TIGER

Journal Articles: 345 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
Borohydride Reduction of Estrone  Animesh Aditya, David E. Nichols, and G. Marc Loudon
This experiment presents a guided-inquiry approach to the demonstration of diastereoselectivity using chiral hindered ketones that undergo facile reduction with sodium borohydride. The resulting diastereomeric estradiols can be analyzed and differentiated by thin-layer chromatography and melting point.
Aditya, Animesh; Nichols, David E.; Loudon, G. Marc. J. Chem. Educ. 2008, 85, 1535.
Aldehydes / Ketones |
Diastereomers |
IR Spectroscopy |
Microscale Lab |
Stereochemistry |
Steroids |
Thin Layer Chromatography
A One-Pot, Asymmetric Robinson Annulation in the Organic Chemistry Majors Laboratory  Kiel E. Lazarski, Alan A. Rich, and Cheryl M. Mascarenhas
Describes a one-pot, enantioselective, Robinson annulation geared towards the second-year organic chemistry major and demonstrating aspects of green chemistry.
Lazarski, Kiel E.; Rich, Alan A.; Mascarenhas, Cheryl M. J. Chem. Educ. 2008, 85, 1531.
Aldehydes / Ketones |
Asymmetric Synthesis |
Catalysis |
Chirality / Optical Activity |
Gas Chromatography |
HPLC |
NMR Spectroscopy |
Synthesis |
Green Chemistry
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
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
Acid-Catalyzed Enolization of β-Tetralone  Brahmadeo Dewprashad, Anthony Nesturi, and Joel Urena
This experiment allows students to use 1H NMR to compare the rates of substitution of benzylic and non-benzylic a hydrogens of -tetralone and correlate their findings with predictions made by resonance theory.
Dewprashad, Brahmadeo; Nesturi, Anthony; Urena, Joel. J. Chem. Educ. 2008, 85, 829.
Aldehydes / Ketones |
Isotopes |
Mechanisms of Reactions |
NMR Spectroscopy |
Reactive Intermediates |
Resonance Theory |
Synthesis
The Baeyer–Villiger Oxidation with Trifluoroacetic Acid and Household Sodium Percarbonate  Richard A. Kjonaas and Anthony E. Clemons
Reports a method for carrying out the BaeyerVilliger oxidation of cyclopentanone to d-valerolactone in a large-section introductory organic chemistry laboratory course.
Kjonaas, Richard A.; Clemons, Anthony E. J. Chem. Educ. 2008, 85, 827.
Aldehydes / Ketones |
Esters |
NMR Spectroscopy |
Oxidation / Reduction |
Synthesis
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
Why Are 1H NMR Integrations Not Perfect? An Inquiry-Based Exercise for Exploring the Relationship Between Spin Dynamics and NMR Integration in the Organic Lab  Haim Weizman
When FT-NMR is used to collect data without a sufficient delay time between subsequent pulses, the integrated area under certain peaks may result in a lower value than should be observed under appropriate conditions. This exercise is designed to raise awareness of this issue in students and to serve as an inquiry-based stepping-stone into basic FT-NMR.
Weizman, Haim. J. Chem. Educ. 2008, 85, 294.
Aldehydes / Ketones |
Microscale Lab |
NMR Spectroscopy
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
Microwave-Assisted Organic Synthesis in the Organic Teaching Lab: A Simple, Greener Wittig Reaction  Eric Martin and Cynthia Kellen-Yuen
A microwave-assisted Wittig reaction has been developed for the organic teaching laboratory. Utilizing this technique, a variety of styrene derivatives have been synthesized from aromatic aldehydes in good yields. The mixture of cis and trans alkenes produced also provides instructors with opportunities to emphasize the spectroscopic analysis of product mixtures.
Martin, Eric; Kellen-Yuen, Cynthia. J. Chem. Educ. 2007, 84, 2004.
Aldehydes / Ketones |
Alkenes |
Chromatography |
Green Chemistry |
Mass Spectrometry |
NMR Spectroscopy |
Spectroscopy |
Synthesis
Using Ozone in Organic Chemistry Lab: The Ozonolysis of Eugenol  Bruce M. Branan, Joshua T. Butcher, and Lawrence R. Olsen
This organic laboratory involves the ozonolysis of eugenol (clove oil) followed by a reductive workup that generates an aldehyde easily identified by its NMR and IR spectra.
Branan, Bruce M.; Butcher, Joshua T.; Olsen, Lawrence R. J. Chem. Educ. 2007, 84, 1979.
Aldehydes / Ketones |
Gases |
IR Spectroscopy |
Laboratory Equipment / Apparatus |
Natural Products |
NMR Spectroscopy |
Synthesis |
Oxidation / Reduction
Determination of Solvent Effects on Keto—Enol Equilibria of 1,3-Dicarbonyl Compounds Using NMR  A. Gilbert Cook and Paul M. Feltman
Expands the classic physical chemistry experiment using of proton NMR to determine the equilibrium position of tautomeric 1,3-dicarbonyl compounds in various solvents.
Cook, A. Gilbert; Feltman, Paul M. J. Chem. Educ. 2007, 84, 1827.
Aldehydes / Ketones |
Equilibrium |
Hydrogen Bonding |
Molecular Modeling |
Molecular Properties / Structure |
NMR Spectroscopy |
Solutions / Solvents |
Thermodynamics
Probing the Rate-Determining Step of the Claisen–Schmidt Condensation by Competition Reactions  Kendrew K. W. Mak, Wing-Fat Chan, Ka-Ying Lung, Wai-Yee Lam, Weng-Cheong Ng, and Siu-Fung Lee
This article describes a physical organic experiment to identify the rate-determining step of the ClaisenSchmidt condensation of benzaldehyde and acetophenone by studying the linear free energy relationship.
Mak, Kendrew K. W.; Chan, Wing-Fat; Lung, Ka-Ying; Lam, Wai-Yee; Ng, Weng-Cheong; Lee, Siu-Fung. J. Chem. Educ. 2007, 84, 1819.
Aldehydes / Ketones |
Aromatic Compounds |
Gas Chromatography |
Kinetics |
Mechanisms of Reactions |
Synthesis
Synthesis and Characterization of Aldol Condensation Products from Unknown Aldehydes and Ketones  Nicholas G. Angelo, Laura K. Henchey, Adam J. Waxman, James W. Canary, Paramjit S. Arora, and Donald Wink
Describes an experiment in which students perform the aldol condensation on an unknown aldehyde and ketone and make use of TLC, column chromatography, recrystallization, and characterization by 1H NMR, GCMS, and FTIR.
Angelo, Nicholas G.; Henchey, Laura K.; Waxman, Adam J.; Canary, James W.; Arora, Paramjit S.; Wink, Donald. J. Chem. Educ. 2007, 84, 1816.
Aldehydes / Ketones |
Chromatography |
Gas Chromatography |
IR Spectroscopy |
Mass Spectrometry |
NMR Spectroscopy |
Spectroscopy |
Thin Layer Chromatography
Hydration of Acetylene: A 125th Anniversary  Dmitry A. Ponomarev and Sergey M. Shevchenko
The discovery the hydration of alkynes catalyzed by mercury ions by Mikhail Kucherov made possible industrial production of acetaldehyde from acetylene and had a profound effect on the development of industrial chemistry in the 1920th centuries.
Ponomarev, Dmitry A.; Shevchenko, Sergey M. J. Chem. Educ. 2007, 84, 1725.
Addition Reactions |
Aldehydes / Ketones |
Alkynes |
Catalysis |
Industrial Chemistry |
Reactions
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
A Knoevenagel Initiated Annulation Reaction Using Room Temperature or Microwave Conditions  A. Gilbert Cook
The product of a Knoevenagel initiated annulation reaction is identified through a guided prelab exercise of the synthesis of the Hagemann ester, and then through the analysis of GCMS, NMR, and IR spectra. The stereochemistry of the product is determined through the NMR spectrum and Karplus curve, and the student is required to write a mechanism for the reaction.
Cook, A. Gilbert. J. Chem. Educ. 2007, 84, 1477.
Aldehydes / Ketones |
Conformational Analysis |
Gas Chromatography |
IR Spectroscopy |
Mass Spectrometry |
Mechanisms of Reactions |
NMR Spectroscopy |
Stereochemistry |
Synthesis
A Guided-Inquiry Approach to the Sodium Borohydride Reduction and Grignard Reaction of Carbonyl Compounds  Robert E. Rosenberg
Students teams identify unknowns and their reaction products and use their data to deduce that esters are less electrophilic than the other carbonyl compounds present, that Grignard reagents are more nucleophilic than sodium borohydride, and that carboxylic acid derivatives do not undergo the nucleophilic addition reactions that are characteristic of aldehydes and ketones.
Rosenberg, Robert E. J. Chem. Educ. 2007, 84, 1474.
Addition Reactions |
Aldehydes / Ketones |
Esters |
Grignard Reagents |
IR Spectroscopy |
Oxidation / Reduction |
Reactions |
Student-Centered Learning
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
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
CARBOHYDECK: A Card Game To Teach the Stereochemistry of Carbohydrates  Manuel João Costa
This paper describes CARBOHYDECK, a card game that may replace or complement lectures identifying and differentiating monosaccharide isomers.
Costa, Manuel João. J. Chem. Educ. 2007, 84, 977.
