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Mechanism
Calculations
Sample weight = (Vial weight with sample) – (Weight of empty vial) = 9.294 g - 9.028g = 0.098g
Percent yield = (sample weight/ Theoretical yield) * 100 = (0.098 / 0.14) *100 = 40.16%
Discussion
The goal of this lab was to teach us the Diel-Alder by carrying out the final step of the reaction. This
experiment silicone oil was used as a solvent for diphenylacetylene as dienophile to react it with
tetraphenyl cyclopentadienone to get hexaphenylbenzene.
The yield of this experiment was 70%. There are several ways that the yield could have been improved.
Product could have been lost during the Hirsch filtration step; to avoid this, it’s important to ensure that
the right filter paper is used and its pre wetted before pouring the product on to it, enough hexane and ice
cold water wasn’t added to sperate out the final product. The glass rod used to break the product should
have been rinsed to recover as much product as possible. Other sources of error include not boiling and
cooling the solution long enough. The final product was a tan color.