Chem 35.

1 TEG
Espiritu, Walter Aljhon
Silong, Rafaelle
Tumimbang, Glenn Vincent

Experiment 5: Aldol Condensation

February 18, 2014

I. Abstract
Some organic compounds like ketones, carboxylic acids and esters contain a carbonyl group
(C=O). In these compounds, Greek letters are used to approximate each carbon atom to the carbonyl
group (Klein, 2012). The labeling starts after the carbonyl group. Also, hydrogen atoms are named with
the Greek letter of the carbon in which they are attached, for example for a methyl group in alpha
position, there are -hydrogens. In this experiment, one of the most important reactions at the alpha
position is observed, which is aldol condensation.
II. Keywords: -carbon, aldol condensation, nucleophilic addition, base-catalyzed reaction

III. Introduction
Aldol condensations are important
in organic synthesis, providing a good way to
form carboncarbon
bonds.
The Robinson
annulation reaction sequence features an aldol
condensation;
the Wieland-Miescher
ketone product is an important starting material
for
many
organic
syntheses.
Aldol
condensations are also commonly discussed in
university level organic chemistry classes as a
good bond-forming reaction that demonstrates
important reaction mechanisms. In its usual
form, it involves the nucleophilic addition of
a ketone enolate to an aldehyde to form a hydroxy ketone, or "aldol" (aldehyde + alcohol),
a structural unit found in many naturally
occurring molecules and pharmaceuticals.
IV. Methodology
In a 50mL Erlenmeyer flask, combine
0.80 mL (0.83 g, 8mmol) of benzaldehyde, 0.30
mL acetone and 2 mL 95% ethanol. Then add 2
mL of 10& NaOH and swirl for 20 minutes. After
swirling, collect the solid by suction filtration
then break up the solid and remove the suction.
Add the gathered residue to 3 mL water then
apply suction, repeat this process twice. Finally,
recrystallize the solid using 95% ethanol and
determine its melting point and %yield.

V. Results and Discussion

In an acidic or basic medium followed by
heating, an aldol addition will yield an
elimination
product,
an
,-unsaturated
product.
This product is achieved under higher
temperature to yield the product.

Figure 1. Aldol condensation

Condensation is used to refer to any to a

reaction in which two molecules undergo
addition which is followed by a loss of a small
molecule such as water.
There are two parts in aldol
condensation. The first is the addition of a
ketone with either a ketone or an aldehyde
(nucleophilic attack), an example is the attack
of acetone to benzaldehyde. The product is a
protonated alkoxide.
The next step is the loss of water
molecule. The hydroxyl group is eliminated by
the hydroxide ion, resulting to the elimination of
water molecule.
When the reaction is proceeded under
low temperature, the aldol addition product is

Chem 35.1 TEG

obtained (-hydroxy alkane) but has poor
yield. In the experiment, acetone is used and
the equilibrium does not favor formation of an
aldol addition product. On the other hand, in
higher temperature, the aldol condensation
product is obtained because the equilibrium
favors its formation as well as the formation of a
conjugated system.

Experiment 5: Aldol Condensation

2. Write the reactions that may take place

during the synthesis. How can these reactions
be minimized or avoided?

VI. Guide Questions

1. Write a mechanism for the base-catalyzed
aldol condensation of dibenzalacetone. Do the
same for the acid-catalyzed aldol condensation.
a. base-catalyzed

b. acid-catalyzed

One of the side reactions that may occur is the

formation of ,-unsaturated ketone, which
limits the concentration of ketone in the
solution. To minimize this, one should add
enough acetone in the solution.
3. Why is the -hydrogen in a carbonyl
compound more acidic than any other hydrogen
in the alkyl chain?
The reason is related with the stability of the
anion and the possibility of resonance
stabilization via delocalization of the negative
charge to the more electronegative oxygen
atom like in the case of the carbonyl group. In
the case of alkyl chain, you cannot delocalize
the negative charge of the anion, and it is
always "focused" on the carbon atom. In short,
the alpha-hydrogen atoms are more acidic
because the resulting anion is resonance
stabilized.
4. Why is the -hydrogen in an ,-unsaturated
carbonyl compound also acidic?
Because the conjugated double bonds of the
C=C-C=O part of the molecule allow the
electron-attracting effect of the carbonyl group
to be extended weakening the bond to the
gamma-hydrogen.

Chem 35.1 TEG

5. Ketones with non-equivalent -hydrogens are
not
usually
made
to
undergo
aldol
condensation. Explain the rationale behind this.
If a ketone is to undergo aldol condensation,
there must be a presence of equivalent
hydrogen that will both be used to form two
products. One of the alpha hydrogen is required
in the formation of the enolate and the other is
for the dehydration reaction.

Experiment 5: Aldol Condensation

I hereby certify that I substantially contribute to
this report.
_____________________
Walter Aljhon Espiritu

_____________________
Rafaelle Silong

VII. Conclusion and Recommendation

Aldol condensation is an important
reaction in organic chemistry due to the
formation of C-C bonds. The experiment
showed that the reaction proceeds in two steps,
the first involving the attack of acetone to
benzaldehyde which produces an alkoxide. The
second part of the reaction is the loss of water
molecule. It shows that high temperature favors
the formation of the product in the experiment.
It is recommended to use pure acetone
to have better yield. The use of ethanol must
also be kept at a minimal to have better
recrystallization of the product.
References
Klein, D. (2012). Organic Chemistry.
Chapter 19. (n.d) Retrieved from:
http://cas.umkc.edu/chemistry/Faculty/cours
es/Kilway/Ch19.pdf
Enols and enolates. (2000) Retrieved from:
http://www.mhhe.com/physsci/chemistry/car
ey/student/olc/ch18acidity.html
Aldol
condensation.
Retrieved
from:
http://research.cm.utexas.edu/nbauld/teach/
emphtopB2.html

_____________________
Glenn Vincent Tumimbang