TIGER

Journal Articles: 229 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
Evaluating Mechanisms of Dihydroxylation by Thin-Layer Chromatography  Benjamin T. Burlingham and Joseph C. Rettig
Presents a microscale experiment in which cyclohexene is dihydroxylated under three sets of conditions and the products determined through thin-layer chromatography. Teams of students evaluate proposed mechanisms for each dihydroxylation in light of the data collected.
Burlingham, Benjamin T.; Rettig, Joseph C. J. Chem. Educ. 2008, 85, 959.
Addition Reactions |
Alkenes |
Diastereomers |
Mechanisms of Reactions |
Microscale Lab |
Stereochemistry |
Synthesis |
Thin Layer Chromatography
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
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
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
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
Reaction-Map of Organic Chemistry  Steven Murov
The Reaction-Map of Organic Chemistry has been designed to provide an overview of most of the reactions needed for the organic chemistry course and should help students develop synthetic routes from one functional group to another.
Murov, Steven. J. Chem. Educ. 2007, 84, 1224.
Addition Reactions |
Electrophilic Substitution |
Elimination Reactions |
Nucleophilic Substitution |
Oxidation / Reduction |
Periodicity / Periodic Table |
Reactions |
Synthesis |
Enrichment / Review Materials
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
Markovnikov's Rule  Predrag-Peter Ilich
More insight into the mechanisms of addition reactions to alkenes is needed before completely abandoning Markovnikov and anti-Markovnikov terminology
Ilich, Predrag-Peter. J. Chem. Educ. 2007, 84, 1109.
Addition Reactions |
Reactions |
Mechanisms of Reactions
Markovnikov's Rule  Robert C. Kerber
The use of Markovniknov and anti-Markovnikov to describe addition reactions and their products has long outlived its utility.
Kerber, Robert C. . J. Chem. Educ. 2007, 84, 1109.
Addition Reactions |
Reactions |
Mechanisms of Reactions
Markovnikov's Rule  Robert C. Kerber
The use of Markovniknov and anti-Markovnikov to describe addition reactions and their products has long outlived its utility.
Kerber, Robert C. . J. Chem. Educ. 2007, 84, 1109.
Addition Reactions |
Reactions |
Mechanisms of Reactions
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
Polar Addition to C=C Group: Why Is Anti-Markovnikov Hydroboration–Oxidation of Alkenes Not "Anti-"?  Predrag-Peter Ilich, Lucas S. Rickertsen, and Erienne Becker
The authors redefine Markovnikov or anti-Markovnikov regioselectivity and propose that the teaching of organic chemistry should be based on robust and portable concepts such as energy difference and atomic charge rather than historical labels.
Ilich, Predrag-Peter; Rickertsen, Lucas S.; Becker, Erienne. J. Chem. Educ. 2006, 83, 1681.
Addition Reactions |
Alkenes |
Computational Chemistry |
Mechanisms of Reactions |
Molecular Modeling
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
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
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
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
Electrophilic Additions to Alkenes  Thomas M. Bertolini and Phuc D. Tran
A worksheet of 18 reactions is presented as a learning aid to comprehend the regiochemistry and stereochemistry of alkene electrophilic addition.
Bertolini, Thomas M.; Tran, Phuc D. J. Chem. Educ. 2006, 83, 590.
Addition Reactions |
Alkenes |
Reactions
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
Derivatization of Fullerenes: An Organic Chemistry Laboratory  Charles T. Cox Jr. and Melanie M. Cooper
Presents two undergraduate organic chemistry laboratories detailing the synthesis of fullerene derivatives, using the Bingel (carbene insertion) and Prato (1,3-dipolar addition) protocols.
Cox, Charles T., Jr.; Cooper, Melanie M. J. Chem. Educ. 2006, 83, 99.
Acids / Bases |
Addition Reactions |
Chromatography |
Heterocycles |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
UV-Vis Spectroscopy
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
Diels–Alder Synthesis of endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide  Marsha R. Baar and Kristin Wustholz
endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide was synthesized by a DielsAlder cycloaddition of 1,3-cyclohexadiene and N-phenylmaleimide in ethyl acetate. 1,3-Cyclohexadiene and N-phenylmaleimide were selected to illustrate the Alder rule, which reflects a preference for endo products and to overcome the difficulties associated with the traditional combination of 1,3-cyclopentadiene and maleic anhydride.
