9, 10-Dihydroanthracene Lab Report

The objective of the experiment completed was to form the product 9,10-dihydroanthracene-9,10-α,β-succinic anhydride from anthracene and maleic anhydride. The reaction that took place is named a Diels-Alder reaction, defined as an addition reaction in which a diene unites with a double or triple bond of an unsaturated compound to form a 6-membered-ring. The following reactions below depict the ways in which dienes and dienophiles join to form products. Anthracene functioned as a diene and maleic anhydride functioned as the dienophile. Xylene was used as a solvent that provided a quicker way of reaction between the two starting materials. The Diels-Alder reaction is stereospecific with respect to both the diene and the dienophile. A cis-dienophile gives cis-substituents in the product and a trans-dienophile gives trans-substituents. If the diene substituents have the same stereochemistry, the diene substituents would be on the same face of the product. If the diene substituents have opposite stereochemistry, the diene substituents would be on opposite faces of the product. The limiting reagent in the case of the experiment was the maleic anhydride. The

In order for a substance to be pure, its melting point, from start to finish, must stay within 3 oC or 4 oC because more pure organic substances melt within the range of 1 oC – 2 oC. (Craine et al., 2012) The range of the crude was 5.3 oC, a clear indication of impurity. In addition, it was well below the literature melting point of 9,10-dihydroanthracene-9,10-α,β-succinic anhydride at 262 oC – 264 oC, which was another indication of impurity. However, the pure product had a melting point of 260.3 oC – 263.9 oC, which was much closer to the melting point of the pure product and stays within the range of 3 oC – 4 oC, which could indicate that there was still a small amount of impurity, but the product attained was close to a pure