17.4. What Are the Characteristic Reactions of Aldehydes and Ketones?, 462
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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
A One-Pot, Asymmetric Robinson Annulation in the Organic Chemistry Majors LaboratoryKiel E. Lazarski, Alan A. Rich, and Cheryl M. Mascarenhas Describes a one-pot, enantioselective, Robinson annulation geared towards the second-year organic chemistry major and demonstrating aspects of green chemistry. Lazarski, Kiel E.; Rich, Alan A.; Mascarenhas, Cheryl M. J. Chem. Educ.2008, 85, 1531.
Aldehydes / Ketones |
Asymmetric Synthesis |
Catalysis |
Chirality / Optical Activity |
Gas Chromatography |
HPLC |
NMR Spectroscopy |
Synthesis |
Green Chemistry
Polymer-Supported Reagents and 1H–19F NMR Couplings: The Synthesis of 2-FluoroacetophenoneNicola Pohl and Kimberly Schwarz Describes an experiment in which 2-bromoacetophenone is converted to 2-fluoroacetophenone using a solid-phase nucleophilic fluorine source. The experiment introduces students to the utility of solid-phase reagents in organic synthesis, to NMR-active nuclei other than 1H without the requirement of a special NMR probe, and to the unique uses of fluorine in molecular design. Pohl, Nicola; Schwarz, Kimberly. J. Chem. Educ.2008, 85, 834.
