The Cherry On Top

Aldol Condensation Reaction

Arvind Narayan
GSI: Luke Peterson
Section 216-133
11/12/13

Introduction:
Benzalacetophenones belong to a class of compounds called chalcones. Chalcones are
characterized by their diphenyl structure [1] and can be synthesized by an aldol condensation
between a benzaldehyde and acetophenone. These structures have important antitumor properties
and have the ability to block potassium channels. Benzalacetophenones can be prepared without
a solvent, but by using a very strong base [2]. The reaction contains an enolate intermediate that is
generated from a carbonyl compound. Aldol condensation reactions are also characterized by the
loss of water which gives the final product of the reaction.
Lab Objective:
The purpose of this lab is to generate this compound with substituted benzaldehydes and
acetophenones. To do this lab, an aldehyde and ketone were selected from a list and the product
of the reaction was characterized with melting point, TLC and IR spectroscopy. In table 3-1, a
list of known aldol product melting points were listed for comparison.
Reaction:

BASE

Reagents:
Compound
Benzaldehyde

Molecular Weight (g)

106.12

Melt temp/ boiling temp C

175.1 (boiling point)

4-chloropheyehtnanone
Sodium hydroxide
Ethanol

154.60
34.447
46.07

18-20 (melting point)

78 (boiling point)

Procedure:
4-chloroacetophenone (0.1546 g, 1 mmol) was chosen as the ketone derivative and benzaldehyde
(0.10612 g, 1 mmol) was chosen as the aldehyde derivative and mixed in a conical dram vial
with a spin vane. Ethanol (1 mL, 95%) was added to vial and stirred. Sodium hydroxide (.10 mL,
50% w/w) was added. The solution was stirred at room temperature until a solid precipitated
completely. The solid was broken up with a spatula and diluted with 2mL of ice water. It was
then transferred to another vial with an additional 3 mL of ice water. The solution was vacuum
filtered and allowed to dry. The product was then recrystallized.
Results and Discussion:
Initial observations of the starting materials and product:
Benzaldehyde smells like cherries. The product of the reaction was a pink yellow color. This is
cause by the excitation of an electron in the pi bond system. This is an indicator that a reaction
happened because pi-bonds are only in double bonds and triple bonds.
Yield
Starting material
0.1206 g

Theoretical Yield
0.271 g

Actual Yield
0.2065 g

% yield
76 %

IR Peaks:
4-chloroacetophenone: 3020 cm-1, 1680.1 cm-1, 1605.9 cm-1
benzaldehyde: 3073.5 cm-1, 2957 cm-1 , 1696.8 cm-1
product: 3020.3 cm-1 , 2259 cm-1, 2178 cm-1, 2129, 1658.91 cm-1, 1585.35 cm-1
The IR peaks of the ketone, aldehyde, and the product show a peak ~1650 - 1700 cm-1 which
represents the carbon-oxygen double bond that is present in all three compounds. The cluster of
peaks in the fingerprint region of the spectra represents the two benzene rings in the product. The
peak at 2259 cm-1 is indicative of the carbon-carbon double bond that formed as results of the
condensation reaction. This peak is not present in the IR spectra of the other two reactants which
indicated that a new bond was formed as part of the reaction.
The melting point of the product was measured to be 98-103 C. Table 3-1 in the lab manual lists
the melting point for the product of benzaldehyde and 4-chloroacetophenone as 100 C. The

difference in the melting ranges could be explained by impure product. The low starting
temperature for the melting range could be due to the fact that there is excess water in the
product.
The TLC plates showed separation of the product and the benzaldehyde. The product was
originally dissolved in a 3:2 mixture of ethyl acetate to hexanes. This did not work because there
was too much ethyl acetate and the spots ran too close to the solvent line. The solvent was
changed to a 1:4 ethyl acetate to hexanes mixture. The Rf value for the starting material,
benzaldehyde is 0.9 and the Rf values for the product is 0.78. Although the TLC plate showed
separation, the Rf are still very high to be definitive.
The reaction only took 10 minutes. A possible way to increase yield would have been to let the
reaction stir longer until more product, or possibly purer product formed before moving on to the
dilution step. By creating a more acidic environment, the condensation and thus the elimination
of water would have increased, and thus decreased the melting range of the product.
As a result of this information, it can be concluded that a reaction did happen and that an aldol
product was formed. However, it is inconclusive to what degree of purity the product formed
has. The yield was fairly low and may account for not the entire product forming.

Works Cited
1. Toda, F., et al., J. Chem. Soc. Perkin Trans. I, 1990, 3207.
2. Palleros, D. R., J. Chem. Educ., 81, 1345 (2004).
3. Klein, David R. "Chapter 17." Organic Chemistry. Hoboken, NJ: John Wiley, 2012. N.
pag. Print.