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 via aldol condensation reaction

between acetone and
The aldol condensation relies on
benzaldehyde. This is by mixing
the reactivity of a carbonyl group
the two
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 reactants with NaOH and ethanol
of aldol condensation, and for this and swirled occasionally for 15
experiment the cross aldol minutes to allow reaction. The
condensation was employed. This crystals were then collected by
reaction is between aldehydes and vacuum filtration while washing it
ketone that produces a mixed with water and chilled ethanol to
condensation products. encourage recrystalization.
The purpose of this experiment
was to synthesize dibenzaldehyde
 METHODOLOGY calculating the theoretical yield,
the following calculations were
A. Materials/Chemicals/Apparatus
made:
This experiment used the →
following: (a) 50-mL Erlenmeyer Conversion: mL of A grams of
flask, (b) beaker, (c) aspirator, (d) A → moles of A → moles of D
pipette, (e) Buchner funnel, (f) filter
paper, (g) wash bottle, (h) 0.4 g → grams of D
NaOH (in 2-mL water), (i) 0.3-mL
acetone , (j) 0.8-mL benzaldehyde, 0.731 g A 1 mol A 1 mol D 244 g D
0.3−mL A x x x x
and (k) 95% ethanol. 1−mL A 58.08 g A 1mol A 1 mol D

B. Procedure ¿ 0 . 846 g D
A solution of 0.4 g NaOH in 2-mL
H2O + 2-mL 95% ethanol was where A denotes acetone and D
prepared in an Erlenmeyer flask. denoted dibenzaldehyde.
The solution was then cooled. Into
And in the calculation of the
the solution, a 0.3 mL acetone and
percentage yield the following
a 0.8 mL benzaldehyde was added.
calculation was made:
The flask was then swirled from
time to time for 15 minutes to experimental value
yield= x 100
allow reaction. The product was t h eoretical value
then filtered using a Buchner
funnel via vacuum filtration. The 0. 700 g
crystals were then washed with yield= x 100
0.8460 g
H2O and then with chilled 95%
ethanol. The crystals were then
= 82.74%
weighted and the percentage yield
was calculated.

DISSCUSSION/ INTERPRETATION
OF RESULTS
RESULTS
Aldol condensation reactions
The final product obtained
represent an important class of
dibenzaldehyde crystals from aldol
reaction for forming carbon-carbon
condensation. The crystal product
bonds. In this experiment the cross
weighed 0.700g. In the calculation
aldol condensation was performed.
of the theoretical yield, the limiting
The synthesis began with a strong
reagent acetone was used as the
base, NaOH, which was mixed with
basis for the theoretical value. In
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 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 α-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:
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
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 α-carbon resulting the
formation of C=C double bond at
the α and β carbon. At the same
time, the hydroxide group attached
to the β 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 Figure 6
which attached to the carbon at
benzylic position.
The aldol condensation reaction
between acetone and
benzaldehyde yielded
dibenzaldehyde crystals. The
percentage yield for the reaction
Figure 5 was 82.74%. The lower percentage
yield was due to the fact that many
crystals were lost during the
The ketone undergone the same removal of the solvent from the
enolate condensation reactions reaction mixture during the
with the second mole of condensation of acetone with
benzaldehyde since this ketone still benzaldehyde. Some crystals were
have the α -hydrogen, which is also lost during the washing of
crystals with water. Also, not all of
acidic, and produced the
the crystals remained in the filter
dibenzaldehyde. The
paper. Some was filtered right
benzalacetone enolate ion acts as
through the paper with the solvent
a nucleophile which attacks
and ended up in the bottom of the
another benzaldehyde. The
flask. These errors contributed to
protonation of the aldol took place
the lower percentage yield
followed by the hydroxide groups
obtained. On loophole, in theory,
being eliminated as leaving groups.
was that the reaction is a mixture
As a result, the nucleophilic
of product thus it was expected to
addition and base-catalyzed
produce a lower yield and therefore
dehydration led to the formation of
contributed to the low percentage
the desired product which is
yield.
 CONCLUSION AND 2. Give the mechanism involved in
RECCOMENDATION the reaction.

The purpose of this experiment Acetone has α-hydrogens (on

was to synthesize dibenzaldehyde both sides) and thus can be
through aldol condensation of deprotonated to give a nucleophilic
acetone and benzaldehyde. The enolate anion. The aldehyde
experiment yielded crystals which carbonyl is much more electrophilic
was an indication of a successful than that of a ketone, and
experiment. Though there were therefore reacts rapidly with the
errors that resulted to lower enolate. The alkoxide produced is
percentage yield it can be avoided protonated by solvent, giving a β-
by considering the lapses hydroxyketone, which undergoes
mentioned earlier. One thing to base-catalyzed dehydration. The
avoid such errors is by carefully elimination process is particularly
selecting the starting materials fast in this case because the alkene
where only one reactant has an is stabilized by conjugation to not
enolized α -hydrogen and can only the carbonyl but also the
benzene.
minimize the formation of
mixtures. The other one is the
proverbial of most
3. What product should be formed by
recommendations – handling and
mixed aldol condensation of
performing the experiments more
benzaldehyde woth
vigilantly.
proionaldehyde? With acetone
(excess)?

ANSWERS TO QUESTIONS The products formed by the

mixed aldol condensation of
1. Calculate the percentage yield of benzaldehyde with proionaldehyde
the reaction. and acetone (excess) are 3-
experimental value hydroxy-1-phenyl-2-butanone and
yield= x 100 dibenzaldehyde, respectively.
t h eoretical value
4. Mixed aldol condensation using
0.700 g ketones having methyl groups
yield= x 100
0.8460 g often led to a possibility of forming
mono or disubstituted products.
= 82.74% What product is formed if
benzaldehyde and acetone (in
excess amount) are allowed to
 Chang, Reymond. Chemistry. 10th
ed. McGraw-Hill. 2010

Wade, L. G. Organic Chemistry (6th

react? Give the reaction equation ed.). Upper Saddle River, NJ:
and describe the mechanism. Prentice Hall. 2005

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 α-carbon
of ketone usually adds to the
carbonyl carbon of aldehyde,
leading to only one major product.
REFERENCE
Books
Journals
Mahrwald, R. (2004). Modern Aldol
Reactions, Volumes 1 and 2.
Weinheim, Germany: Wiley-VCH
Verlag GmbH & Co. KGaA. pp.
1218–23. ISBN 3-527-30714-1.
Nielsen, A. T.; Houlihan., W. J.
(1968). "The Aldol Condensation".
Organic Reactions 16: 1–438.
doi:10.1002/0471264180.or016.01.
Web
Aldol Condensation.
SynArchive:The Organic Synthesis
Archive. Retrived on 11 April 2015,
from
http://www.synarchive.com/named-
reactions/Aldol_Condensation

Bruice, Paula Y. Organic Chemistry.

4th ed. Pearson Prentice Hall. 2004 Aldol Cendensation. Organic
Chemistry Portal. Retrieved on 11
Boyd, R. N. & Morrison, R.T. April 2015, from
Organic Chemistry. 6th Ed. Prentice http://www.organic-
Hall. 1992 chemistry.org/namedreactions/aldol
-condensation.shtm
Carey, Francis A. Organic
th
Chemistry. 4 ed. McGraw-Hill.
2000
Aldol Reaction. ChemWiki. retrived
on 11 April 2015, from
http://chemwiki.ucdavis.edu/Organi
c_Chemistry/Reactivity_of_Alpha_H
ydrogens/Aldol_Reaction