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Journal Articles: 42 results
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
A Simple Assignment That Enhances Students' Ability To Solve Organic Chemistry Synthesis Problems and Understand Mechanisms  Jennifer Teixeira and R. W. Holman
Describes an original, easily implemented approach in which students construct a "functional group transformation" notebook which helps them to think about organic reactions in both the forward and the reverse (retrosynthetic) sense.
Teixeira, Jennifer; Holman, Robert W. J. Chem. Educ. 2008, 85, 88.
Mechanisms of Reactions |
Synthesis |
Student-Centered Learning
Vanillin Synthesis from 4-Hydroxybenzaldehyde  Douglass F. Taber, Shweta Patel, Travis M. Hambleton, and Emma E. Winkel
Describes a simple and safe preparation of vanillin from 4-hydroxybenzaldehyde appropriate for undergraduate organic chemistry laboratories.
Taber, Douglass F.; Patel, Shweta; Hambleton, Travis M.; Winkel, Emma E. J. Chem. Educ. 2007, 84, 1158.
Aldehydes / Ketones |
Ethers |
Food Science |
Microscale Lab |
Natural Products |
Synthesis |
Thin Layer Chromatography |
Transition Elements
Chemical Aspects of General Anesthesia: Part II. Current Practices  Robert Brunsvold and Daryl L. Ostercamp
With the basic elements of balanced general anesthesia in place by the 1950s, the focus turned to developing safer and more effective agents and to improving procedures. During the last half-century a new generation of intravenous induction anesthetics, inhalational anesthetics, and muscle relaxants has emerged.
Brunsvold, Robert; Ostercamp, Daryl L. J. Chem. Educ. 2006, 83, 1826.
Bioorganic Chemistry |
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Synthesis
Acetal Protecting Groups in the Organic Laboratory: Synthesis of Methyl 4,6-O-Benzylidene-α-D-Glucopyranoside  Alexei V. Demchenko, Papapida Pornsuriyasak, and Cristina De Meo
The synthesis of methyl 4,6-O-benzylidene-a-D-glucopyranoside provides an opportunity to synthesize a cyclic acetal; stereoselectively introduce a chirality center; and learn extraction, evaporation, precipitation, optical rotation, melting point measurement, thin-layer chromatography, IR-spectroscopy, mass spectrometry, and various NMR techniques.
Demchenko, Alexei V.; Pornsuriyasak, Papapida; De Meo, Cristina. J. Chem. Educ. 2006, 83, 782.
Carbohydrates |
IR Spectroscopy |
Medicinal Chemistry |
NMR Spectroscopy |
Thin Layer Chromatography |
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
Diastereoselectivity in the Reduction of α-Hydroxyketones. An Experiment for the Chemistry Major Organic Laboratory  David B. Ball
Describes a research type, inquiry-based project where students synthesize racemic ahydroxyketones using umpolung, a polarity-reversal approach; investigate chelating versus non-chelating reducing agents; and determine the diastereoselectivity of these reducing processes by NMR spectroscopy.
Ball, David B. J. Chem. Educ. 2006, 83, 101.
Addition Reactions |
Aldehydes / Ketones |
Chirality / Optical Activity |
Chromatography |
Conferences |
Constitutional Isomers |
Enantiomers |
NMR Spectroscopy |
Stereochemistry |
Synthesis |
Conformational Analysis
Fluorous Compounds and Their Role in Separation Chemistry  Maria Angeles Ubeda and Roman Dembinski
Reviews fluorous technology and outlines strategies towards organic synthesis.
Ubeda, Maria Angeles; Dembinski, Roman. J. Chem. Educ. 2006, 83, 84.
Amino Acids |
Catalysis |
Esters |
Green Chemistry |
Separation Science |
Synthesis
Just Click It: Undergraduate Procedures for the Copper(I)-Catalyzed Formation of 1,2,3-Triazoles from Azides and Terminal Acetylenes  William D. Sharpless, Peng Wu, Trond Vidar Hansen, and James G. Lindberg
In keeping with the defining aspects of click chemistry, this reaction is high-yielding, requires no chromatography, is easily monitored by TLC, and displays distinct peaks in both IR and 1H-NMR. Virtually all products precipitate, and with just a few different starting blocks, every student, or pair of lab partners, can produce a unique "clicked" compound.
