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SYNTHESIS OF BENZALDEHYDE
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1. AIM
The main objective of this experiment is to synthesis dibenzalacetone through a base
catalysed aldol condensation of acetone and benzaldehyde using lithium hydroxide
monohydrate as the base.

2. INTRODUCTION
The aldol condensation is an example of exothermic and spontaneous reaction. Due to
this exothermic character, the reaction products are placed in the ice bath with addition
of a reagent to avoid the formation of the side products and the evaporation of the
acetone. All of the afore mentioned information was highlighted by (Jin, F. and
Enomoto, H., 2011,) whom further that it is a reaction between two aldehydes or
ketones which are catalysed by a base or acid giving out a molecule having both alcohol
and aldehyde functional groups. Moreover (Nielsen,A.T and Hauliham,W.J.,2004) also
stated that the response of the ketone in utilizing sodium hydroxide as a base is a case of
blended aldol condensation reaction and for the reaction, the two mixed aldol
condensation reaction between acetone and benzaldehyde will be put into play. In
addition, they further explained acetone to contain the alpha hydrogens on both sides
and therefore can be deprotonated to give allowance for the nucleophilic enolate ion as
shown by the reaction mechanism below.

Hull, 2001 indicated that in this type of reaction, large molecule tends to be formed from
the carbon-carbon in a way that the alpha carbon of the first molecule is attached to the
carbonyl carbon of the second molecule. Conjunction of the double bond with the
carbonyl group stabilizes the unsaturated products and provides the driving force for the
dehydration process hence resulting in the overall reaction that involves idol formation
and dehydration. He further stated that the term aldol condensation comes from the loss
of H+ and OH- which represents the loss of water during the reaction where the enolate
attacks the carbonyl group. The aldol therefore undergoes the acid base reaction with the
remaining alpha hydrogen and hydroxide as a leaving group to give an enol, (Raston,
C.L. and Scott, J.L., 2000). Depending on the structure and reaction condition, the
equilibrium for the aldol reaction can lie in the reaction of either reactants or products,
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3. EXPERIMENTAL

a) CHEMICALS REQUIRED
¨      Acetone: 0.81ml (11mmol)
¨      Benzaldehyde: 2.3ml (20mmol)
¨      LiOH.H2O:42mg (1mmol, 10mol%)

a) PROCEDURE
In 25 ml round bottom flask containing a magnetic stirrer, 2.3 ml of benzaldehyde, 0.81
ml of acetone, 5ml of ethyl alcohol and 42mg of LiOH monohydrate were added. The
reaction mixture was vigorously stirred for 10 minutes until a pale-yellow solid
precipitated out. 5 g of crushed ice was added and the reaction mixture was stirred once
more then the solid was allowed to settle down. The pale-yellow precipitate was filtered
out, washed with water, suction dried and the product was recrystallised with ethanol.
The yield as well as the melting point were recorded.

4. RESULTS
Table 1; Mass of Li OH used

Mass of weighing boat 0.46 g

Mass of LiOH 0.0418 g

Table 2; Mass of the dibenzalacetone obtained

Mass of filter paper 0.47 g

Mass of filter paper + product 2.0570 g
Mass of product 1.5826 g
 
CALCULATING THE PERCENTAGE YIELD OF DIBENZALACETONE

Mass of acetone = density * volume

                           = 0.791g/mL * 0.81 mL
                           = 0.64071 g
Mass of benzaldehyde = density * volume
                                    = 1.044g/mL * 2.3 mL
                                    = 2.4012 g
Moles of acetone = mass / molar mass
                            = 0.64071g / 58.08g
                           = 0.011037209 mol
Moles of benzaldehyde = mass / molar mass
                                      = 2.4012g / 106.124g/mol
                                      = 0.022626361 mol
Acetone has the least number of moles hence acetone is the limiting reactant in the
reaction of synthesis of dibenzalacetone
The ratio of acetone to the product is 1:1
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The moles of the product are therefore = 0.011037209 mol

 
Theoretical yield of dibenzalacetone = moles * molar mass
                                                           = 0.011037209 mol * 234.29 g/mol
                                                           = 2.585907697 g
Percentage yield = actual yield / theoretical yield
                           = 1.5826 g / 2.58907697 g
                           = 61.3%
 
The percentage yield of the product is 61.3 %
 
Table 2 recording melting point of dibenzalacetone

Starts melting 94.0˚C

Finishes melting 111.0˚C

5. DISCUSSION
The experiment was successfully carried out and the results were collected but before
that, it was crucial to understand that according to (Hull,2001), carbonyl condensation
takes place between two carbonyl partners and involves a combination of the
nucleophilic addition and substitution steps, the nucleophilic donor being converted to
its enolate and undergoes a- substitution reaction.
In this experiment, acetone and benzaldehyde were mixed in the presence of LiOH.H2O
because it acts as dual activation catalyst for the reaction and the dibenzalacetone was
obtained as the product following a stepwise mechanism shown below:

As the dibenzalacetone was formed, a yellow precipitate was obtained from the
experiment in the process. This statement has been supported by (Raston, C.L. and
Scott, J.L., 2000) whom made it clear that the theoretical range of the melting point of
dibenzalacetone is found at 108- conjugated pi bond system which causes it to absorb
light in its visible region having a gamma max of 330nm, absorbs blue/ violet light and
gives yellow precipitate. After attaining the precipitate, it was then recrystallised and
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this is one of the crucial steps of the experiment as it reduces at trace impurities that may
deviate the desired results. Furthermore, determine the scale at which the
dibenzalacetone was formed, the percentage yield of the product was calculated and
found to be 61.3%. The 100% percentage yield could not be attained due to some errors
encountered during the procedure and these errors are inclusive of incomplete reactions
and loss of the product during recrystallisation. Furthermore, though the melting point
attained (94 -111) ℃ is partially within the theoretical range (110-111) ℃, it is actually
lower due to some impurities within the product lowering the melting point. To further
verify the purity of the product obtained, the IR spectra was supposed to be used to
detect the ketone and the aldehyde that was started when the experiment was initiated.

Though the experiment was successfully conducted, quite a number of errors were
encountered such as loss of the product during recrystallisation and the presence
impurities in the product that lowered the melting point. However, to improve the
results the produts of the reaction can be regenerated and reutilised for efficiency.

6. CONCLUSION
Acetone and benzaldehyde were reacted with the use of LiOH.H 2O as a base and
dibenzalacetone was attained as the product of this base catalysed aldol condensation
reaction. The percentage yield of the product was calculated and found to be 61.3%.
Again, the melting point of the product of the reaction was measured as 94℃-111℃.
7. REFERENCES

1. Hull, L.A., 2001. The dibenzalacetone reaction revisited. Journal of Chemical

Education, 78(2), p.226.

2. Jin, F. and Enomoto, H., 2011. Rapid and highly selective conversion of biomass into
value-added products in hydrothermal conditions: chemistry of acid/base-catalysed
and oxidation reactions. Energy & Environmental Science, 4(2), pp.382-397.

3. Nielsen, A.T. and Houlihan, W.J., 2004. The aldol condensation. Organic

reactions, 16, pp.1-438.
4. Raston, C.L. and Scott, J.L., 2000. Chemoselective, solvent-free aldol condensation
reaction. Green Chemistry, 2(2), pp.49-52.

ANSWERS TO QUESTIONS
A) Recrystallisation removes impurities from the compound that changes the melting and
the boiling point of the sample.
B) It is significant to constantly release the pressure in the vessel to allow the reaction to
occur at normal conditions
C) Reaction mechanism
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