| Journal Articles: 33 results |
|
|
A Simple Assignment That Enhances Students' Ability To Solve Organic Chemistry Synthesis Problems and Understand Mechanisms Jennifer Teixeira and R. W. Holman
Describes an original, easily implemented approach in which students construct a "functional group transformation" notebook which helps them to think about organic reactions in both the forward and the reverse (retrosynthetic) sense.
Teixeira, Jennifer; Holman, Robert W. J. Chem. Educ. 2008, 85, 88.
Mechanisms of Reactions |
Synthesis |
Student-Centered Learning
|
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
|
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
|
Stereospecific Synthesis of the Geometrical Isomers of a Natural Product T. Grove, D. DiLella, and E. Volker
Presents an experiment for the synthesis of (Z) and (E) isomers that is presented to students as a puzzle in which they must determine the identity of the major component in anise oil. A necessary part of the analysis is the preparation the (E) and (Z) isomers of anethole. Molecular modeling is used to explore the conformation of and energy difference between isomers.
Grove, T.; DiLella, D.; Volker, E. J. Chem. Educ. 2006, 83, 1055.
Alkenes |
Computational Chemistry |
Gas Chromatography |
IR Spectroscopy |
NMR Spectroscopy |
Stereochemistry |
Synthesis
|
The Virtual ChemLab Project: A Realistic and Sophisticated Simulation of Organic Synthesis and Organic Qualitative Analysis Brian F. Woodfield, Merritt B. Andrus, Gregory L. Waddoups, Melissa S. Moore, Richard Swan, Rob Allen, Greg Bodily, Tricia Andersen, Jordan Miller, Bryon Simmons, and Richard Stanger
Describes a set of sophisticated and realistic laboratory simulations for use in freshman- and sophomore-level chemistry classes and laboratories called Virtual ChemLab. The purpose of these simulations is to reinforce concepts taught in the classroom, provide an environment for creative learning, and emphasize the thinking behind instructional laboratory experiments.
Woodfield, Brian F.; Andrus, Merritt B.; Waddoups, Gregory L.; Moore, Melissa S.; Swan, Richard; Allen, Rob; Bodily, Greg; Andersen, Tricia; Miller, Jordan; Simmons, Bryon; Stanger, Richard. J. Chem. Educ. 2005, 82, 1728.
IR Spectroscopy |
NMR Spectroscopy |
Qualitative Analysis |
Synthesis |
Reactions |
Thin Layer Chromatography
|
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
|
Ethanol Metabolism and the Transition from Organic Chemistry to Biochemistry Richard D. Feinman
Introducing alcohol dehydrogenase and aldehyde dehydrogenase reactions in organic chemistry to ease transition to biochemistry.
Feinman, Richard D. J. Chem. Educ. 2001, 78, 1215.
Metabolism |
Oxidation / Reduction |
Reactions |
Mechanisms of Reactions |
Alcohols |
Carbohydrates
|
Synthesis of Substituted Butenolides. An Undergraduate Organic Laboratory Experiment Utilizing Two 3-Step Preparatory Sequences Géraldine Maheut, Liang Liao, Jean-Marie Catel, Paul-Alain Jaffrès, and Didier Villemin
The synthesis of substituted butenolide in two, 3-step sequences that illustrate five basic organic reactions (alkyne hydration, Knoevenagel condensation, lactonization, aldolization-type reaction, and hydration of nitrile); the products have pedagogical interest for IR and NMR spectroscopy (diastereotopic effect).
Maheut, Géraldine; Liao, Liang; Catel, Jean-Marie; Jaffrès, Paul-Alain; Villemin, Didier. J. Chem. Educ. 2001, 78, 654.
IR Spectroscopy |
Molecular Modeling |
NMR Spectroscopy |
Synthesis |
Undergraduate Research |
Reactions
|
Computational Investigations for Undergraduate Organic Chemistry: Modeling Markovnikov and anti-Markovnikov Reactions for the Formation of Alkyl Halides and Alcohols Rita K. Hessley
This paper describes how the early introduction of molecular modeling for the study of reaction mechanisms leading to alcohols from alkenes can increase students' involvement in their own learning and can effectively challenge their misapprehension about memorization.
