ALDOL CONDENSATION

Traya Levie Grace M.

Abstract: The purpose of this laboratory experiment was to synthesize
dibenzaldehyde using aldol condensation rection between benzaldehyde and
acetone. 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. After the filtration we obtained
crystals of dibenzaldehyde. The obtained crystals weighed 0.700g and
resulted to a 82.74% yield. The lower percentage yield was due to the fact
that many crystals were lost during the removal of the solvent from the
reaction mixture during the condensation 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 filtered right
through the paper with the solvent and ended up in the bottom of the flask.
These personal errors contributed to the lower 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
lower percentage yield.

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 carboncarbon 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.
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
crystals were then collected by
vacuum filtration while washing it
with water and chilled ethanol to
encourage recrystalization.

METHODOLOGY
A. Materials/Chemicals/Apparatus
This
experiment
used
the
following: (a) 50-mL Erlenmeyer
flask, (b) beaker, (c) aspirator, (d)
pipette, (e) Buchner funnel, (f) filter
paper, (g) wash bottle, (h) 0.4 g
NaOH (in 2-mL water), (i) 0.3-mL
acetone , (j) 0.8-mL benzaldehyde,
and (k) 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
H2O and then with chilled 95%
ethanol. The crystals were then
weighted and the percentage yield
was calculated.

RESULTS
The
final
product
obtained
dibenzaldehyde crystals from aldol
condensation. The crystal product
weighed 0.700g. In the calculation
of the theoretical yield, the limiting
reagent acetone was used as the
basis for the theoretical value. In

calculating the theoretical yield,

the following calculations were
made:
Conversion: mL of A

moles of A

grams of

moles of D

grams of D

0.3mL A x

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

x
x
x
1mL A 58.08 g A 1mol A 1 mol D

0 . 846 g D

where A denotes acetone and D

denoted dibenzaldehyde.
And in the calculation of the
percentage yield the following
calculation was made:
yield=

experimental value
x 100
t h eoretical value

yield=

0. 700 g
x 100
0.8460 g
= 82.74%

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, which was mixed with

distilled water then was used to

react with enough ethanol. The
particular reaction is an exothermic
reaction which released the heat
energy to the surrounding from the
reaction. The base functioned as a
catalyst in the reaction. The
ethanol acts as a solvent which
allows
the
acetone
and
benzaldehyde to dissolve and react
with each other. After that, acetone
and benzaldehyde were mixed in
the solvent which turns to yellow
color
quickly.
Eventually,
the
product was formed with a yellow
precipitate.

Figure 2

The acetaldehyde enolate ion

attacks the benzylic carbon of
benzaldehyde
via
nucleophilic
addition to form the intermediate
as shown in below:

Figure 3

Figure 1. Before and after addition of

benzaldehyde

Acetone is considered as a stable

and unreactive compound, so it
should be converted into anionic
form to increase its nucleophile
properties to initiate the reaction.
The base dissolved in water
produces hydroxide ion and tends
to attack the -hydrogen in
acetone form water molecule. The
deprotonation of acetone caused
by the enolate ion was produced as
nucleophile. An enolate ion was
formed
which
it
exists
as
resonance-stabilized structure that
is shown in the following figure:

The oxygen attached to the

benzylic position of carbon tends to
attract one proton from water
molecule to form hydroxide group
in the intermediate. This is the
formation of an aldol since the
molecule consists of a carbonyl
group and an alcohol group. In the
basic condition, the hydroxide ion
tends to remove one proton from
the
-carbon
resulting
the
formation of C=C double bond at
the and carbon. At the same
time, the hydroxide group attached
to the carbon forms a leaving
group. After the condensation,
benzalacetone was formed after
two water molecules leaved as
shown:

dibenzaldehyde. The mechanism of

dibenzaldehyde
formation
was
shown in the figure 6:

Figure 4

The benzalacetone tends to form

benzalacetone enolate ion after the
hydroxide
group
from
the
surrounding attack the proton
which attached to the carbon at
benzylic position.

