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Organic Chemistry 1 Laboratory

4
th
Quarter SY 13-14

Experiment 10 | Group 3 | 10 June 2014 Page 1

ISOMERIZATION OF AN ALKENE
Martin, Marilen
1
, Lovenia, Melden D.
2
1
Professor, School of Che-Chm-BE-MSE, Mapua Institute of Technology;
2
Students, Chm145L/A41, School of Che-Chm-BE-
MSE, Mapua Institute of Technology

ABSTRACT
The experiment was conducted to accomplish the following objectives. The first objective aims to synthesize
an isomer of alkenes. This was done by converting maleic acid to fumaric acid. This conversion was
accomplished by applying a heat-catalyzed reaction on maleic acid diluted in distilled water and mixing it
with HCl using a reflux set-up. A reflex set up is a distillation set up wherein the set up differed because it is
inverted vertically. This was done in order to break the pi bond to allow the rotation about the remaining
sigma bond since rotation about a pi bond is not possible. After the acid has been refluxed, a white
precipitate has formed and the solution was filtered using a Buchner funnel. Where the product had been
tested for melting point and calculated its percentage yield.
Keywords : Reflux set up, isomerization of alkenes
INTRODUCTION
Isomers which differ only in the orientations of
substituents around a carbon to carbon double bond
are known as geometric isomers. When a pair of
identical groups is attached to the central carbon with
the double bond it could be classified as cis or trans.
The classification of the cis and the trans
stereoisomer are basically relative to the position of
the identical substituents attached to the given carbon
double bond.
Since the rotation about a double bond is not possible,
conversion of geometric isomer into another form of
isomer is possible only by breaking the pi bond and
then rotating about the remaining sigma bond. This
shows that geometric isomers are not interconvertible
and different from conformational isomers.
Breakage and rotation of bonds, forming a new form
of the substance can lay effects on the chemical.
Since orientation of the initial group was changed,
the relative properties of the isomer also changed,
these are the melting point, the boiling point and the
solubility. This is because there is now huge
differences in the structure of the compound since it
undergo breakage and rotation of bonds.



In the experiment the isomerization of alkenes was
exhibited by the maleic acid forming the fumaric acid.
A set up known as reflux set up was used to
transform the maleic acid to the fumaric acid and this
process was catalyzed by heat.
METHODOLOGY
A reflux set-up was assembled using a condenser, a
pear-shaped flask, an iron clamp, iron stand, a hot
plate, and a cotton stopper. 1 g of maleic acid was
dissolved in the pear-shaped flask using 1.5 ml of
distilled water. This mixture was then added with
1.25 ml of concentrated HCl. The mixture was then
refluxed for 30-45 minutes. The solution was
allowed to cool and it was filtered using a Buchner
funnel. The solid was air dried and its weight was
determined. A portion of the solid was taken for
melting point determination.




Organic Chemistry 1 Laboratory
4
th
Quarter SY 13-14

Experiment 10 | Group 3 | 10 June 2014 Page 2

RESULTS
Table 1.1
Melting point
(sample)
140-
144 °C
Color of product White
Meling point
(product)
296-
298°C
% yield of product 83.2 %
Weight of maleic
acid
1.00 g
Weight of by-
product
0.168g
Weight of product
0.832
% yield of the by-
product
16.8%

Observations:

 A cloudy solution formed (mixture of maleic
acid, water and concentrated HCl).

 Formation of precipitate slowly occurred as
the solution started to boil.
 Heat is directly proportional to the rate of
the reaction.
Mechanism:

DISCUSSION
As seen above, the melting point of the sample which
is maleic acid, was 144 degrees Celsius and when it
was converted to fumaric acid through the reflux set
up accompanied by the heat that catalyzed the
reaction, the melting point of the fumaric acid
became 296 degrees Celsius thus, having a huge
difference between the two boiling points.
Considering the isomers, given are two chemicals,
with both chemical formula and molecular weight.
Having the bonds broken and single bonds rotated,
the sample was then converted to another substance
which is the fumaric acid, which had different
structural orientations that made the boiling point and
melting points different.
Considering the weight of maleic acid, 1 g, and the
weight of fumaric acid, 0.832 g. The conversion of
maleic acid to fumaric acid theoretically should yield
also to 1 g because they both have the same
molecular weight and also having one is to one ratio
for the maleic acid and the fumaric acid. But of
course, the pure maleic acid used became impure due
to different factors. Making the yield about 83.2 %,
but it can be deduce through the data that the
isomerization of the given maleic acid should more
or less result into a high percentage yield.
Considering the observations made the mixture of
maleic acid, water and the concentrated HCL formed
a cloudy solution upon mixing together. The
formation of the precipitate slowly occurred as the
solution started to boil, because the reaction is
catalyzed by heat. The higher the heat the faster the
reaction would be or heat is directly proportional to
the rate of the reaction.
CONCLUSION AND RECOMMENDATION
Isomers which differ only in the orientations of
substituents around a carbon to carbon double bond
are known as geometric isomers. In the experiment,
geometric isomerism was displayed by the maleic
acid and the fumaric acid.
Having the results of the experiment, the boiling
point and the melting point of the sample greatly
differed from the product although both posses the
same molecular formula and molecular weight. This
Organic Chemistry 1 Laboratory
4
th
Quarter SY 13-14

Experiment 10 | Group 3 | 10 June 2014 Page 3

is because, the conversion of geometric isomer into
another form of isomer is possible only by breaking
the pi bond and then rotating about the remaining
sigma bond making the initial chemical form another
isomer which have different structural orientation
that could make the boiling and melting point
different.
Since the chemical underwent breakage and rotation
of bonds just to make a new isomer, the initial
properties of the chemical would change including
the melting and the boiling points and of course the
solubility would change as well.
To conclude the experiment, alkenes are organic
compounds that have at least a carbon-carbon double
bond. Although some alkenes have the same number
of atoms and molecules in their structure, some may
have a different configuration leading up to different
chemical properties.

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