Aldehydes / Ketones |
Carbohydrates |
Molecular Properties / Structure |
Stereochemistry |
Enrichment / Review Materials |
Student-Centered Learning
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
Using a Premade Grignard Reagent To Synthesize Tertiary Alcohols in a Convenient Investigative Organic Laboratory Experiment  Michael A. G. Berg and Roy D. Pointer
Describes the use of a commercially available Grignard reagent in a Grignard synthesis that avoided the failures typically associated with the Grignard reaction.
Berg, Michael A. G.; Pointer, Roy D. J. Chem. Educ. 2007, 84, 483.
Aldehydes / Ketones |
Grignard Reagents |
IR Spectroscopy |
NMR Spectroscopy |
Organometallics |
Synthesis
The Aldol Addition and Condensation: The Effect of Conditions on Reaction Pathway  R. David Crouch, Amie Richardson, Jessica L. Howard, Rebecca L. Harker, and Kathryn H. Barker
Describes an experiment offering the opportunity for students to observe the critical role that reaction temperature and base strength have in determining the product of the base-mediated addition of a ketone to an aldehyde.
Crouch, R. David; Richardson, Amie; Howard, Jessica L.; Harker, Rebecca L.; Barker, Kathryn H. J. Chem. Educ. 2007, 84, 475.
Addition Reactions |
Aldehydes / Ketones |
Green Chemistry |
NMR Spectroscopy |
Reactions |
Synthesis
A Green Enantioselective Aldol Condensation for the Undergraduate Organic Laboratory  George D. Bennett
The proline-catalyzed aldol condensation between acetone and isobutyraldehyde proceeds in good yield and with high enantioselectivity at room temperature. This multi-week experiment also illustrates a number of principles and trade-offs of green chemistry.
Bennett, George D. J. Chem. Educ. 2006, 83, 1871.
Addition Reactions |
Aldehydes / Ketones |
Asymmetric Synthesis |
Catalysis |
Chirality / Optical Activity |
Green Chemistry |
Mechanisms of Reactions |
Stereochemistry
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
Photochemical Dimerization of Dibenzylideneacetone. A Convenient Exercise in [2+2] Cycloaddition Using Chemical Ionization Mass Spectrometry  G. Nageswara Rao, Chelli Janardhana, V. Ramanathan, T. Rajesh, and P. Harish Kumar
Presents a laboratory procedure for the photochemical dimerization of dibenzylideneacetone, a dienone. The dimerization is confirmed by chemical ionization mass spectrometry, and other spectroscopic techniques are used to establish the structure of the product.
Rao, G. Nageswara; Janardhana, Chelli; Ramanathan, V.; Rajesh, T.; Kumar, P. Harish. J. Chem. Educ. 2006, 83, 1667.
Aldehydes / Ketones |
Alkenes |
Chromatography |
IR Spectroscopy |
Mass Spectrometry |
NMR Spectroscopy |
Photochemistry |
Thin Layer Chromatography
Synthesis of meso-Diethyl-2,2′-dipyrromethane in Water. An Experiment in Green Organic Chemistry  Abilio J. F. N. Sobral
In this laboratory activity, students are introduced to the synthesis of dipyrromethanes important precursors for porphyrin and calix[4]pyrrolethrough the acid-catalyzed condensation of pyrrole and 3-pentanone to produce meso-diethyl-2,2'-dipyrromethane.
Sobral, Abilio J. F. N. J. Chem. Educ. 2006, 83, 1665.
Aldehydes / Ketones |
Aqueous Solution Chemistry |
Green Chemistry |
Synthesis
A Discovery-Learning 2,4-Dinitrophenylhydrazone Experiment  Bruno M. Vittimberga and Ben Ruekberg
Selections of liquid aldehydes and ketones are proposed for students to determine what property is the best predictor of the color (yellow to red) of their 2,4-dinitrophenylhydrazone derivative. Students may use a computer (spreadsheet or word processor) to analyze their results.
Vittimberga, Bruno M.; Ruekberg, Ben. J. Chem. Educ. 2006, 83, 1661.
Aldehydes / Ketones |
Molecular Properties / Structure |
Physical Properties |
Qualitative Analysis
Microwave-Mediated Synthesis of Lophine: Developing a Mechanism To Explain a Product   R. David Crouch, Jessica L. Howard, Jennifer L. Zile, and Kathryn H. Barker
Describes the microwave-mediated preparation of lophine (2,4,5-triphenylimidazole). The experiment also provides an opportunity for students to employ the principles of carbonyl chemistry in devising a mechanism to explain the formation of the product.
Crouch, R. David; Howard, Jessica L.; Zile, Jennifer L.; Barker, Kathryn H. J. Chem. Educ. 2006, 83, 1658.
Aldehydes / Ketones |
Amines / Ammonium Compounds |
Aromatic Compounds |
Microscale Lab |
Molecular Modeling |
Synthesis |
NMR Spectroscopy
Developing Critical Thinking Skills: The "Sabotaged" Synthesis of Methyl p-Bromobenzoate  Eric J. Mahan and Mary Alice Nading
Before beginning an experiment, students are told that someone might have sabotaged their experiment to produce other-than-expected results. The objective is to perform the experiment, determine if any sabotage has occurred, and, if so, identify the changes that were made to the reagents as well as the person responsible.
Mahan, Eric J.; Nading, Mary Alice. J. Chem. Educ. 2006, 83, 1652.
Alcohols |
Carboxylic Acids |
Esters |
IR Spectroscopy |
NMR Spectroscopy |
Mass Spectrometry |
Synthesis
Synthesis and Analysis of a Versatile Imine for the Undergraduate Organic Chemistry Laboratory  Jacqueline Bennett, Kristen Meldi, and Christopher Kimmell II
In this experiment students prepare and analyze N-p-methoxyphenyl (N-PMP) alpha-imino ethyl glyoxalate, an imine that has been used in the synthesis of biologically active molecules. The stability and versatility of this imine allow it to be used in subsequent reactions, offering a variety of possible multistep synthetic strategies.
Bennett, Jacqueline; Meldi, Kristen; Kimmell, Christopher, II. J. Chem. Educ. 2006, 83, 1221.
Aldehydes / Ketones |
Gas Chromatography |
Green Chemistry |
Mass Spectrometry |
NMR Spectroscopy |
Synthesis
Methanol  Jay A. Young
The hazards of methanol are discussed.
Young, Jay A. J. Chem. Educ. 2006, 83, 1131.
Alcohols |
Laboratory Management
Enantioselective Reduction by Crude Plant Parts: Reduction of Benzofuran-2-yl Methyl Ketone with Carrot (Daucus carota) Bits  Silvana Ravía, Daniela Gamenara, Valeria Schapiro, Ana Bellomo, Jorge Adum, Gustavo Seoane, and David Gonzalez
Presents the enantioselective reduction of a ketone by crude plant parts, using carrot (Daucus carota) as the reducing agent.
Ravía, Silvana; Gamenara, Daniela; Schapiro, Valeria; Bellomo, Ana; Adum, Jorge; Seoane, Gustavo; Gonzalez, David. J. Chem. Educ. 2006, 83, 1049.
Aldehydes / Ketones |
Biotechnology |
Catalysis |
Chromatography |
Green Chemistry |
Oxidation / Reduction |
Stereochemistry |
Separation Science
Reductive Amination: A Remarkable Experiment for the Organic Laboratory  Kim M. Touchette
The synthesis of N-(2-hydroxy-3-methoxybenzyl)-N-p-tolylacetamide is a fast, simple three-step sequence that serves as a useful example of the reductive amination reaction for the organic chemistry laboratory.
Touchette, Kim M. J. Chem. Educ. 2006, 83, 929.
Aldehydes / Ketones |
Amines / Ammonium Compounds |
Green Chemistry |
Instrumental Methods |
IR Spectroscopy |
NMR Spectroscopy |
Oxidation / Reduction |
Solids
A Simple Combinatorial Experiment Based on Fischer Esterification. An Experiment Suitable for the First-Semester Organic Chemistry Lab  Peter A. Wade, Susan A. Rutkowsky, and Daniel B. King
Describes a combinatorial experiment for the synthesis of esters by Fischer esterification in which a total of eight esters are prepared as six mixtures.
Wade, Peter A.; Rutkowsky, Susan A.; King, Daniel B. J. Chem. Educ. 2006, 83, 927.
Alcohols |
Carboxylic Acids |
Combinatorial Chemistry |
Equilibrium |
Esters |
Gas Chromatography |
Synthesis
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
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
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
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
Using Building-Block Puzzles To Practice Drawing Organic Mechanisms  Ender Erdik
This pencil-and-paper activity is designed to test the ability of students in writing intermediates and products in the reactions of ketones. An undergraduate student who is successful in organic chemistry at the sophomore level is expected to fill in empty boxes with the appropriate "building blocks", which are atoms and atom groups (neutral or ionic). Solving the puzzle will give the formulas of reactants, reactive intermediates, and products. Students test their understanding of reaction mechanisms while having fun.
Erdik, Ender. J. Chem. Educ. 2005, 82, 1325.
