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Journal Articles: 13 results
The Comparative Nucleophilicity of Naphthoxide Derivatives in Reactions with a Fast-Red TR Dye  Cheryl M. Mascarenhas
In this experiment, organic chemistry students perform reactions between three naphthyl acetate derivatives and the diazonium salt Fast-Red TR. Students discover under what conditions the hydrolysis and electrophilic aromatic substitution is fastest and slowest, allowing them to conclude that latter, rather than the former, is rate-limiting.
Mascarenhas, Cheryl M. J. Chem. Educ. 2008, 85, 1271.
Alcohols |
Aromatic Compounds |
Dyes / Pigments |
Esters |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography |
UV-Vis Spectroscopy
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
Weak Acid pKa Determination Using Capillary Zone Electrophoresis  Mike Solow
In this experiment, students use capillary zone electrophoresis to determine the effective mobility of benzoic acid at two different hydrogen ion concentrations. A plot of these data yields the pKa of benzoic acid.
Solow, Mike. J. Chem. Educ. 2006, 83, 1194.
Acids / Bases |
Aqueous Solution Chemistry |
Carboxylic Acids |
Electrophoresis |
Instrumental Methods
A Greener Approach to Aspirin Synthesis Using Microwave Irradiation  Ingrid Montes, David Sanabria, Marilyn García,, Joaudimir Castro, and Johanna Fajardo
Presents an inquiry-based laboratory experience based on the use of a microwave oven as a means for a comparative study of the effect of different catalysts in the synthesis of aspirin.
Montes, Ingrid; Sanabria, David; García,, Marilyn; Castro, Joaudimir; Fajardo, Johanna. J. Chem. Educ. 2006, 83, 628.
Drugs / Pharmaceuticals |
Esters |
Green Chemistry |
NMR Spectroscopy |
Reactions |
Synthesis |
Thin Layer Chromatography
4-Dimethylaminopyridine or Acid-Catalyzed Syntheses of Esters: A Comparison  Annemieke W. C. van den Berg and Ulf Hanefeld
Students compare acid-catalyzed ester synthesis and the 4-dimethylaminopyridine-catalyzed reaction. Based on the outcome of the experiments, students discuss the different reaction mechanisms and reason why different products are formed.
van den Berg, Annemieke W. C.; Hanefeld, Ulf. J. Chem. Educ. 2006, 83, 292.
Acids / Bases |
Catalysis |
Chromatography |
Esters |
IR Spectroscopy |
NMR Spectroscopy |
Mass Spectrometry |
Synthesis |
Mechanisms of Reactions
An Unexpected Event When Chymotrypsin Performs Its Physiological Role  Ivan G. Darvey
One of the events that occur during the chymotrypsin-catalyzed hydrolysis of proteins is an example of an exception to a rule of thumb taught in introductory organic chemistry courses, namely, that amides can't readily be converted to esters. If biochemistry teachers and the authors of textbooks of biochemistry commented on this unusual reaction, it would emphasize further the remarkable part chymotrypsin plays as a catalyst in carrying out its main perceived "physiological role".
Darvey, Ivan G. J. Chem. Educ. 2000, 77, 422.
Catalysis |
Enzymes |
Amides |
Esters
Microwave Irradiation Reactions: Synthesis of Analgesic Drugs  Gholam A. Mirafzal and Jolene M Summer
Over-the-counter analgesics such as aspirin, acetanilide, phenacetin, and acetaminophen are conveniently prepared in a microwave at 30% power for five minutes. Recrystallization from appropriate solvents results in solid products in good to excellent yields.
Mirafzal, Gholam A.; Summer, Jolene M. J. Chem. Educ. 2000, 77, 356.
Drugs / Pharmaceuticals |
Synthesis |
Medicinal Chemistry |
Aromatic Compounds |
Amines / Ammonium Compounds |
Esters
Replacing mineral acids in the laboratory: Nafion-catalyzed dehydration and esterification  Doyle, Michael P.; Plummer, Benjamin F.
The advantage of Nafion is that unlike mineral acids, this perfluorinated ion-exchange polymer is a solid resin that can be handled without the safety hazards usually associated with strong acids.
Doyle, Michael P.; Plummer, Benjamin F. J. Chem. Educ. 1993, 70, 493.
Esters |
Laboratory Management
Introducing plastic in the laboratory: Synthesis of a plasticizer, dioctylphthalate and evaluation of its effects on the physical properties of polystyrenes  Caspar, A.; Gillois, J.; Guillerm, G.; Savignac, M.; Vo-Quang, L.
These authors are proposing a two-stage experimental approach that combines preparative organic chemistry and polymer characterization.
Caspar, A.; Gillois, J.; Guillerm, G.; Savignac, M.; Vo-Quang, L. J. Chem. Educ. 1986, 63, 811.
Esters |
Reactions |
IR Spectroscopy |
UV-Vis Spectroscopy |
NMR Spectroscopy |
Mass Spectrometry |
Thin Layer Chromatography
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
The hydrolysis of 4-nitrophenol phosphate. A freshman class investigation  Hopkins, Harry P., Jr.; Mather, Jane H.
A study of the hydrolysis of 4-nitrophenol phosphate is made the basis of a biochemistry-oriented quarter in freshman chemistry; after completing the simple hydrolysis studies, the student proceeds to investigate the enzymatic hydrolysis of 4-nitrophenol phosphate.
Hopkins, Harry P., Jr.; Mather, Jane H. J. Chem. Educ. 1972, 49, 126.
Reactions |
pH |
Esters |
Enzymes |
Catalysis
Kinetics of condensation polymerization: Preparation of a polyester  McCaffery, Edward L.
This experiment involves determining the reaction-rate constant for a condensation polymerization.
McCaffery, Edward L. J. Chem. Educ. 1969, 46, 59.
Kinetics |
Polymerization |
Synthesis |
Esters |
Rate Law
Preparation and crosslinking of an unsaturated polyester: An organic chemistry experiment  Stevens, M. P.
Unsaturated polyesters are ideally suited for introducing students to polymer chemistry in the laboratory because they are easy to prepare, the use both condensation and addition polymerization, and they serve to demonstrate the techniques involved in preparing the most widely used polymers.
Stevens, M. P. J. Chem. Educ. 1967, 44, 160.
Polymerization |
Esters