Hessley, Rita K. J. Chem. Educ. 2000, 77, 794.
Computational Chemistry |
Alcohols |
Molecular Modeling |
Mechanisms of Reactions
|
Side Reactions in a Grignard Synthesis Hilton M. Weiss
This experiment describes a standard Grignard synthesis of a secondary alcohol, 3-heptanol. It brings attention to a significant side product, 3-heptanone, and suggests ways of understanding and utilizing the formation of this product. The experiment is intended to stimulate creative thought in the undergraduate organic chemistry course.
Weiss, Hilton M. J. Chem. Educ. 1999, 76, 76.
Mechanisms of Reactions |
Synthesis |
Grignard Reagents
|
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
|
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
|
Synthesis and Characterization of Potassium Tris(oxalato)ferrate(III) Trihydrate: A Spectrophotometric Method of Iron Analysis Richard F. Dallinger
A general chemistry experiment that combines titrimetric, gravimetric, and spectrophotometric analysis in two, three-hour lab periods.
Dallinger, Richard F. J. Chem. Educ. 1995, 72, 936.
Spectroscopy |
Synthesis |
Titration / Volumetric Analysis |
Gravimetric Analysis
|
The Synthesis and Analysis of Copper (II) Carboxylates Yoder, Claude H.; Smith, Wendy D.; Katolik, Vera L.; Hess, Kenneth R.; Thomsen, Marcus W.; Yoder, Carolyn S.; Bullock, Elizabeth R.
Several different methods for synthesizing and analyzing copper (II) carboxylates; includes sample data and analysis.
Yoder, Claude H.; Smith, Wendy D.; Katolik, Vera L.; Hess, Kenneth R.; Thomsen, Marcus W.; Yoder, Carolyn S.; Bullock, Elizabeth R. J. Chem. Educ. 1995, 72, 267.
Synthesis |
Laboratory Management
|
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
|
An operationally simple hydroboration-oxidation experiment Kabalka, George W.; Wadgaonkar, Prakash P.; Chatla, Narayana
The reactions involve the use of in situ generated diborane as the hydroborating reagent and sodium perborate as the oxidizing agent to convert cyclopentene to cyclopentanol.
Kabalka, George W.; Wadgaonkar, Prakash P.; Chatla, Narayana J. Chem. Educ. 1990, 67, 975.
Synthesis |
Mechanisms of Reactions |
Alkenes |
Alcohols
|
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
|
Steric course of lactonization in the deamination of glutamic acid: An organic mechanism experiment Markgraf, J. Hodge; Davis, Howard A.
The stereochemical consequences of a reaction at a chiral center offer a unique way to distinguish among mechanistic hypothesis.
Markgraf, J. Hodge; Davis, Howard A. J. Chem. Educ. 1990, 67, 173.
Mechanisms of Reactions |
Stereochemistry |
Alcohols
|
Reinecke's salt revisited: An undergraduate project involving an unknown metal complex Searle, Graeme H.; Bull, Graham S.; House, Donald A.
With five components, Reinecke's salt allows a variety of analyses and measurements; this article describes 10 such experiments.
Searle, Graeme H.; Bull, Graham S.; House, Donald A. J. Chem. Educ. 1989, 66, 605.
Metals |
Coordination Compounds |
Synthesis |
Spectroscopy |
Ion Exchange |
Conductivity |
Magnetic Properties |
Quantitative Analysis
|
Preparation and analysis of potassium tris(oxalato)ferrate(III)trihydrate: A general chemistry experiment Olmsted, John, III
The analysis of this compound combines gravimetric and titrimeric methods and includes a unique and colorful photoredox reaction.
Olmsted, John, III J. Chem. Educ. 1984, 61, 1098.
