Diels Alder Lab Report

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The Diels-Alder Reaction
Submitted by: Joe Student Partner: Jill Student
Date: February 8, 2005 TA: Super TA
Reaction +OOOxylene140 oCOOO
Data Table
Reagents
MW
Grams used
Lit. Mp
Anthracene
178.23 g/mol
1.023 g
216-218ºC
Maleic anhydride
98.06 g/mol
0.497 g
54-56ºC
Products
MW
Grams obtained
Lit. Mp
Observed Mp
Crude product
276.29 g/mol
1.362 g
261-262ºC
260.2-261.3ºC
Recryst. Product
276.29 g/mol
1.283 g
261-262ºC
261.3-261.9ºC
Results and Discussion
Discuss the data that your team obtained in this section. Be sure to address any questions posed in the lab procedure as well as any additional questions that your TA wants you to answer. You should also analyze any NMR spectra that you have from the reaction (if applicable). Spectra of starting materials are available on the Vista site. This reaction was carried out using standard reflux conditions. Both the anthracene and maleic anhydride dissolved immediately in xylene to give a slightly yellow solution. As the reflux was conducted, the reaction mixture appeared to darken a bit in color, and after 30 minutes, it was a distinct yellow color. Crystal formation occurred almost immediately after removing the round-bottomed flask from the heating mantle, with even more crystals forming during the time the flask was in the ice bath. The crystals were a pale yellow color, with an irregular, powdery shape. The crude material was recrystallized from boiling xylene. Xylene is an excellent solvent for both anthracene and maleic anhydride, as evidenced by their complete solubility in the early part of the synthesis. Due to this fact, any unreacted starting materials would remain soluble throughout the recrystallization process. Additionally, the Diels-Alder product is soluble in boiling xylene, but insoluble in cool xylene. This makes for an ideal recrystallization solvent. The purified crystals that were collected from the recrystallization were a faint off-white color, with a regular,...
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