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A More Challenging Interpretative Nitration Experiment Employing Substituted Benzoic Acids and AcetanilidesEdward M. Treadwell and Tung-Yin Lin An experiment is described involving the nitration of ortho or meta, monosubstituted benzoic acids and monochlorinated acetanilides with nitric acid to evaluate the regioselectivity of addition through computational methods and 1H NMR spectroscopy. Treadwell, Edward M.; Lin, Tung-Yin. J. Chem. Educ.2008, 85, 1541.
Aromatic Compounds |
Computational Chemistry |
Electrophilic Substitution |
Molecular Modeling |
NMR Spectroscopy |
Synthesis
Isolation of Betulin and Rearrangement to AllobetulinBrian Green, Michael D. Bentley, Bong Y. Chung, Nicholas G. Lynch, and Bruce L. Jensen Betulin is obtained by extraction from birch bark and converted to allobetulin. Both compounds display 1H NMR spectra that include axialequatorial coupling characteristic of a C3-alcohol, conformational analysis by the use of dihedral angles and the Karplus equation, coupling patterns caused by diastereotopic protons and long-range interactions, and chemical shift values that are influenced by electronegativity and stereochemistry. Green, Brian; Bentley, Michael D.; Chung, Bong Y.; Lynch, Nicholas G.; Jensen, Bruce L. J. Chem. Educ.2007, 84, 1985.
Biosynthesis |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Natural Products
A Green Alternative to Aluminum Chloride Alkylation of XyleneGrigoriy A. Sereda and Vikul B. Rajpara Presents a simple laboratory experiment that introduces organic chemistry students to the basic principles of green technologies, such as lack of toxic or bulk byproducts, nontoxicity, and reusability of the catalyst. Sereda, Grigoriy A.; Rajpara, Vikul B. J. Chem. Educ.2007, 84, 692.
Mechanisms That Interchange Axial and Equatorial Atoms in Fluxional ProcessesMarion E. Cass, Henry S. Rzepa, King Kuok Hii The Berry pseudorotation is a classical mechanism for interchanging axial and equatorial ligands in molecules with trigonal bipyramidal geometry. Teaching this mechanism presents particular pedagogic problems due to both its dynamic and three dimensional character. The approach taken here illustrates these processes using interactive animations embedded in a Web page and overcomes many limitations of a printed page.
