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Organic Chemistry 3 (CHEM 22200) Hexaphenylbenzene Lab Report-2

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Sandra Watson
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University of Chicago

Organic Chemistry 3 (CHEM 22200)

Synthesis of Hexaphenylbenzene
Purpose: The purpose of this experiment is to understand and perform a multistep parallel
synthesis of hexaphenylbenzene

1. Yield of Multistep Synthesis:
Synthesis of meso-dibromostilbene:
1.0 g trans-stilbene (5.55E-3 mol) used with 2.0 g pyridinium tribromide (6.25E-3 mol); thus,
trans-stilbene is expected to be limiting reagent. By stoichiometry, we would have a theoretical
yield of 1.89 g meso-dibromostilbene. We obtained 1.79 g meso-stilbene, thus there was a very
high yield of 94.7%.

2. We have two reactants in the final synthesis of hexaphenylbenzene: one is diphenylacetylene
and the other is tetraphenylcyclopentadienone. We conducted a parallel synthesis of both of
these reagents. The synthesis of diphenylacetylene had an overall yield of 94.7% x 47.0%, or
44.5%. The synthesis of tetraphenylcyclopentadienone had an overall yield of 38.0%. Thus, we
will use the lower of these two percents, 38.0% in calculating our overall yield for the synthesis
of hexaphenylbenzene.

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Organic Chemistry 3 (CHEM 22200) Hexaphenylbenzene Lab Report-2

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