Experiment 15.docx - Experiment 15 Diels-Alder Reaction...

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Experiment 15: Diels-Alder Reaction: 9,10-Dihydroanthracene-9,10-α,β-succinic Acid Anhydride Objective : 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. Experimental Procedure : 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 o C instead of 200 o C Reaction Scheme : Data and Results : anthracene maleic anhydride xylenes 9,10-dihydroanthracene-9,10- α,β -succinic acid anhydride mol. formula C 14 H 10 C 4 H 2 O 3 C 8 H 10 C 18 H 12 O 3 amount (mg) 80 40 113 (TY) N/A (EY)

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