Benzil Synthesis:

The objective of this experiment was to synthesize benzil from benzoin via copper acetate oxidation. In
order to determine the purity of the compound, the molar mass of the compound was found using mass
spectrometry, gas chromatography, IR spectroscopy.

In order to determine the amount of product synthesized in the reaction we must perform the following
limiting reagent calculation:
𝑚
𝑛 = 𝑀 , where n represents the number of moles of the compound, m the sample mass and M the molar
mass of the product.
0.3171𝑔
Using the above formula we can calculate that nbenzoin 212.2𝑔 = 0.00015𝑚𝑜𝑙.

3.76𝑔
nCopper acetate= 181.63𝑔 = 0.021𝑚𝑜𝑙.

We see from the above calculations that the benzoin is the limiting reagent. The moles of benzil formed
is the same as the number of moles of benzoin due to the nature of the oxidation reaction.

In order to see the efficiency of the reaction we can use the percentage yield of the experiment. The
theoretical yield of the experiment is 0.00015mol of benzil which is 0.314g. The experimental yield of
the experiment is 0.1781g. We can find the percentage yield of the experiment using the formula:
𝑒𝑥𝑝𝑒𝑟𝑖𝑚𝑒𝑛𝑡𝑎𝑙 𝑦𝑖𝑒𝑙𝑑 0.1781
% 𝑦𝑖𝑒𝑙𝑑 = 𝑡ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
× 100 = 0.314
× 100 = 57%. As we can see the experiment is successful
in producing 60% of pure product. In order to time the reaction, samples of the reaction intervals were
taken and spotted on a TLC plate. 5 samples were taken, one at the start of the experiment and the
next four were taken at 10 minute intervals and were spotted against samples of the reactant benzoin
and the product benzil.

Spot Rf of spot 1 Rf of spot 2

1 0.367347 0.673469
2 0.387755 0.714286
3 0.367347 0.734694
4 0.346939 0.755102
5 0.408163 0.77551
benzoin 0.204082 0.653061
benzil 0.367347 0.673469

The Rf is calculated by dividing the distance travelled by the spotted compound by the distance travelled
by the solvent.
As we can see all the spots taken from the reaction mixture had two spots with one corresponding to
the benzoin remaining and the benzil being created. What we cannot see from the quantitative data is
the progression of the reaction, but by observing the size of the spots on the TLC plate, we can see that
as the reaction progresses, the top-most spot begins to grow in size while the lower spot decreases in
size due to the fall in concentration of the reactants as the reaction progresses. We see that the reagent
has a lower Rf than the product indicating that the product is less polar than the reactant. This is due to
the alcohol having the ability to form hydrogen bonds with electronegative atoms in the surrounding
environment while the ketone is only capable of interacting via dipole interactions.

In order to assess the purity of the product made in the lab, the sample was tested using IR spectroscopy
and GC/MS. If we observe the IR spectrum of the product obtained in the experiment we see a group of
peaks after 1700 wavenumber corresponding to the bonds present in the benzene rings. There is no
peak in the 3300-3600 range that is a broad u shaped peak therefore we can safely assume that the
compound synthesized in the reaction has no hydroxyl groups. The GC data contains only one peak in
indicating that the sample used is very pure. The mass spectrometry data shows that the mass
spectrometry data corresponds greatest with 2-chloroacetophenone at 80% and the desired product
diphenyl-ethanedione at 78%. In conclusion, we can say that the reaction is successful in synthesizing a
pure product with a yield of 60% and the purity of the product is verified using the IR and GC/MS of the
product.