Baar, Marsha R.; Wustholz, Kristin. J. Chem. Educ. 2005, 82, 1393.
Asymmetric Synthesis |
Microscale Lab |
Stereochemistry |
Addition Reactions |
Alkenes |
IR Spectroscopy |
NMR Spectroscopy
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
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
The Addition of Bromine to 1,2-Diphenylethene   Judith C. Amburgey-Peters and LeRoy W. Haynes
We investigated the reaction of (Z)-1,2-diphenylethene (cis-stilbene) with various brominating reagents and solvents following directions in standard organic chemistry manuals. We were particularly interested in learning which combination of brominating reagent and solvent gave the best yield of (d,l)-1,2-dibromo-1,2-diphenylethane without the formation of significant amounts of meso-1,2-dibromo-1,2-diphenylethane, which is essentially the sole product from the reaction of bromine with (E)-1,2-diphenylethene (trans-stilbene). Based on the results from the standard preparatory methods, some permutations of solvent and brominating reagent were tried.
Amburgey-Peters, Judith C.; Haynes, LeRoy W. J. Chem. Educ. 2005, 82, 1051.
Addition Reactions |
Alkenes |
Carbocations |
Diastereomers |
Enantiomers |
Mechanisms of Reactions |
Stereochemistry
"You're Repulsive!"Teaching VSEPR in a Not-So-Elegant Way  Robert S. H. Liu
Valence shell electron pair repulsive (VSEPR) interaction is an important concept particularly in discussing structural properties of molecules. In this article we showed five organic examples not commonly associated with VSEPR but yet all involving repulsive interactions of valence electrons, which provides ready explanations for altered chemical reactivity and spectroscopic properties of organic compounds. The ready catchy phrase Youre Repulsive! is the common thread used throughout these five examples.
Liu, Robert S. H. J. Chem. Educ. 2005, 82, 558.
Mechanisms of Reactions |
UV-Vis Spectroscopy |
Reactions |
Addition Reactions |
Electrophilic Substitution
The Evolution of a Green Chemistry Laboratory Experiment: Greener Brominations of Stilbene  Lallie C. McKenzie, Lauren M. Huffman, and James E. Hutchison
We describe two new greener alkene bromination reactions that offer enhanced laboratory safety and convey important green chemistry concepts, in addition to illustrating the chemistry of alkenes. The two alternative reactions, one involving pyridinium tribromide and a second using hydrogen peroxide and hydrobromic acid, are compared to the traditional bromination of stilbene through the application of green metrics, including atom economy, percent experimental atom economy, E factor, and effective mass yield.
McKenzie, Lallie C.; Huffman, Lauren M.; Hutchison, James E. J. Chem. Educ. 2005, 82, 306.
Synthesis |
Green Chemistry |
Aromatic Compounds |
Addition Reactions |
Alkenes
The Sharpless Asymmetric Dihydroxylation in the Organic Chemistry Majors Laboratory  Christopher J. Nichols and Melissa R. Taylor
A six-period laboratory exercise has been developed that uses the convenient Sharpless asymmetric dihydroxylation (AD) to illustrate the principles of a chiral synthesis. Using one particular alkene, students perform a racemic dihydroxylation, an AD using a commercially available AD-mix, and then an AD using an ester derivative of dihydroquinidine that they synthesized themselves. The structures of the products are confirmed with 1H NMR spectroscopy and the enantiomeric excesses of the diols are determined using a chiral GC column.
Nichols, Christopher J.; Taylor, Melissa R. J. Chem. Educ. 2005, 82, 105.
Chirality / Optical Activity |
Chromatography |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Alkenes |
Addition Reactions
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
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
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
A Series of Small-Scale, Discovery-Based Organic Laboratory Experiments Illustrating the Concepts of Addition, Substitution, and Rearrangement  Judith S. Moroz, Janice L. Pellino, and Kurt W. Field
Multistep, microscale organic laboratory experiments are presented that illustrate addition, substitution, and rearrangement reactions.
