Chem 2204- Diels Alder Rxn.docx - Experiment 15 Diels-Alder...

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Experiment 15: Diels-Alder Reaction: 9,10-Dihydroanthracene-9,10-α, β-succinic Acid Anhydride Objective: To investigate the Diels-Alder reaction by demonstrating a 1,4 addition by an activated alkene dienophile across the 9,10 positions of anthracene. This experiment also aims to introduce the student to the drying tube. Experimental procedure: The procedure was followed as described in Mayo, pages 271-272, with the modifications listed in the posted Canvas document. Reaction Scheme: Data and Results: anthracene maleic anyhydride xylenes 9,10- dihydroanthracene- 9,10- α,β-succinic acid anhydride Mol. formula C14H10 C4H2O3 C8H10 C18H12O3 Amount (mg) 80 40 - 110 (TY) 58 (EY) Amount (mL) - - 1.0 - mmoles 0.45 0.41 0.106 0.41 (TY) 0.21 (EY) Molar mass 178.23 98.06 106.16 276.30 density - - 0.86 - lit. bp (°C) - - 137-140 - lit. mp (ºC) 216 60 262-266 Observations: Mixture was yellow in color before boiling.
After boiling and reflux took place, mixture became a clear color. Boiling seemed to begin as the thermometer in the sand bath reached approximately 135 degrees. After the solution cooled to room temperature, white crystal like structures began to form in the conical vial.

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