Sharpless, William D.; Wu, Peng; Hansen, Trond Vidar; Lindberg, James G. J. Chem. Educ. 2005, 82, 1833.
Catalysis |
Heterocycles |
Alkynes |
IR Spectroscopy |
NMR Spectroscopy |
Reactions |
Thin Layer Chromatography |
Synthesis
Polypyrazolylborates: Scorpionates  Swiatoslaw Trofimenko
Key features of polypyrazolylborates (also known as scorpionates because of certain specific features of their coordination chemistry) and examples of their use in modeling biologically active compounds are briefly presented.
Trofimenko, Swiatoslaw. J. Chem. Educ. 2005, 82, 1715.
Coordination Compounds |
Heterocycles |
Synthesis |
Bioinorganic Chemistry |
Molecular Properties / Structure
Spectroscopic Properties of Some Simple Esters. A Practical Application of Synthesis and Spectroscopy in the Undergraduate Organic Laboratory  David P. Brown, Haris Durutlic, and Didier Juste
This exercise, the synthesis and spectroscopic analysis of the allyl esters of some aromatic carboxylic acids, consists of a series of open-ended experiments.
Brown, David P.; Durutlic, Haris; Juste, Didier. J. Chem. Educ. 2004, 81, 1016.
Esters |
Synthesis |
NMR Spectroscopy |
IR Spectroscopy |
Chromatography
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
Organic Functional Group Playing Card Deck  Michael J. Welsh
Organic functional group playing card deck used for review of the name and structure of organic functional groups that can be used to play any game that a normal deck of cards is used for.
Welsh, Michael J. J. Chem. Educ. 2003, 80, 426.
Nomenclature / Units / Symbols |
Nonmajor Courses |
Enrichment / Review Materials |
Alcohols |
Aldehydes / Ketones |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes |
Amides |
Amines / Ammonium Compounds |
Aromatic Compounds |
Carboxylic Acids |
Esters |
Ethers |
Mechanisms of Reactions |
Synthesis
Semi-Microscale Williamson Ether Synthesis and Simultaneous Isolation of an Expectorant from Cough Tablets  Ryan G. Stabile and Andrew P. Dicks
Procedure for synthesis of the active ingredient in many well-known, over-the-counter cough syrups - 3-(2-methoxyphenoxy)-1,2-propanediol, an aromaric ether.
Stabile, Ryan G.; Dicks, Andrew P. J. Chem. Educ. 2003, 80, 313.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Mathematics / Symbolic Mathematics |
Microscale Lab |
Synthesis |
Stereochemistry |
Applications of Chemistry |
Ethers |
Aromatic Compounds |
Medicinal Chemistry
Epoxide Reactions  Thomas Bertolini
Puzzle involving epoxide reactions.
Bertolini, Thomas. J. Chem. Educ. 2002, 79, 828.
Synthesis |
Epoxides |
Ethers
Synthesis and Characterization of a Gasoline Oxygenate, Ethyl tert-Butyl Ether  Craig J. Donahue, Teresa D'Amico, and Jennifer A. Exline
Procedure for the synthesis and characterization of ethyl tert-butyl ether.
Donahue, Craig J.; D'Amico, Teresa; Exline, Jennifer A. J. Chem. Educ. 2002, 79, 724.
Chromatography |
Synthesis |
Ethers |
Gas Chromatography |
IR Spectroscopy |
Qualitative Analysis
A Phthalocyanine Synthesis Group Project for General Chemistry  Darren K. MacFarland, Christopher M. Hardin, and Michael J. Lowe
A group experiment synthesizing phthalocyanine dyes in one step from commercially available starting materials is described. The importance of a metal template is explored. The experiment is suitable for a second-semester general chemistry course.
MacFarland, Darren K.; Hardin, Christopher M.; Lowe, Michael J. J. Chem. Educ. 2000, 77, 1484.
Aromatic Compounds |
Synthesis |
Organometallics |
UV-Vis Spectroscopy |
Aromatic Compounds
Synthesis of the Sweetener Dulcin from the Analgesic Tylenol  Brian D. Williams, Birute Williams, and Louise Rodino
A sequence suitable for the synthesis of the sweetener dulcin from the analgesic acetaminophen. The analgesic phenacetin is isolated during the synthesis as an intermediate and consequently the experiment can be adopted as a multistep synthesis or as either of two single-period transformations.
