Dicyclopentadiene

The Diels-Alder product obtained in this experiment had a measured melting point of 154°C, which has a discrepancy of 11degrees from the literature value of 165°C. These values show an experimental flaw in the process of drying the solid product obtained from the vacuum filtration portion of the method of experimentation. Because the product was not fully dry during the melting point portion of the experiment, the melting point results were skewed. The reactants and solvents in the reaction each have significantly lower melting points than the product. Specifically, cold petroleum ether was used to wash the crystals in the drying portion of the experiment. Petroleum ether has a melting point of ~-73.0°C.9 It is possible the product was not dried thoroughly via vacuum filtration and
This is a significantly lower yield than was expected. The major experimental flaw in the drying of the product may have been a contributor to this lower percentage yield because the product was still wet and contained impurities. It is also possible crystals were brought into the pipette in error and discarded. The dimerization of cyclopentadiene is the side reaction because this compound is both a diene and a dienophile capable of reacting with itself which is evidenced by the product of such reaction, dicyclopentadiene, which was used in the fractional distillation portion of the experiment to obtain cyclopentadiene. Thus, the purpose of the fractional distillation in this experiment was to prevent the side reaction from occurring by cracking this compound into its monomer cyclopentadiene.10 The desired product was procured as evidenced by the completion of the reaction into crystal product and the melting point of the product being in a wide range of the literature value. The reaction was decidedly inefficient as the low percent yield supported the fact that product was either lost or not