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ALDOL CONDENSATION
OBJECTIVE
• To synthesize α,β-unsaturated ketone from an
aldehyde and ketone
• To purify product through recrystallization.
• To identify and analyze purity through tlc and melting
point analysis
• To analyze the product using IR spectrum
Dibenzalacetone
• It consist of two
aromatic rings with
unsaturated chain
• Many biological
activities have been
attributed to this group.
• such as,
1. Anticancer
2. Antioxidant
3. Antifungal
4. Anti-inflammatory
5. Antibacterial
6. Antimicrobial
Techniques
• TLC analysis
• Recrystallization
• Melting point analysis
Introduction
• Aldol condensations are nucleophilic
additions of an enolate ion,which are
strong nucleophiles, to another C=O
group under basic conditions
• Protonation gives the aldol product
• Abstration of a proton gives an enolate
that can expel an -OH ion to give a
conjugate product
• Dehydration is usually exothermic
because it leads to a very stable
conjugated product.
CHEMICAL EQUATION
Mechanism
•
General Aldol Condensation
• Aldol condensation reaction is carried out in an
organic solvent,such as ethanol
• Isolation of the product requires a much more
involved workup
• Another challenge is that solution phase reaction is
reversible,so low product yield may result.
Experimental Procedure
• Place aldehyde and
ethanol in Erlenmeyer
flask
• Stir the mixture
• Slowly add 6M NaOH
• Add acetone in the last.
• Continue to react for 15
minutes at room
temperature
Purification and product isolation
• Filter the precipitate
through suction
filtration.
• Wash precipitate with
mixture of 4% acetic
acid and 95% ethanol.
• Recrystallize crude
product in hot ethanol.
• Collect the purified
solid and allow it to dry.
• determine the melting
point.
• Obtain final product
mass and calculate %
yield
TABLE 1
theoretical
yield (g)
4-(4-
nitrophenyl)-
3-buten-2-
one
1,5-
bis(phenyl)-
1,4-
pentadien-3-
one
1,5-bis(4-
nitrophenyl)-
1,4-
pentadien-3-
one
1,5-bis(2-
hydroxyphenyl)
-1,4-pentadien-
3-one
1,5-bis(4-
methoxyphen
yl)-1,4-
pentadien-3-
one
Actual
yield(g)
1.7 1.7 5 4.5 2.5
% yield 89 30 92 81 49.5
Melting
range( ͦͦͦͦͦͦ C)
110-112 110-111 128
Product
appearance
black solid
light yellow
solid
brownish-
black solid
blackish green
solid
yellow solid
Table 2
Compound
TLC Rf value
refernce
TLC Rf value
product
4-(4-nitrophenyl)-3-buten-
2-one
0.88 0.69
1,5-bis(phenyl)-1,4-
pentadien-3-one
0.38 0.5
1,5-bis(4-nitrophenyl)-1,4-
pentadien-3-one
0.44 0.26
1,5-bis(2-hydroxyphenyl)-
1,4-pentadien-3-one
0.6 0.19
1,5-bis(4-methoxyphenyl)-
1,4-pentadien-3-one
0.5 0.4
IR SPECTRUM
Function
al Group
Base
Values
(cm-1)
4-(4-
nitrophen
yl)-3-
buten-2-
one
1,5-
bis(pheny
l)-1,4-
pentadien
-3-one
1,5-
bis(4-
nitrophen
yl)-1,4-
pentadie
n-3-one
1,5-
bis(2-
hydroxyp
henyl)-
1,4penta
dien-3-
one
1,5-bis(4-
methoxyphenyl
)-1,4-
pentadien-3-
one
sp3 CH
Stretch
2800-
3000
sp2CH
stretch
3000-
3100
C=O
Stretch
1680-
1740
Aromatic
C=C
Stretch
1500-
1600
C-O
Stretch
1000-
1200
Aldehyd
e CH
stretch
2700-
2800

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Aldol condensation 2