The Diels-Alder Reaction of Anthracene with Maleic Anhydride

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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
Abstract:
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 that some of the crude product was not recrystallized and was instead used to take a melting point of the crude product. It was also low due to several of the crystals being stuck inside the flask and not going into the funnel. The percent recovery from recrystallization was 54.21%. The melting point of the crude product was 261 - 264°C. The melting point of the recrystallized product was 261 - 263°C. Comparing these values with the literature melting point of 262 - 264°C shows that the product was indeed 9, 10-dihydroanthracene-9, 10-α, β-succinic anhydride and that recrystallization yielded a purer product. Upon examination of an infrared spectrum of the product and comparison with anthracene and maleic anhydride spectra, it was found that the product spectrum had similarities with both the anthracene spectrum and the maleic anhydride spectrum. This indicated that the product was an adduct of both anthracene and maleic anhydride, and thus that the experiment was successful. The Diels-Alder Reaction of Anthracene with Maleic Anhydride 2 Introduction: The purpose of this experiment is to form 9, 10-dihydroanthracene-9,10-α, β-succinic anhydride by way of a Diels Alder reaction between anthracene and maleic anhydride. Anthracene acts as the diene and maleic anhydride functions as the dienophile. Following the reaction, the crude product will be recrystallized. Melting points of both the crude product and recrystallized product will be taken and compared with the literature value. Also, an infrared spectrum of the recrystallized product will be taken. Both melting points and the infrared spectrum will be used to characterize the product. Materials Used:

150-mL beaker Hirsch funnel, with adapter
boiling chip 2 melting point capillary tubes
Condenser, with tubing Pasteur pipet, with latex bulb
5-mL conical vial microspatula
2 Erlenmeyer flasks, 10-mL 1-mL pipet
25-mL filter flask, with vacuum tubing sand bath
filter paper support stand
glass stirring rod 13 x 100-mm test tube
thermometer, -10 to 260°C

Substances Formula Weight
g/mol Quantity Moles Used Mole Ratio Melting Point
°C Boiling Point
°C
anthracene 178.23 100 mg 5.611 x 10-4 1 to 1 216 – 218 N/A 9,10-dihydroanthracene-
9, 10-α, β-succinic anhydride 276.29 product N/A 1 to 1 262 – 264 N/A maleic anhydride 98.06 55 mg 5.609 x 10-4 1 to 1 54 – 56 N/A potassium bromide 119.01 100 mg 8.4 x 20-4 N/A N/A N/A xylene 106.17 6 mL N/A N/A N/A 137 – 144

Reagents and Properties:
Reaction and its Mechanism:
Overall Reaction: C14H10 + C4H2O3 􀃆C18H12O3 C O C O O + Anthracene (diene) Maleic anhydride (dienophile) C O H H C O O 9,10-dihydroanthracene-9,10-α, β-succinic anhydride Maleic anhydride (dienophile) C O O C O C O H H C O O Anthracene (diene) 9,10-dihydroanthracene-9,10-α, β-succinic anhydride The Diels-Alder Reaction of Anthracene with Maleic Anhydride 3 Procedure:

Part 1 – Reacting Anthracene with Maleic Anhydride
Tare a 5-mL conical vial (or 10x 100-mm reaction tube) and record the mass. Weigh 100 mg of anthracene and 55 mg maleic anhydride and place them in the vial or reaction...
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