Renita Alexander

Hughes- WED PM
Oxidation Lab
Results:
Figure 1 is the IR spectrum of unknown As product. Figure 2 is
the MS of unknown As product. Figure 3 is the experimental 1H NMR of
unknown As product. Figure 4 is the predicted 1H NMR of benzoic acid.
Figure 5 is the

13

C NMR of unknown As product.

Discussion:
The goal of this weeks lab was to oxidize an unknown aldehyde
into a carboxylic acid, using a microwave. The unknown used was
unknown A. In Figure 1, there is a C-H sp2 hybridized peak at 3050 cm1

, a C-H sp3 peak at 2825 cm-1, an RCO-OH peak at 2552 ppm,

aromatic overtones from 2000-1800 cm-1, a C=O peak at 1679 cm-1,

and a monosubstituted benzene hydrogen bending at 700 cm-1. In
Figure 2, the parent ion is 122 M/Z; this corresponds to the molecular
weight of benzoic acid, which could be the identity of unknown As
product. In Figure 2 there were three significant fragment peaks; a
monosubstituted benzene peak at 77 M/Z, a carbonyl group from 77
M/Z to 105 M/Z, and an OH peak from 105 M/Z to 122 M/Z. Figure 3 has
3 total peaks that are in the aromatic region. In Figure 3, peak A has a
doublet of triplets at 8.12 ppm, with an integration of 1.90 and J values
of 8.5 and 1.5 Hz. This peak represents two hydrogens that have 1
ortho and 2 meta coupling hydrogens. Peak B has a triplet of triplets at
7.62 ppm, with an integration of 1.00 and J values of 8.7, 6.9, 1.4 Hz.
This peak represents 1 hydrogen, with 2 ortho neighbors and 2 meta

Renita Alexander
Hughes- WED PM
Oxidation Lab
neighbors as well. Peak C has a broad triplet at 7.48 ppm, with an
integration of 2.09 and J values of 7.9, 7.5, 1.7 Hz. This peak
represents 2 hydrogens, with 2 ortho neighbors and 1 meta neighbor.
Figure 4 also has 3 peaks that are in the aromatic region. Peak A is a
doublet of triplets that represents 2 hydrogens, peak B is also a triplet
of doublet doublets that represents 1 H, and peak C is a broad triplets
that represents 2 hydrogens. Figure 5 has a total of 5 peaks. Because
of the similarities between Figure 3 and Figure 4, and the IR and MS
data, this means the product of unknown A was benzoic acid. This
would make unknown A benzaldehyde. Figure 5 is the

13

C NMR of

unknown As product, and Figure 5 has a total of 5 peaks. Peak A is at

172.6 ppm and is the carbonyl carbon of the compound, peak B is at
133.8 ppm and is attached to carbon A, peak C is at 130.2 ppm and
represents the two carbons attached to carbon B, peak D is at 129.3
ppm and also represents 2 carbons that are meta to carbon B, peak E
is at 126.4 ppm and is the carbon para to carboxylic acid group. Figure
5 further solidifies that the product is benzoic acid. Since the product is
benzoic acid, unknown A is benzaldehyde.
The melting point of the product was 115.4-118.0 oC. This
melting point is lower than the melting point for benzoic acid, which is
121-125 oC. Because the experimental melting point of the product is
lower than the literature value, there were impurities in the product
sample that had not been removed during recrystallization. The

Renita Alexander
Hughes- WED PM
Oxidation Lab
impurity could have been from the presence of the starting material,
benzaldehyde, which has a very low melting point of -26 oC. This could
have caused a lower melting point, and an impure product sample. The
crude % yield was 78.6&. The % yield of this reaction is 21.7%. There
was a huge difference between the crude yield and the % yield due to
inefficient recrystallization. The % yield was so low, because while
cooling the microwave reaction tube on ice, some of the mixture spilled
into the fume hood. In order to increase % yield and improve this
experiment, the spilled mixture would have to be added back into the
reaction vessel.