Reactive Intermediates |
Synthesis |
Aldehydes / Ketones |
Mechanisms of Reactions
An Improved Preparation of 2,4-Dinitrophenylhydrazine Reagent  Ben Ruekberg and Eric Rossoni
In the analysis of aldehydes and ketones (both for characterizing the functional group and identifying such compounds by the melting points of their derivatives), 2,4-dinitrophenylhydrazine reagent is often used. Of the several formulations of this reagent, the most popular uses sulfuric acid. The method involves making a paste of 2,4-dinitro-phenylhydrazine in concentrated sulfuric acid, dispersion of the paste in ethanol, addition of water, and the filtration of the reagent. This improvement uses milder conditions, which may obviate the need for the final filtration. Those responsible for preparation of stock reagent solutions for classes should note that this method facilitates scaling up the preparation.
Ruekberg, Ben; Rossoni, Eric. J. Chem. Educ. 2005, 82, 1310.
Aldehydes / Ketones |
Laboratory Equipment / Apparatus |
Laboratory Management
Capillary Electrophoresis Analysis of Substituted Benzoic Acids. An Experiment for the Organic Synthesis Laboratory  Nancy S. Mills, John D. Spence, and Michelle M. Bushey
We have introduced an experiment into the organic chemistry sequence, in the synthesis laboratory, that utilizes capillary electrophoresis to evaluate the pKa shift on a series of student-prepared substituted benzoic acids. The pKa shift is examined in reference to the electrophoretic-migration behavior of benzoic acid and is a result of the electron-withdrawing or electron-donating characteristics of the substituent. This strategy allows us to increase the exposure of students to modern methods of separation. We are using repeated exposure to increase students' knowledge of separation strategies and techniques.
Mills, Nancy S.; Spence, John D.; Bushey, Michelle M. J. Chem. Educ. 2005, 82, 1226.
Synthesis |
Electrophoresis |
Grignard Reagents |
Instrumental Methods |
Separation Science
The Ethylene Ketal Protecting Group Revisited: The Synthesis of 4-Hydroxy-4,4-diphenyl-2-butanone  Marsha R. Baar, Charles E. Russell, and Kristin L. Wustholz
The multistep synthesis of 4-hydroxy-4,4-diphenyl-2-butanone from ethyl acetoacetate illustrates the use of a ketal protecting group. Reaction of ethyl acetoacetate with ethylene glycol with p-TsOH in toluene produced the ketal ester. Reaction of the crude ketal ester with two equivalents of phenyl magnesium bromide followed by an aqueous acid workup generated the tertiary alcohol and simultaneously removed the ketal protecting group to produce the hydroxyketone. Our procedure is a modification of a previously published synthesis whose end product was 4,4-diphenyl-3-buten-2-one, the dehydrated analog.
Baar, Marsha R.; Russell, Charles E.; Wustholz, Kristin L. J. Chem. Educ. 2005, 82, 1057.
Synthesis |
Grignard Reagents |
IR Spectroscopy |
Mechanisms of Reactions |
NMR Spectroscopy
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
Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory Experiment  Sam H. Leung and Stephen A. Angel
In this experiment (E)- and (Z)-1-(4-bromophenyl)-2-phenylethene are synthesized by a solvent-free Wittig reaction. The reaction is effected by grinding the reactants in a mortar with a pestle. Both the E and Z isomers of the product are produced as evidenced by thin-layer chromatography and 1H NMR analysis. The E isomer is isolated by crystallization with ethanol in this experiment. In addition to learning about the Wittig reaction, students are also introduced to the ideas of mechanochemistry and green chemistry.
Leung, Sam H.; Angel, Stephen A. J. Chem. Educ. 2004, 81, 1492.
Chromatography |
Green Chemistry |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Reactions |
Aldehydes / Ketones |
Alkenes
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
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
The Darzens Condensation: Structure Determination through Spectral Analysis and Understanding Substrate Reactivity  R. David Crouch, Michael S. Holden, and Candice A. Romany
The Darzens condensation involves two steps that are typically included in the sophomore organic curriculum: an aldol reaction followed by an intramolecular nucleophilic substitution.
Crouch, R. David; Holden, Michael S.; Romany, Candice A. J. Chem. Educ. 2004, 81, 711.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Mechanisms of Reactions |
Aldehydes / Ketones
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
Methyl Ethyl Ketone  Jay A. Young
The hazards of methyl ethyl ketone are described.
Young, Jay A. J. Chem. Educ. 2004, 81, 630.
Laboratory Management |
Aldehydes / Ketones |
Laboratory Equipment / Apparatus
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
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
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
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
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
Preparing Students for Research: Synthesis of Substituted Chalcones as a Comprehensive Guided-Inquiry Experience  James R. Vyvyan, Donald L. Pavia, Gary M. Lampman, and George S. Kriz Jr.
An aldol condensation of substituted benzaldehydes with substituted acetophones to produce substituted benzalacetophenones (chalcones) in a guided-inquiry approach.
Vyvyan, James R.; Pavia, Donald L.; Lampman, Gary M.; Kriz, George S., Jr. J. Chem. Educ. 2002, 79, 1119.
Medicinal Chemistry |
Microscale Lab |
Natural Products |
NMR Spectroscopy |
Synthesis |
Aromatic Compounds |
Aldehydes / Ketones
1H NMR Measurement of the Trans–Cis Photoisomerization of Cinnamic Acid Derivatives  Basil Danylec and Magdy N. Iskander
Procedure that illustrates trans-cis photoisomerization.
Danylec, Basil; Iskander, Magdy N. J. Chem. Educ. 2002, 79, 1000.
NMR Spectroscopy |
Photochemistry |
Stereochemistry |
Aromatic Compounds |
Alcohols |
Esters |
Alkenes |
Molecular Properties / Structure
Discovery-Oriented Approach To Organic Synthesis: Tandem Aldol Condensation-Michael Addition Reactions. Identifying Diastereotopic Hydrogens in an Achiral Molecule by NMR Spectroscopy  Nanette Wachter-Jurcsak and Kendra Reddin
Procedure illustrating aldol condensation and Michael addition reactions.
Wachter-Jurcsak, Nanette; Reddin, Kendra. J. Chem. Educ. 2001, 78, 1264.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Aromatic Compounds |
Aldehydes / Ketones |
Addition Reactions |
Mechanisms of Reactions
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
The TCICA Test for Distinguishing Aldehydes and Ketones  Gene A. Hiegel, Christine Juska, and Michelle Kim
Distinguishing aldehydes from ketones through their reaction with TCICA (trichloroisocyanuric acid).
Hiegel, Gene A.; Juska, Christine; Kim, Michelle. J. Chem. Educ. 2001, 78, 1105.
Qualitative Analysis |
Aldehydes / Ketones
Diastereoselective Synthesis of (+/-)-1,2-Diphenyl-1,2-propanediol. A Discovery-Based Grignard Reaction Suitable for a Large Organic Lab Course  James A. Ciaccio, Roxana P. Bravo, Antoinette L. Drahus, John B. Biggins, Rosalyn V. Concepcion, and David Cabrera
An experiment that probes the diastereoselectivity of the reaction between a Grignard reagent and a common, inexpensive alpha-chiral ketone; introduces students to pi-facial discrimination by having them establish the stereochemical course of kinetically controlled nucleophilic addition to a carbonyl.
Ciaccio, James A.; Bravo, Roxana P.; Drahus, Antoinette L.; Biggins, John B.; Concepcion, Rosalyn V.; Cabrera, David. J. Chem. Educ. 2001, 78, 531.
Mechanisms of Reactions |
Synthesis |
Organometallics |
Stereochemistry |
Grignard Reagents |
Aldehydes / Ketones
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
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
Introducing Chiroscience into the Organic Laboratory Curriculum  Kenny B. Lipkowitz, Tim Naylor, and Keith S. Anliker
"Chiroscience" is a young but robust industry linking science and technology with chemistry and biology; includes description of an asymmetric reduction of a ketone followed by an assessment of the enantiomeric excess by GC using a chiral stationary phase.
Lipkowitz, Kenny B.; Naylor, Tim; Anliker, Keith S. J. Chem. Educ. 2000, 77, 305.
Chirality / Optical Activity |
Chromatography |
Mechanisms of Reactions |
Synthesis |
Separation Science |
Stereochemistry |
Gas Chromatography |
Aldehydes / Ketones
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
Grignard Reactions in "Wet" Ether  David H. Smith
A small laboratory ultrasonic bath can be used to initiate the Grignard reaction of alkyl or aryl bromides in regular laboratory-quality, undried, diethyl ether and in simple undried test tubes.
Smith, David H. J. Chem. Educ. 1999, 76, 1427.
Synthesis |
Microscale Lab |
Grignard Reagents |
Ethers
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
Side Reactions in a Grignard Synthesis  Hilton M. Weiss
This experiment describes a standard Grignard synthesis of a secondary alcohol, 3-heptanol. It brings attention to a significant side product, 3-heptanone, and suggests ways of understanding and utilizing the formation of this product. The experiment is intended to stimulate creative thought in the undergraduate organic chemistry course.
Weiss, Hilton M. J. Chem. Educ. 1999, 76, 76.
Mechanisms of Reactions |
Synthesis |
Grignard Reagents
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
Vanillin (the author replies)  Hocking, Martin
Additional information regarding salicylic acid.
Hocking, Martin J. Chem. Educ. 1998, 75, 1203.
Aldehydes / Ketones |
Applications of Chemistry |
Medicinal Chemistry |
Molecular Properties / Structure
Vanillin  Calloway, Dean
Incorrect structural formula for methyl salicylate.
Calloway, Dean J. Chem. Educ. 1998, 75, 1203.
