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Diels-Alder - Amy Linkous CHEM 2556 CRN 91653 Diels-Alder...

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Amy Linkous 11/4/09 CHEM 2556, CRN: 91653 Diels-Alder Reaction Objective: Prepare cis -cyloxex-4-ene-1,2-dicarboxylic acid via the Diels-Alder reaction. General Reaction: Procedure: 2.4 g of 2,5-dihydrotriophene-1,1-dioxide, 2.0 g butenedioic anhydride and 2.0 mL bis(2- methoxyethyl) ether were placed in a round-bottom flask with a stir bar and thermometer. The reaction was stirred with heat until sulfur dioxide gas evolved around 140 C, at which time the heat was removed. When the temperature began to drop, the reaction was placed back on the heat and kept between 150-160 C for about 5 minutes until the evolution of sulfur dioxide ceased. The reaction flask was then cooled in a water bath and stirred, upon which partial crystallization occurred. 25 mL cold water was added with stirring and the crystals were filtered out by suction.
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The crystals were washed twice with 25 mL of water each time while still on the filter. The product was left on the funnel under suction for a few minutes to dry, after which it was weighed. 1.0 g of the product was then placed in a round-bottom flask with boiling stones and 10
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