CHM145L Organic Chemistry 1 Laboratory

2nd Quarter SY 2014-2015

PREPARATION AND CHARACTERIZATION OF ALKENE

Miranda, Marilyn1, Ancot, Rachel, C2,
Professor, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; 2CHM145L/C21, School of Chemical Engineering, Chemistry
and Biotechnology, Mapua Institute of Technology
1

The experiment aimed to prepare cyclohexene from cyclohexanol and know the properties of alkene. Alkenes are
chains of hydrocarbons with at least one c=c bond in their structure. They are more saturated than alkynes but are
less saturated than of those alkanes because the alkenes only have double bonds. Some of the characteristics of
alkenes are: it has lower boiling point than of the corresponding alkane, it only shows Van der Waals interaction
which is dependent on the shape of the molecule and the number of electrons it contains, an alkene has two fewer
electrons than the alkane with same number of carbons and lastly, an alkene is insoluble in water but is soluble in
most organic solvents. Dehydration of the alcohol was involved in the preparation of the alkene. 1,2- or elimination reaction was involved for the dehydration process. When alcohols are heated with strong acids,
alcohols typically undergo a 1,2-elimination reactions to generate alkene and water. Reaction of secondary or
tertiary alcohols usually proceeds via an E1 mechanism in which generates a carbocation intermediate which can
undergo a rearrangement. Primary alcohols will proceed via an E2 mechanism since the primary carbocation is
highly unfavorable. In this experiment, the cycloalkene was prepared through the said mechanism. In order to
achieve the dehydration, anhydrous calcium chloride was used which is responsible in the removal of water. Then
the prepared cycloalkene was then characterized by its properties such as the flammability, solubility against water,
bromination, oxidation with the potassium permanganate and sulfur acid test.
Keywords:

E1

mechanism,

E2

mechanism,

cyclohexanol,

cyclohexene,

1,2-

or

-elimination,

dehydration

INTRODUCTION
Alkenes are unsaturated hydrocarbons with one double
bond between two carbons from a homologous series with
the general formula CnH2n where n is the number of
carbons. Alkenes follow the naming convention of the
alkanes but this time a suffix ene is used instead of an
ane. There are many comparisons between alkanes and
alkenes few are: (1) alkenes are more reactive than alkanes
because of its reactive double bond wherein the pi
electrons were not as fully under the control of the carbon
nuclei as the electrons of sigma bond and because they lie
exposed above and below the rest of the molecule. They
are relatively open to attack by other molecules making
them more reactive. (2) Alkenes boiling point is lesser by a
few degrees than that of the alkanes and alkenes have 2
less electrons than that of the alkane with the same number
of carbon
An alkene is any of the series of unsaturated hydrocarbons
containing a double bond. Alkenes contain a double bond
that is composed of one sigma and one pi bond between
two carbon atoms. The sigma bond has similar properties to
those found in alkanes, while the pi bond is more reactive.
The carbon atoms in the double bond are sp2hybridized,
forming a planar structure. Rotation around the double is

Experiment 09 Group No.1 November 27, 2014

disfavored, so alkenes form fairly stable isomers depending

on the positioning of substituents on the same (cis) or
opposite (trans) sides of the double bond. These isomers
are diastereoisomers.
The melting and boiling points of alkenes are determined by
the regularity of the packing of these molecules. Alkene
isomers that can achieve more regular packing have higher
melting and boiling points than molecules with the
same molecular formula but weaker dispersion forces.
Alkenes are non-polar, and they are both immiscible in
water and less dense than water. They are generally
soluble in organic solvents. In addition, they do not conduct
electricity.
Alkenes can be produced through the dehydration of their
respective aliphatic alcohols.
Alkenes are more reactive than their related alkanes due to
the relative instability of the double bond. They are more
likely to participate in a variety of reactions including
combustion,
addition, hydrogenation,
and halogenation reactions. Alkenes can also be reacted,
typically in the presence of a catalyst, to form polymers.
In this experiment an alkene, which is the cyclohexene, will
be prepared by dehydration of an alcohol, which is the

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CHM145L Organic Chemistry 1 Laboratory

2nd Quarter SY 2014-2015

cyclohexanol. Dehydration of an alcohol is done to remove

any water from the solution. This experiment is done with
the aid of phosphoric acid and sulfuric acid. These two
acids serve as the acid catalysts. This is one of the most
common methods of preparing alkenes. The crude product
is contaminated with water, unreacted alcohol, phosphoric
acid and some side products. Washing with water removes
most of the impurities.