Moroz, Judith S.; Pellino, Janice L.; Field, Kurt W. J. Chem. Educ. 2003, 80, 1319.
IR Spectroscopy |
Mass Spectrometry |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Addition Reactions |
Mechanisms of Reactions
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
Dendrimers: Branching Out of Polymer Chemistry  Eric E. Simanek and Sergio O. Gonzalez
Addresses synthetic concepts surrounding dendrimers including the use of protecting groups, functional group interconversions, and convergent and divergent synthetic strategies.
Simanek, Eric E.; Gonzalez, Sergio O. J. Chem. Educ. 2002, 79, 1222.
Materials Science |
Synthesis |
Molecular Properties / Structure |
Addition Reactions |
Aromatic Compounds |
Alkylation |
Nucleophilic Substitution
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
Moving Past Markovnikov's Rule  E. Eugene Gooch
Extension of the Markovnikov Rule for addition reactions across a carbon-carbon double bond.
Gooch, E. Eugene. J. Chem. Educ. 2001, 78, 1358.
Synthesis |
Reactions |
Alkenes |
Addition Reactions |
Mechanisms of Reactions
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
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
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
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
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
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
Mechanism Templates: Lecture Aids for Effective Presentation of Mechanism in Introductory Organic Chemistry  Brian J. McNelis
To promote active student learning of mechanism in introductory organic chemistry, hand-outs have been developed with incomplete structures for reaction processes depicted, which are called mechanism templates. The key to these lecture aids is to provide only enough detail in the diagram to facilitate notetaking, ensuring that these templates are dynamic learning tools that must be utilized by an engaged and alert student.
Brian J. McNelis. J. Chem. Educ. 1998, 75, 479.
Learning Theories |
Mechanisms of Reactions |
Reactions |
Addition Reactions |
Acids / Bases |
Electrophilic Substitution |
Nucleophilic Substitution
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
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
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
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
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
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
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
Further Comments upon the Electrophilic Addition to Alkynes: A Response to Criticism from Professor Thomas T.Tidwell  Hilton M. Weiss
This paper responds to the preceding article by Professor T. Tidwell in which he provides arguments for vinyl cations being an intermediate in most electrophilic additions to alkynes.
Weiss, Hilton M. J. Chem. Educ. 1996, 73, 1082.
Addition Reactions |
Alkynes |
Mechanisms of Reactions
The Electrophilic Addition to Alkynes Revisited  Thomas T. Tidwell
A recent claim that vinyl cations are not the predominant intermediates in the electrophilic addition to alkynes is disputed.
Tidwell, Thomas T. J. Chem. Educ. 1996, 73, 1081.
Addition Reactions |
Alkynes |
Mechanisms of Reactions
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 New Photochemistry Experiment, A Simple 2+2 Photocycloaddition that Poses an Interesting NMR Problem   John T. Magner, Matthias Selke, Arlene A. Russell, Orville L. Chapman
The cycloaddition of -nitrostyrene to 2,3-dimethyl-1,3-butadiene provides an extremely clean example of 2 + 2 cycloaddition. This laboratory exercise combines theory, technique, spectroscopy, and data interpretation.
J. Chem. Educ. 1996, 73, 854.
Photochemistry |
NMR Spectroscopy |
Qualitative Analysis |
Instrumental Methods |
Addition Reactions |
Mechanisms of Reactions
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
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
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
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
The Addition of Hydrogen Bromide to Simple Alkenes  Hilton M. Weiss
Synthesis of 1-bromohexane.
Weiss, Hilton M. . J. Chem. Educ. 1995, 72, 848.
Synthesis |
Mechanisms of Reactions |
Addition Reactions |
Alkenes
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
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
Use of Multimedia in an Introductory Chemistry Course for Student Analysis of Real-Life Situations  Joesten, Melvin D.
Award in the Course and Curriculum Development (CCD) program for FY1994.
Joesten, Melvin D. J. Chem. Educ. 1994, 71, 508.
Addition 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
A New Approach To Teaching Organic Chemical Mechanisms  Wentland, Stephen H.
Describing the mechanisms of organic reactions using five simple steps or operations.
