Abstract

Aim

This experiment aims to use the cannizzaro reaction to create benzoic acid and benzyl alcohol
from benzaldehyde.

Introduction

In the cannizzaro reaction, two molecules of a non-enolizable aldehyde are disproportionated by

a base, resulting in the formation of a primary alcohol on a carboxylic acid. The procedure is a
redox reaction in which one substrate molecule transfers a hydride to the other. Oxic alcohol is
one kind of aldehyde.

The reaction is a nucleophilic acyl substitution on an aldehyde, and in the second step, the
leaving group simultaneously attaches to another aldehyde. A carbonyl is attacked first by
hydroxide. The carbonyl is subsequently reformed and the hydride is transferred to attack
another carbonyl when the ensuing tetrahedral intermediate collapses. The acid and alkoxide ions
generated in the reaction's last stage exchanged a proton. The aldehyde that produces a doubly
charged anion in the presence of a very high concentration of base transfers a hydride ion to the
second molecule of aldehyde to form carboxylate and alkoxide ions. The alkoxide ion then takes
up the proton from the solvent. (Gardner Swain et al., 1979)
Procedure
Results and analysis

Product IR (cm-1 ) 1H NMR(CDCl3) 13C NMR Mass(g)

ppm
Benzoic acid O-H 3499 11.67s 172.60 0.87
C=O 2919 7.68 t 133.89
130.28
129.39
128.55
Crude Benzyl O-H 3329 2.66 s 140.86 2.03
alcohol C-H 3036 128.55
C-H 2882 127.63
benzaldehyde C=O 2817.78 10s 134.4 2.01
1701.89 7.4 qt 129
129.7
136.5

ANALYSIS;

Calculations of percentage yield

2C7H7O + KOH C7H5O2K+ C7H7OH

Calculation of Theoretical yield acid

mass
Moles=
molar mass

= 2.99g / 56.106g mol-1

= 0.0533 mol

From the reaction equation, 1 mole of KOH reacts to give 1 mole of alcohol

KOH: C7H5O2-

1 : 1
0.0533: 0.0533

Mass of acid = moles x molar mass

= 0.0533 mol x 121.116 g.mol-1

= 6. 46g

Percentage yield =(actual mass/theoretical mass) x 100 %

= (0.87g/ 6.46g) x 100%

= 13.5 %

Theoretical yield of the alcohol

Form the reaction equation;

KOH: C7H8O

1 : 1

0.0533: 0.0533

Mass of the acid=moles x molar mass

¿ 0.05507 mol x 108.140 g .mol−1

¿ 5.76 g

Percentage yield = (actual mass / theoretical mass) x 100%

= (0.87g/ 5.76g) x 100%

= 15.1 %

Answers to questions
Discussion

If there are no alpha hydrogens (hydrogens on the carbon next to the carbonyl carbon) in
benzaldehyde, it does not go through self-disproportionation, making it an exception to the
Cannizzaro reaction. Alpha hydrogens are needed for the hydride transfer step of the process.
Under typical circumstances, benzaldehyde won't experience the Cannizzaro reaction. To
perform a Cannizzaro reaction using an aldehyde that is devoid of alpha hydrogens, you would
require using an external source of hydride ions or employ a different method.

After the experiment, 1.99g of benzoic acid were recovered, from which 13.5 % of the
percentage could be computed. A calculation of the benzyl alcohol yield revealed that it was
15.1%. The fact that the percentages do not approach the 100% yield indicates that the accuracy
of the experimental data was lower. Errors that happened throughout the experiment could have
been the reason for this. It's possible that some of the products were lost in the separation funnel
during the shaking and filtering process. It's possible that some of the products were lost to the
stopper lid as the reaction mixture was being heated and shaken. Additionally, there was a
chance that the reaction might not be finished, producing incomplete and impure products due to
the addition of the boiling stones. Although the reaction mixture was only given roughly 20
minutes to react, literature claims that the reaction mixture needs 24 hours to complete. National
Center for Biotechnology Information (2024) states that benzoic acid has a melting point range
of 121–123 ˚C. This literature value is closer to the experimental value, which was found to be
117-121˚C, demonstrating the precision of the experiment.

Conclusion

Benzylaldehye underwent Cannizzaro reaction to form a crude benzyl alcohol and benzoic acid
References

National Center for Biotechnology Information (2024). PubChem Compound Summary for CID
243, Benzoic Acid.

Swain, C. G., Powell, A. L., Sheppard, W. A., & Morgan, C. R. (1979). Mechanism of the
Cannizzaro reaction. Journal of the American Chemical Society, 101(13), 3576–3583.