Chem 2204 Report 1.docx - Experiment 15 The Diels-Alder...

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Experiment 15: The Diels-Alder Reaction: 9,10-Dihydroanthracene-9,10-,-succinic Acid Anhydride Objective: The purpose of this experiment is to examine how aromatic rings behave as the diene substrate of this reaction. This is technically classified as a 100% atom economic 1,4 addition across the 9,10 positions of anthracene. Experimental Procedure: The procedure was followed as described in Mayo, pages 269-272, with the modifications listed in the Canvas document. Additional modifications to the procedure included the following Instead of using calcium chloride as a drying agent, use drierite in the drying tube. Heat the reaction at reflux for 30 minutes in a sand bath of 180-185ºC while making sure the reaction doesn’t exceed 200 ºC. There will be no recrystallization step. Reaction Scheme: Data:
anthracene maleic anhydride xylenes 9,10- dihydroanthrace ne-9,10 , -succinic acid anhydride mol Mol. formula C 14 H 10 C 4 H 2 O 3 C 18 H 12 O 3 Amount (mg) 80 40 (TY, 110) (EY, 36) Amount (mL) 1.0 mmoles 0.45 0.41 (TY, 0.41) (EY, 0.13) Molar mass 178.23 98.06 276.30 density 0.86 lit. bp (°C) 137-140

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