Aldol Condensation

I.
INTRODUCTION
The aldol condensation relies on the reactivity of a carbonyl group that

can build a new carbon-carbon bond. This reaction is considered as one of the
most proficient method that is used to form a carbon-carbon bond. There are
many types of aldol condensation, and for this experiment the cross aldol
condensation was employed. This reaction is between aldehydes and ketone that
produces a mixed condensation products. In this reaction, the enolate ion of one
compound undergoes nucleophilic addition to the carbonyl carbon of a different
compound. Its products are usually detrimental since there is atendency of
reduced yielded product due to the mixture of products. Below is the figure of
the crossed aldol condensation main reaction of this experiment. This
experiment condensation produces an
, -unsaturated ketone
dibenzaldehyde.
The purpose of this experiment was to synthesize dibenzaldehyde via

aldol condensation reaction between acetone and benzaldehyde. This is by
mixing the two reactants with NaOH and ethanol and swirled occasionally for 15
minutes to allow reaction. The crystal s were then collected by vacuum filtration
while washing it with water and chilled ethanol to encourage recrystalization.
II.
METHODOLOGY
A. MATERIALS/ CHEMICALS/ APPARATUS
50-mL Erlenmeyer flask
Beaker
Aspirator
Pipet
Buchner funnel
Filter paper
Wash bottle
0.4 g NaOH (in 2-mL water)

0.3-mL acetone
0.8-mL benzaldehyde
Ethyl acetate
95% ethanol
B. PROCEDURE
A solution of 0.4 g NaOH in 2-mL H2O + 2-mL 95% ethanol was
prepared in an erlenmeyer flask. The solution was then cooled. Into the
solution, a 0.3 mL acetone and a 0.8 mL benzaldehyde was added. The
flask was then swirled from time to time for 15 minutes to allow
reaction. The product was then filtered using a Buchner funnel via
vacuum filtration. The crystals were then washed with H 2O and then
with chilled 95% ethanol. The crystals were then weighted and the
percentage yield was calculated.
III.
DATA/ RESULTS/ CALCULATIONS

Table 1. Reagents and properties
Substance
Aetone
Benzaldehyde
NaOH
Dibenzalacetone
Formula, g/mol
58.08
106.12
40
224
Amount used
0.3-mL
0.8-mL
0.4
product
Mole ratio
1:1
2:1
N/A
N/A
Density, g/mL
0.731
1.044
N/A
N/A
Solving for theoretical yield.

Conversion: mL of A
grams of A
moles of A
moles of D
grams of D
Note: A-acetone; D- dibenzaldehyde
0.3mL A x
Acetone:
Conversion: mL of B
0.731 g A 1 mol A 1 mol D 244 g D

x
x
x
=0.846 g D
1mL A 58.08 g A 1mol A 1 mol D
grams of B
moles of B
moles of D
grams of D
Note: B-benzaldehyde; D- dibenzaldehyde
Benzaldehyde:
0.8mL B x
1.044 g B
1 mol B
1 mol D 244 g D
x
x
x
=0.8815 g D
1mL B 106.12 g B 1 mol B 1 mol D
Since Acetone was the limiting reagent thus will be the theoretical value as
well.
Table 2. Weight of NaOH

Weight of watchglass + NaOH (g)
Weight of watchglass (g)
Weight of NaOH (g)
32. 07
31.67
0.400
Table 3. Weight of crystals/product

Weight of filter paper + crystals (g)
Weight of filter paper (g)
Weightof crystals (g)
0.9463
0.3500
0.5963
Calculation of percentage yield
yield=
experimental value
x 100
theoretical value
yield=
0.5963 g
x 100
0.8460 g
= 70. 48%
IV.
DISSCUSSION/ INTERPRETATION OF RESULTS
Aldol condensation reactions represent an important class of reaction for

forming carbon-carbon bonds. In this experiment the cross aldol condensation
was performed. The synthesis began with a strong base, NaOH, to generate the
acetone enolate ion. Water then forms as a byproduct of the reaction. This
reaction strongly favors the starting acetone and based in the shown calculation
acetone here was the limiting reagent and thus produces only on small quantity
but because the enolate is nucleophilic, it attacks the carbonyl of the
benzaldehyde and formed a
-carbonyl alkoxide ion. This alkoxide ion attacks
the protons from the water molecule and formed a

other hand, NaOH attracks another acidic
carbocation and formed an
- hydroxyl ketone. On the
-hydrogen and stabilizes the
, -unsaturated ketone. The ketone undergone
the same enolate condensation reaction with the second mole of benzaldehyde
since this ketone still have the
-hydrogen, which is acidic, and produced the
dibenzalacetone.
The aldol condensation reaction between acetone and benzaldehyde
yielded dibenzalacetone crystals. The percentage yield for the reaction was
70.48%. The low percentage yield was due to the fact that many crystals were
lost during the removal of the solvent from the reaction mixture during the
comdensation of acetone with benzaldehyde. Some crystals were also lost
during the washing of crystals with water. Also, not all of the crystals remained in
the filter paper. Some was filterd right through the paper with the solvent and
ended up in the bottom of the flask. These personal error contributed to the low
percentage yield obtained. On loophole, in theory, was that the reaction is a
mixture of product thus it was expected to produce a lower yield and therefore
contributed to the low percentage yield.
V.
CONCLUSION AND RECCOMENDATION
The purpose of this experiment was to synthesize dibenzalacetone

through aldol condensation of acetone and benzaldehyde. The experiment
yielded the crystals which was an indication of a successful experiment. Though
there were errors that resulted to low percentage yield it can be avoided by
considering the lapses mentioned earlier. One thing to avoid such errors is by
carefully selecting the starting materials where only one reactant has an
enolized
-hydrogen and can minimize the formation of mistures. The other
one is the SOP of most recommendations handling and performing the

experiments more vigilantly.

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I.

The aldol condensation relies on the reactivity of a carbonyl group that

The purpose of this experiment was to synthesize dibenzaldehyde via

0.4 g NaOH (in 2-mL water)

DATA/ RESULTS/ CALCULATIONS

Solving for theoretical yield.

0.731 g A 1 mol A 1 mol D 244 g D

Table 2. Weight of NaOH

Table 3. Weight of crystals/product

Calculation of percentage yield

DISSCUSSION/ INTERPRETATION OF RESULTS

Aldol condensation reactions represent an important class of reaction for

-carbonyl alkoxide ion. This alkoxide ion attacks

the protons from the water molecule and formed a

- hydroxyl ketone. On the

-hydrogen and stabilizes the

, -unsaturated ketone. The ketone undergone

-hydrogen, which is acidic, and produced the

CONCLUSION AND RECCOMENDATION

The purpose of this experiment was to synthesize dibenzalacetone

-hydrogen and can minimize the formation of mistures. The other

one is the SOP of most recommendations handling and performing the

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