Jiara Laine Montano

November 10 2016

Chem 26AA

November 17 2016
Experiment no. 9: Cannizzaro Reaction

Data and Results

Mass of Beaker
& Funnel (g)

Mass with
Product (g)

Benzoic
132.98
134.60
Acid
Benzyl
7.39
8.08
Alcohol
Table 1 Percent Recovery of Products

Mass of
Product (g)

Theoretical
Yield (g)

Percent
Yield (%)

1.62

3.0

54.0%

0.69

2.7

25.6%

Melting Point Start Temperature

Melting Point Stop Temperature
o
Trial 1
122.3 C
123.3 oC
Trial 2
122.3 oC
123.5 oC
Trial 3
122.5 oC
124.0 oC
o
Mean
122.4 C
123.6 oC
Table 2 Melting Point Range of Recrystallized Benzoic Acid
Discussion
The Cannizzaro Reaction is a redox disproportionation of aldehydes to carboxylic acids and
alcohols in the presence of a strong base. In this reaction, the nucleophilic addition of the
hydroxide ion to the aldehyde yields a tetrahedral intermediate. This intermediate expels the
hydride ion as a leaving group and is oxidized to yield a carboxylic acid salt. The other
aldehyde molecule accepts the expelled hydride ion and is reduced into an alcohol. However,
even under ideal conditions the Cannizzaro reaction usually produces low yields. To avoid
low yields, one usually conducts a crossed Cannizzaro reaction, in which a sacrificial
aldehyde (i.e. formaldehyde) is used in combination with another aldehyde (i.e.
benzaldehyde). In this reaction, formaldehyde will act as a reducing agent and will be
oxidized to sodium formate while the benzaldehyde will be reduced benzyl alcohol.
In this experiment, the Cannizzaro reaction was carried out with benzaldehyde and sodium
hydroxide to yield sodium benzoate (later protonated and isolated in the form of benzoic
acid) and benzyl alcohol. Benzaldehyde and sodium hydroxide was first mixed and shaken
until an emulsion was formed. It was then dissolved with water and washed with water
then hexane. Since the reaction was done in a basic environment, the other product of
the reaction is not benzoic acid but sodium benzoate instead. Since sodium benzoate is a
charged molecule it is best solvated by polar solvents. Thus sodium benzoate ended up
in the aqueous layer. Since benzyl alcohol is relatively non-polar (since the benzene ring
has no dipole and is the largest constituent of the molecule) and has a high pKa, it will
not be deprotonated by the sodium hydroxide and will be more soluble in the nonpolar
hexane. Thus the addition of hexane separated the two products using liquid-liquid
extraction.
The organic layer was then washed to remove excess benzaldehyde and dried to remove
excess water. The product was then distilled to hexane present in the organic layer. On the
other hand, hydrochloric acid was added into the aqueous layer to protonate sodium
benzoate into benzoic acid. The presence of benzoic acid was indicated by the white

precipitate produced during the addition of hydrochloric acid. After a while of adding
hydrochloric acid, there was no longer any white precipitate formed. This indicates that
there was no longer any sodium benzoate to be protonated. However, there is also a
chance that an excess addition of hydrochloric acid formed sodium chloride instead of
benzoic acid, thus recrystallization was done to obtain a purer product.
The white benzoic acid crystals collected weighed 1.62 grams yielding a percent yield of
54.0% while the aqueous benzyl alcohol collected was 0.69 grams and yielding a percent
yield of 25.6%. To test for the purity of the products qualitative tests were used. To test for
the relative of benzoic acid a melting point test was done. Through the test it was determined
that the mean melting point range of the benzoic acid collected was 122.4123.6 oC which is
well within the literature values for the melting point of benzoic acid which is 121-125 oC.
Thus it can be said that the benzoic acid produced is relatively pure. In contrast, qualitative
tests on the benzyl alcohol was not accomplished due to the lack of qualitative test reagents.
However, in the msds of benzyl alcohol it should be a clear colorless to white liquid but the
benzyl alcohol yielded had a bright yellow color. This means that further purification of this
product was needed.
Conclusion
Through the procedures illustrated in the experiment, approximately 1.62 grams of benzoic
acid while 0.69 grams of benzyl alcohol was obtained. The recrystallized benzoic acid was
then determined to have a melting point range of approximately 122.4 oC 123.6 oC which is
well within the literature value of 121 oC 123 oC. The benzyl alcohol produced had a yellow
color which deviated from its MSDS physical characteristics. This indicates that this product
was not as pure as it should be.
As the melting point of benzoic acid and the theoretical yield of both products has been
obtained it can be said that the objectives of the experiment has been met. However,
although, benzyl alcohol had a maximum theoretical yield of ~98.5%, there was only a 25.6%
yield. This discrepancy has been attributed to several experimental errors executed during the
experiment. It is recommended that to replicate better results the mixture of NaOH and
Benzaldehyde be shaken more vigorously and regulated. Furthermore, movements should be
more standardized and cautious especially during the suction filtration and decantation to
avoid any spillages that may have contributed to a lower turnout percentage.
References
McMurry, John. Organic Chemistry: 5th Edition. USA: Brooks/Cole, 2000.
W. C. Wilson (1941). 2-Furancarboxylic Acid and 2-Furylcarbinol. Org. Synth.; Coll.
Vol., 1, p. 276
Appendix
1. Mass of Product
mass of beaker andfunel :132.98 g
mass of benzoic acid , beaker funnel :134.08 g

mass of acetanilide=134.6 0 g132.98 g

1.6 2 g

2. Theoretical Yield
Benzoic Acid :
5.3 grams C 6 H 5 CHO

1 mol C 6 H 5 CHO 1 mol C 6 H 5 COONa 1 mol C 6 H 5 COOH 122.12 gram

106.13 grams
2 mol C 6 H 5 CHO
1 mol C 6 H 5 COONa
1mol C

Benzyl Alcohol:

5.3 grams C 6 H 5 CHO

1 mol C 6 H 5 CHO 1 mol C 6 H 5 CH 2 OH 108.14 g 1 mol C 6 H 5 CH 2 OH

=2.
106.13 grams
2mol C 6 H 5 CHO
1 mol C6 H 5 CH 2 OH

3. Percent Yield
Benzoic Acid :
1.6 2 grams
100=54.0
3.0 grams
Benzyl Alcohol:

0.69 grams
100=25.556 =25.6
2.7 grams
4. Mean Starting/ Final Temperature
start temperature , trial one :122.3
start temperature , trialtwo :122.3

start temperature , trialthree :122.5

mean=

122.3 +122.3 +122.5

3

122.3667=122.4

Figure 1 Benzoic Acid Crystals

Figure 2 Benzyl Alcohol