Orgo Diels-Alder

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University of Louisville *

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343

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Chemistry

Date

Feb 20, 2024

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docx

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2

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1. Write the reaction mechanism for the Diels-Alder reaction that occurs between furan and maleic anhydride. Use the curved-arrow notation to show the movement of electrons. Label the diene and dienophile and show the product(s). 5 pt Diene Dienophile Product 2. The Diels-Alder reaction was set up last lab session and crystals should have formed over the past week. However, if there hasn’t been any crystal formation, what could be done to induce crystallization. Give 3 possible ways to induce crystallization. 3 pt If crystals don’t form over the week that the reaction has been allowed to sit, you can try to retrieve the crystals through placing the flask in ice water, scraping the flask with a glass stir rod or evaporating some of the THF. 3. A 1H NMR will be taken of the Diels-Alder product of the reaction of furan and maleic anhydride. How many signals are expected in the 1H NMR? Draw the product and label the hydrogens. What splitting pattern is expected for each hydrogen? 3 pt
Three signals are expected Carbon 1: 2H, doublet Carbon 2: 2H, triplet Carbon 3: 2H, doublet of doublet Carbon 4: 2H, doublet of doublet Carbon 5: 2H doublet Carbon 6: 2H doublet
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