| Journal Articles: 23 results |
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Determination of the Rotational Barrier for Kinetically Stable Conformational Isomers via NMR and 2D TLC Gregory T. Rushton, William G. Burns, Judi M. Lavin, Yong S. Chong, Perry Pellechia, and Ken D. Shimizu
After the synthesis of a N,N'-diaryl naphthalene diimide, students estimate the rotational barrier about a CarylNimidesingle bond by studying the reequilibration of the two resulting isomers using two-dimensional thin-layer chromatography, followed by a more accurate determination through a 1H NMR time study.
Rushton, Gregory T.; Burns, William G.; Lavin, Judi M.; Chong, Yong S.; Pellechia, Perry; Shimizu, Ken D. J. Chem. Educ. 2007, 84, 1499.
Alcohols |
Chromatography |
Conformational Analysis |
Equilibrium |
Kinetics |
NMR Spectroscopy |
Physical Properties |
Rate Law |
Thin Layer Chromatography
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Measuring Breath Alcohol Concentrations with an FTIR Spectrometer Adam Kneisel and Michael K. Bellamy
Students use aqueous ethanol solutions to make a calibration curve that relates absorbance signals of breath samples with blood alcohol concentrations. Students use their calibration curve to determine the time needed for their calculated blood alcohol levels to drop below the legal limit following use of a commercial mouthwash.
Kneisel, Adam; Bellamy, Michael K. J. Chem. Educ. 2003, 80, 1448.
Forensic Chemistry |
Instrumental Methods |
IR Spectroscopy |
Fourier Transform Techniques |
Alcohols
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A Puzzling Alcohol Dehydration Reaction Solved by GC–MS Analysis Michael W. Pelter and Rebecca M. Macudzinski
The reaction of 2-methyl-2-propanol with ~50% sulfuric acid at 100 C yields isobutylene, which reacts further by a "puzzling" reaction. By coupling the GC/MS analysis of the product mixture with their knowledge of the mechanism of alcohol dehydration and alkene reactivity, students are able to identify the major products of this reaction.
Pelter, Michael W.; Macudzinski, Rebecca M. J. Chem. Educ. 1999, 76, 826.
Synthesis |
Microscale Lab |
Mass Spectrometry |
Gas Chromatography |
Alcohols |
Alkenes
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The Chemical Adventures of Sherlock Holmes: The Baker Street Burning Thomas G. Waddell and Thomas R. Rybolt
A chemical mystery featuring Sherlock Holmes and Dr. Watson.
Thomas G. Waddell and Thomas R. Rybolt. J. Chem. Educ. 1998, 75, 484.
Enrichment / Review Materials |
Forensic Chemistry |
Qualitative Analysis |
Oxidation / Reduction |
Alcohols |
Dyes / Pigments
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Microscale Dehydration of Cyclohexanol Using a Macroreticular Cation Exchange Resin as Catalyst Harriet P. Moeur, Sharon A. Swatik, and Robert P. Pinnell
In this experiment, cyclohexanol is dehydrated to cyclohexene using Amberlyst 15 macroreticular resin as an acid catalyst. The procedure is carried out with partners, one student using phosphoric acid-sulfuric acid catalyst, the other student using the resin. Yields and ease of manipulation between the two options are compared.
Moeur, Harriet P.; Swatik, Sharon A. ; Pinnell, Robert P. J. Chem. Educ. 1997, 74, 833.
Microscale Lab |
Alcohols |
Catalysis
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The TCICA Test for Distinguishing Primary and Secondary Alcohols Gene A. Hiegel and Afshin K. Chaharmohal
Simple primary and secondary alcohols can easily be distinguished by their rate of oxidation with trichloroisocyanuric acid (TCICA). The TCICA test is conducted by adding the unknown to a solution of TCICA in acetonitrile containing hydrochloric acid and measuring the time for a precipitate to form. Primary alcohols react slowly and secondary alcohols react rapidly.
Hiegel, Gene A.; Chaharmohal, Afshin K. J. Chem. Educ. 1997, 74, 423.
Alcohols |
Molecular Properties / Structure
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The Acid Catalyzed Dehydration of an Isomeric 2-Methylcyclohexanol Mixture: A Kinetic and Regiochemical Study of the Evelyn Effect John J. Cawley and Patrick E. Linder
This paper details an experiment which serves as an introduction to organic laboratory research. The reaction is the dehydration of a cis, trans mixture of 2-methylcyclohexanols. At intervals of times the reactant mixture is sampled for the cis and trans reactants. At those same intervals of times the receiver flasks of product cyclohexanes being collected are changed, such that sequential fractions of material are obtained.
