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OBJECTIVES:

 To study the aldol condensation reaction between a substituted benzaldehyde and a


ketone in presence of α, β- unsaturated ketone
 To determine the percentage yield, melting point and NMR spectrum of 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, 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-
hydoxyketone. The intermediate is, for aromatic aldehyde at least, instable and undergoes
base-catalysed dehydration to yield the unsaturated product

.
PROCEDURE:

1. 0.7501g of nitrobenzaldehyde was mix with 0.6mL acetophenone and 4mL of 95%
ethanol in a 50mL 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 80°C for 30
minutes. The weight of the solid product was recorded.
7. About 0.5g of the solid product was recrystallized with 20mL 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 was weighed and the percentage yield was calculated.
9. The melting point and NMR test were done with the solid product.

RESULT:

Mass of nitrobenzaldehyde (g) 0.7501


Mass of filter paper (g) 0.6747
Mass of watch glass (g) 36.2481
Mass of product + filter paper + watch glass 38.3675
(g)
Mass of product 1.4447
Melting point of product (°C) 142

CALCULATION:

Molar mass of acetophenone = 120.15g/mol

Molar mass of nitrobelzaldehyde = 151.12g/mol

Molar mass of chalcone = 208.26g/mol

Density of acetophenone = 1.03g/cm3


Mol of nitrobenzaldehyde =0.7501g/151.12 g/mol = 0.004963mol

Theoretical yield = 0.004963mol × 208.26g/mol = 1.0335g

Percentage yield = actual/theoretical × 100%

Percentage yield of the product (chalcone) = 0.7501g/1.0335g × 100% = 72.57%

DISCUSSION:

In this experiment, 0.7501 of nitrobenzaldehyde was used to prepare


benzalacetophenones (Chalcones). The theoretical mass is calculated by referring to the
mole of the chalcone. From the result obtained, the product seems to be pure enough by
comparing the actual melting point, 142°C with the theoretical melting point that around
146°C. The percentage yield of the product chalcone is72.57%.

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.

QUESTION:

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 isomer?

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)
The difference between Cis and Trans isomers can be determined by the help of coupling
constants in the 1H NMR spectra. If it is a trans the J-Coupling constant of the
unsaturated protons in the spectrum shows nearly 13-16 Hz, and it is nearly 10-12 in
case of Cis isomers

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

O

a) CH3CH2CH=C-C-H
l
CH3
b) CH3
C=CHC-CH3

CH3 O

O
c) Ph ‖
C=CH-C-Ph
CH3
O
d) ‖
CH3O CH=CH-C-CH=CH OCH3

O

e) O2N-Ph-CH=CH-C-Ph-Br
O

f) Cl-Ph-CH=CH-C

NO2

CONCLUSION:

In conclusion, we can study the aldol condensation reaction between a substituted


benzaldehyde and a ketone in presence of α, β- unsaturated ketone. We can also determine
the percentage yield which is 72.57%, melting point that is 142° and NMR spectrum of
product (chalcone).

REFERENCES:

https://www.scribd.com/doc/249342064/THE-ALDOL-CONDENSATION-REACTION-
PREPARATION-OF-BENZALACETOPHENONES-CHALCONES (accessed on Nov 23,
2018)

http://en.wikipedia.org/wiki/Aldol_condensation (accessed on Nov 23, 2018)

http://en.wikipedia.org/wiki/Chalcone (accessed on Nov 23, 2018)