Medicinal Chemistry |
Applications of Chemistry |
Aldehydes / Ketones |
Molecular Properties / Structure
Letters  
Incorrect structural formula for methyl salicylate.
J. Chem. Educ. 1998, 75, 1203.
Medicinal Chemistry |
Applications of Chemistry |
Aldehydes / Ketones |
Molecular Properties / Structure
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
A Simple Organic Microscale Experiment Illustrating the Equilibrium Aspect of the Aldol Condensation  Ernest A. Harrison Jr.
A simple microscale experiment has been developed that illustrates the equilibrium aspect of the aldol condensation by using two versions of the standard preparation of tetraphenylcyclopentadienone from benzil and 1,3-diphenyl- 2-propanone.
Harrison, Ernest A., Jr. J. Chem. Educ. 1998, 75, 636.
Equilibrium |
Reactions |
Mechanisms of Reactions |
Microscale Lab |
Aldehydes / Ketones
Cinnamaldehyde by Steam Distillation of Cinnamon  Douglass F. Taber and Andrew J. Weiss
Powdered cinnamon foams badly on attempted steam distillation. It has been demonstrated that preliminary iterative evacuation of the aqueous mixture allows smooth distillation of cinnamaldehyde (I).
Taber, Douglass F.; Weiss, Andrew J. J. Chem. Educ. 1998, 75, 633.
Aldehydes / Ketones |
Aromatic Compounds
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
An Aldehyde Derivative  J. Hodge Markgraf and Bo Yoon Choi
A system in which aldehydes are condensed with 1,2-benzenedimethylthiol in the presence of anhydrous ferric chloride on silica gel to give 3-substituted 1,5-dihyhdro-2,4-benzodithiepines. Melting points of the derivatives were taken as a means of identification of unknown compounds.
Markgraf, J. Hodge; Choi, Bo Yoon. J. Chem. Educ. 1998, 75, 222.
Aldehydes / Ketones |
Synthesis
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
Acetone and Ethyl Acetate in Commercial Nail Polish Removers: A Quantitative NMR Experiment Using an Internal Standard  David W. Clarke
The qualitative and quantitative analysis of commercial nail polish removers is performed on a 60 MHz NMR spectrometer. After taking NMR spectra of the polish removers, students can make peak assignments for the known components of acetone and ethyl acetate. Using these spectra, students are also able to identify the unknown alcohol present in the remover as ethanol.
Clarke, David W. J. Chem. Educ. 1997, 74, 1464.
Laboratory Equipment / Apparatus |
NMR Spectroscopy |
Aldehydes / Ketones
Determination of Formaldehyde in Cigarette Smoke  Jon W. Wong, Kenley K. Ngim, Jason P. Eiserich, Helen C. H. Yeo, Takayuki Shibamoto, and Scott A. Mabury
This experiment involves the collection, derivatization, extraction, and analysis of formaldehyde from cigarette smoke using two methods. Formaldehyde is extracted from smoke and derivitized with a solution of 2,4-DNPH with subsequent cleanup by solid-phase extraction and analysis of the hydrazone by HPLC with UV detection; additionally a solution of cysteamine yields the corresponding thiazolidine derivative that is liquid/liquid extracted and subsequently analyzed by either GC with NPD or FPD (sulfur mode).
Wong, Jon W.; Ngim, Kenley K.; Eiserich, Jason P.; Yeo, Helen C. H.; Shibamoto, Takayuki; Mabury, Scott A. J. Chem. Educ. 1997, 74, 1100.
Learning Theories |
Chromatography |
Quantitative Analysis |
Separation Science |
Aldehydes / Ketones |
Applications of Chemistry
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
An Experiment to Demonstrate Magnetic Nonequivalence in Proton NMR  Christopher J. Welch
The bicyclic compound, 3a,6a-diethoxycarbonyl-2,5-dimethyl-1,4-dioxo-octahydropyrrolo[3,4-c]pyrrole, prepared by a literature procedure is used to demonstrate magnetic nonequivalence for methylene protons in the proton NMR experiment.
Welch, Christopher J. J. Chem. Educ. 1997, 74, 247.
Spectroscopy |
NMR Spectroscopy |
Stereochemistry |
Aldehydes / Ketones
A -78°C Sequential Michael Addition for the Organic Lab  Michael W. Tanis
This paper introduces a cold-temperature enolate alkylation reaction that can be performed safely and inexpensively by undergraduate students in approximately two 3-hour lab sessions.
Tanis, Michael W. J. Chem. Educ. 1997, 74, 112.
Addition Reactions |
Alkenes |
Aldehydes / Ketones |
Synthesis
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
Following Microscale Organic Reactions Using FT-IR  Ems-Wilson, Janice
The progress of two microscale reactions, the reduction of cyclohexanone with sodium borohydride and the photochemical formation of benzopinacol, was monitored, qualitatively, using FT-IR.
Ems-Wilson, Janice J. Chem. Educ. 1996, 73, A171.
Microscale Lab |
Aldehydes / Ketones |
Photochemistry |
Oxidation / Reduction |
IR Spectroscopy
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
Grignard Reaction of an Epoxide: A Mechanistic Study  James A. Ciaccio, Sabrina Volpi, Ransford Clarke
Unlike most undergraduate Grignard experiments which are performed merely for the sake of illustrating a textbook reaction, this Grignard synthesis is performed to probe the reactivity of styrene oxide. Students are required to analyze their products by TLC and NMR spectroscopy (instead of just submitting them for a grade) in order to obtain the data necessary for making mechanistic conclusions.
Ciaccio, James A.; Volpi, Sabrina; Clarke, Ransford. J. Chem. Educ. 1996, 73, 1196.
Grignard Reagents |
Epoxides |
Thin Layer Chromatography |
NMR Spectroscopy |
Synthesis
Carbonyl and Conjugate Additions to Cyclohexenone: Experiments Illustrating Reagent Selectivity  Michael G. Organ and Paul Anderson
Undergraduate students leaving an organic chemistry program should have exposure to these concepts and hands-on experience in dealing practically with the issue of selectivity. In this paper, selective addition of a nucleophile to either end of the enone moiety in cyclohexenone is examined.
Organ, Michael G.; Anderson, Paul. J. Chem. Educ. 1996, 73, 1193.
Addition Reactions |
Aldehydes / Ketones |
Mechanisms of Reactions
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
Epoxidation of Alpha-Methylstyrene and its Lewis Acid Rearrangement to 2-Phenylpropanal  David L. Garin, Melissa Gamber, and Bradley J. Rowe
This undergraduate organic lab experiment includes procedures for the peracid epoxidation of an olefin and the Lewis acid rearrangement of an epoxide to a carbonyl compound.
Garin, David L.; Gamber, Melissa; Rowe, Bradley J. J. Chem. Educ. 1996, 73, 555.
Lewis Acids / Bases |
Spectroscopy |
NMR Spectroscopy |
UV-Vis Spectroscopy |
Gas Chromatography |
IR Spectroscopy |
Aldehydes / Ketones
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
A Mixed Aldol Condensation-Michael Addition Experiment  Thomas P. Clausen, Beverly Johnson, and Jim Wood
This article describes the analysis of the recrystallized products of a mixed aldol condensation between symmetrical ketones and aromatic aldehydes.
Clausen, Thomas P.; Johnson, Beverly; Wood, Jim. J. Chem. Educ. 1996, 73, 266.
Aldehydes / Ketones |
NMR Spectroscopy |
Mechanisms of Reactions
The Mechanism of NaBH4 Addition to Aldehydes: A Labeling Experiment  Rolland K. Robinson and Karl De Jesus
In order to determine the sources of hydrogens in NaBH4 reductions of aldehydes, a series of reductions were carried out using differentially deuterated reagents and solvents.
Robinson, Rolland K.; De Jesus, Karl. J. Chem. Educ. 1996, 73, 264.
Aldehydes / Ketones |
Oxidation / Reduction
A Colorful Grignard Reaction: Preparation of the Triarylmethane Dyes from 4-Bromo-N,N-Dimethylaniline  Douglass F. Taber, Robert P. Meagley, and Danielle Supplee
The Grignard reagent is readily prepared from 4-bromo-N,N-dimethylaniline. A procedure suitable for an undergraduate laboratory course is presented.
Taber, Douglass F.; Meagley, Robert P.; Supplee, Danielle. J. Chem. Educ. 1996, 73, 259.
Dyes / Pigments |
Grignard Reagents
Experimental Illustration of the Utility of Lewis Structures: An FTIR Experiment for Introductory Chemistry  James E. Swartz and Kurt Schladetzky
An experiment is described in which students record the FTIR spectra of a series of organic liquids which contain a carbonyl group and to predict the strength of the carbonyl bonds based upon drawing and examination of various Lewis structures.
Swartz, James E.; Schladetzky, Kurt. J. Chem. Educ. 1996, 73, 188.
Fourier Transform Techniques |
Aldehydes / Ketones |
Lewis Structures
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
An Efficient Microscale Procedure for the Preparation of 3,5-Dinitrobenzoates  Richard F. Smith and Gaetano M. Cristalli
A laboratory to introduce the concept and technique of mass spectroscopy to introductory organic students; sample data and analysis included.
Smith, Richard F.; Cristalli, Gaetano M. J. Chem. Educ. 1995, 72, A160.
