Tetraphenylcyclopentadienone
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Tetraphenylcyclopentadienone Abstract: The purpose of this lab is to perform an Aldol Condensation reaction where Benzil reacts with dibenzyl to deprotonate it and produce tetraphenylcyclopentadienone. To begin this lab, Benzil and diphenylacetone are combined with the addition of a catalyst, Ethanolic KOH, to quickly complete the reaction. The solvents are mixed on a hot plate for 15 min which creates a reflux helping the solution mix evenly and gently. After the reflux, the solution was washed down with 95% cold ethanol were the crystals would get collected using vacuum filtration twice.
Finally, the collected crystals would be left to dry until the next day. The dried crystals were then
weighed for their mass, and used to determine its melting point and percent yield. Any sources of
error are not drying the product well or contamination of the product. Overall, the product of tetraphenylcyclopentadienone was achieved for this lab period. Chemical Mechanism Figure 1: Mechanism for Wittig reaction
Property Table: Compounds Melting Point Boiling
Point Density Compound Structure Molecular Weight Benzil 94.8
o
C
346
o
C
1.2 g/cm
3
180.4g/mol
Ethanolic
KOH
-114.1
o
C
78.37
o
C
1.02g/cm
3
68.05g/mol
Absolute
ethanol -114.1
o
C
78.37
o
C
789kg/m
3
46.07g/mol
Dibenzyl
Ketone
(diphenylaceto
ne)
32-34
o
C
330
o
C
1.07g/cm
3
210.28 g/mol
Tetraphenyl
Cyclopenta
dienone
219-220
o
C
617
o
C
1.2g/cm
3
384.48g/mol
Procedure: For this lab, 0.1066g of Benzil and 0.1021g diphenyl acetone are dissolved with 1ml of absolute ethanol in a 3ml reaction vial. A magnetic spin vane is added to the vial were the solution is mixed over the hot plate just before it reaches boiling point. Then, 0.20ml of Ethanolic KOH is added using a Pasteur pipet through the condenser in which the reaction will take place to achieve the product. When the product is made, the solution should change to a purple color in which the temperature of the hot plate can be increased to produce a reflux. The reflux will take around 15min. After the time is done, the vial is placed in ice bath were crystals form. The crystalized solution is then collected using vacuum filtration using 95% ethanol get all
the crystals out of the vial. The crystals are recollected with 95% ethanol to wash them. Add the finalized crystals into a vial to dry overnight. Then weigh the product to collect the mass and test
for melting point and percent yield. Data: Table 1: Number of measured compounds used and final mass results with percent yield Mass of Benzil
0.1066g Mass of diphenylacetone
0.1021g
Melting Point 220.5-221.3
o
C
Experimental mass of product 0.1895g
Theoretical mass of product 0.1866
Percent Yield
98%
Calculations: .1021
g
210.28
g
/
mol
=
4.85
mol
4.85
mol x
384.48
g
mol
=
.1866
theoretical massof product
%
yieldof product
=
Experiment mass of product
Theoretical Mass
x
100
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0.1895
g
0.1866
g
=
0.544
x
100%
=
101.5%
yield of product
Atomeconomy
=
Mass of atoms
∈
desired product
Massof atoms
∈
reactants
=
¿
384.48
(
210.28
+
180.4
)
=
98%
atomeconomy
Discussion: This experiment focused on conducting an Aldol Condensation Reaction between Benzil and diphenylacetone to produce the molecule tetraphenylcyclopentadienone. To speed up the reaction between the two, the catalyst Ethanolic KOH was also used in this experiment. The reflux induced for the mixture allowed the mixture to properly mix in order to set it aside for crystallization. The crystallized solution created was then collected using vacuum filtration to then let the crystals dry overnight. The product was weighed giving a mass of 0.1895g and the melting point was seen at 220.5-221.3C. The melting point showed accuracy as the theoretical melting point of tetraphenylcyclopentadienone is between 219-220. Using the mass of the product, the percent yield was calculated at a 101.5% while the atom economy was at a 98%. The percent yield was higher than 100% because of impurities in the product or not dried enough. Any sources of error are not drying the product well or contamination of the product. Overall, the product of tetraphenylcyclopentadienone was achieved for this lab period.
Conclusion: In conclusion, the process of Aldol Condensation was efficient to produce the product tetraphenylcyclopentadienone with Benzil and Dibenzyl. The melting point of the product was very similar to the theoretical melting point of the product which indicates a good outcome for the experiment. On top of that the percent yield equaled higher than 100% with a high atom economy proving again the successful product collection when performing this experiment due to complete product collection. Any sources of error this experiment can be too low heat to the mixture causing no reflux or the product was not properly dried enough. Reference: 1.
Katz/Schwartz pp. 201-204 Organic Chemistry
, Laboratory Manual, Fourth Edition.
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