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Borohydride Reduction of EstroneAnimesh Aditya, David E. Nichols, and G. Marc Loudon This experiment presents a guided-inquiry approach to the demonstration of diastereoselectivity using chiral hindered ketones that undergo facile reduction with sodium borohydride. The resulting diastereomeric estradiols can be analyzed and differentiated by thin-layer chromatography and melting point. Aditya, Animesh; Nichols, David E.; Loudon, G. Marc. J. Chem. Educ.2008, 85, 1535.
Aldehydes / Ketones |
Diastereomers |
IR Spectroscopy |
Microscale Lab |
Stereochemistry |
Steroids |
Thin Layer Chromatography
Acid-Catalyzed Enolization of β-TetraloneBrahmadeo Dewprashad, Anthony Nesturi, and Joel Urena This experiment allows students to use 1H NMR to compare the rates of substitution of benzylic and non-benzylic a hydrogens of -tetralone and correlate their findings with predictions made by resonance theory. Dewprashad, Brahmadeo; Nesturi, Anthony; Urena, Joel. J. Chem. Educ.2008, 85, 829.
Aldehydes / Ketones |
Isotopes |
Mechanisms of Reactions |
NMR Spectroscopy |
Reactive Intermediates |
Resonance Theory |
Synthesis
The Baeyer–Villiger Oxidation with Trifluoroacetic Acid and Household Sodium PercarbonateRichard A. Kjonaas and Anthony E. Clemons Reports a method for carrying out the BaeyerVilliger oxidation of cyclopentanone to d-valerolactone in a large-section introductory organic chemistry laboratory course. Kjonaas, Richard A.; Clemons, Anthony E. J. Chem. Educ.2008, 85, 827.
