Herein, we describe the in-situ cracking of dicyclopentadiene with the subsequent reaction of the resulting monomer with maleic anhydride in a Diels-Alder cycloaddition.  The Diels-Alder cycloaddition product was then hydrolyzed to the diacid product, consistent with the traditional lab exercise in the undergraduate organic chemistry sequence.  The rigid structure of both the anhydride and hydrolyzed diacid make these products ideal candidates for analysis by 2D-NMR and molecular modeling.  Such an analysis would be inappropriate for a large class but is ideal in a smaller, advanced lab setting or as a special collaboration project between a small portion of a larger undergraduate organic chemsitry lab and a physical chemistry lab.  The findings and complications encountered during our 2D-NMR and molecular modeling analyses will be presented.

Microwave-assisted in-situ cracking of dicyclopentadiene and subsequent reaction with maleic anhydride and the analysis of the Diels-Alder cycloaddition product via 2D-NMR and molecular modeling: A laboratory exercise for an advanced lab course or inter-course collaboration

245th National Meeting (2013)

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