Experiment 15: Diels-Alder Reaction: 9,10-Dihydroanthracene-9,10-α,β-succinic Acid
The objective of this experiment is to explore the role of an aromatic ring system as the diene
substrate in this addition reaction, which is an example of a 100% atom economic 1,4 addition by
an activated alkene dienophile across the 9,10 positions of anthracene. Techniques that are used
in this experiment include the use of the Hirsch funnel for crystallization.
The procedure was followed as described in Mayo, pages 269-273, with the modifications listed
in the Blackboard document. Additional modifications to the procedure included the following:
Anhydrous calcium sulfate was substituted for calcium chloride in the drying tube.
The sand bath was heated to a temperature of 180-185
C instead of 200
Data and Results
α,β -succinic acid anhydride