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In the Laboratory
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Diels–Alder Synthesis of endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide
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Marsha R. Baar and Kristin Wustholz
Department of Chemistry, Muhlenberg College, Allentown, PA 18104
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September 2005
Vol. 82 No. 9
p. 1393
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| Abstract |
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endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide was synthesized by
a Diels–Alder cycloaddition of 1,3-cyclohexadiene and N-phenylmaleimide in ethyl
acetate. 1,3-Cyclohexadiene and N-phenylmaleimide were selected to illustrate
the Alder rule, which reflects a preference for endo products and to overcome
the difficulties associated with the traditional combination of 1,3-cyclopentadiene
and maleic anhydride. This Diels–Alder reaction can be performed on macro-
or miniscale, at room temperature for a week or under reflux for 2.5 hours
to produce a 91% yield of a white solid that precipitates from solution and
can be analyzed without further purification. Typical student results after
1.5 hours of reflux were 1.05 g (78%), mp 203.4–205.3 °C (lit. 204–206 °C).
Results from IR and 1H and 13C NMR were consistent with literature values.
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| Supplement |
The student handout and report sheet, CAS numbers, and IR, 400 MHz 1H and 13C NMR spectra for endo-cis-N-phenylbicyclo-[2.2.2]-oct-5-en-2,3-dicarboximide (VI) are available.
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 Contents |
JCE2005p1393W.doc (Microsoft Word)
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| More Information |
Citation |
Baar, Marsha R.; Wustholz, Kristin. J. Chem. Educ. 2005 82 1393.
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Keywords |
Addition Reactions; Alkenes; Asymmetric Synthesis; Hands-On Learning / Manipulatives; IR Spectroscopy; Laboratory Instruction; Microscale Lab; NMR Spectroscopy; Organic Chemistry; Second-Year Undergraduate; Stereochemistry
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History |
Created:
Last Updated: |
August 2, 2005
August 10, 2005
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