We used this one in Fall 2010 since the Bruice textbook has Diels Alder rather early.
In Fall 2010 we used N-phenylmaleimide, and diethyl maleate as dienophiles in addition to the traditional maleic anhydride
+ The lab is a great experiment to reinforce the classroom instruction related to the Diels-Alder Reaction.
+ The experiment is a traditional synthesis experiment and lends itself to a classical lab report format.
+/- It is maybe too simple and straightforward, it needs an aspect of "problematization" to strengthen it.
- It is not a very environmentally friendly reaction both reactants and solvents.
- The product is very difficult to draw in two dimensions and visualize appropriately.
there certainly may be ways to explore a variety of reactants since the Diels Alder is such as popular reaction.
further reactions can be done to the anhydride Diels Alder product - hydrolysis and esterification, for example.
The 1H NMR analysis of the product was very interesting on several counts.
It definitely is a challenging structure to verify given the level of spectroscopy instructions typically given in Organic Chemistry.
2010 UV data
2010 IR data
2009 1H NMR data
(The handout contains a highly fictitious 13C NMR table.
We are working on obtaining a more realistic 13C NMR data set.)
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