Figure 5

The ketone undergone the same

enolate condensation reactions
with
the
second
mole
of
benzaldehyde since this ketone still
have the -hydrogen, which is
acidic,
and
produced
the
dibenzaldehyde.
The
benzalacetone enolate ion acts as
a
nucleophile
which
attacks
another
benzaldehyde.
The
protonation of the aldol took place
followed by the hydroxide groups
being eliminated as leaving groups.
As a result, the nucleophilic
addition
and
base-catalyzed
dehydration led to the formation of
the desired product which is

Figure 6

The aldol condensation reaction

between
acetone
and
benzaldehyde
yielded
dibenzaldehyde
crystals.
The
percentage yield for the reaction
was 82.74%. The lower percentage
yield was due to the fact that many
crystals were lost during the
removal of the solvent from the
reaction
mixture
during
the
condensation 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 filtered right
through the paper with the solvent
and ended up in the bottom of the
flask. These errors contributed to
the
lower
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.

CONCLUSION
RECCOMENDATION

AND

2. Give the mechanism involved in

the reaction.

The purpose of this experiment

was to synthesize dibenzaldehyde
through aldol condensation of
acetone and benzaldehyde. The
experiment yielded crystals which
was an indication of a successful
experiment. Though there were
errors that resulted to lower
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
-hydrogen and can
enolized

Acetone has -hydrogens (on

both sides) and thus can be
deprotonated to give a nucleophilic
enolate
anion.
The
aldehyde
carbonyl is much more electrophilic
than that of a ketone, and
therefore reacts rapidly with the
enolate. The alkoxide produced is
protonated by solvent, giving a hydroxyketone, which undergoes
base-catalyzed dehydration. The
elimination process is particularly
fast in this case because the alkene
is stabilized by conjugation to not
only the carbonyl but also the
benzene.

minimize
the
formation
of
mixtures. The other one is the
proverbial
of
most
recommendations handling and
performing the experiments more
vigilantly.

ANSWERS TO QUESTIONS
1. Calculate the percentage yield of
the reaction.
yield=

yield=

experimental value
x 100
t h eoretical value
0.700 g
x 100
0.8460 g
= 82.74%

3. What product should be formed by

mixed
aldol
condensation
of
benzaldehyde
woth
proionaldehyde?
With
acetone
(excess)?
The products formed by the
mixed
aldol
condensation
of
benzaldehyde with proionaldehyde
and acetone (excess) are 3hydroxy-1-phenyl-2-butanone and
dibenzaldehyde, respectively.
4. Mixed aldol condensation using
ketones having methyl groups
often led to a possibility of forming
mono or disubstituted products.
What
product
is
formed
if
benzaldehyde and acetone (in
excess amount) are allowed to

Chang, Reymond. Chemistry. 10th

ed. McGraw-Hill. 2010

react? Give the reaction equation

and describe the mechanism.
The
reaction
between
benzaldehyde and acetone in
excess via aldol condensation
produces
disubstituted
product
which is the dibenzaldehyde. This
mixture of addition products that
are formed when 2 different
enolizable carbonyl compounds are
subjected to aldol conditions. Since
the carbonyl carbon of aldehyde is
more electrophilic than that of
ketone, the reaction between an
aldehyde
an
a
ketone
is
synthetically viable. The -carbon
of ketone usually adds to the
carbonyl carbon of aldehyde,
leading to only one major product.

REFERENCE

Wade, L. G. Organic Chemistry (6th

ed.). Upper Saddle River, NJ:
Prentice Hall. 2005

Journals
Mahrwald, R. (2004). Modern Aldol
Reactions, Volumes 1 and 2.
Weinheim, Germany: Wiley-VCH
Verlag GmbH & Co. KGaA. pp.
121823. ISBN 3-527-30714-1.
Nielsen, A. T.; Houlihan., W. J.
(1968). "The Aldol Condensation".
Organic Reactions 16: 1438.
doi:10.1002/0471264180.or016.01.
Web
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4th ed. Pearson Prentice Hall. 2004
Boyd,
R. N. & Morrison,
R.T.
Organic Chemistry. 6th Ed. Prentice
Hall. 1992
Carey,
Francis
A.
Organic
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Chemistry. 4
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Organic
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April
2015,
from
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on
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from

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