Titles:

Properties of hydrocarbons

Objectives:

To study the chemical properties of hydrocarbons.

To differentiate between saturated and unsaturated hydrocarbons.
To investigate the reactivity of saturated and unsaturated hydrocarbons.

Theory:
Hydrocarbons are compounds that comprised of hydrogen and carbon only. Hydrocarbon are
widely varied depending on their structure and can be classified into several group. Aliphatic
hydrocarbons are divided into three classes. Firstly is alkane, have only single bonds and are
said to be saturated. Secondly are alkenes and thirdly are alkynes have carbon-carbon double
bonds or triple bonds are said to unsaturated. Aromatic hydrocarbons are cyclic compounds
whose structure is related to that of benzene with six-electrons in a six-membered ring.
For this experiment, n-hexane was used as an example of saturated hydrocarbon, cyclohexene
was used as an unsaturated hydrocarbon and toluene as an aromatic hydrocarbon. These three
hydrocarbons are reacted differently toward the same reagent or condition, in which case it
may be used to distinguish between them. Three methods that used to determine the
properties of hydrocarbons are combustion, reaction with Bromine (Br2) and reaction with
Potassium Permanganate (KMnO4).
Results:
Chemical reaction of hydrocarbons
1. Combustion

Appearance of
flame
Duration for the
flame to diminish
Condition of
evaporating dish

n-hexane
Vigorous bright
orange flame
Very short time to
diminish
Slight amount of
black residue at the
mouth of dish

Cyclohexene
Bright orange flame
Diminishes after
hexane
More black residue
around the
evaporating dish

Toluene
Very sooty orange
flame
Longer time to
diminish
Heavy black residue
all over the
evaporating dish

cyclohexene
Brown colour of
bromine turns
colourless

toluene
Brown colour of
bromine remain
unchanged

Brown colour of
bromine turns
colourless

Brown colour of
bromine remain
unchanged

2. Reaction with Bromine

(A). In the presence of light
Presence of light

Absence of light

n-hexane
Brown colour of
bromine turns
colourless after a few
minutes
Brown colour of
bromine remain in
the same condition

3. Reaction with Potassium Permanganate

Substances
Hexane
Toluene
Cyclohexene
Unknown liquid A
Unknown liquid B

Observations
No visible colour change of purple potassium permanganate.
No visible colour change of purple potassium permanganate.
Purple colour of potassium permanganate decolourized.
Brown colour precipitate formed.
No visible colour change of purple potassium permanganate.
No visible colour change of purple potassium permanganate.

Discussion:
Hydrocarbon is an organic compound that consists of hydrogen and carbon only and
is being sourced from crude oil on Earth. Hydrocarbon can divided into two types aliphatic
and aromatic hydrocarbons. Aliphatic hydrocarbons contains alkanes; have only single bond
and said to be saturated, alkenes and alkynes; contains double or triple bond and said to be
unsaturated, whereas aromatic hydrocarbons are cyclic compounds which evolves around
benzene, a compound of six-membered ring and six-electrons.
In this session of laboratory, an investigation on the reactivity of a selected hydrocarbon was
conducted. Among the selected hydrocarbons are hexane as an representative for alkane as
saturated hydrocarbon, cyclohexene as representative for alkene as unsaturated hydrocarbons
and toluene as representative for aromatic hydrocarbons. Several reactions that were used to
test the reactivity of these chemicals are combustion, reaction with bromine water and
reaction with potassium permanganate.
Firstly, combustion was carried out to test the reactivity of these compounds. From the results
obtained, it observed that hexane, cyclohexene and toluene burns incompletely in air with a
sooty flame. This phenomena is due to the high percentage bymass of carbon present in the
hydrocarbons. The interpretation is as below;
Percentage of carbon in hexane:

[6(12)/6(12)+14(1)] x 100%= 83.71%

Percentage of carbon in cyclohexene:

[6(12)/6(12)+10(1)] x 100%= 87.80%

Percentage of carbon in toluene:

[7(12)/7(12)+8(1)] x 100%= 91.30%

From the calculation above, it is obvious that toluene is more saturated in carbon mass
followed by cyclohexene and hexane. This caused the excessive amount of soot residue left in
the evaporating dish at the end of combustion of toluene.
Secondly, bromine test was conducted on these hydrocarbons. It is observed that
bromine water remained unchanged with and without the presence of light due to absence of
double bonds or triple bonds to undergo addition reaction of halogens. Cyclohexene, on the
other hand reacts with bromine in the presence of light as well as without the presence of
light as it has double bond area to accommodate bromine. Thus this will decolourise the
bromine solution at once. Hexane, is conditionally reactive when in the presence of light,
where bromine solution was decolourized by the free-radical substitution mechanism.
Therefore, when kept in dark, no reaction takes place as no energy is supplied to carry out the
fission of bonds.

Halogenation of alkanes is by a free-radical mechanism. Free radicals are formed by

hemolytic fission of the bromine molecule. The Br-Br bond cleaves in a symmetrical way, so
that each bromine atom retains its own electron from the shared pair. Energy from UV light is
needed to carry out the fission. Free radicals are actually bromine atoms. The bromine radical
which is also a bromine atom with seven electrons is extremely reactive because of its
urgency to complete its octet. When bromine is exposed to light and heat, it will break into
two bromine radicals. These radicals will abstract hydrogen atom from hexane molecule to
hydrogen bromide and producing hexane radical, this reaction continues and eventually
decolourize the bromine solution
In alkenes however, addition of halogens occurs as there are presence of double bonds or
triple bonds. When cyclohexene reacts with bromine in tetrachloromethane, reddish colour of
bromine turns colourless immediately. According to the mechanism of electrophilic addition,
although the bromine molecule is non-polar, random movements of electrons within the
bromine molecule may cause an unsymmetrical distribution of electrons at one end of the
molecule. Even though this occurs only for a short while, a small dipole is formed. This
momentary dipole alters the electron distribution of neighboring bromine molecules. The
momentary bromine dipole is said to induce an oppositely-oriented dipole to its surrounding
bromine molecules. The partially-charged positive ends of the momentary and induced
bromine dipoles will behave as electrophiles to attack the double bond of alkene. Thus the
first step for the electrophilic addition mechanism is to attack an electron-seeking reagent ar
electrophiles. The C=C bond is the reactive site that supplies the electron. This has caused the
adjacent C atom to lose its electron in the shared pair and to consequently become C+. A
positively charged C atom is called a carbonium ion. There is a pair of bonding electrons in
the bromine molecule being transferred to the Br- atom. This gives the Br- atom another
electron besides its own electron contribution to the bonding pair. The Br- atom breaks away
as the Br- ion. Then, Br- ion will combine with the carbonium ion to form 1,2dibromocyclohexane.
Finally, test with potassium permanganate was carried out on these hydrocarbons. Only
cyclohexene shows positive test results for this test. Cyclohexene readily decolourize the
purple colour of the potassium permanganate due to the presence of the double bonds in the
cyclohexene. This phenomena occurs because cyclohexene is unsaturated hydrocarbon and
addition reaction reaction prominently occurs at this region. Thus, cyclohexene is oxidized
into glycols. This decolourize purple colour of permanganate solution and the reaction creates
the Baeyers Test.
While conducting this experiment several precautionary steps need to be taken into
consideration for an enhanced environment. All combustion experiments was conducted in
the fume chamber, the bromine solution was dispensed in the fume chamber as it is strong
oxidizing agent. Lastly, all hydrocarbon was covered with stopper to avoid from being
evaporated.

Conclusion:
The reactivity and the properties of the hydrocarbons was studied.
The saturated and unsaturated hydrocarbon was differentiated.

UNIVERSITI TUNKU ABDUL RAHMAN

FACULTY OF SCIENCE
BACHELOR OF SCIENCE (HONS) BIOCHEMISTRY
YEAR 1 TRIMESTER 3
UDEC1164 ORGANIC CHEMISTRY

NAME

SRI SANGLISWARAN S/O SUBRAMANIAM

ID

1203776

EXPERIMENT

PROPERTIES OF HYDROCARBON

DATE

21 JANUARY 2015

COMBUSTION

Unkno
wn B

Cyclohxe

Tolue
hexan

Unkno
wn A

Bromine test