Anthracene Report

The experiment consisted of a Diels Alder reaction between anthracene and maleic anhydride to produce 9,10-dihydroanthracene-9,10-α,β-succinic anhydride. This is called a cycloaddition reaction because the reaction between the two products creates a cyclic product. The conjugated diene (called diene) was anthracene (consisted of 2 double bonds) and the dienopile was maleic anhydride (consisted of 1 double bond). The reaction occured between the alkene group of maleic anhydride and the alkene group of anthracene. The reaction is:

Source: Melvil, 2014.

The solvent used was xylene (dimethyl benzene) and the reactants were boiled in it. Since the boiling point for xylene is high, it assisted in the reaction proceeding rapidly. For the

After recrystallization and purification, the percent yield was 63.620% (0.724 grams) and the melting point was 262-263°C (see Table 1). The literature melting is 262-264°C. The low percent yield could be due to lack of recrystallization of the crude product. In addition, some of the crystals may not have been transferred to the funnel from the flask. The IR analysis indicated a distinctive peak at 1778.43 representing ketone, and another peak at 1226.73 representing ether. The peak at 1400-1600 was indicative of either a ring structure or an alkene group. The reactants were dissolved in xylene since they have more solubility compared to the product which undergoes crystallization. Thereafter the mixture was refluxed to maintain constancy in temperature and ensure mixing. Since xylene has a high boiling point of 140 °C, the reaction proceeded speedily. Crystallization of the product took place as the mixture underwent cooling. Filtration was used to isolate the product. The tests with regards to the melting point and spectra led to the determination that 9,10-dihydroanthracene-9,10-α,β-succinic anhydride was produced. The Diels Alder reaction is a high yield reaction and can be used to form as many as 4 carbons. It has wide applications in the industry because it is considered a very effective synthesis