Exp 2

Action plan
Apparatus required Chemicals required

Suction filtration apparatus Potassium hydroxide
25 ml round bottom flask Benzaldehyde
Separatory funnel Water
Filter paper Boiling chip
Short stem funnel Ether
Rotary evaporator Magnesium sulphate
Balance
400ml beaker
Plan
 Mix KOH and water with into benzaldehyde the round bottom flask
 Attach round bottom flux to reflux condenser and heat mixture for one hour
 Cool mixture to room temperature and transfer to a separatory funnel and extract the mixture
with ether
 Acidify mixture and collect crystals via suction filtration And let it air dry
 Dry the ether extract with magnesium sulfate
 Gravity filter the benzyl alcohol into around bottom flask and evaporate
the ether On the rotary evaporator and record the weights for both and
compare the spectra for both
Aim
This experiment aims to use the cannizzaro reaction to create potassium benzoate from benzaldehyde.
Introduction
In the cannizzaro reaction, two molecules of a non-enolizable aldehyde are disproportionate 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.
Procedure
In this experiment three grams of potassium hydroxide was added into water into a round bottom flask
of 25ml. Thereafter 2ml of Benzaldehyde was added a boiling chip was added to help quicken the
reaction and then it was attached to the reflex condenser which was heated for about an hour.
Afterwards the mixture was cooled to room temperature and then transferred into a separatory funnel.
The mixture was extracted with two 25ml volumes of ether and separated into two phases whereby the
aqueous phase was acidified with hydrochloric acid to pH 3 and the organic phase was to be used later
on. The acidified mixture was cooled in an ice bath and the crystals were collected by section filtration
and then the benzoic acid was led to air dry and while this was happening the Ether was dried using
magnesium sulfate. The benzo alcohol was filtered by gravity into another separate 100ml round bottom
flask. The ether was evaporated On a rotary evaporator and the weight was recorded After air drying the
mixture and the ether melting point, IR, NMR Spectrum was recorded And for the ether too.
Results and analysis
Product IR NMR(CDCl3) Mass

Benzoic acid
Crude Benzyl alcohol
benzyladehyde
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
0.05347: 0.05507
Mass of acid = moles x molar mass
= 0.05347 mol x 121.116 g.mol-1
= 6. 670g
Percentage yield =(actual mass/theoretical mass) x 100 %
= (1.62g/ 6.670g) x 100%
= 29.8 %
Theoretical yield of the alcohol
Form the reaction equation;
KOH: C7H8O
1 : 1
0.05507: 0.05507
Mass of the acid=moles x molar mass
¿ 0.05507 mol x 108.140 g .mol−1
¿ 5.955 g
Percentage yield = (actual mass / theoretical mass) x 100%
= (2.61g/ 5.955g) x 100%
= 43.8 %
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 29.8% of the percentage
could be computed. A calculation of the benzyl alcohol yield revealed that it was 43.8%. 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 (Niemen,
2008). Simpson (2016) 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.

Exp 2

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Exp 2

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Action plan

Apparatus required Chemicals required

Product IR NMR(CDCl3) Mass

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