Mass Spectrometry |
Gas Chromatography |
Aldehydes / Ketones |
Instrumental Methods |
Qualitative Analysis |
Microscale Lab
Discovery-Based Microscale Catalytic Decarbonylation of Aldehydes  Pearsall, Mary-Ann; Rosen, Alan M.; Conrad, Jennifer S.; Hendrickson, Carrie A.; Pacchia, Ann Marie L.; Schantz, Daniel J.
Experimental procedure for decarbonylation of aldehydes by heating over a palladium/carbon catalyst.
Pearsall, Mary-Ann; Rosen, Alan M.; Conrad, Jennifer S.; Hendrickson, Carrie A.; Pacchia, Ann Marie L.; Schantz, Daniel J. J. Chem. Educ. 1995, 72, A29.
Synthesis |
Catalysis |
Aldehydes / Ketones |
Microscale Lab
Baeyer-Villiger Oxidation of Indane-1-ones: Monitoring of the Reaction by VPC and IR Spectroscopy  Elie Stephan
Procedure for the Baeyer-Villiger oxidation of indane-1-ones.
Stephan, Elie. J. Chem. Educ. 1995, 72, 1142.
IR Spectroscopy |
Synthesis |
Mechanisms of Reactions |
Oxidation / Reduction |
Aldehydes / Ketones
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
"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
A Centenary Synthesis of Carone and Dicarvelone  Armstead, D. E. F.
Procedure for synthesizing carone and dicarvelone.
Armstead, D. E. F. J. Chem. Educ. 1995, 72, 550.
Synthesis |
Aldehydes / Ketones
Baker's Yeast Reduction of alpha-Diketones: A Four-Hour Experiment for Undergraduate Students  Besse, Pascale; Bolte, Jean; Veschambre, Henri
Procedure for quickly and efficiently reducing alpha-diketones using bakers' yeast.
Besse, Pascale; Bolte, Jean; Veschambre, Henri J. Chem. Educ. 1995, 72, 277.
Oxidation / Reduction |
Synthesis |
Aldehydes / Ketones
Preparation of (S)-(+)-5,8a-Dimethyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione: An Undergraduate Experiment in Asymmetric Synthesis  Markgraf, J. Hodge; Fei, John F.; Ruckman, Robert E.
An asymmetric Robinson annelation suitable for the undergraduate organic laboratory.
Markgraf, J. Hodge; Fei, John F.; Ruckman, Robert E. J. Chem. Educ. 1995, 72, 270.
Synthesis |
Chirality / Optical Activity |
Aldehydes / Ketones
Hydrogen-Bonding Equilibrium in Phenol Analyzed by NMR Spectroscopy  Lessinger, Leslie
Experimental procedure for determining the equilibrium constant for the hydrogen-bonding equilibrium of phenol in carbon tetrachloride solution; data and analysis included.
Lessinger, Leslie J. Chem. Educ. 1995, 72, 85.
Equilibrium |
Noncovalent Interactions |
NMR Spectroscopy |
Hydrogen Bonding |
Aromatic Compounds |
Alcohols
The Distribution of Cyclohexanone between Cyclohexane and Water  Worley, John D.
A microscale experiment that may be used to demonstrate extraction, spectrophotometric analysis, and the determination of a distribution constant.
Worley, John D. J. Chem. Educ. 1994, 71, A145.
Microscale Lab |
Aqueous Solution Chemistry |
Aldehydes / Ketones |
Alkanes / Cycloalkanes |
Separation Science |
Spectroscopy
A More Affordable Undergraduate Experiment on the Reduction of Acetophenone by Yeast  Lee, Moses; Huntington, Martha
Preparation of Mosher's esters through the reduction of acetophenone with baker's yeast.
Lee, Moses; Huntington, Martha J. Chem. Educ. 1994, 71, A62.
Microscale Lab |
Aromatic Compounds |
Aldehydes / Ketones |
Oxidation / Reduction |
Stereochemistry |
Chirality / Optical Activity |
Esters |
Synthesis
Synthesis and Spectroscopic Study of Plant Growth Regulators Phenylpyridylureas: An "Agrorganic" Undergraduate Laboratory Experiment  Hocquet, Alexandre; Tohier, Jacques; Fournier, Josette
This lab could represent an undergraduate comparative synthesis and analysis of biologically active molecules, suitable for an introductory lab session.
Hocquet, Alexandre; Tohier, Jacques; Fournier, Josette J. Chem. Educ. 1994, 71, 1092.
Agricultural Chemistry |
Drugs / Pharmaceuticals |
Aldehydes / Ketones |
Aromatic Compounds |
Synthesis
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
Models of 2-Butanone: Using Graphics To Illustrate Complementary Approaches to Molecular Structure and Reactivity  Hanks, T. W.
157. Ways in which a graphics workstation can be used to illustrate various concepts of molecular structure.
Hanks, T. W. J. Chem. Educ. 1994, 71, 62.
Aldehydes / Ketones |
Molecular Properties / Structure |
Molecular Modeling |
Molecular Mechanics / Dynamics |
Stereochemistry |
Quantum Chemistry |
MO Theory
The stereochemistry of commercial 2,6-dimethylcyclohexanone: An application of capillary gas chromatography   Garner, Charles M.
One example of how capillary gas chromatography can be employed in undergraduate organic laboratories.
Garner, Charles M. J. Chem. Educ. 1993, 70, A310.
Gas Chromatography |
Microscale Lab |
Laboratory Equipment / Apparatus |
Aldehydes / Ketones |
Diastereomers |
Stereochemistry
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
Products of aldol addition and related reactions: Notation for their prediction  Nwaukwai, Stephen O.
A simple method that can be used to predict products of aldols and aldol-tye addition reactions.
Nwaukwai, Stephen O. J. Chem. Educ. 1993, 70, 626.
Addition Reactions |
Aldehydes / Ketones |
Nomenclature / Units / Symbols
A puzzle within a puzzle   Silversmith, Ernest F.
Author expresses gratitude for Josef G. Krause's suggested improvements (appear earlier on the page in this Journal) and offers further clarifications on his article which appeared in this Journal (August 1991, page 688).
Silversmith, Ernest F. J. Chem. Educ. 1993, 70, 605.
Grignard Reagents
A puzzle within a puzzle   Krause, Josef G.
Author points out a change that should be made to a lab in a previously published paper in this Journal (August 1991, page 688).
Krause, Josef G. J. Chem. Educ. 1993, 70, 605.
Grignard Reagents
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
The microscale synthesis and the structure determination of endo-9-methoxycarbonyl-3-oxatricyclo[4,2,1,0 4,5]-2-nonanone.  Lee, Moses.
The microscale synthesis and the structure determination of endo-9-methoxycarbonyl-3-oxatricyclo[4,2,1,0 4,5]-2-nonanone.
Lee, Moses. J. Chem. Educ. 1992, 69, A172.
Microscale Lab |
Synthesis |
Aldehydes / Ketones |
Fourier Transform Techniques |
NMR Spectroscopy |
IR Spectroscopy |
Gas Chromatography |
Thin Layer Chromatography |
Instrumental Methods
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
Preparing and purifying 2,4-dinitrophenylhydrazones: Alternatives to the Brady procedure  Zhang, Juan; Hertzler, Russell L.; Eisenbraun, E. J.
Problems with and an alternative to the Brady procedure for preparing 2,4-dinitrophenylhydrazone; using a sulfonic acid ion-exchange resin in refluxing toluene.
Zhang, Juan; Hertzler, Russell L.; Eisenbraun, E. J. J. Chem. Educ. 1992, 69, 1037.
Synthesis |
Catalysis |
Aldehydes / Ketones
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
Identification of methylcyclohexanones by NMR  Gurst, Jerome E.
Distinguishing between three isomeric methylcyclohexanones using NMR.
Gurst, Jerome E. J. Chem. Educ. 1992, 69, 774.
Aldehydes / Ketones |
NMR Spectroscopy |
Diastereomers
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
Three methods for studying the kinetics of the halogenation of acetone.  Birk, James P.; Walters, David L.
Three methods for carrying out a kinetic study of the reaction between propanone and elemental iodine.
Birk, James P.; Walters, David L. J. Chem. Educ. 1992, 69, 585.
Aldehydes / Ketones |
Kinetics |
Spectroscopy |
Rate Law
Schiff base puzzle project.  Todd, David.
Students pick an unknown substituted aniline and a substituted benzaldehyde, produces the corresponding Schiff base from them, and compares its melting point to those of 25 possible Schiff bases (their structures and melting points being given).
Todd, David. J. Chem. Educ. 1992, 69, 584.
Qualitative Analysis |
Aldehydes / Ketones |
Amines / Ammonium Compounds
Corn chip aroma: A classroom demonstration on the preparation of a Schiff base  Sartori, Antony T.; Wood, William F.
Preparing 3-methylimino-2-butanone.
Sartori, Antony T.; Wood, William F. J. Chem. Educ. 1992, 69, 572.
Aldehydes / Ketones |
Synthesis |
Reactions |
Mechanisms of Reactions
The importance of temperature control in the preparation of phencyclone (1,3-diphenyl-2-H-cyclopenta[I]phenanthrene-2-one).  Harrison, Ernest A., Jr.
The addition of a methanolic alkali solution to the reactant mixture increases yields to 80%.
Harrison, Ernest A., Jr. J. Chem. Educ. 1992, 69, 571.
Synthesis |
Aromatic Compounds |
Aldehydes / Ketones
Phenol and the importance of dose.  Crute, Thomas D.
