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Journal Articles: 12 results
The Synthesis of a Cockroach Pheromone  Patty L. Feist
This paper describes the synthesis of gentisyl quinone isovalerate or blattellaquinone, a sex pheromone of the German cockroach and a compound with real-world applications. The experiment also affords students practice in extraction as well as IR and NMR spectroscopy.
Feist, Patty L. J. Chem. Educ. 2008, 85, 1548.
Esters |
IR Spectroscopy |
Natural Products |
NMR Spectroscopy |
Oxidation / Reduction |
Synthesis
Grubbs's Cross Metathesis of Eugenol with cis-2-Butene-1,4-diol To Make a Natural Product. An Organometallic Experiment for the Undergraduate Lab   Douglass F. Taber and Kevin J. Frankowski
Describes the ruthenium catalyzed cross metathesis of eugenol with cis-1,4-butenediol. The experiment is an excellent example of the powerful selectivity possible with the Grubbs' catalyst, demonstrating the preference for trans over cis alkene formation and for cross metathesis over homodimerization.
Taber, Douglass F.; Frankowski, Kevin J. J. Chem. Educ. 2006, 83, 283.
Alkenes |
Catalysis |
IR Spectroscopy |
Mass Spectrometry |
Mechanisms of Reactions |
Microscale Lab |
Natural Products |
NMR Spectroscopy |
Organometallics |
Stereochemistry |
Synthesis |
Thin Layer Chromatography |
Transition Elements
Monoterpene Unknowns Identified Using IR, 1H-NMR, 13C-NMR, DEPT, COSY, and HETCOR  Lisa T. Alty
This set of NMR experiments can be a capstone experience for a spectroscopy or advanced laboratory course following organic chemistry. Students are given a monoterpene to identify using IR, 1H-NMR, 13C-NMR, and DEPT data. Once the unknown is identified, they can fully interpret and assign each carbon and each proton signal to the structure using COSY and HETCOR along with the one-dimensional NMR data. The rigidity of the ring systems and the chiral centers in all of the compounds present diastereotopic hydrogens and, in some cases, diastereotopic methyl groups.
Alty, Lisa T. J. Chem. Educ. 2005, 82, 1387.
Natural Products |
NMR Spectroscopy |
Diastereomers |
Chirality / Optical Activity |
IR Spectroscopy |
Undergraduate Research
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 selective electroantennography cell for testing the activity of pheromones  Rozas, Roberto; Perez, Dagor
Design, construction, and use of a elective electroantennography cell for testing the activity of pheromones.
Rozas, Roberto; Perez, Dagor J. Chem. Educ. 1987, 64, 356.
Laboratory Equipment / Apparatus |
Natural Products
Synthesis and evaluation of the sex pheromone of the bagworm moth  Schwarz, Meyer; Klun, J. A.
Several possible student-oriented experiments at different educational levels can look into the interesting chemistry involved in a naturally occurring optically active pheromone.
Schwarz, Meyer; Klun, J. A. J. Chem. Educ. 1986, 63, 1014.
Undergraduate Research |
Natural Products |
Synthesis |
Qualitative Analysis |
Chirality / Optical Activity
Mammalian Semiochemistry: The Investigation of Chemical Signals Between Mammals (Albone, Eric S.)  Oliver, George V.
Surveys our knowledge of the chemical signals employed by mammals.
Oliver, George V. J. Chem. Educ. 1985, 62, A270.
Natural Products
Sulcatol: Synthesis of an aggregation pheromone  Black, Shirley-Ann; Slessor, Keith N.
Synthesis of the aggregation pheromone of the ambrosia beetle, an insect pest of harvested timber in the Pacific North Coast.
Black, Shirley-Ann; Slessor, Keith N. J. Chem. Educ. 1982, 59, 255.
Synthesis |
Natural Products |
Molecular Properties / Structure |
Chirality / Optical Activity |
NMR Spectroscopy |
IR Spectroscopy |
Applications of Chemistry
Glutamic acid in pheromone synthesis: A useful chiral synthon  Smith, Leverett R.; Williams, Howard J.
Outlines synthetic routes for the formation of various pheromones from glutamic acid.
Smith, Leverett R.; Williams, Howard J. J. Chem. Educ. 1979, 56, 696.
Synthesis |
Chirality / Optical Activity |
Natural Products |
Stereochemistry |
Enantiomers |
Amino Acids
A student synthesis of the housefly sex attractant  Cormier, Russell A.; Duc Phan, M.; Graddis, Thomas; Singer, Richard
This multi-step synthetic sequence illustrates several important laboratory techniques, including ir and nmr spectroscopy, thin-layer and column chromatography, rotary evaporation, recrystallization, and vacuum distillation.
Cormier, Russell A.; Duc Phan, M.; Graddis, Thomas; Singer, Richard J. Chem. Educ. 1979, 56, 345.
Synthesis |
Natural Products |
IR Spectroscopy |
NMR Spectroscopy |
Chromatography |
Thin Layer Chromatography
Questions [and] Answers  Campbell, J. A.
309-314. Six questions involving practical applications of chemistry.
Campbell, J. A. J. Chem. Educ. 1977, 54, 437.
Enrichment / Review Materials |
Toxicology |
Alcohols |
Gases |
Natural Products
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