| Journal Articles: 44 results |
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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
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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
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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 ClaisenSchmidt 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
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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 1920th centuries.
Ponomarev, Dmitry A.; Shevchenko, Sergey M. J. Chem. Educ. 2007, 84, 1725.
Addition Reactions |
Aldehydes / Ketones |
Alkynes |
Catalysis |
Industrial Chemistry |
Reactions
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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 GCMS, 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
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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
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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
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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
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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
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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 ahydroxyketones 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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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