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IR ANALYSIS FOR MULTI-STEP SYNTHESIS

Functional Group Group Name Signal Position (


R-C=O-R ketone ~1694.34

phenyl ~1592.65
C-H Alkanes/IR card ~2915.43 and ~2850.50
Benzil


Functional Group Group Name Signal Position
(


R-C=O-R ketone ~1701.67

phenyl ~1463.79
C-H Alkanes/IR card ~2915.50 and ~2850.67

Tetraphenylcyclopentadienone



Functional Group Group Name Signal Position
(


-OH alcohol ~3415.68 and ~3377.53
R-C=O-R ketone ~1699.89

phenyl ~1595.63
C-H Alkanes/IR card ~2915.02 and ~2849.19

Benzoin

One of the possible reasons why benzil was not obtained
from the oxidation of benzoin is probably because maybe not
all the N
2
O gas fumes are removed or maybe because it needed
more time (more than 30 minutes) for all the fumes to be
removed on the reaction mixture because the desired product
wont be obtained if the oxidation process is not done.

First Reaction:




Second Reaction:





Benzoin
Obtained m.p: 137C
Lit. value: 132-137 C
% error from m.p: 1.86%
Obtained yied: 92 mg
Theoretical yield: 1.558 g
% yield: 5.905%

Benzil
Obtained m.p: 90-94 C
Lit. value: 94-97 C
% error from m.p: 3.16 %
Obtained yied: None (from 1
st
reaction)
93 mg (from ready-made)
Theoretical yield: 91 mg (from the supposed 1
st
reaction)
% yield: 0%


Final Reaction:




























Tetraphenylcyclopentadienone
Obtained m.p: 120 C
Lit. value: 117-120 C
% error from m.p: 0.7 %
Obtained yied: 102 mg
Theoretical yield: 165 mg
% yield: 61.81 %


Multistep Synthesis of 2,3,4,5-Tetraphenylcyclopentadienone
The multistep synthesis of 2,3,4,5-tetraphenylcyclopentadienone is divided into three
consecutive steps. The first step is to run a benzoin condensation using two equivalents of
benzaldehyde and thiamine as the catalyst of the reaction. Since benzaldehyde does not have any
-hydrogen to undergo aldol condensation, benzoin condensation takes place since the term
'condensation' means that two molecules are being combined together to form a larger molecule.
The next step is oxidizing benzil from benzoin using nitric acid as the oxidizing agent. In the
oxidation reaction, the alcohol function of the benzoin is then oxidized to form the carbonyl
function while the nitric acid is reduced into complex mixture of nitrogen oxides in the form of
toxic brown fumes that will be formed in the condenser. The third step of the reaction is
performing a double aldol condensation; which is accompanied by dehydration, due to the highly
conjugated molecule that is formed. This then leads to the formation of
tetraphenylcyclopentadienone as the final product.
On the first workup procedure, ice bath was used on the crystallization of benzoin from
benzaldehyde to finish the crystallization process and isolate the pure crystal after it was cooled
at room temperature. The product was filtered thrice using 2 mL of ice-cold 50% EtOH/
2
O to
remove the unreacted benzaldehyde. It was then recrystallized using 95% EtOH in order to
increase the purity of the crude benzoin. The second workup procedure was performed after the
oxidation of benzoin to benzil using nitric acid. After the mixture was cooled at rm. temperature,
~3 mL of water was added to the product and was rinsed using additional water. The reason why
water was used, is to replace the COH into C=O group. The reaction was then stirred vigorously
using glass rod in order for the oily benzene to form and crystallize as yellow solid. Cold water
was also used in order to remove the nitric acid. The third workup procedure was performed after
the synthesis of tetraphenylcyclopentadienone from benzil and diphenylacetone. The reaction
mixture that contained the final product was first cooled at room temperature to settle the
crystals. Ice bath was then used to finish the crystallization process and separate the crystals from
the other components of the mixture. The crystals were filtered and washed thrice using 0.5 mL
of 95% EtOH to purify the final product. It was also recommended that if the product was not as
pure, recrystallization using 1:1 mixture of absolute ethanol and toluene is recommended.
The first reaction performed which is the condensation of benzoin from benzaldehyde
using thiamine as the base catalyst turned out to be effective because the desired compound was
obtained, the obtained m.p is quite close to the lit. value, and the IR spectra of the product
suggests that all the important functional groups were determined. The second reaction
performed which is the oxidation of benzil from benzoin, didnt turn out to be as effective
because there wasnt enough product obtained from the reaction. It is vague whether the
oxidation process was successful because even though nitric oxide fumes were no longer visible,
it is still hard to tell if all the nitric acid on the mixture was removed after washing it with cold
water. The last reaction which is the double aldol condensation using benzil and diphenylacetone
turned out to be very effective because the desired compound was obtained, the obtained m.p is
close to the lit. value, and the IR spectrum identifies all the important functional groups.
The first intermediate product, benzoin, was successfully synthesized because the
obtained m.p (137C) is close to the range of the lit.value (132-137C), and all the important
functional groups were identified using its IR spectra. The second intermediate product which is
the benzil, was not obtained from the oxidation reaction due to some experimental errors that
might have been committed while performing the reaction. In order to compensate for the benzil,
a ready-made benzil was used to finish the reaction. The benzils obtained m.p (90-94C) is close
to range of the lit. value (94-96C) which may corresponds to slight impurity, and all the
important functional groups were also determined using IR. The final product was also
successfully performed because the desired product after performing the aldol condensation was
synthesized; the m.p (120 C) was very close to range of the lit. value (117-120C), and all the
important functional groups were also obtained using IR.

References
Bruice, P. Organic Chemistry, 7
th
ed.; Pearson: New Jersey, 2013.
Padias, A. Making The Connections, 2nd ed.; Hayden-McNeil Publishing: Plymouth, MI, 2013.
Padias, A. Organic Chemistry Laboratory Manual, 4th ed.; Hayden-McNeil Publishing:
Plymouth, MI, 2013.