Wentland, Stephen H. J. Chem. Educ. 1994, 71, 3.
Mechanisms of Reactions |
Addition Reactions |
Nucleophilic Substitution |
Electrophilic Substitution |
Elimination Reactions |
Resonance Theory |
Molecular Properties / Structure
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
The electrophilic addition to alkynes  Weiss, Hilton M.
Electrophilic additions to alkynes traditionally do not receive as much attention in organic textbooks as electrophilic addition to alkenes.
Weiss, Hilton M. J. Chem. Educ. 1993, 70, 873.
Addition Reactions |
Alkynes
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
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
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
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
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 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
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
Synthesis of trans-2-tert-butylcyclohexanol via hydroboration: A microscale organic experiment demonstrating syn addition  Wigal, Carl T.; Hopkins, William T.; Ronald, Bruce P.
This microscale experiment demonstrates the relative stereochemistry of the titled addition.
Wigal, Carl T.; Hopkins, William T.; Ronald, Bruce P. J. Chem. Educ. 1991, 68, A299.
Synthesis |
Microscale Lab |
Addition Reactions |
Aromatic Compounds |
Stereochemistry
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 quick and effective demonstration of anti-Markovnikov addition to alkenes  Brown, Trevor M.; Dronsfield, Alan T.; Hitchcock, Ian
This reaction can be performed in less then 10 minutes and the product is easily identifiable.
Brown, Trevor M.; Dronsfield, Alan T.; Hitchcock, Ian J. Chem. Educ. 1991, 68, 785.
Alkenes |
Addition Reactions
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
A laboratory study of 1,3-dipole-dipolarophile addition: An extension of the Diels Alder reaction  Gingrich, Henry L.; Pickering, Miles
Some easy organic reactions that can also be used as the basis for puzzles, or as facile heterocyclic syntheses: an area neglected in the student experiment literature.
Gingrich, Henry L.; Pickering, Miles J. Chem. Educ. 1991, 68, 614.
Mechanisms of Reactions |
Addition Reactions |
Synthesis |
Heterocycles |
Physical Properties |
NMR Spectroscopy
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
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
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
Reaction of bromine with hydrocarbons on the overhead, real or simulated  Solomon, Sally; Gregory, Michael; Padmanabhan, Sandeep; Smith, Kurt
A simulation that looks like the addition of bromine to hydrocarbons but is not (the bromine is simulated using a mixture of food colorings).
Solomon, Sally; Gregory, Michael; Padmanabhan, Sandeep; Smith, Kurt J. Chem. Educ. 1990, 67, 961.
Alkanes / Cycloalkanes |
Aromatic Compounds |
Addition Reactions
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
The stereochemistry of additions to trans-anethole  McGahey, Lawrence
Trans-anethole is brominated with pyridinium bromide perbromide in dichloromethane.
McGahey, Lawrence J. Chem. Educ. 1990, 67, 554.
Addition Reactions |
Stereochemistry |
Mechanisms of Reactions |
Alkenes |
Diastereomers |
Enantiomers
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
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
Availability of video tape to clarify the method of standard abbreviations  Williams, Kathryn R.
The method of standard addition is recognized as an important calibration technique in instrumental analysis.
Williams, Kathryn R. J. Chem. Educ. 1989, 66, 247.
Calibration |
Addition Reactions |
Instrumental Methods
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
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
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
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
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
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
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
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
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
Who is anti-Markovnikov?  Tedder, J. M.
What are the factors that control the rate and orientation of free radical addition to alkenes?
Tedder, J. M. J. Chem. Educ. 1984, 61, 237.
Mechanisms of Reactions |
Addition Reactions |
Free Radicals |
Alkenes
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
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
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
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
Isobutylene revisited: An experiment introducing both qualitative and quantitative application of NMR spectroscopy  Tremelling, Michael J.; Hammond, Christina N.
The product distribution is a contradiction to the general rule that the more highly substituted alkene is more stable.
Tremelling, Michael J.; Hammond, Christina N. J. Chem. Educ. 1982, 59, 697.
