Synthesis Of Hexaphenylcyclopentadienone

Objective
The objective of this experiment is to produce a sample of hexaphenylbenzene from the Diels-Alder addition of tetraphenylcyclopentadienone and diphenylacetylene, both of which were synthesized from previous lab procedures.

Procedure Part A- Preparation of Hexaphenylbenzene
• In a 25 mL round-bottom flask, 0.50 g (0.0013 mol) of tetraphenylcyclopentadienone and 0.50 g (0.0028 mol) of diphenylacetylene were poured, and with a heating mantle and a ring stand, the flask was vigorously heated. This heating was performed for a continuous 20 minutes in order to allow the reaction to occur thoroughly, which required a large amount of energy, and the melting solids were stirred from time to time with a spatula. It was observed that the solids melted into a purple liquid, which at around 10-12 minutes, turned into a distinct brown color. After the allotted time, 10 mL

Afterwards, the mixture was allowed to cool to room temperature, at which point an additional 15 mL of “hexanes” were added, and the flask was placed in an ice bath. After allowing the flask to cool to room temperature, a layer of light brown crystals was observed at the bottom of the flask. These crystals were collected with a vacuum filtration setup (which was created from a Buchner funnel and Buchner flask, which was attached with a hose to a vacuum), and were further washed with about 10-15 mL of diphenyl ether. After collecting, washing, and allowing the crystals to dry, a yield of 0.25 g of a whitish powder was recorded, presumably hexaphenylbenzene. The product was disposed of, as this