Williams, Brian D.; Williams, Birute; Rodino, Louise. J. Chem. Educ. 2000, 77, 357.
Synthesis |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Aromatic Compounds
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
Protecting Groups in Carbohydrate Chemistry  Sigthór Pétursson
The most important protecting groups in carbohydrate chemistry are reviewed. The paper is aimed at those beginning to specialize in synthetic carbohydrate chemistry and at teachers with other specialties who wish to go beyond the content of general organic chemistry textbooks.
Petursson, Sigthor. J. Chem. Educ. 1997, 74, 1297.
Carbohydrates |
Molecular Properties / Structure |
Synthesis
Microscale Synthesis of the Natural Products Carpanone and Piperine  Sloop, Joseph C.
Experimental procedure for synthesizing carpanone and piperine.
Sloop, Joseph C. J. Chem. Educ. 1995, 72, A25.
Synthesis |
Microscale Lab |
Ethers
Other Publications on C6Cl6 and C2Cl6  Keiter, Richard L.
Previous JCE articles on the formation of C6Cl6 and C2Cl6.
Keiter, Richard L. J. Chem. Educ. 1995, 72, 956.
Synthesis
The AC Rule: An Algorithm for Organic Reactions  Edgar F. Kiefer
Algorithm for predicting organic reaction mechanisms.
Kiefer, Edgar F. J. Chem. Educ. 1995, 72, 906.
Mechanisms of Reactions |
Synthesis |
Reactions
The Sassafras Tree and Designer Drugs: From Herbal Tea to Ecstasy  French, Larry G.
Using historical development of material from the sassafras tree and elicit synthesis of the drug ecstasy (MDMA) as a venue for presenting methodology for amine synthesis in organic chemistry.
French, Larry G. J. Chem. Educ. 1995, 72, 484.
Drugs / Pharmaceuticals |
Synthesis |
Enrichment / Review Materials |
Molecular Properties / Structure
Synthesis of metal halides   Grube, Karl; Leffler, Amos J.
Procedure for micro preparation of metal halides.
Grube, Karl; Leffler, Amos J. J. Chem. Educ. 1993, 70, A204.
Laboratory Equipment / Apparatus |
Metals |
Synthesis |
Microscale Lab
A synthesis of indane musk Celestolide  Kagabu, Shinzo; Kojima, Yuka
This convenient operation using only a calculated amount of tetrahydrofuran will help students understand that one of the real operative species in Grignard reaction is a complex of alkylmagnesium halogenide with ether molecules.
Kagabu, Shinzo; Kojima, Yuka J. Chem. Educ. 1992, 69, 420.
Synthesis |
Grignard Reagents
A serendipitous two-step synthesis from a Grignard reaction: 1-ethoxy-1,1,1-triphenlymethane from the reaction of phenylmagnesium bromide with benzophenone  Abhyankar, Sudhir B.; Dust, Julian M.
To illustrate the potential products of a Grignard reaction, students prepared phenylmagnesium bromide from bromobenzene and magnesium turnings in diethyl ether. The Grignard reagent was then allowed to react with benzophenone.
Abhyankar, Sudhir B.; Dust, Julian M. J. Chem. Educ. 1992, 69, 76.
Synthesis |
Grignard Reagents
Synthesis of 5-nitrofurfural diacetate and 5-nitrofurfural semicarbazone: An undergraduate laboratory experiment  Li, Xiaorong; Liu, Qianguang; Chang, James C.
Demonstrates how to nitrate an aromatic compound having an aldehyde group that can be oxidized by nitrating agents.
Li, Xiaorong; Liu, Qianguang; Chang, James C. J. Chem. Educ. 1990, 67, 986.
Synthesis |
Aldehydes / Ketones |
Esters |
Ethers |
Electrophilic Substitution |
Aromatic Compounds |
NMR Spectroscopy
Disconnect by the numbers: A beginner's guide to synthesis  Smith, Michael B.
A protocol for planning organic syntheses using the disconnection method.
Smith, Michael B. J. Chem. Educ. 1990, 67, 848.
Synthesis |
Mechanisms of Reactions
The synthesis of substituted benzyl phenyl ethers: An undergraduate organic chemistry experiment  Dilts, Kimberly; Durand, Marc
The experiment presented here presents a convenient and safe procedure for the semimicro SN2 Williamson synthesis of benzyl phenyl ethers.