Alkenes |
NMR Spectroscopy |
Addition Reactions |
Molecular Properties / Structure
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
Pi bonding without tears  Akeroyd, F. Michael
A non-mathematical treatment of sigma-pi bonding applied to conjugation, hyperconjugation, Markovnikoff addition, aromaticity, and aromatic substitution.
Akeroyd, F. Michael J. Chem. Educ. 1982, 59, 371.
Alkenes |
Mechanisms of Reactions |
Addition Reactions |
Aromatic Compounds
The problem of syn- versus anti-addition: An organic chemistry laboratory experiment  Silversmith, Ernest F.
An experiment that allows a student to determine whether an addition to a carbon-carbon double bond proceeds in syn- or anti-fashion.
Silversmith, Ernest F. J. Chem. Educ. 1982, 59, 346.
Addition Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure |
Stereochemistry |
Synthesis |
Alkenes
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
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
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
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
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
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
Project for problem-oriented undergraduate organic or integrated undergraduate laboratory  Silveira, Augustine, Jr.
This paper reports on an open-ended project which allows a great degree of flexibility in the laboratory. The project provided about a 6-week study for groups of 24 students each.
Silveira, Augustine, Jr. J. Chem. Educ. 1978, 55, 57.
Synthesis |
Undergraduate Research |
Spectroscopy |
Diastereomers |
Addition Reactions |
MO Theory |
Elimination Reactions |
Thermodynamics |
Kinetics
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
Molecular design of compounds via intermolecular Diels-Alder reactions  Mehta, Goverdhan
The Diels-Alder reaction involving a cycloaddition between a diene and dienophile is one of the most versatile and useful reactions in the armory of the synthetic organic chemists.
Mehta, Goverdhan J. Chem. Educ. 1976, 53, 551.
Synthesis |
Addition Reactions |
Aromatic Compounds
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
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
Free-radical addition of tetrahalomethanes to [beta]-pinene. Experiments in organic chemistry  Kaye, Irving Allan; Odum, Robert A.
This laboratory provides a much needed learning opportunity about free-radicals.
Kaye, Irving Allan; Odum, Robert A. J. Chem. Educ. 1976, 53, 60.
Free Radicals |
Addition Reactions
The hydroboration-oxidation of alkenes. A convenient anti-Markownikoff hydration experiment  Kabalka, George W.; Hedgecock, Herbert C., Jr.
A hydroboration-oxidation sequence that relies on the borane dimethylsulfide complex as the hydroborating agent and trimethylamine-N-oxide dihydrate as the oxidizing agent.
Kabalka, George W.; Hedgecock, Herbert C., Jr. J. Chem. Educ. 1975, 52, 745.
Alkenes |
Oxidation / Reduction |
Addition Reactions
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
Classification of the electrophilic addition reactions of olefins and acetylenes  Wilson, Michael A.
Summarizes a wide variety of electrophiles and substrates and the mechanisms by which they react.
Wilson, Michael A. J. Chem. Educ. 1975, 52, 495.
Addition Reactions |
Reactions |
Mechanisms of Reactions
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
Stereospecific thermal cycloadditions and catalyzed isomerizations: An organic laboratory project  Pasto, D. J.; Duncan, J. A.; Silversmith, E. F.
The authors have prepared a sequence of experiments for their undergraduate organic chemistry laboratory concerned with the preparation of cis and trans 1,4-diphenyl-2-butene-1,4diones, their cycloadditions reactions with cyclopentandiene, and with related isomerization reactions of both the sequence, which has met with much success experimentally, clearly and collectively demonstrates certain aspects of the concepts of thermodynamics, kinetics, and stereochemistry and photochemistry.
Pasto, D. J.; Duncan, J. A.; Silversmith, E. F. J. Chem. Educ. 1974, 51, 277.
Photochemistry |
Constitutional Isomers |
Addition Reactions
A crossed aldol condensation for the undergraduate laboratory  Angres, Isaac; Zieger, Herman E.
This two-step experiment for undergraduate organic chemistry students illustrates three basic ideas: organic chemistry students illustrate three basic ideas (1) crossed aldol condensation; (2) the acidity of benzylic hydrogen in hydrocarbons; and (3) reduction of a double bond in hydride transfer.
Angres, Isaac; Zieger, Herman E. J. Chem. Educ. 1974, 51, 64.
