The Diels-Alder Reaction of Anthracene with Maleic Anhydride

2942 Words Mar 10th, 2008 12 Pages
The Diels-Alder Reaction of Anthracene with Maleic Anhydride 1 The Diels-Alder Reaction of Anthracene with Maleic Anhydride
Microscale Diels-Alder Reaction
Leah Monroe
March 6, 2003
Organic Chemistry Lab II
Experiment performed on February 25 and 27, 2003
This experiment involved a reaction between anthracene and maleic anhydride via a Diels Alder reaction to yield 9, 10-dihydroanthracene-9,10-α, β-succinic anhydride. Anthracene was the diene and maleic anhydride was the dienophile. The percent yield of the crude product was 69.03%. Following recrystallization of the product using xylene and vacuum filtration, a percent yield of 37.42% for the recrystallized product was collected. This was low due to the fact
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Turn on the water to the condenser or add a wet pipe cleaner around the reaction tube. Use a 200°C sand bath to heat the mixture at reflux for 30 minutes, boiling vigorously to ensure good mixing. Cool the mixture to room temperature and prepare an ice bath using a 150-mL beaker. Then cool the mixture in the ice bath for approximately 5 minutes. At the same time, pour 2 mL xylene into a test tube and chill the xylene in the ice bath. Collect the recrystallized solid by vacuum filtration using a Hirsch funnel and rinse the crystals with 1 mL of ice-cold xylene. Weigh the crude product and set aside a small sample to dry. This sample will later be used to measure the melting point of the crude product.
Part 2 – Purifying the Product
To perform recrystallization, place the product in a 10-mL Erlenmeyer flask. Add 1 – 2 mL of xylene and heat the mixture gently in a sand bath until the xylene boils. Gradually add more xylene until all the product dissolves or until no more appears to be dissolving. Be sure not to exceed 3 mL of total volume xylene. If solid impurities are still present, use a Pasteur pipet to transfer the solution to another 10-mL Erlenmeyer flask. Allow the solution to cool to room temperature and then cool the solution in an ice bath for 5 minutes. If it's necessary, scratch the bottom of the flask with a glass rod to induce crystallization. Collect the crystallized solid by vacuum filtration, using a Hirsch funnel. Rinse the crystals with 1 mL

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