Orgo II Lab 1.docx - Experiment 15 Diels-Alder Reaction...

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Experiment 15: Diels-Alder Reaction: 9,10-Dihydroanthracene- 9,10-,-succinic AcidAnhydrideObjective: The purpose of this experiment is to investigate the Diels-Alder reaction and explore the role of an aromatic ring system as the diene substrate in this addition reaction. This demonstrates a 100% atom economic 1,4 addition by an activated alkene dienophile across the 9,10 positions of anthracene.Experimental Procedure:The procedure was followed as described in Mayo, pages 271-272, with the modifications listed in the posted Canvas document. Additional modifications to the procedure included the following: A drying tube will be used for the first time in lab. This is used to protect moisture-sensitive reaction components from atmospheric water vapor while allowing the system to remain unsealed. The setup for this will be demonstrated by the TA. Drierite, or anhydrous calcium sulfate, will be substituted for calcium chloride in the drying tube. This will always be used as the drying tube agent in Chem 2204. The cotton and Drierite from the drying tube is to be disposed of in the regular trash bin. The reaction mixture will be heated at reflux for 30 minutes by immersing in a sand bath at 180-185 oC and should not exceed 200 oC.

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