Exp 3 Otww

ABSTRACT
AIM
The objective of this lab was to successfully oxidize benzoin through the reaction with nitric acid
which should synthesize the compound benzil.
INTRODUCTION
Benzoin can be oxidized to the a-diketone benzil very efficiently by nitric acid or by copper(II)
sulfate in pyridine. On oxidation with sodium dichromate in acetic acid, the yield is lower
because some material is converted into benzaldehyde by cleavage of the bond between two
oxidized carbon atoms that is activated by both phenyl groups . Similarly, hydrobenzoin on
oxidation with dichromate or perrrnanganate yields chiefly benzaldehyde and only a trace of
benzil . The oxidation reaction also releases a concerning amount of nitrogen dioxide, so be
careful to make sure all fumes are taken up by the fume hood. Ultraviolet spectroscopy is used
to help characterize aromatic molecules such as benzoin. The absorption band at 247 nm in the
UV spectra is attributable to the presence of the phenyl ketone group C6H5-C=O, in which the
carbonyl group is conjugated with the benzene ring. Aliphatic a,b-unsaturated ketones,
RCH=CH-C=O, show selective absorption of ultraviolet light of comparable wavelength. The IR
spectrum of benzoin shows a peak at 1664 cm-1 for the conjugated carbonyl. Benzil is used as a
pharmaceutical intermediate and uv curing resin photosensitizer. In polymer chemistry, it is
used as a photoinitiator. Further, it serves as a potent inhibitor of human carboxylesterases. It is
used in the preparation of diketimines by reacting with amines.
REACTION SCHEM:
PROCEDURE
2.00g of benzoin and 7.5ml of concentrated nitric acid were placed in a 50ml round bottomed
flask in a fume hood. Boiling chips were added before attaching the condenser fitted with T-
tube and gas trap to remove any vapours generated from nitric acid. The contents of round
bottomed were then heated at reflux for 30 minutes. The mixture was then allowed to cool
before being poured into 40ml of water. The suspension was swirled for few minutes and then
the product was collected by means of suction filtration. The yellow solid was washed with
water on the buchner funnel before the product was air dried for a few minutes. The still moist
product was then recrystallized by dissolving the product in 5ml hot ethanol and then water
was added dropwise until the solution became turbid. This hot solution was then clarified with
two drops of hot ethanol. After allowed to cool, the product was collected by suction filtration,
its colour was noted and the yield was recorded together with melting point of the product. The
TLC on silica gel using toluene was then carried to determine the purity of the product by
means of Rf value. This was done by marking two lines (1cm from both ends) with a pencil on
TLC plate and the dissolving small amount of the product in ethanol. The capillary tube was
used to place the dissolved product in ethanol on the TLC plate which was then inserted in the
TLC bank after the saturation was observed using filter paper. The spot on the TLC plate was
circled with a pencil.
RESULTS
Table 1: The preparation of Benzil
Mass of Benzoin 2.00g

Vol of nitric acid 7.5ml
Mass of the petri-dish + filter paper 48.98g
Mass of the petri-dish + filter paper + mass of 51.42g
the product
mass of the product 2.44g
Colour of the product yellow
Melting point of the product
DISCUSSION
mechanism:
4ml of ice-cold water is added in procedure because water is needed to wash away the
Remaining acid that is still in the solid product, it is ice cold because it is an exothermic reaction
and nitric acid with water will generate heat so ice cold water will help keep it in control.
Improvement to this may be increasing reaction time would have given a better result, drying
the product over a longer period of time, while transferring solid to the funnel by make sure to
wash the funnel. Compared to literature value of 94.8°C, the results obtained was 72.0°C-
78.2°C. Benzil is used as a pharmaceutical intermediate, insecticide and curing agent. They are
also used in the free radical curing of polymer networks. Benzil mechanism is formed from
Benzoin oxidation with molecular weight of 212.24g/mol to form benzil and oxidation of
asecondary alcohol with ketone
CONCLUSION
Benzil was synthesized from the oxidation of Benzoin with Nitric Acid. The crude product was
purified via recrystallization. The product was obtained as a pale yellow crystalline solid, in high
yield. Spectrum and melting point data showed close correspondence with literature values,
ascertaining the formation and purity of the product. Experiment was successful. Benzil was
synthesized in high yield by the procedure described in this experiment. The product was
successfully characterized using the melting point and IR data, sharp range of melting point
displayed its purity.

Exp 3 Otww

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ABSTRACT

Table 1: The preparation of Benzil

Mass of Benzoin 2.00g

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