CHM 556

ORGANIC CHEMISTRY II
EXPERIMENT 4: THEALDOL CONDENSATION REACTION:
PREPARATION OF BENZALACETOPHENONES (CHALCONES)

NAME
AMAR SAFWAN BIN MOHD ALI HANAPIAH (2015272222)
LAB PARTNER
SALMA IZZATI BINTI SINAR MASHURI (2015839778)
NURUL SHAZREENA BINTI ZULKAFLY (2015258246)
CLASS: AS2453D1
LECTURES NAME: PN. NUR VICKY BIHUD

LABORATORY REPORT MARKING SCHEME

Objective of the Experiment

Introduction
Experimental Procedure
Results and Observations
Calculations
Discussion
Conclusion
Answers to Questions
References
Pre-laboratory preparations
Laboratory techniques
Total Marks

Full
Marks
Mark(s) (to be filled by lecturer)
1.0
2.0
1.0
3.0
3.0
2.0
1.0
3.0
1.0
2.0
1.0
20

Objective
Performing

aldol

condensation

reaction

between

3-nitrobenzaldehyde

and

acetophenone in the presence of base (ethanol) to produce an , -unsaturated ketone (3nitrochalcone) and calculate the percentage yield of the crude and purified product and obtain
the NMR spectrum for the pure product.
Introduction
An aldol condensation is an organic reaction in which an enol or an enolate ion reacts
with a carbonyl compound to form a -hydroxyaldehyde or -hydroxyketone, followed by a
dehydration to give a conjugate enone. Benzaldehyde reacts with a ketone in the presence of
base to give , -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 -carbon to form an enolate ion, which
attacks the carbonyl carbon of the aldehyde to yield, after protonation, , -hydoxy ketone.
The intermediate is, for aromatic aldehyde at least, instable and undergoes base-catalysed
dehydration to yield the unsaturated product.

Aldol condensations are important in organic synthesis, providing a good way to form
carboncarbon bonds. For example, 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.

Procedure
1. 0.7515g of 3-nitrobenzaldehyde was mix with 0.6mL acetophenone and 4mL of 95%
ethanol in a conical flask. The mixture was stirred until the entire solid is dissolved.
2. 0.5mL of sodium hydroxide solution (6g NaOH solid in 10mL water) was added into
the mixture and the stirring process continued.
3. 10mL of ice water was added and scratching was performed to induce to
crystallization process.
4. The mixture then was transferred into a beaker containing 15mL 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 80C for
30 minutes. The weight of the solid product was recorded.
7. The entire solid (1.0633g) was recrystallized with 42.5mL hot methanol solution,
and the solid was filtered again. The solid was dried again in oven at temperature of
about 80C 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).

Calculation:
Molar mass of acetophenone = 120g/mol
Molar mass of 3-nitrobelzaldehyde = 151g/mol
Molar mass of 3-nitrochalcone = 253g/mol
Density of acetophenone = 1.03g/cm3
Mol of 3-nitrobenzaldehyde =

0.75 g
151 g/mol

= 0.004967mol
0.6mL of acetophenone = 0.6cm3 of acetophenone
Mass of acetophenone = 0.6cm3 1.03g/cm3
= 0.618g
Mol of acetophenone =
= 0.00515mol

0.618 g
120 g/mol

Result and observation:

i.

Observation
Colourless solution turns to reddish yellow and the precipitate
form after the addition of sodium hydroxide solution.

Description
Weight of 3-nitrobenzaldehyde
Weight of crude solid
Weight of crude solid to recrystallize
Weight of dry pure product

Weight (g)
0.7555
1.9171
0.500
0.2513

Mass of product (3-nitrochalcone) = 0.2513g

Melting point of product (3-nitrochalcone) =57 C

Percentage yield =

mass of product
molar mass of product
mass ofstarting material
molar mass of starting material
0.2513 g
253 g /mol
0.7555 g
151.12 g /mol

x 100%

x 100%

= 19.88%

ii.

NMR result for chalcone

Signal
1H doublet

Chemical shift (ppm)

7.84-7.71

Frequency (Hz)
15.6

Discussion

The result for melting point that obtain from the experiment is 57 oC, and the melting
point from the reference is 146oC. It is due to some error while handling this experiment.
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 15.6Hz. From the literature review, the
frequency of signal for trans compound is between 12-18Hz, so that it is proven that the
compound yield is that trans-compound. This frequency is compared to cis-compound
frequency that is lower, 6-12Hz. There some error in the integration of this NMR peaks based
on the result that obtain. It is due to some human error during run the sample in NMR. To
overcome this error, when run the sample in the machine need to follow the procedure to
avoid the error in integration of NMR peaks. The mechanism of this reaction is show on
below:

O H

CH 2

CH3

O
CH 2

O
O

O
O

N aO H

OH

O
4

-H 2O

OH

Reference:
1. CHM 556 Organic Chemistry 2 lecture notes prepared by Prof.
Faujan.
2. T.W. Graham Solomons, Craig B. Fryhle, Organic Chemistry, Asia,
John Wiley and Sons, 2011.
3. Aldol
condensation,

16/11/2014,

http://en.wikipedia.org/wiki/Aldol_condensation.
4. Chalcone, 16/11/2014, http://en.wikipedia.org/wiki/Chalcone.