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EXPERIMENT 2A DIELS-ALDER REACTION OF ANTHRACENE REFERENCES Pavia et al (4/e): Tech. 6.1/6.2, 7.2-7.4 Klein (1/e)...


EXPERIMENT 2A DIELS-ALDER REACTION OF ANTHRACENE REFERENCES Pavia et al (4/e): Tech. 6.1/6.2, 7.2-7.4 Klein (1/e) pp. 784-792
EXP. 2: SUPPLEMENTARY LAB QUESTIONS y is the reaction carried out in xylene rather than ethanol? 2. As the reflux poeds durin
EXPERIMENT 2A DIELS-ALDER REACTION OF ANTHRACENE REFERENCES Pavia et al (4/e): Tech. 6.1/6.2, 7.2-7.4 Klein (1/e) pp. 784-792 EQUATION heat Diels-Alder Adduct 9,30-dihydroanthracene-9,10- endo-o B-seccinic anhydride mp 262264 PROCEDURE Place 0.200 grams of anthracene and an equal molar amount of maleic anhydride in 5 mL of xylenes in a 10-mL round-bottom flask with a magnetic stir bar. Attach a water-cooled condenser and reflux for 60 minutes. Allow the solution to cool to room temperature and then place the flask in an ice bath. Filter the ppt., dry it, and take the melting point of the product. Calculate the % yield. Obtain both the IR and UV spectra of the product. We will use 2-propanol for the UV solvent. You will need to heat the solution to get the Diels-Alder adduct to completely dissolve, so initially make the solution in a small beaker using approximately 5 mL of 2-propanol. After heating, allow the solution to cool to room temperature and transfer the solution to a 10 ml. volumetric flask. Carefully fill the volumetric flask with solvent to the 10-mL mark. The IR and UV spectra of the starting materials are provided at the end of this lab. These spectra should be removed and attached to your notebook. You will refer to them as you discuss any similarities or differences between them and the spectra of your Diels-Alder product. 19
EXP. 2: SUPPLEMENTARY LAB QUESTIONS y is the reaction carried out in xylene rather than ethanol? 2. As the reflux poeds during the reaction,the color of the solution changes from yllow to colorless. Explain. 3. In general, the exo form of a Diels-Alder product is more stable, yet the endo product is formed almost exclusively. Explain. 4. Which would be more reactive in a Diels-Alder reaction: cis-2-methyl-2,4-hexadiene or trans-2-methyl-2,4-hexadiene? Explain. 5. The following reaction gives two products in unequal amounts. CHO Identify the major product and explain why it is favored.
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