Objectivity Of Diels-Alder Reaction

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Diels-Alder Reaction

Objective: The objective of this lab was to do a diels-alder reaction using anthracene, maleic anhydride, and xylene to create 9,10-dihydroanthracene, 10-, -succinic acid anhydride.

Experimental: Anthracene (1.00g, 5.61x 10-3 mol), maleic anhydride (0.75g, 7.61x 10-3 mol), xylene (5mL, 4.71x 10-2 mol), and a stir rod were added into a round-bottomed flask. The round-bottom flask was then moved to the hood where the it was attached to a distillation column, placed on top of a sand bath. The sand bath temperature was placed between 30C to 40C. At the initial sight of reflux, a timer was set for 40 minutes. The mixture’s appearance was initially green, but darken over time as the experiment proceeded. After 40 minutes,
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Theoretical Yield = Theoretical moles x Molecular weight of product (g/mol) Example: Theoretical Yield = 0.00597 (mol) x 276.29 (g/mol)= 1.65 g 3. % Yield= (Actual Yield (g)/ Theoretical Yield (g)) x 100 Example: % Yield = (1.65 (g)/ 1.65 (g)) x 100= 100% 4. Rf value = Distance spot traveled (cm) / Distance solvent traveled (cm)
Example: Rf value = 1.3 (cm) / 4 (cm) = 0.325 cm
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From the experiment, 1.65g of the product was retrieve and the percent yield was then calculated using the following equations above to be 100.0% . What the percent yield may have identified was that all of the product was obtained or that the product may have had some solvents still in it. To indicate if the product was pure, a TLC, melting point, and IR spectrum was ran. A comparative TLC was done for both the anthracene and the maleic anhydride. For anthracene the Rf value was 0.62cm, whereas the product was shown to have an Rf value of 0.22cm. Maleic anhydride present an Rf value of 0.0cm, while the product’s Rf value was calculated to be at 0.31cm. Observing both comparative TLC plates only the product compound was expressed within its lane, thus showing that the product was pure. Using the slow ramp, the melting point for the pure product was identified to be at 259.1-262.6 C. The melting point for the product was shown to be 260C, which is in range of the experimental product’s melting point. When comparing the IR spectrum of the product with anthracene, the two compounds both expresses C=C and C-H. However, the product also have a C=O peak whereas anthracene have a =C-H peak. The difference in peaks showed that the anthracene was successfully converted into the

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