Title

The production of 2.5-dibenzyalidene cyclopentanone through the aldol

reaction.

Abstract

2.5-dibenzyalidene cyclopentanone was synthesised using a base catalysed aldol

reaction. An aldehyde (benzaldehyde) and a ketone (cyclopentane) was mixed
together 95% ethanol and 2M aqueous sodium hydroxide in an Erlenmeyer
flask. The yellow crystals formed with mass of 1.94 g. the product was
recrystallized using ethanol which was heated to boil. The light-yellow crystals
were produce which in case was pure with a mass of 1.35 g. The percentage
yield of crude product is 98% with the melting point ranging from 178°C -
190°C whereas that of a pure compound is 94% with a melting point ranging
from 185°C - 191°C. Both crude and pure samples was dissolved separately
using acetone and the TLC plate was ran. The retention factor of both
compound spots was 86.

Introduction

Aldol reaction is another way to form a Carbon-Carbon bond in organic

chemistry. Mostly used is where there is a loss of water, dehydration takes place
and the alkene is formed this is called aldol condensation and is also type of
aldol reaction. Aldol reaction was discovered by a Russian Chemist named,
Alexander Borodin in 1869 and by the French Chemist, Charles-Aldophe
Wurtz. The reaction involves combination carbonyl compound (aldehydes and
ketones) to form a new β-hydroxy carbonyl compound, β-hydroxy aldehyde (or
ketone). These products are known as aldols. The word ‘aldol’ comes from
aldehyde + alcohol.

Scheme1: formation of an aldol product from two equivalent aldehydes

Aldol products are usually found in every necessarily molecules. They can
occur either naturally or they can be synthesised. Aldol products have many
application in industries, one of the mostly important is the synthesis of the
Lipitor drug (Atorvastatin Calcium) which belongs to group of HMG CoA
reductase inhibitors, it reduces levels of “bad” cholesterol and triglyrides in the
blood.

Scheme 2: synthesis of Lipitor drug

The aldol reaction is broadly divided into two types, aldol condensation reaction
an aldol addition reaction. they are all occurring in the presence of LDA that
makes an anion deprotonation of an aldehyde and it get protonated again. In the
aldol reaction, the resulting product is dehydrated after protonation. The product
synthesized is α,β-unsaturated carbonyl.

Scheme 3: condensation aldol reaction

Scheme 4: addition aldol reaction

Results

Synthesis of 2.5-dibenzylidenecyclopentane

Melting point: 191-194ºC

Molar mass: 260.33 g/mol

n = m/M and d = m/v

Criteria Aldehyde(benzaldehyde) Ketone(cyclopentane)

Volume (ml) 2.0 0.5

Density (g/ml) 1.044 0.951
Mass (g) 2.088 0.4755
Molar mass (g/mol) 106.121 84.12
Moles (mol) 0.0197 0.00565

Mole ratio is 3: 1

Benzaldehyde is the limiting reagent.

Crude product Pure products

Mass (g) 1.44 1.35

Theoretical mass of 2.5-dibenzylidene cyclopentane

M=n×M
 = 0.00565 × 260.33

=1.47

% percentage yield (crude) = actual mass (g)/ theoretical mass(g) × 100

= 1.44/ 1.47 × 100

= 98%

% percentage yield (pure) =1.35/ 1.47 × 100

= 92%

The TLC plate

Rf (crude) = distance travelled by spot (mm) / distance travelled by solvent

(mm)

=38 mm/ 44mm

= 0.86
Rf (pure) = 38 mm/ 44mm

= 0.86

Discussion

In this experiment, the synthesis of 2.5-dibenzylidene cyclopentanone occurred.

The sample was prepared from 0.5 ml cyclopentane (ketone), 2ml benzaldehyde
(aldehyde), 10ml of 95% ethanol and 7.5 ml of 2M aqueous sodium hydroxide.
The yellow crystals resulted from the mixture which is the crude product. The
reaction was conducted at room temperature. Small amount, about a full tip of a
spatula was dissolved in a glass beaker with ethanol which was heated to boil.
The mixture was cooled in ice for 10 min to allow for recrystallization, it was
then filtered using a vacuum. Again, light yellow crystals were formed which
was then pure.

The purpose of the recrystallization was to purify the product. The percentage
yield of the recrystallized product proved it very well that there were no more
impurities in the sample, this is because the percentage yield of it is smaller
compared to that of a crude product. The reason is that the product contains
some impurities. The melting point of a crude product was found to be 179ºC-
191ºC with the literature of 191-194ºC. Comparing the two temperature ranges,
they are little bit the same, this proves that the sample was well synthesised.

The crude and recrystallized (pure) samples was dissolved in the acetone
separately then they were spotted on the TLC plate. This was done to prove that
the recrystallized product is pure compared to the crude product. The
appropriate solvent (70:30 ethyl acetate) was used to run the test. The retention
factor appears the same for both compound spots as 0.86. This tells us that the
two samples are similarly polar, meaning the crude product is also pure.

As it was said earlier that the product is synthesise from benzaldehyde and
cyclopentanone using aqueous sodium hydroxide. Therefore, the reaction is a
base catalysed reaction.

The aldol reaction mechanism is:

Scheme 5

The α,β- unsaturated carbonyl is formed

 OH⁻ acts as a base it deprotonates α-hydrogen, the negatively charged α-

hydrogen attach to a carbon which is slightly positive.
 An alkoxide ion is formed by the attacking of a nucleophile to a slightly
positive carbon.
 An alkoxide deprotonates to form a hydroxide and aldol product.
 The hydroxide ion act as a base, removing α-hydrogen forming an
enolate. Water is removed and an alkene is formed.
 Double bond and hydroxide ion are generated by enolate electrons.
Scheme 6: the overall reaction for the formation 2.5-dibenzylidene
cyclopentanone

Conclusion

An aldehyde (benzaldehyde) and a ketone (cyclopentane) was reacted through

aldol reaction to produce 2.5-dibenylidene cyclopentanone. The
recrystallization of a sample was successful because the percentage yield of a
recrystallized product appears small than that of a crude product. Rf of both
samples is 0.86 meaning thy are similarly polar.

References

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