EXPERIMENT 4 – THE ALDOL CONDENSATION REACTION : PREPARATION OF

BENZALACEROPHENONES (CHALCONES)

OBJECTIVE OF THE EXPERIMENT

 To perform the aldol condensation reaction between a substituted benzaldehydes and a
ketone in the presence of base to produce an α,β-unsaturated ketone.

INTRODUCTION
An aldol condensation is an organic reaction in which an enol or an enolate ion reacts with a
carbonyl compound to form a β-hydroxyaldehyde or β-hydroxyketone, followed by a dehydration
to give a conjugate enone. Benzaldehyde reacts with a ketone in the presence of base to give α, β-
unsaturated ketones. This reaction is an example of a crossed aldol condensation where the
intermediate dehydrates to produce the resonance-stabilized unsaturated ketone. Ketone loses a
proton from an α-carbon to form an enolate ion, which attacks the carbonyl carbon of the aldehyde
to yield, after protonation, α, β-hydoxy ketone. The intermediate is, for aromatic aldehyde at least,
instable and undergoes base-catalysed dehydration to yield the unsaturated product.

LIST OF APPARATUS AND CHEMICALS

 50 mL Erlenmeyer flask
 Glass rod
 100 mL beaker
 Distilled water
 Buchner funnel
 Spatula
 Vacuum filtration
 3-nitrobenzaldehyde
 Acetophenone
 95% ethanol
 Sodium Hydroxide (NaOH) solution
 Hot Methanol
PROCEDURE

1. 0.7503 g of 3-nitrobenzaldehyde was mixed with 0.6 mL acetophenone and 4 mL of 95%

ethanol in a conical flask. The mixture was stirred until the entire solid is dissolved.

2. 0.5 mL of sodium hydroxide solution (6 g NaOH solid in 10mL water) was added into the
mixture and the stirring process continued.

3. 10 mL of ice water was added and scratching was performed to induce to crystallization
process.

4. The mixture then was transferred into a beaker containing 15 mL of ice water.

5. The mixture was filtered to collect the solid by using Buchner funnel filtration set.

6. The solid collected was allowed to dry in oven with temperature of about 80°C for 30
minutes. The weight of the solid product was recorded.

7. The entire solid was recrystallized with 20 mL hot methanol solution, and the solid was
filtered again. The solid was dried again in oven at temperature of about 80°C overnight to
make sure complete drying process.

8. The dried solid product (3-nitrochalcone) was weighed and the percentage yield was
calculated.

9. The melting point and NMR test were done with the solid product (3-nitrochalcone).
RESULT
CALCULATION :
Molar mass of acetophenone = 120 g/mol
Molar mass of 3-nitrobelzaldehyde = 151 g/mol
Molar mass of 3-nitrochalcone = 253 g/mol
Density of acetophenone = 1.03 g/cm3
0.75 𝑔
Mol of 3-nitrobenzaldehyde = = 0.004967 mol
151 𝑔/𝑚𝑜𝑙

0.6 mL of acetophenone = 0.6 cm3 of acetophenone

Mass of acetophenone = 0.6 cm3 × 1.03 g/cm3 = 0.618 g
0.618 𝑔
Mol of acetophenone = = 0.00515mol
120 𝑔/𝑚𝑜𝑙

Limiting reagent: 3-nitrobenzaldehyde

Theoretical yield = 0.004967 mol × 253 g/mol = 1.2667 g

OBSERVATIONS :
 Colorless solution turns to reddish yellow and the precipitate form after the addition of
sodium hydroxide solution.

Mass of product (3-nitrochalcone) = 0.7503 g

Melting point of product (3-nitrochalcone) =140 °C
𝑎𝑐𝑡𝑢𝑎𝑙
Percentage yield = × 100%
𝑡ℎ𝑒𝑜𝑟𝑒𝑐𝑡𝑖𝑐𝑎𝑙
0.7503
Percentage yield of the product (3-nitrochalcone) = × 100% = 59.23%
1.2667

Signal Chemical Shift (ppm) Frequancy (Hz)

1H doublet
DISCUSSION

From the experiment, the limiting reagent is the 3-nitrobenzaldeyde. The theoretical mass is
calculated by referring to the mole of the 3-nitrochalcone. From the result obtained, the product
seems to be pure enough by comparing the actual melting point, 140°C with the theoretical melting
point that around 146°C. Errors may occur during the filtration process by using the Buchner
funnel vacuum filtration. The pressure used to collect the solid is too high until the filter paper
form holes that can pass through the solid with the liquid into the conical flask. This then will
make the actual yield mass will decrease. To make sure there is no error in weighing the product,
the solid must be dry at least overnight to evaporate all the water moisture
From the NMR result the 1H doublet signal was observed with frequency of Hz. From the
literature review, the frequency of signal for trans compound is between Hz, so that it is
proven that the compound yield is that trans-compound. This frequency is compared to cis-
compound frequency that is lower, Hz.

CONCLUSION
The product yield from this experiment is 3-nitrobenzaldehyde that proven with the H1 NMR
spectrum. The percentage yield of the crude product obtained is 59.23% and the melting point of
the product is 140 °C.
QUESTIONS
1. Give a mechanism for the preparation of the appropriate benzalacetophenone using the
aldehyde that you selected in this experiment.

2. Draw the structure of the cis and trans isomers of the compound that you prepared. Why
did you obtain the trans isomers?
3. Using proton NMR, how could you experimentally determine that you have the trans
isomer rather than the cis one? (Hint: Consider the use of coupling constants for the vinyl
hydrogens)

4. Provide the starting materials needed to prepare the following compounds

O
||
a. CH3CH2CH=C ̶ C ̶ H
|
CH3

CH3
\
b. C=CHC ̶ CH3
∕ ||
CH3 O
REFFERENCES
 T.W. Graham Solomons, Craig B. Fryhle, Organic Chemistry, Asia, John Wiley and Sons,
2011.
 Aldol condensation, 16/11/2014, http://en.wikipedia.org/wiki/Aldol_condensation.
 Chalcone, 16/11/2014, http://en.wikipedia.org/wiki/Chalcone.