Antonio Catalig, Gian Gamboa

Chem 35.1

BS Biochemistry

Experiment No. 5: Aldol Condensation: Synthesis of Dibenzalacetone

I. Abstract
Dibenzalacetone is an organic compound typically found in sunscreen. In this experiment, Acetone
and Benzaldehyde reacted to form Dibenzalacetone via Aldol condensation. This type of organic reaction
typically involves aldehydes or ketones, which form larger molecules with alcohol and aldehyde functional
groups. This reaction can also be furthered using catalysis via acids, bases or aldolases.
Keywords:

Aldol condensation, functional groups, organic molecules, catalysis, aldolases

II. Introduction
Dibenzalacetones ability to absorb UV
rays and its insolubility in water make it a
common component of sunscreen. This organic
molecule can be formed via Aldol condensation,
which is the case in this experiment. Aldol
condensation results from the condensation of
carbonyl and enolate compounds into larger
molecules. The term Aldol comes from the fact
that these larger molecules have alcohol and
aldehyde functional groups.
Typical of Aldol condensations a ketone
and an aldehyde; acetone and benzaldehyde
were used in this experiment to form
dibenzalacetone. The crude dibenzalacetone
formed from the condensation was refined via
recrystallization, and the melting point of the
recrystallized
product
was
obtained
for
comparison in order to analyze its purity.
III. Methodology
The materials and apparatus used in this
experiment were Acetone, Benzaldehyde, Sodium
Hydroxide, Ethanol, water, Glacial Acetic acid,
Pipettes, Pasteur pipettes, Erlenmeyer flasks, and
a filtration set-up.
The first step of the experiment was the
combination of 0.8 mL (0.82 g, 8 mmol) of
Benzaldehyde , 0.3 mL (0.24 g, 4 mmol) of
Acetone, and 2 mL of 95% ethanol in a 50 mL
Erlenmeyer flask. Two (2) mL of 10% Sodium
Hydroxide was then added before swirling the
mixture for at least 20 min. The next step was the
collection of the solid component of the solution
via suction filtration. The solid was broken up
before the suction was removed.

using 95% ethanol, and the determination of the

percent yield and melting point afterward.

IV. Results
The crude product weighed 0.5965 g
before recrystallization. The recrystallized product
weighed 0.3281 g. The percent yield was equal to
(0.3281/0.936 x 100%) 35.05%, and the melting
point ranged from 94 to 102oC.
V. Discussion:
The synthesis begins by using NaOH (a
strong base) to react with acetone to form an
enolate. Water is also a product in this reaction.

Although the reaction favors the left side, the

enolate ion reacts with the benzaldehyde. This
results in the production of the B-carbonyl
alkoxide ion, which pushes the reaction forward.
The alkoxide ion forms a B-hydroxy ketone after
reacting with water, while NaOH forms a
stabilized carbanion after abstracting an acidic Ahydrogen. The electron pair on carbon is used to
eliminate the hydroxide ion, forming an alpha-beta
unsaturated ketone in an irreversible step. This is
an example of an E1CB mechanism which is made
possible via the stabilization of the intermediate
carbanion by the carbonyl group, and this is all
done under basic conditions, unlike the E1
mechanism which is done under acidic conditions.

The third step was the addition of the

residue to 3 mL of distilled water. The mixture was
allowed to stand for about a minute before
reapplying suction. This step was repeated twice.
The last step was the recrystallization of the solid

Chem 35.1 Free-Radical Polymerization of Styrene

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Due to the presence A-hydrogens, the ketone

product can still condense with another
benzaldehyde molecule to form dibenzalacetone.

VIII. References
Bruice, P. (2006). The essentials of organic
chemistry. Pearson Education, inc.

The
melting
point
range
of
dibenzalacetone is 110-111 oC. The broad 94-102
o
C range of the experimental yield implies
impurities were present in the recrystallized solid.

Chiu, H.H. & Villarante, N.R. Laboratory manual

in Organic Chemistry II.

VI. Guide Questions

Pahlavan, Cherif (Date unknown). Experiment 7

(Organic
Chemistry
II).
Retrieved
from:
http://swc2.hccs.edu/pahlavan/2425L7.pdf

1. Write the mechanisms for the acidcatalyzed and base-catalyzed aldol

condensation of dibenzalacetone.
2. Write the side-reactions that may take
place during synthesis. How are they
minimized or avoided?
3. Why is the A-hydrogen more acidic than
any other hydrogen in the alkyl chain?
4. Why is the Y-hydrogen also acidic?
5. Explain how ketones with non-equivalent
A-hydrogens are not usually made to
undergo aldol condensation.
VII. Conclusion and Recommendation
(The 0.2684 g diff in the recrystallized
yield calls for a better purification process/
improved protocol)

Chem 35.1 Free-Radical Polymerization of Styrene

Klein, D. (2012). Organic Chemistry. John Wiley &

Sons, inc.

Snelling, C. R., Neilan, J. (August 7, 2006). Aldol

Condensation.
Retrieved
from:
http://www2.volstate.edu/chem/2020/Labs/Aldol_
Condensation.html
I hereby certify that I have given substantial
contribution to the report.

Catalig, Antonio Mari P.

_____________________________________Ga
mboa, Gian Wyatt

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