Synthesis |
Photochemistry |
Oxidation / Reduction |
Gravimetric Analysis |
Titration / Volumetric Analysis
|
Metallo complexes: An experiment for the undergraduate laboratory Kauffman, George B.; Karbassi, Mohammad; Bergerhoff, Gunter
Theory, nomenclature, structure, and preparative methods of metallic complexes; the experiment prepares several metallo complexes according to procedures modified from the literature and their properties are observed.
Kauffman, George B.; Karbassi, Mohammad; Bergerhoff, Gunter J. Chem. Educ. 1984, 61, 729.
Coordination Compounds |
Metals |
Nomenclature / Units / Symbols |
Molecular Properties / Structure |
Synthesis
|
An easy student synthesis of a substituted 1,3-dioxane by use of an ion-exchange resin as catalyst: Clean illustration of the Prins reaction Delmas, Michel; Kalck, Phillipe; Gorrichon, Jean-Pierre; Gaset, A.
The preparation of 4-(4-hydroxy, 3-methoxy-phenyl) 5-methyl 1,3-dioxane from isoeugenol via the Prins reaction.
Delmas, Michel; Kalck, Phillipe; Gorrichon, Jean-Pierre; Gaset, A. J. Chem. Educ. 1982, 59, 700.
Synthesis |
Catalysis |
Natural Products
|
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
|
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
|
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 polyhalide experiment and the Open University summer school Mason, Joan
The problem is to make a polyhalide and identify it by simple quantitative tests.
Mason, Joan J. Chem. Educ. 1975, 52, 244.
Synthesis |
Quantitative Analysis
|
Synthesis of sulfuric acid by the contact process. A student laboratory experiment Martin, J. A.; Baudot, P.; Monal, J. L.; Lejaille, M. F.
Experimental apparatus and details for the synthesis of sulfuric acid by the contact process.
Martin, J. A.; Baudot, P.; Monal, J. L.; Lejaille, M. F. J. Chem. Educ. 1975, 52, 188.
Synthesis |
Catalysis |
Oxidation / Reduction |
Industrial Chemistry
|
The preparation of 3-phenylanthranil. A sequential experiment for the undergraduate organic laboratory Kenny, David H.; Strieter, Jeffrey C.
A sequence of reactions that can be completed by the average student over ten weeks and involves a Friedel-Crafts reaction and Hofmann rearrangement.
Kenny, David H.; Strieter, Jeffrey C. J. Chem. Educ. 1972, 49, 130.
Synthesis |
Reactions
|
The preparation and analysis of some double salts. An introductory experiment Snavely, Fred A.; Yoder, Claude H.
The introduction of analytical techniques into the general chemistry laboratory has too often meant the addition of routine analysis of "unknowns." Chemists are generally more concerned with the identification and characterization of their own preparations, and thus it would seem more desirable to adopt the same approach in the student laboratory.
Snavely, Fred A.; Yoder, Claude H. J. Chem. Educ. 1971, 48, 621.
Synthesis
|
Stereochemical correlations in the norbornane system Markgraf, J. Hodge; Leung, Pak-Tong
In this experiment 2-norbornanone is converted to the epimeric 2-methyl-2-norbornanols by two routes; the structural assignments of the products are not specified, but must be determined from comparisons of various physical properties.
Markgraf, J. Hodge; Leung, Pak-Tong J. Chem. Educ. 1970, 47, 707.
Stereochemistry |
Molecular Properties / Structure |
Synthesis
|
The dehydration of 3,3-dimethyl-2-butanol Taber, Richard L.; Grantham, Gary D.; Champion, William C.
Presents an experiment that demonstrates the usefulness of gas chromatography as an analytical technique, emphasizes structural rearrangement, makes use of elementary thermodynamics, and gives the student some experience in the original literature.
Taber, Richard L.; Grantham, Gary D.; Champion, William C. J. Chem. Educ. 1969, 46, 849.
Alcohols |
Alkenes |
Gas Chromatography
|
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
|
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
|
|