Cawley, John J.; Linder, Patrick E. J. Chem. Educ. 1997, 74, 102.
Catalysis |
Kinetics |
Alcohols |
Stereochemistry
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Chemical Magic: Polymers from a Nonexistent Monomer Seymour, Raymond B.; Kauffman, George B.
Synthesis, properties, and applications of polyvinyl alcohol and related polymers.
Seymour, Raymond B.; Kauffman, George B. J. Chem. Educ. 1994, 71, 582.
Polymerization |
Alcohols
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The Dehydration of 2-Methylcyclohexanol Revisited: The Evelyn Effect Todd, David
Modification to an earlier procedure that allows students to observe the results of a hydride shift mechanism.
Todd, David J. Chem. Educ. 1994, 71, 440.
Alcohols |
Mechanisms of Reactions |
Gas Chromatography |
Alkenes |
Elimination Reactions
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Microscale elimination reactions: Experiments for organic chemistry using the small scale approach Gilow, Helmuth M.
Procedure illustrating E1 and E2 reactions.
Gilow, Helmuth M. J. Chem. Educ. 1992, 69, A265.
Microscale Lab |
Reactions |
Elimination Reactions |
Alcohols |
Alkenes |
Catalysis
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Drying ethanol by azeotropic distillation Mattson, Guy; Hertel, George R.
The commercial process for producing absolute ethanol can be used as a basis for an unusual homework or take-home exam problem.
Mattson, Guy; Hertel, George R. J. Chem. Educ. 1990, 67, 46.
Separation Science |
Alcohols
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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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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
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Which will evaporate first? Stenmark, Allan
The evaporation rate of various short-chain alcohols and diethyl ether are compared.
Stenmark, Allan J. Chem. Educ. 1987, 64, 351.
Physical Properties |
Noncovalent Interactions |
Hydrogen Bonding |
Molecular Properties / Structure |
Alcohols |
Ethers
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Microscale organic laboratory: IV: A simple and rapid procedure for carrying out Wittig reactions Pike, R. M.; Mayo, D. W.; Butcher, D. W.; Butcher, S. S.; Hinkle, R. J.
This paper offers two examples that illustrate a new synthetic method. This synthesis is the first feasible preparation of a particular group available for the introductory organic laboratory.
Pike, R. M.; Mayo, D. W.; Butcher, D. W.; Butcher, S. S.; Hinkle, R. J. J. Chem. Educ. 1986, 63, 917.
Synthesis |
Aromatic Compounds |
Heterocycles |
Alkenes |
Alcohols
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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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A modification of the copper catalysis demonstration apparatus Olsen, Edwin S.; Ashmore, R. E.
A modification to an earlier device for illustrating the oxidation of alcohols to carbonyl compounds over a copper catalyst.
Olsen, Edwin S.; Ashmore, R. E. J. Chem. Educ. 1982, 59, 1042.
Catalysis |
Alcohols |
Laboratory Equipment / Apparatus
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A new synthesis of tertiary alkyl N-aryl-carbamates from isocyanates Bailey, William J.; Griffith, James R.
A simple, convenient, and fast procedure has been developed for the synthesis of tertiary alkyl N-acrylcarbamate from phenyl and 1-naphthyl isocyanates as solid derivatives of tertiary alcohols by the use of lithium tertiary alkoxides as catalysts.
Bailey, William J.; Griffith, James R. J. Chem. Educ. 1978, 55, 809.
Catalysis |
Alcohols |
Synthesis
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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
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Conversions from cyclohexanol. An undergraduate laboratory project Hanna, Samir B.; Wrobleski, James T.; Bohanon, Joseph T.; Peace, Bab W.
A procedure for a laboratory in conversions from cyclohexanol.
Hanna, Samir B.; Wrobleski, James T.; Bohanon, Joseph T.; Peace, Bab W. J. Chem. Educ. 1971, 48, 556.
Alkanes / Cycloalkanes |
Alcohols
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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
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A unique laboratory-lecture in organic chemistry Nienhouse, Everett J.
The laboratory-lecture considered centers about the products obtained from the dehydration of 4-methyl-2-pentanol.
Nienhouse, Everett J. J. Chem. Educ. 1969, 46, 765.
Alcohols |
Alkenes
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Dehydration of 2-methylcyclohexanol Taber, Richard L.; Champion, William C.
This short article describes a simple alcohol dehydration that illustrates the Saytzeff Rule.
Taber, Richard L.; Champion, William C. J. Chem. Educ. 1967, 44, 620.
Alcohols |
Gas Chromatography |
Alkenes
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