Solubility
It changes color into dark orange
Bromination
Dark/ black precipitate formed.
Oxidation
Sulfuric Acid

Heat evolved in micro test tube and

change its color to orange.
REACTIONS INVOLVED

MATERIALS AND METHODS

For the preparation of cyclohexene, 6.0 mL of cyclohexanol
was mixed with 1.50 mL of 85% phosphoric acid and 0.25 L
of sulfuric acid inside a pear-shaped flask. The solution was
heated until small amount of the original solution remained
in the flask. The hydrocarbon layer of the distillate was
obtained and was washed with cold water. This process is
called extraction. The hydrocarbon layer was then dried
with small amount of anhydrous calcium chloride for about
6 minutes. The solid was allowed to settle down. The liquid
portion of the mixture was then gathered and was filtered
using quick fit filter funnel.
The same procedure did earlier was repeated again, this
time using the gathered liquid portion from the previous
mixture. The distillate was collected between the
temperature ranges of 82 to 85 degrees Celsius.
For the determination of the properties of the prepared
cyclohexene, the compound was tested for its flammability,
solubility, bromination, oxidation and the sulfuric acid test.

Br

Br
Br

Scheme 9.2 Bromination

OH

KM nO

COOH

COOH

OH

Scheme 9.3 Oxidation

H
O

H
O

Boiling Point of
Cyclohexene

78C82C

Weight of
Cyclohexanol
Actual Yield of
Cyclohexene

5.808 g

Scheme 9.4 Sulfuric Acid Test

1.06 g

Theoretical
Yield of
Cyclohexene
Mole of
Cyclohexene
Percentage
Yield

4.7633 g
0.0580 mol

COMPUTATION
I Weight of the Cyclohexanol

22.25%

II Properties of Alkene
TESTS
Flammability

S
O

I Preparation of Cyclohexene

OBSERVATIONS
Flammable and produces a yelloworange flame color
Insoluble in water

Experiment 09 Group No.1 November 27, 2014

Br

RESULTS

Scheme 9.1 Flammability Test

RESULTS and DISCUSSIONS

II Moles of Cyclohexene

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O
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CHM145L Organic Chemistry 1 Laboratory

2nd Quarter SY 2014-2015

reversible);
2.

by losing a proton to yield cyclohexene;

3.

with cyclohexanol to yield dicyclohexyl ether.

III Theoretical Yield

IV Percentage Yield

Dicyclohexyl ether then is a probable side product of the

dehydration of cyclohexanol. It is immiscible with water is
likely to co-distill and may therefore be present in the first
distillate. To remove dicylcohexy ether completely a second
distillation of the product is usually carried out.
DISCUSSION
These should be the result of the experiment but at some
point we were not able to synthesize cyclohexene and for
this mistake will be discuss on recommendation part.

In this experiment an alkene (cyclohexene) was prepared

by dehydration of an alcohol (cyclohexanol) using an acid
catalyst such as phosphoric acid. This is one of the most
common methods of preparing alkenes.

The crude product was contaminated with water, unreacted

alcohol, phosphoric acid and some side products. Washing
with water removes most of the impurities. Treatment with
sodium carbonate solution removes traces of acid and a
final wash with water removes any remaining carbonate.
The mechanism of the dehydration of cyclohexanol
probably involves the formation of a carbocation.
This carbocation can react in any of the ways shown below:

Figure1. Mechanism for the preparation from cyclohexanol to

cyclohexene

The anhydrous calcium chloride is an inorganic drying

agent that binds strongly with water and thus removes any
traces of water from the solution. Also, it removes water in
cyclohexene since CaCl2 can form hydrate complex.
Since alkenes are generally flammable, the cyclohexane
showed positive result in the flammability test and it gave a
yellow orange flame color. Combustion reaction was
involved.