Dilts, Kimberly; Durand, Marc J. Chem. Educ. 1990, 67, 74.
Synthesis |
Ethers |
Titration / Volumetric Analysis
The use of fluoromethanes in organic synthesis  Everett, T. Stephen
A review of advances in selective fluorination; mechanisms and applications of fluoromethanes in organic synthesis.
Everett, T. Stephen J. Chem. Educ. 1987, 64, 143.
Synthesis |
Mechanisms of Reactions
Guidebook to organic synthesis (Mackie, R.K.;Smith, D.M.)  Wade, L. G., Jr.
A review of a text that was designed as a text for an advanced undergraduate course in organic synthesis.
Wade, L. G., Jr. J. Chem. Educ. 1983, 60, A320.
Synthesis
An Ether Synthesis Using Phase Transfer Catalysis  Hill, John W.; Corredor, Jorge
Williamson syntheses may be carried out under milder conditions by employing phase-transfer catalyst; anhydrous solvents are nor needed.
Hill, John W.; Corredor, Jorge J. Chem. Educ. 1980, 57, 822.
Ethers |
Synthesis |
Catalysis
The preparation of p-cresyl propyl ether by phase transfer catalysis  Rowe, Jeffrey E.
Modifying the referenced procedure to produce aromatics ethers.
Rowe, Jeffrey E. J. Chem. Educ. 1980, 57, 162.
Catalysis |
Synthesis |
Aromatic Compounds |
Ethers
"Crown ether" synthesis: An organic laboratory experiment  Field, Kurt W.; Glover, A. Donald; Moroz, Judith S.; Collander, Deborah J.; Kolb, Kenneth E.
The starting materials are readily available and the product, a cyclic polyether, belongs to a class of compounds that has aroused interest in both chemists and biologists.
Field, Kurt W.; Glover, A. Donald; Moroz, Judith S.; Collander, Deborah J.; Kolb, Kenneth E. J. Chem. Educ. 1979, 56, 269.
Ethers |
Synthesis
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
Quarternary ammonia salts: Some recent applications in organic synthesis  Varughese, Pothen
Presents a variety of applications for quarternary ammonia salts, including as reaction media, a reagent for mesylation, catalytic hydrogenation, and micellar and phase-transfer catalysis.
Varughese, Pothen J. Chem. Educ. 1977, 54, 666.
Synthesis |
Amines / Ammonium Compounds |
Micelles |
Catalysis
The Gabriel synthesis of benzylamine: An undergraduate organic experiment  Nigh, W. G.
The Gabriel synthesis involves the reaction of the conjugate base of phthalimide and an alkyl halide to give an alkyl phthalimide which is subsequently hydrolyzed to the primary alkyl amine; the reaction is important historically for the synthesis of pure primary amines uncontaminated by secondary or tertiary by-products.
Nigh, W. G. J. Chem. Educ. 1975, 52, 670.
Synthesis |
Aromatic Compounds |
Amines / Ammonium Compounds
Constitutional Problems in Organic Chemistry (Watson, M. B.; Youngson, G. W.)  Haynes, LeRoy W.

Haynes, LeRoy W. J. Chem. Educ. 1964, 41, 691.
Reactions |
Synthesis
Principles of chemical reaction  Sanderson, R. T.
The purpose of this paper is to examine the nature of chemical change in the hope of recognizing and setting forth the basic principles that help us to understand why they occur.
Sanderson, R. T. J. Chem. Educ. 1964, 41, 13.
Reactions |
Thermodynamics |
Mechanisms of Reactions |
Kinetics |
Synthesis |
Covalent Bonding |
Ionic Bonding |
Metallic Bonding
Student preparation and manipulation of a gasMethyl ethyl ether  Casanova, Joseph, Jr.
This laboratory involves the preparation of methyl ethyl ether by a Williamson synthesis.
Casanova, Joseph, Jr. J. Chem. Educ. 1963, 40, 41.
Ethers |
Synthesis |
Gases
A student preparation of butyl ether  Smith, William B.
This preparation uses a Dean-Stark tube to separate water from the reaction mixture as it is formed.
Smith, William B. J. Chem. Educ. 1962, 39, 212.
Ethers |
Synthesis |
Laboratory Equipment / Apparatus