23.3 Dehydration of Aldol Products: Synthesis of Enones
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Photochemical Dimerization of Dibenzylideneacetone. A Convenient Exercise in [2+2] Cycloaddition Using Chemical Ionization Mass SpectrometryG. Nageswara Rao, Chelli Janardhana, V. Ramanathan, T. Rajesh, and P. Harish Kumar Presents a laboratory procedure for the photochemical dimerization of dibenzylideneacetone, a dienone. The dimerization is confirmed by chemical ionization mass spectrometry, and other spectroscopic techniques are used to establish the structure of the product. Rao, G. Nageswara; Janardhana, Chelli; Ramanathan, V.; Rajesh, T.; Kumar, P. Harish. J. Chem. Educ.2006, 83, 1667.
Aldehydes / Ketones |
Alkenes |
Chromatography |
IR Spectroscopy |
Mass Spectrometry |
NMR Spectroscopy |
Photochemistry |
Thin Layer Chromatography
The Base-Induced Reaction of Salicylaldehyde with 1-Bromobutane in Acetone: Two Related Examples of Chemical Problem SolvingHolly D. Bendorf and Chriss E. McDonald Each student performs his or her own experimental work, running one of the two reactions, and acquiring the proton and carbon NMR, IR, and mass spectra. The students work in groups to propose structures for the products and mechanisms for their formation. The students are also asked to address why the reactions take different courses. Bendorf, Holly D.; McDonald, Chriss E. J. Chem. Educ.2003, 80, 1185.
Chromatography |
Mass Spectrometry |
NMR Spectroscopy |
Aromatic Compounds |
Aldehydes / Ketones |
Ethers |
Phenols |
IR Spectroscopy
Carbonyl and Conjugate Additions to Cyclohexenone: Experiments Illustrating Reagent SelectivityMichael 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.