Aromatic Compounds |
Aldehydes / Ketones |
Acids / Bases |
Alcohols
Dihalocarbene addition reaction  Goh, S. H.
This experiment illustrates the synthetic utility of carbenes and that of phase transfer catalysis.
Goh, S. H. J. Chem. Educ. 1973, 50, 678.
Alkenes |
Addition Reactions |
Reactions |
Mechanisms of Reactions |
Catalysis |
Synthesis
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
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
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
Donor-acceptor interactions in organic chemistry  Sunderwirth, S. G.
The purpose of this article is to aid teachers in making even more effective use of theoretical considerations in teaching organic chemistry; the primary objective is to emphasize the underlying principles that are common to the following four basic types of reactions: substitution, addition, elimination, and rearrangement.
Sunderwirth, S. G. J. Chem. Educ. 1970, 47, 728.
Reactions |
Mechanisms of Reactions |
Addition Reactions |
Elimination Reactions |
Nucleophilic Substitution
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
A modern look at Markovnikov's rule and the peroxide effect  Isenberg, Norbert; Grdinic, Marcel
Presents a "carbonium ion" definition of Markovnikov's Rule and examines the peroxide effect.
Isenberg, Norbert; Grdinic, Marcel J. Chem. Educ. 1969, 46, 601.
Mechanisms of Reactions |
Stereochemistry |
Diastereomers |
Free Radicals |
Alkenes |
Addition Reactions
Organic chemistry  Dolbier, William R., Jr.
Presents an explanation that encompasses all electrophilic additions to alkenes within a single, unifying picture.
Dolbier, William R., Jr. J. Chem. Educ. 1969, 46, 342.
Addition Reactions |
Alkenes |
Mechanisms of Reactions |
Stereochemistry
Preparation of p-anisole: An organic chemistry experiment  Smith, Richard F.; Bates, Alvin C.
In this experiment, p-anisaldehyde is converted to p-anisonitrile by a modification of the three-step aldehyde-nitrile synthesis of Smith and Walker.
Smith, Richard F.; Bates, Alvin C. J. Chem. Educ. 1969, 46, 174.
Synthesis |
Mechanisms of Reactions |
Addition Reactions |
Nucleophilic Substitution |
Elimination Reactions |
Catalysis
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
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
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
Hydration of an alkyne: Undergraduate organic chemistry experiment  Rose, Norman C.
The hydration of 2-methyl-3-butyn-2-ol to yield 3-hydroxy-3-methyl-2-butanone is a very suitable reaction for undergraduates who have had little prior experience in the organic laboratory.
Rose, Norman C. J. Chem. Educ. 1966, 43, 324.
Alkynes |
Aldehydes / Ketones |
Alcohols
Reaction mechanisms in organic chemistry. I. The experimental approach  Caserio, Marjorie C.
Reviews a variety of method that may be employed to determine the mechanism of organic reactions.
Caserio, Marjorie C. J. Chem. Educ. 1965, 42, 570.
Reactions |
Mechanisms of Reactions |
Reactive Intermediates |
Kinetics |
Nucleophilic Substitution |
Addition Reactions |
Elimination Reactions
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
Nucleophilic reactions at trigonally bonded carbon  Cash, R. Vincent
Examines the mechanisms of nucleophilic displacement reactions, nucleophilic addition reactions, and nucleophilic addition with elimination, all at trigonally bonded carbon.
Cash, R. Vincent J. Chem. Educ. 1964, 41, 108.
Nucleophilic Substitution |
Reactions |
Mechanisms of Reactions |
Addition Reactions |
Elimination Reactions
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
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
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
Textbook errors: Guest column- XIX. The relative reactivity of acetylenes and olefins toward bromine  Mysels, Karol J.; Daniels, Ralph; Bauer, Ludwig
Many contemporary textbooks and laboratory manuals in organic chemistry either state explicitly or imply that bromine ass much faster to acetylenes than to olefins.
Mysels, Karol J.; Daniels, Ralph; Bauer, Ludwig J. Chem. Educ. 1958, 35, 444.
Reactions |
Addition Reactions |
Alkylation |
Alkynes
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
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