Kaitlyn Tom AH

3-Step Synthesis Lab

Discussion:
In step 1 of this 3-step synthesis, I made benzil by oxidizing benzoin with nitric acid. Progression of
the reaction was monitored using TLC. After crystallization in an ice bath followed by vacuum
filtration, a melting point of the crude product was taken to determine its purity. The products
melting point, 64.4-71.0 C, was wide-ranging and depressed. The crude product was then
recrystallized with 95% ethanol. The melting point of the purified product, 86-91.9 C, was much
closer to the literature value of benzil (94.4-95.1 C). Few crystals were recovered however,
resulting in a low yield of 18.17%.
In step 2, I prepared tetraphenylcyclopentadienone from the aldol reaction of benzil (step1) and
dibenzylketone. Due to my low yield from day 1, I supplemented my product with additional
prepared benzil to make 0.1 g. After heating and refluxing the reaction, crystallization and filtration
were performed to isolate the crude product. The crude melting point, 213.6-215 C, was slightly
depressed. After recrystallization with 95% ethanol and toluene, a melting point of the purified
product was taken and determined to be 218.6-219 C. This value is sharp, narrow, and very close to
the expected melting point of tetraphenylcyclopentadienone (219-220 C). My % recovery was
determined to be 25.16%.
In the last step, I synthesized tetraphenylnaphthalene from the diels-alder reaction of
tetraphenylcyclopentadienone (day 2) and benzyne. Due to my low yield from day 2, I
supplemented my product with additional prepared tetraphenylcyclopentadienone to make 0.1 g
After heating and refluxing the reaction, I noticed a color change from deep purple to orange
(signifying completion of the reaction). The melting point of the crude product (crystallized and
filtered) was revealed to be 199.6-201.5 C, which, compared to tetraphenylnaphthalenes expected
melting point value of 199-201 C, is sharp, narrow, and nearly identical. My calculated % recovery
was 47.11%.
Conclusion:
Despite my low % yields, the overall reaction was a success. The expected color changes were
observed, and the relative sharpness and proximity of my melting points to the literature values of
the expected products indicated few impurities were present and that benzil,
tetraphenylcyclopentadienone, and tetraphenylnaphthalene were produced (respectively). The one
exception was the depressed and wide-ranging melting point of my crude benzil product from step
1, which indicated that impurities remained. Recrystallization, however, successfully removed these
impurities (thus explaining the sharper melting point of the purified product). In step 1, my low
yield may have resulted from removing the reaction mixture from the heat prematurely (before all
of the red gases disappeared). This would have resulted in lesser product being formed. In step 2,
my low yield may have been due to dissolving my product in too much solvent (this would have
resulted in more product staying in solution) and secondly, some of my solid escaping the filter
paper and ending up in the bottom of the filter flask. My low yield from step 3 may have resulted
from the loss of product in the transfer from the funnel to the watch glass. In the future, I can
improve my recrystallization technique and chances of % recovery by using a minimum amount of
solvent, waiting until the entire reaction has run to completion, and transferring product carefully to
minimize loss.