953, 30, 315.
Phenols |
Esters |
Qualitative Analysis