The Diels-Alder Reaction of Anthracene with Maleic Anhydride
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
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