Diels-Alder cycloadditions: A MORE experiment in the organic laboratory including a diene identification exercise involving NMR spectroscopy and molecular modeling

Journal of Chemical Education

Volumn 82, Issue 4, 2005, Pages 625-629

  Shaw, Roosevelt ^a   Severin, Ashika ^a   Balfour, Miguel ^a   Nettles, Columbus ^a  

^a MORGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CALCULATIONS; COMPUTER SIMULATION; CURRICULA; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; SYNTHESIS (CHEMICAL);

DIELS-ALDER CYCLOADDITIONS; MOLECULAR MODELING; ORGANIC CHEMISTRY; ORGANIC LABORATORY;

PHYSICAL CHEMISTRY;

EID: 17244367738     PISSN: 00219584     EISSN: None     Source Type: Journal    
DOI: 10.1021/ed082p625     Document Type: Article

References (17)

1. All chemicals, except cyclopentadiene used in this experiment, are available from The Aldrich Chemical Company. See ref 6, p 488 for synthesis of cyclopentadiene.
2. 13C NMR spectra were recorded on a Varian Unity Plus 600 MHZ NMR spectrometer at the Johns Hopkins University School of Medicine, Baltimore, Maryland by Michael Massiah.
3. Product structure determination by NMR showed that the stereochemistry of the reactant trans-1,2-dibenzoylethylene in both reactions is maintained in the Diels-Alder adducts. Students were given Figures 1 and 3, and also Figures 2 and 4 without the indicated structures or names.
4. The PC Spartan Pro and Spartan'02 computer software packages with accompanying tutorial guides of molecular structure building and obtaining best stable conformation from a potential energy-dihedral angle diagram can be acquired from Wavefunction, Inc. (http:// www.wavefun.com; accessed Jan 2005). Both software packages can be used on an 800-MHz Pentium III personal computer running Windows 98 or other compatible PCs to achieve the same results. Execution time for producing energy-dihedral angles diagrams is rapid (within minutes). A detailed step-by-step procedure for obtaining diagrams is given in the Supplemental Material.
5. The Allyn and Bacon organic molecular model set, available from Fisher Scientific, was used to build the handheld molecular models for 1/2 and 3/4. These models were constructed well in advance of the lab experiment by the student authors of this article.
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