Phenol is highly toxic, but the active ingredient in Chloraseptic lozenges.
Crute, Thomas D. J. Chem. Educ. 1992, 69, 553.
Phenols |
Aromatic Compounds |
Alcohols |
Toxicology |
Consumer Chemistry |
Medicinal Chemistry
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
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 new method for the oxidation of 4-phenylurazole to 4-phenyltriazolinedione.  Mallakpour, Shadpour E.
The procedures describe the synthesis of 4-phenyl-urazole from ethyl carbazate and then the oxidation of the urazole with NO2-N2O4 to yield 4-phenyl-1,2,4-trizoline-3,5-dione.
Mallakpour, Shadpour E. J. Chem. Educ. 1992, 69, 238.
Oxidation / Reduction |
Aldehydes / Ketones |
Synthesis |
Aromatic Compounds
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 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
Beta-keto esters from tin(II) chloride catalyzed reactions of aldehydes with ethyl diazoacetate: An undergraduate laboratory experiment drawn from the current literature  Brockwell, Joyce C.; Holmquist, Christopher R.
This is an experimental procedure for producing longer-chain keto esters from unconjugated aldehydes on reaction with ethyl diazoacetate catalyzed by Lewis acids for use in an undergraduate laboratory.
Brockwell, Joyce C.; Holmquist, Christopher R. J. Chem. Educ. 1992, 69, 68.
Catalysis |
Synthesis |
Lewis Acids / Bases |
Aldehydes / Ketones |
Esters
A mild and convenient oxidation of alcohols: Benzoin to benzil and borneol to camphor  Straub, Thomas S.
A traditional organic chemistry laboratory poses threat to both student safety and the environment: this author provides an alternative procedure.
Straub, Thomas S. J. Chem. Educ. 1991, 68, 1048.
Heterocycles |
Oxidation / Reduction |
Alcohols
A novel ketone derivative  Melamedi, Dan; Pickering, Miles
The authors propose the use of thioketals as derivatives as a safer alternative that also illustrates an interesting but rarely visited corner of undergraduate organic chemistry.
Melamedi, Dan; Pickering, Miles J. Chem. Educ. 1991, 68, 1046.
Aldehydes / Ketones
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
The malonic ester synthesis in the undergraduate laboratory  Hoogenboom, Bernard E.; Ihrig, Phillip J.; Langsjoen, Arne N.; Linn, Carol J.; Mulder, Stephen D.
The versatile reactions of diethyl malonate represent an important lecture topic in introductory organic courses, but are only rarely performed in the lab because of several problems associated with performing these reactions. These authors present a lab the circumvents some of the typical problems.
Hoogenboom, Bernard E.; Ihrig, Phillip J.; Langsjoen, Arne N.; Linn, Carol J.; Mulder, Stephen D. J. Chem. Educ. 1991, 68, 689.
Aromatic Compounds |
Aldehydes / Ketones |
Amino Acids |
Heterocycles |
Amides
A puzzle-solving experiment utilizing a Grignard reagent  Silversmith, Ernest F.
Puzzle-solving experiments get away from typical organic laboratories that involve more of a cookbook methodology.
Silversmith, Ernest F. J. Chem. Educ. 1991, 68, 688.
Grignard Reagents |
Addition Reactions
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
The synthesis of 2-methyl-4-heptanone  de Jong, Elma A.; Feringa, Ben L.
2-methyl-4-heptanone is an ant pheromone used to alarm fellow ants. The synthesis described in this article is greeted with interest by students.
de Jong, Elma A.; Feringa, Ben L. J. Chem. Educ. 1991, 68, 71.
Aldehydes / Ketones |
Natural Products |
Synthesis |
Grignard Reagents
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
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
Sherlock Holmes and the fraudulent ketone  Waddell, Thomas G.; Rybolt, Thomas R.
A chemical mystery featuring Sherlock Holmes and Dr. Watson.
Waddell, Thomas G.; Rybolt, Thomas R. J. Chem. Educ. 1990, 67, 1006.
Enrichment / Review Materials |
Aldehydes / Ketones
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
Preparation of 1-phenyl-3-phenylaminopyrrolidine-2,5-dione: An organic laboratory experiment on the Michael addition  Ram, Ram N.; Varsha, Kiran
Acylation of aniline with maleic anhydride to give maleanilic acid followed by Michael addition of aniline and cyclization to yield 1-phenyl-3-phenylaminopyrrolidine-2,5-dione.
Ram, Ram N.; Varsha, Kiran J. Chem. Educ. 1990, 67, 985.
Addition Reactions |
Aldehydes / Ketones |
Synthesis
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
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
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
A simple procedure for the base-catalyzed cleavage of benzopinacolone to triphenylmethane: An undergraduate experiment  Stranberg, Michael; Anselme, J. -P.
A simple procedure for the base-catalyzed cleavage of benzopinacolone to triphenylmethane: An undergraduate experiment.
Stranberg, Michael; Anselme, J. -P. J. Chem. Educ. 1990, 67, 616.
Catalysis |
Aldehydes / Ketones |
Mechanisms of Reactions |
Synthesis
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
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
The palladium-catalyzed oxidation of 2-vinylnaphthalene: A microscale organic synthesis experiment   Byers, Jeffrey H.; Ashfaq, Aalla; Morse, Wendy R.
The Wacker oxidation experiment as described is cost-efficient due to the small scale employed, and is a valuable addition to the undergraduate organic curriculum.
Byers, Jeffrey H.; Ashfaq, Aalla; Morse, Wendy R. J. Chem. Educ. 1990, 67, 340.
Microscale Lab |
Synthesis |
Alkynes |
Aldehydes / Ketones |
Oxidation / Reduction
The subjection of glutaraldehyde to the Tollens test  Hill, William D., Jr.
Redox equations have been established for the Tollens test with respect to compounds containing two aldehyde groups such as glutaraldehyde.
Hill, William D., Jr. J. Chem. Educ. 1990, 67, 329.
Aldehydes / Ketones |
Oxidation / Reduction
Laboratory experiments on phase-transfer-catalyzed reactions of neutral molecules  Mathur, Nawal K.; Narang, Chander K.
In order to illustrate the application of a phase transfer catalyst (PTC), the preparation of benzophenone oxime was attempted under different conditions.
Mathur, Nawal K.; Narang, Chander K. J. Chem. Educ. 1990, 67, 273.
Catalysis |
Aromatic Compounds |
Aldehydes / Ketones |
Phases / Phase Transitions / Diagrams
Grignard reagent additions to alpha, beta-ethylenic nitriles: 1,4- vs. 1,2- additions  Kulp, Stuart S.; DiConcetto, Joseph A.
The easily synthesized alpha-phenylcinnamonitrile serves as an excellent starting material to illustrate conjugate (1,4) vs. simple (1,2) addition of various reactants.
Kulp, Stuart S.; DiConcetto, Joseph A. J. Chem. Educ. 1990, 67, 271.
Grignard Reagents |
Aromatic Compounds |
IR Spectroscopy |
NMR Spectroscopy
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
g-Nonanoic lactone: Synthesis of a fragrance and flavor enhancer in the undergraduate laboratory  Bunce, Richard A.; Reeves, Henry D.
The experiment describes the synthesis of ?-nonanoic lactone, an un-natural compound having the odor and flavor of coconuts.
Bunce, Richard A.; Reeves, Henry D. J. Chem. Educ. 1990, 67, 69.
Synthesis |
Aldehydes / Ketones
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
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
Example of the Robinson annulation procedure via phase transfer catalysis a beginning organic synthesis experiment  Soriano, D. S.; Lombardi, A. M.; Persichini, P. J.; Nalewajek, D.
A brief description of the procedure.
Soriano, D. S.; Lombardi, A. M.; Persichini, P. J.; Nalewajek, D. J. Chem. Educ. 1988, 65, 637.
Catalysis |
Aromatic Compounds |
Synthesis |
Aldehydes / Ketones
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
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
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
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
An aldol condensation experiment using a number of aldehydes and ketones  Hathaway, Bruce A.
Four aldehydes and four ketones can be used to synthesize sixteen different products via an aldol condensation reaction.
Hathaway, Bruce A. J. Chem. Educ. 1987, 64, 367.
Aldehydes / Ketones
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
An improved preparation of a Grignard reagent  Eckert, Timothy S.
An improved preparation of phenylmagnesium bromide, a Grignard reagent.
Eckert, Timothy S. J. Chem. Educ. 1987, 64, 179.
Grignard Reagents |
Synthesis
Tollens's test, fulminating silver, and silver fulminate  Jenkins, Ian D.
Preparation, application, and misinformation regarding Tollens's test for aldehydes and reducing sugars.
Jenkins, Ian D. J. Chem. Educ. 1987, 64, 164.
Aldehydes / Ketones |
Carbohydrates |
Qualitative Analysis |
Laboratory Management
A visual manifestation of the Norrish Type I reaction: The cyclohexanone sunburn dosimeter  Carroll, Felix A.; Strouse, Geoffrey F.; Hain, Jon M.
Irradiation of aqueous cyclohexanone solutions produces hex-5-enal and butylketene; the latter reacts with water to form caproic acid, which lowers the pH of the solution and thus can be used to measure the progress of the reaction.
Carroll, Felix A.; Strouse, Geoffrey F.; Hain, Jon M. J. Chem. Educ. 1987, 64, 84.
