...The purpose of this lab was to perform a Diels Alder reaction by using anthracene and maleic anhydride to form 9,10-dihydroanthracene-9,10-α,β-succinic acid anhydride. At the end of the experiment, the mass of the final product was used to calculate the percent yield in order to examine the efficiency of the reaction. In addition, the melting point range was measured of the final product and compared with the literature value to determine the purity of the product. To a 10 mL round bottom flask was added 0.406 g, 0.200 g and 5mL of toluene. The solution had a yellowish color when the reactants were mixed. Then, the flask was attached to the condenser and heated at 160° C to maintain reflux for an hour. After the hour, the reaction was allowed to cool to room temperature. As the reaction cool down, small crystal formed in the reaction. The crystals (product) of the reaction were collected in the Buchner funnel by vacuum filtration for 15minutes. Finally, the...
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...β – Succinic Anhydride Reactions: Reaction Mechanism Physical Properties Table: Chemical | Formula | M.W (g/mol) | Quantity (g or ml) | Amount( moles) | Molar Equivalent | M.P(OC) | B.P (OC) | Density\(g/cm3) | Yield (g) | % yield | Anthracene | C14H10 | 178.23 | 2.018 g | 0.0113 | 1 | 215 | 339 | 1.28 | | | Xylene | C8H10 | 106.16 | 2.5 ml | 0.0022 | 1 | -47.4 | 138.5 | 0.864 | | | Maleic Anhydride | C4H2 O3 | 98.06 | 1.001 g | 0.0102 | 1 | 52.8 | 202 | 1.480 | | | Hexane | C6H14 | 86.18 | - | - | | -96 | 68 | 0.655 | | | DCM | C10Cl2 | 84.93 | - | - | | -96.7 | 39.6 | 1.327 | | | Ethyl Acetate | C4H8O2 | 88.11 | - | - | | -83.6 | 77 | 0.897 | | | 9,10-Dihydroanthracene-9,10-Endo-α,β – Succinic Anhydride | C18H12O3 | 276.29 | - | - | | 262-264 | | | 2.326 | 82.43 | Calculations: * Calculating the number of moles of Anthracene Mass of Anthracene Used is 2.018 g Molar Mass is 178.23 g/mol Number of moles = MassMolar mass = 2.018 g 178.23gmol = 0.0113 moles * Calculating the number of moles of Maleic Anhydride Mass of Maleic Anhydride Used is 1.001 g Molar Mass is 98.06 g/mol Number of moles = MassMolar mass = 1.001 g 98.06gmol = 0.01021 moles * Calculating the Theoretical Yield C14H10 + C4H2O3 → C18H12O3 Based on the Number of moles calculated the limiting reagent is the Maleic Anhydride. Theoretical...
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...The Diels-Alder Reaction of Anthracene with Maleic Anhydride The Diels-Alder reaction is a member of a class of reactions called cycloadditions. The reaction involves three π bonds, two from the diene and one from the dienophile in a concerted reaction to form a six-membered ring. Since the reaction involves four π electrons in the diene and two π electrons from the dienophile, it is sometimes referred to as a 4 + 2 cycloaddition. Normal Diels-Alder reactions are favored by electron donating groups on the diene and electron withdrawing groups on the dienophile. The diene must be capable of achieving an s-cis conformation to generate the cis double bond in the cyclohexene product. Acyclic dienes may rotate around a single bond, but dienes locked in the s-trans conformation do not react. [pic] 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 anhydride, as shown in the reaction below. Anthracene acts as the diene and maleic anhydride functions as the dienophile. Xylene (dimethylbenzene) is used as a high boiling temperature solvent so that the reaction will proceed quickly. Melting temperature analysis will be used to characterize the product. Anthracene Maleic anhydride 9,10-dihydroanthracene- ...
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...Synthesis of the Diels-Alder Adduct Purpose: To investigate the methods behind Diels-Alder chemistry through the laboratory synthesis of 4- cyclohexene-cis- ,2-dicarboxylic anhydride from butadiene sulfone with maleic anhydride. By utilizing the theoretical concepts in a hands-on approach through laboratory synthesis, I hope to gain a better understanding of the reaction concepts governing Diels- Alder chemistry. Theory: The Diels-Alder reaction is a cycloaddition, chemical reaction that occurs between a conjugated diene, a molecule with two alternating double bonds, and dienophile, an alkene, to form rings and bicyclic compounds. Because it involves the interaction of four π electrons that are supplied by the diene and the two π electrons supplied by the dienophile, the Diels-Alder reaction is often called [4 + 2] cycloaddition. In the reaction, two new σ bonds are formed and one π bond is formed at the expense of two π bonds, which results in a cyclic product. The Diels-Alder reaction is a member of a larger class of reactions called pericylic reactions, which are reactions that take place in a single step, without intermediates and that involve the flow or redistribution of bonding electrons. The reaction proceeds through a cyclic transition state and is concerted, meaning bonds in the transition state are simultaneously made or broken. The Diels-Alder reaction is favored when the dienophile is the substituted with electron withdrawing groups such as nitriles, amines...
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...β – Succinic Anhydride Reactions: Reaction Mechanism Physical Properties Table: Chemical | Formula | M.W (g/mol) | Quantity (g or ml) | Amount( moles) | Molar Equivalent | M.P(OC) | B.P (OC) | Density\(g/cm3) | Yield (g) | % yield | Anthracene | C14H10 | 178.23 | 2.018 g | 0.0113 | 1 | 215 | 339 | 1.28 | | | Xylene | C8H10 | 106.16 | 2.5 ml | 0.0022 | 1 | -47.4 | 138.5 | 0.864 | | | Maleic Anhydride | C4H2 O3 | 98.06 | 1.001 g | 0.0102 | 1 | 52.8 | 202 | 1.480 | | | Hexane | C6H14 | 86.18 | - | - | | -96 | 68 | 0.655 | | | DCM | C10Cl2 | 84.93 | - | - | | -96.7 | 39.6 | 1.327 | | | Ethyl Acetate | C4H8O2 | 88.11 | - | - | | -83.6 | 77 | 0.897 | | | 9,10-Dihydroanthracene-9,10-Endo-α,β – Succinic Anhydride | C18H12O3 | 276.29 | - | - | | 262-264 | | | 2.326 | 82.43 | Calculations: * Calculating the number of moles of Anthracene Mass of Anthracene Used is 2.018 g Molar Mass is 178.23 g/mol Number of moles = MassMolar mass = 2.018 g 178.23gmol = 0.0113 moles * Calculating the number of moles of Maleic Anhydride Mass of Maleic Anhydride Used is 1.001 g Molar Mass is 98.06 g/mol Number of moles = MassMolar mass = 1.001 g 98.06gmol = 0.01021 moles * Calculating the Theoretical Yield C14H10 + C4H2O3 → C18H12O3 Based on the Number of moles calculated the limiting reagent is the Maleic Anhydride. Theoretical...
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...The experiment involved a Diel-Alder reaction and is also known as a [4+2] cycloaddition because the reaction takes place between two different π Systems, one of which is associated with 4 atoms and the other one having two atoms. We synthesized 9,10-dihydroanthracene-9,10α,β 13-succinic acid anhydride from anthracene (diene) and meleic anhydride (dienophile). The use of maleic anhydride as the dienophile allows for a relatively high yield because the carbonyl substituents remove electron density from the reactive site through resonance and ultimately lowers the energy of the lowest unoccupied molecular orbital of the maleic acid anhydride molecule. By using anthracene as the diene, the conjugated π bonds are able to donate electron density...
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