Colleen Samantha Dioquinoa, Christopher Jay Robidillob

Abstract

Aldehydes and ketones react with each other or themselves via aldol addition where a hydroxyl
aldehyde or ketone is formed. Aldol condensation is possible due to the presence of heat. This
experiment aimed to synthesize dianisalacetone, identify unknown and understand aldol’s mechanism.
The test compounds underwent simple mixing, heating, recrystallization and vacuum filtration. The base
had deprotonated β-hydrogen of acetone and this would attack the aldehyde to produce hydroxyl ketone.
Under heat, this would be condensed to form unsaturation. The process would be repeated with another
aldehyde to for dianisalacetone. This experiment had produced a considerable yield of dianisalacetone
and unknowns.

Keywords: aldol addition, aldol condensation, dianisalacetone, recrystallization, unsaturation

Aldol condensation is the elimination of the

hydroxyl group to produce an unsaturated bond.
Aldol addition reactions happen when aldehyde
is treated with a base. This reaction produces a This experiment aims to:
hydroxy-aldehyde or ketone. However, retro
 Synthesize 1,5-Diphenyl-1,4-pentadien-
aldol reaction happens for ketones. Products of
3-one
aldol addition could undergo condensation in the
 Identify mixed aldol product from
presence of heat.
condensation of an unknown aromatic
aldehyde with a ketone

a. CHM146L student, School of CHE-CHM-BE-MSE, Mapua Institute of Technology

b. CHM146L professor, School of CHE-CHM-BE-MSE, Mapua Institute of Technology
  Understand the mechanism of Aldol and A. Synthesis of Dibenzalacetone (1, 5-
mixed aldol condensation reaction Diphenyl-1, 4-pentadien-3-one)

The test compounds to be used are in Table 1.

Table 1-test compounds 2.1ml of

benzaldehyde The mixture was
Test Compounds and 0.75 ml of mixed using a
Name Structure acetone was stirrer.
Benzaldehyde placed in a vial

The vial was

5ml of 5M NaOH
capped. A yellow
and 95% ethanol
precipitate was
was added.
formed

Ethanol

The mixture was

Toluene The product was
continuously
vacuum filtrated
stirred for 30-45
using the Buchner
minutes at room
funnel
temperature

Acetone The product was

recrystallized The product was
from ethanol, washed with 1ml
95% ethanol or cold water thrice.
ethyl acetate.
Anisaldehyde
B. Identification of a Mixed Aldol Product
from Condensation of an Unknown Aromatic
Potassium KOH Aldehyde with a Ketone
hydroxide
Sodium hydroxide NaOH
2-propanol

The reagents were prepared by the laboratory

assistant before the experiment was performed.
 4-hydroxy-4--(4-methoxyphenyl)butan-2-one had
undergone aldol condensation to remove the
hydroxyl group and this would produce 4--(4-
methoxyphenyl)-3-buten-2-one (Fig 2).

Figure 2

A. Synthesis of Dianisalacetone

When anisaldehyde was placed in a vial with

acetone, sodium hydroxide and ethanol, a
yellow precipitate was formed. Due to the
presence of hydroxide, it was able to
deprotonate the β-hydrogen of acetone. β-
carbon then would acquire a negative charge,
thus allowing it to attack to the carbonyl carbon
of the aldehyde. The water formed earlier was
used as a work up. The product formed was
assumed to be 4-hydroxy-4-(4-
methoxyphenyl)butan-2-one (Fig. 1).

Figure 1 Figure 3
4--(4-methoxyphenyl)-3-buten-2-one would react
with an excess benzaldehyde via aldol reaction
and this would be condensed into
dianisalacetone (Fig 3).

Table 2

Data
Weight of crude product 9.10 g
Weight of pure product 6.37 g
Percent yield 70%

From table 2, the yield was 70%. The solvent

used for recrystallization is 95% ethanol. This
may have been brought by unsuccessful
recrystallization.

B. Identification of a Mixed Aldol Product

from Condensation of an Unknown Aromatic
Aldehyde with a Ketone

Unknown 1- Benzaldehyde

Benzaldehyde would react in the same

mechanism with anisaldehyde. This would
produce dibenzalacetone (Fig 4).

Figure 4

Unknown 2-Anisaldehyde

This was the same reagent used at part A.

Definitely, these had yield to dianisalacetone.
(Refer to Fig 1-3)

Data
Unknown 1 Unknown 2
Recrystalliz 2-propanol Toluene
ation
solvent
Weight of 3.77 g 6.25 g
crude
product
Weight of 2.98 g 3.94 g
pure
product
% yield 79% 63%
Unknown Benzal- Anisal-
dehyde dehyde
Benzaldehyde had a higher yield than
anisaldehyde. Anisaldehyde at part A was
higher than part B. This might have been
affected by the efficiency of the solvent

Aldol condensation is a reaction between

aldehydes and ketones. This is a follow up
reaction of aldol addition.

Dianisalacetone was produced using acetone

and anisaldehyde. Base deprotonated β-
hydrogen of acetone which enables the
carbanion to attack anisaldehyde at carbonyl
group. This was followed by a work up using
water. Since the aldol addition produc was
subjected to heat, the hydroxyl group had been
eliminated thus producing an unsaturated bond.

The unknowns were benzaldehyde and

anisaldehyde. The yields were considerable
though dibenzalacetone was higher than of
dianisalacetone. Dianisalacetone at part A was
higher than of part B that might have been
affected by the recrystallization solvent.

I would recommend that the other unknown

should be different from the reagent of part A to
explore more on aldol condensation.

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