Photochemistry |
pH |
Aldehydes / Ketones
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
Macro versus microlab: A controlled study of time efficiency  Pickering, Miles; LaPrade, Joseph E.
Various dramatic claims for speed and efficiency in microlabs have been made. However, few studies have been done that have provided concrete data that either supported or refuted these claims. This paper reports a controlled educational experiment in which a Grignard reaction was run by two groups of students at two different scales.
Pickering, Miles; LaPrade, Joseph E. J. Chem. Educ. 1986, 63, 535.
Grignard Reagents |
Microscale Lab
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
Starting recalcitrant Grignard reactions  Clough, S.; Goldman, E.; Williams, S.; George, B.
This note offers a tip on starting a Gringard reaction.
Clough, S.; Goldman, E.; Williams, S.; George, B. J. Chem. Educ. 1986, 63, 176.
Laboratory Management |
Grignard Reagents |
Organometallics
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
Computer-assisted quantitative infrared conformational analysis of alpha, beta-unsaturated ketones  Tisnes, P.; Perry, M.
Investigates the s-cis <> s-trans conformational equilibrium of alpha, beta-unsaturated ketones.
Tisnes, P.; Perry, M. J. Chem. Educ. 1985, 62, 903.
Aldehydes / Ketones |
Conformational Analysis |
IR Spectroscopy |
Stereochemistry |
Molecular Properties / Structure |
Quantitative Analysis
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
Atmospheric formaldehyde levels in an academic laboratory  Clausz, John C.; Maclntyre, Bruce A.; Malone, Elizabeth S.; Twelmeyer, John M.
Study to determine whether improved ventilation and use of "formaldehyde-free" specimens could reduce the levels of formaldehyde in laboratory air.
Clausz, John C.; Maclntyre, Bruce A.; Malone, Elizabeth S.; Twelmeyer, John M. J. Chem. Educ. 1984, 61, A121.
Laboratory Management |
Aldehydes / Ketones
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
The subjection of glutaraldehyde to the Fehling test and to the corrected Benedict test  Hill, William D., Jr.
The molecular and ionic redox equations with respect to the Fehling and Benedict tests (corrected with respect to glutaraldehyde).
Hill, William D., Jr. J. Chem. Educ. 1984, 61, 1085.
Qualitative Analysis |
Aldehydes / Ketones
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
Acetaldehyde: a chemical whose fortunes have changed  Wittcoff, Harold A.
Acetaldehyde is an example of a chemical whose use is declining because chemists have replaced it with superior chemicals.
Wittcoff, Harold A. J. Chem. Educ. 1983, 60, 1044.
Aldehydes / Ketones |
Applications of Chemistry
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
Prediction of the appearance of non-first-order proton NMR spectra   Macomber, Roger S.
Undergraduates generally become equipped only to handle only first-order coupling patterns. This means that they have a hard time understanding a real spectra. By scaffolding students through the synthesis level of Bloom's taxonomy, students can work toward a more expert level of understanding.
Macomber, Roger S. J. Chem. Educ. 1983, 60, 525.
NMR Spectroscopy |
Aldehydes / Ketones |
Learning Theories
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
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
Solvent increment not solvent correction: a suggested modification in the procedure of calculating wavelength of maximum ultraviolet absorption of alpha, beta-unsaturated aldehydes and ketones  Qureshi, Mohammad Ismail
This article describes a procedure for calculating the ? solvent max that removes an unnecessary, but typical source of confusion.
Qureshi, Mohammad Ismail J. Chem. Educ. 1983, 60, 149.
Spectroscopy |
Aldehydes / Ketones |
UV-Vis Spectroscopy
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
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
An early laboratory introduction to IR spectroscopy: Gaseous deuteroalkanes  Braun, Loren L.; Law, Raymond L.
The authors have found that the preparation of deuterated gaseous alkanes is a simple experiment that is a less hazardous experiment than the popular alternatives.
Braun, Loren L.; Law, Raymond L. J. Chem. Educ. 1981, 58, 79.
Isotopes |
Alkanes / Cycloalkanes |
Grignard Reagents |
Gases
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
Preparation of 1,1-Diphenyl-1-hydroxy-3-butanone  Rivett, D. E. A.
Exemplifies the use of a protecting group in organic synthesis.
Rivett, D. E. A. J. Chem. Educ. 1980, 57, 751.
Synthesis |
Molecular Properties / Structure |
Aldehydes / Ketones
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
Diphenylbutadienes syntheses by means of the Wittig reaction: Experimental introduction to the use of phase transfer catalysis  Gillois, J.; Guillerm, G.; Stephen, E.; Vo-Quang, L.
Intended as a project carried out by students at the end of introductory organic chemistry.
Gillois, J.; Guillerm, G.; Stephen, E.; Vo-Quang, L. J. Chem. Educ. 1980, 57, 161.
Synthesis |
Catalysis |
Alkenes |
Aldehydes / Ketones |
Stereochemistry
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
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
Synthesis of chrysanthemic acid: A multistep organic synthesis for undergraduate students  Schatz, Paul F.
This laboratory is geared toward intermediate organic chemistry laboratory courses that will acquaint students, predominantly chemistry majors, with the strategies and techniques in carrying out a multistep synthesis.
Schatz, Paul F. J. Chem. Educ. 1978, 55, 468.
Synthesis |
Acids / Bases |
Aldehydes / Ketones |
Stereochemistry
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
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
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
Classification test for aldehydes involving phase transfer catalysis  Durst, H. Dupont; Gokel, George W.
Although common spectroscopic methods have largely supplanted the more classical methods for distinguishing aldehydes from ketones in many applications, aldehyde classification tests remain very useful in actual laboratory practice as well as important pedagogical device in qualitative organic chemistry.
Durst, H. Dupont; Gokel, George W. J. Chem. Educ. 1978, 55, 206.
Aldehydes / Ketones |
Qualitative Analysis
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
The scope of the Haworth synthesis  Agranat, Israel; Shih, Yu-Shan
The duality of the Haworth synthesis as revealed most conspicuously in the preparation of both anthracene and phenanthrene, widens the scope of the method. On the basis of the reversibility of Friedel-Crafts acylation in PPA, the Haworth synthesis may serve as a route to linearly annelated-as well as to angularly annelated polynuclear aromatic hydrocarbons.
Agranat, Israel; Shih, Yu-Shan J. Chem. Educ. 1976, 53, 488.
Synthesis |
Catalysis |
Aromatic Compounds |
Aldehydes / Ketones
Syntheses and rearrangements of cage molecules related to cubane  Jefford, Charles W.
This article looks at the synthesis of cubane, basketene, miscellaneous homocubane chemistry, snoutene, triqunacene, hypostrophene, tris-homocubane, and catalysis by transition metals.
Jefford, Charles W. J. Chem. Educ. 1976, 53, 477.
Catalysis |
Transition Elements |
Alkenes |
Synthesis |
Aromatic Compounds |
Heterocycles |
Alcohols
Grignard dehydration reactions. An undergraduate organic experiment.  Duty, Robert C.; Ryder, Bernard L.
In this laboratory, the authors have incorporated the Grignard reaction in a step-wise synthesis that has been successful in demonstrating several experimental and instrumental techniques.
Duty, Robert C.; Ryder, Bernard L. J. Chem. Educ. 1976, 53, 457.
Grignard Reagents |
Reactions |
Synthesis |
Alkenes
An undergraduate electroanalytical experiment  Janata, Jiri
This article presents a determination of vanillin and of other aromatic aldehyde can easily be accomplished by amperometric titration with a standard solution of 2,4-dinitrophenylhydazine.
Janata, Jiri J. Chem. Educ. 1976, 53, 399.
Electrochemistry |
Aldehydes / Ketones |
Titration / Volumetric Analysis |
Aromatic Compounds |
Natural Products
Preparation of phenanthridone. A multipurpose experiment for the organic laboratory  Hawbecker, Byron L.; Radovich, David A.; Tillotson, Loyal G.
It is desirable to have a series of multipurpose reactions available which can illustrate a variety of reaction types within a single, three hour lab period.
Hawbecker, Byron L.; Radovich, David A.; Tillotson, Loyal G. J. Chem. Educ. 1976, 53, 398.
Reactions |
Aromatic Compounds |
Aldehydes / Ketones
Imidazole - Versatile today, prominent tomorrow  Matuszak, C. A.; Matuszak, A. J.
Imidazole chemistry has pedagogical utility for all the organic chemistry students pursing careers in the life sciences.
Matuszak, C. A.; Matuszak, A. J. J. Chem. Educ. 1976, 53, 280.
Grignard Reagents |
Aromatic Compounds |
Heterocycles |
Phenols |
Acids / Bases |
Catalysis |
Coordination Compounds |
Hydrogen Bonding
Illustrating gas chromatography and mass spectrometry. An undergraduate experiment  Gross, Michael L.; Olsen, Virgil K.; Forc, R. Ken
One lab period is used to separate and collect the components of a ketone mixture; the second lab period is used to explain and demonstrate the MS instrumentation and the interpretation of ketone spectra; and in part three the spectra of the separated ketones are analyzed by individual students.
Gross, Michael L.; Olsen, Virgil K.; Forc, R. Ken J. Chem. Educ. 1975, 52, 535.