1.
With water to yield cyclohexanol - the starting
material. (Note that all the steps in this reaction are

Experiment 09 Group No.1 November 27, 2014

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CHM145L Organic Chemistry 1 Laboratory

2nd Quarter SY 2014-2015

Brominarion of cyclohexene proceeds with the antistereochemistry. The two bromine atoms add to opposite
faces of the alkene and there are no syn products and
rearrangements observed. Syn addition is the addition of
two substituents to the same side (or face) of a double bond
or triple bond, resulting in a decrease in bond order but an
increase in number of substituents. Also in bromination, no
carbocation intermediate are formed and it can be
intercepted by nucleophilic solvent in which the attack
occurs at most substituted carbon of the original alkene.
The change in the color of the mixture indicates that the
reaction takes place.
For the solubility test, cyclohexene is insoluble in water.
Hydrocarbons are non-polar. Water is polar. So from like
dissolves like you wouldnt expect this to be very soluble in
water.
In the oxidation test, precipitates are evident because
the structure contained multiple bonds. In alkaline solution,
the potassium permanganate would turn green followed by
the formation of a brown precipitate of MnO 2, which is an
alkene that can undergo substitution reaction by cleaving
the double bonds. Because of the cleavage of the double
bonds, it will produce a 6 carbon chain (assuming only one
double bond is present) with carboxylic acids on the ends.
Alkenes react with concentrated sulfuric acid in the cold
to produce alkyl hydrogensulphates. In the reaction
between sulfuric acid and cyclohexane, electrophilic
addition reaction was involved. In this reaction, the pi bond
breaks and the pair of electrons is used to form a bond with
the hydrogen atom; and the electrons in the hydrogenoxygen bond are pushed on to the oxygen atom giving it a
full negative charge. The lower carbon atom in the original
C=C bond becomes positively charged because the
electron it originally supplied to the pi bond has been
moved away to form the new bond.

produced heat but the compounds did not mix, they formed
two layers.
Alkenes are extremely useful because they lead into
production of materials which are needed in everyday life
such as plastics, fuels, illuminants and polymers. Due to
this demand for alkenes many ways for the preparation of
alkenes are made and this includes acid catalyzed
dehydration of an appropriate alcohol which is commonly
used in laboratory preparation of alkenes and passing of
vapor of the alcohol over hot illumine which is commonly
used for large scale preparation of alkenes for industrial
purposes.
For recommendation, collecting of distillate at 130C-140C
of cyclohexanol and maintaining its increasing temperature
should be properly observed. Also, in any distillation, unless
precautions are taken, some of the product will be lost as
hold-up in the apparatus. Hold-up would result in a reduced
yield of product.
REFERENCES
1. Pavia, Donald L.. Introduction to organic
laboratory techniques: a microscale approach.
4th ed. Belmont, CA: Thomson Brooks/Cole,
2007. Print.
2. McMillen, D.W., Grutzner, J.B., Radical
Bromination of Cyclohexene in CCl4 by Bromine:
Addition versus Substitution. The Journal of
Organic Chemistry.
3. Clayden, Jonathan. Organic chemistry. Oxford:
Oxford University Press, 2001. Print.
4. Taylor, Peter. Alkenes and aromatics.
Cambridge, UK: Royal Society of Chemistry :,

CONCLUSIONS AND RECOMMENDATIONS

Cyclohexane is an alkene, an organic compound that
contains at least one carbon-carbon double bond. After
preparation of the cyclohexane sample through the
distillation process, the precipitate was tested for its
properties. It was tested for its flammability, solubility,
bromination, oxidation and the sulfuric acid test. After the
test was run, it was determined that cyclohexane is
flammable, not soluble in water, it changes color in the
bromination test and produced a precipitate and in both the
bromination and precipitation. In the sulfuric acid test, it

Experiment 09 Group No.1 November 27, 2014

2002. Print.
5. Hao, J., Cheng, H., Wang, H., Cai, S., Zhao, F.
Oxidation of cyclohexaneA significant impact of
stainless steel reactor wall. ScienceDirect.com.
6. Klein, D. R., Organic Chemistry. John Wiley &
Sons, Inc., 2010

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