Gas Chromatography |
Mass Spectrometry |
Aldehydes / Ketones
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
Conversion of a primary alcohol to an alkyl halide via a tosylate intermediate  Wiseman, Park A.; Betras, Steve; Lindley, Barry
The experiment in this article was designed primarily for and has been performed successfully by sophomore chemistry majors.
Wiseman, Park A.; Betras, Steve; Lindley, Barry J. Chem. Educ. 1974, 51, 348.
Alcohols |
Alkylation |
Reactions |
Aromatic Compounds |
NMR Spectroscopy
The photoisomerization of cyclic ketones: An experiment in organic chemistry  Haas, J. W., Jr.
This experiment deals with parameters such as the nature of the excited state, effect of triplet quenchers on product formation, chemical structure and reaction rate and quantum yield when cyclopentanone and cyclohexanone are irradiated at 254nm. These cyclic ketones provide a variety of photolysis information in a short time span, are conveniently analyzed by gas chromatography, and are readily available at the requisite levels of purity.
Haas, J. W., Jr. J. Chem. Educ. 1974, 51, 346.
Aldehydes / Ketones |
Aromatic Compounds |
Photochemistry |
Diastereomers |
Gas Chromatography
Preparative reduction of benzil: Use of a polarographic analyzer and simple current booster  Carney, J. H.; Mullis, O. J.
The authors report a simple laboratory experiment which demonstrates some of the preparative and mechanistic electrochemistry of ketones in acid solution. The also describe a simple and inexpensive apparatus for preparative scale electrochemistry.
Carney, J. H.; Mullis, O. J. J. Chem. Educ. 1974, 51, 343.
Electrochemistry |
Aldehydes / Ketones |
Acids / Bases |
Laboratory Equipment / Apparatus
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
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
Molecular weight determination of aldehydes and ketones. A quantitative organic experiment  Steinhaus, Ralph K.
The reaction between semicarbazide and an unknown ketone is used to determine molecular weight.
Steinhaus, Ralph K. J. Chem. Educ. 1973, 50, 293.
Physical Properties |
Quantitative Analysis |
Aldehydes / Ketones |
Oxidation / Reduction
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
Furfural - Ubiquitous natural product  McCullough, CSC, Thomas
Procedure for obtaining 2-furaldehyde from citrus peelings, banana skins, gourd rinds, corn cobs, dried leaves, and other organic wastes.
McCullough, CSC, Thomas J. Chem. Educ. 1972, 49, 836.
Natural Products |
Synthesis |
Aldehydes / Ketones
Visualization of molecular orbitals. Formaldehyde  Olcott, Richard J.
Using a computer to generate three dimensional charge density distributions of the formaldehyde molecule.
Olcott, Richard J. J. Chem. Educ. 1972, 49, 614.
Aldehydes / Ketones |
Molecular Modeling |
Molecular Properties / Structure
Beer, acetone, and diabetes: A story and a demonstration  Isenberg, Norbert
Acetone causes the collapse of beer foam.
Isenberg, Norbert J. Chem. Educ. 1972, 49, 151.
Aldehydes / Ketones |
Medicinal Chemistry
Catalytic hydrogenation of ketones at moderate pressures. An organic demonstration-experiment  Kaye, Irving Allan
This procedure requires a moderate pressure hydrogenator and can be completed as a demonstration or a laboratory with a small number of students.
Kaye, Irving Allan J. Chem. Educ. 1972, 49, 131.
Catalysis |
Aldehydes / Ketones
Alkylations in organic chemistry  Mundy, Bradford P.
Examines some of the subtle factors involved in alkylations, including alkylations via enolates, alkylations via enamines, and alkylation of enolates derived from reduction of enone systems.
Mundy, Bradford P. J. Chem. Educ. 1972, 49, 91.
Synthesis |
Alkylation |
Aldehydes / Ketones |
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
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
Preparation of 2,3-diphenyl-1-indenone and related compounds  Clark, Thomas J.
The author describes a series of preparative experiments which students in organic chemistry have found enjoyable and instructive.
Clark, Thomas J. J. Chem. Educ. 1971, 48, 554.
Synthesis |
Aldehydes / Ketones |
Aromatic Compounds
Recrystallization and melting point determination  Kaye, Irving Allan; Yuska, Henry
This experiment is essentially an exercise in recrystallization and identification, by melting point and mixed melting point determination, an unknown ketone that has been transformed into either its 2,4-dinitrophenylhydrazone or semicarbazone derivative.
Kaye, Irving Allan; Yuska, Henry J. Chem. Educ. 1970, 47, 703.
Crystals / Crystallography |
Aldehydes / Ketones |
Qualitative Analysis
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
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
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
Hazardous chemicals data  National Fire Protection Association
Explains aspects of chemical hazard data and presents hazards associated with acetaldehyde.
National Fire Protection Association J. Chem. Educ. 1968, 45, A115.
Chemometrics |
Aldehydes / Ketones |
Laboratory Management
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
Acids as derivatives of aldehydes prepared with silver oxides  Thomason, Sandra C.; Kubler, Donald G.
Examines the use of silver(i) and silver(II) oxide to convert aldehydes into acid derivatives.
Thomason, Sandra C.; Kubler, Donald G. J. Chem. Educ. 1968, 45, 546.
Acids / Bases |
Aldehydes / Ketones |
Oxidation / Reduction |
Synthesis
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
The preparation of naphthalene-alpha-d: An experiment in organic chemistry  Ziegler, Gene R.
This procedure involves the preparation of a hydrocarbon via the Grignard reagent from the corresponding bromide.
Ziegler, Gene R. J. Chem. Educ. 1967, 44, 609.
Synthesis |
Grignard Reagents |
Alkanes / Cycloalkanes
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
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
Qualitative test for ketones, aromatic aldehydes, and aliphatic aldehydes  Morrison, James D.
The Bordwell-Wellman solution of chromic anhydride in aqueous sulfuric acid is an excellent reagent for distinguishing aldehydes from ketones.
Morrison, James D. J. Chem. Educ. 1965, 42, 554.
Qualitative Analysis |
Aldehydes / Ketones |
Aromatic Compounds
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
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
The pyrolytic decomposition of carboxylate salts to ketones  Schultz, H. P.; Sichels, J. P.
Suggestions for research to accompany a previously published article.
Schultz, H. P.; Sichels, J. P. J. Chem. Educ. 1963, 40, A463.
Undergraduate Research |
Reactions |
Aldehydes / Ketones
The use of the Perkin reaction in organic chemistry classes  Buckles, R. E.
Provides suggestions for student research based on an earlier article published in the Journal.
Buckles, R. E. J. Chem. Educ. 1963, 40, A139.
Undergraduate Research |
Reactions |
Aromatic Compounds |
Aldehydes / Ketones |
Amines / Ammonium Compounds
The theory of the formaldehyde clock reaction  Jones, P.; Oldham, K. B.
Presents a theory for the formaldehyde clock reaction.
Jones, P.; Oldham, K. B. J. Chem. Educ. 1963, 40, 366.
Reactions |
Kinetics |
Rate Law |
Aldehydes / Ketones
The formation of acetone from acetates  Young, Jay A.; Taylor, John K.
Suggests some research activities based on an article published previously in the Journal.
Young, Jay A.; Taylor, John K. J. Chem. Educ. 1962, 39, A962.
Undergraduate Research |
Aldehydes / Ketones |
Reactions
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
The acylation of aliphatic unsaturated hydrocarbons  Sharefkin, Jacob G.
Introductory organic chemistry textbooks discuss the Friedel-Crafts synthesis of aromatic ketones but usually do not treat the corresponding reaction in the aliphatic series.
Sharefkin, Jacob G. J. Chem. Educ. 1962, 39, 206.
Aromatic Compounds |
Aldehydes / Ketones |
Reactions |
Synthesis |
Mechanisms of Reactions
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
Letters  Smith, W. B.
The author suggests two experiments for determining the best method for preparing cyclopentanone from adipic acid.
Smith, W. B. J. Chem. Educ. 1961, 38, 638.
Aldehydes / Ketones |
Synthesis
Letters  Taylor, D. A. H.
Tollens reagent is not an infallible test for aldehydes.
Taylor, D. A. H. J. Chem. Educ. 1961, 38, 102.
Quantitative Analysis |
Aldehydes / Ketones
The Fehling and Benedict tests  Daniels, Ralph; Rush, Clyde C.; Bauer, Ludwig
The commonly cited interpretation of the Fehling and Benedict tests are not in accord with experimental facts.
Daniels, Ralph; Rush, Clyde C.; Bauer, Ludwig J. Chem. Educ. 1960, 37, 205.
Qualitative Analysis |
Aldehydes / Ketones
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
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
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
A synthesis of bis(p-aminophenyl) sulfone for laboratory classes  Buckles, Robert E.
A three-step synthesis of bis(p-aminophenyl) sulfone from p-chloronitrobenzene has been devised on a fairly small scale for laboratory classes in beginning organic chemistry.
Buckles, Robert E. J. Chem. Educ. 1954, 31, 36.
Synthesis |
Aldehydes / Ketones
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
The Friedel-Crafts reaction in elementary organic laboratories  Wright, Oscar L.; Fuhlhage, Donald; Sheridan, Earl
Presents a modification of the Perrier ketone synthesis.
Wright, Oscar L.; Fuhlhage, Donald; Sheridan, Earl J. Chem. Educ. 1952, 29, 620.
Reactions |
Aldehydes / Ketones |
Synthesis