Reactions of Hydrocarbons

Rea Iriz T. Magdayo

Rocel Mae M. Lomeda
Brother Isaie Ky
Group 3
De La Salle University-Dasmarias
Dasmarias City, Cavite, Philippines

ABSTRACT
The chemical reactions observed in this experiment were used to distinguish the different characteristic of
each hydrocarbons samples. Five drops of the four given compounds are used to be tested with the
Bayers, Bromination with light and dark, and Tollens Test. Hexane and Unknown Hydrocarbon 1 are
positive only in Brominations test in light indicating that it belongs to the alkane group. While in Eugenol,
it reacted negative only in Tollens test. On the other hand, Acetylene positively reacted to all the chemical
test which signifies the characteristic of a compound belongs to alkyne group. Lastly, the Unknown
Hydrocarbon 2 obtained a negative result in Tollens test same as the sequence presented in the
Eugenol. Sample 1 was identified as Alkane and Sample 2 was Alkene. The result of the experiment were
concluded as accurate with the original result presented by the laboratory instructor and have been useful
in determining the different types of reaction of each hydrocarbon groups.

INTRODUCTION
Organic compounds are of compounds
that are produced by living organisms. Some of
these organic compounds in their raw states are
useless and toxic unless they converted into
suitable forms and some of these are carried out
by cracking that is in petroleum, and also
synthesis as in polymerization. Hence it is the
duty of chemical engineers to know the
characteristics, classes and type of reaction under
which these compounds undergo in order to convert them
into useful products. Compounded through
carbon, hydrogen, oxygen, nitrogen, Sulphur
and halogens they are divided into classes and
each of them are characterized by a functional group. A
functional group is a chemically bond atoms that
shows characteristics set of properties. Among
organic
compounds,
the
simplest
are
hydrocarbons, contained only of elements
carbon and hydrogen, are classified according to
their structure. So, hydrocarbons are divided into

Aliphatic and Aromatic hydrocarbons.

Aliphatic compounds are carbon compounds
arranged in open chains and can be straight
chained, branched and can contain single,
double or triple bonds which are respectively
Alkanes, Alkenes and Alkynes. Alkanes are of
hydrocarbons saturated and double or triple bonds
alkenes and alkynes are unsaturated. Aromatic
compounds are compounds containing close
rings of carbon atoms in which the pi-electron
are delocalized across the structure. They are
referred to as benzene ring compounds and may
also contain other atoms like oxygen and
nitrogen (4). In this experiment the various
hydrocarbons are analyzed based upon their
fundamental reactions when they are subjected
to various varieties of reagents, with the tests
such as Bayers test, Bromination test and
Tollens test, under some experimental
conditions which would be used to distinguish them,

METHODOLOGY
The various classes of hydrocarbons can be
distinguished from each other by the types of
reactions they undergo. In other words, alkanes
react differently than aromatics, alkenes, and
alkynes under the same conditions. The various
hydrocarbons also have different physical
properties. Their capacity to react with the
solvent or to change of color. For this
experiment, four compounds are subjected each
to the chemical test which concerned the
Bayers test, Bromination test (light and dark),
and Tollens test with their different reactive. And
the compounds were hexane, eugenol acetylene
and two unknowns hydrocarbons 1 and 2). For
beginning their experiment, the students have
introduced 5 drops of each sample into the four
dry test tubes. Then, one by one, they are tested
to 5 drops of each reactive. The mixture are
shacked and observed (visible + result). For
Bayers test, the reagent was potassium
permanganate (KMnO4), 5 drops per each
sample. For the Bromination test light, bromine
(Br2) was used 5 drops per each sample, and for
Bromination test dark the test tubes were
wrapped with paper and added 5 drops of
bromine then placed in the dark immediately. All
tests were subjected to five minutes of
observation. For the Tollens test, 5 drops, per
each sample, of Tollens reagent was used
(shake and observe). As another step, acetylene
generation set-up (Figure 1) was prepared and
with which preparatory funnel contained some
water and distilling flask calcium carbide (CaC2),
in which also was added a small increment of
water. This mixture was to initiate the formation
of acetylene (C2H2) which one was collected into
the each test tubes through inserting the end of
the rubber tubing after opening the pinchcock.
And some minutes for observing the reaction, it
were the process of results and identification of
the sample nature.

Visible +
result
Hexane
Eugenol
Acetylene
Unknown 1
Unknown 2

Brown
precipitate
+
++
++

(in light)
Discoloration
or formation of
gas
+
++
++
+
++

(in dark)
Discoloration
or formation of
gas
++
+
+

Silver mirror

++
-

Legend: ++ fast reaction; +

slow
reaction; no reaction.
Hexane and Unknown Hydrocarbon 1
are positive only in Brominations Test in light,
hence was classified as an alkane compound.
While in the Eugenol, an aromatic compound,
and Unknown Hydrocarbon 2 reacted negatively
in Tollens Test, indicating that it belongs to the
alkene group. On the other hand, Acetylene
positively reacted to all the chemical test which
signifies the characteristic of a compound
belongs to alkyne group. The identity of the two
unknown hydrocarbons were later on classified
as Alkane sample 1, and Alkene - Sample 2.
Hexane and Unkown Hydrocarbon 1 are
expected to react only in Bromination in light
with a reason that the alkane reacts with
halogens with the help of UV light produced by
the sun known as the substitution reaction in
which a hydrogen is removed and a halogen will
occupy the space as illustrated in the figure 2.
Figure 2. The Substitution Reaction in
Hexane and Br2.

Br

RESULTS AND DISCUSSION

Br2

The chemical testing of the four compounds

is used for determining their identity to which
hydrocarbon group they belong. The result in the
chemical test with their visible reaction are
summarized in Table 1.
A. Table 1. The Chemical Test Result
Bayers Test

Bromination

Bromination

Tollens Test

UV light

HBr

Br-Br

Br

Br

UV light

B. Pertinent General Reactions

Alkenes and alkynes are much more reactive
than alkanes. They will react readily with Br2 or
Cl2, and ultraviolet light is not needed for the
reaction. This reaction is an addition reaction
the halogen atoms will add at the site of the
double bond only. Therefore, this reaction is
selective only one product will result. (1)

1. Bayers Oxidation:

(a) Alkene:
CH2

(c) Aromatic Compound

OH

HO

Br

HO

OH
OH

2KMnO4

H2
C

MnO2

2H2O

HO

CH3

OH

HO

OH

OH

CH
CH3

Br2

CH3

UV light

Brown ppt

When a purple solution of the oxidizing agent

KMnO4 is added to an alkene, the alkene is
oxidized to a diol and the KMnO4 is converted to
brown MnO2. Thus, if the purple color changes
to brown in this reaction, it is a positive reaction.
The diol produced has two adjacent alcohol
groups.(1)

Aromatic compounds are not very reactive. They

will not react with Br2 or Cl2 under normal
conditions. If the aromatic compound has an
alkyl substituent, however, the alkyl group can
be halogenated in the presence of UV light. The
benzene ring will not react under these
conditions. (1)

(b) Alkyne:
H

KMnO4
NaOH

HO

OH

3. Bromination (dark)

(a) Alkane
+

2. Bromination (light)

Br

UV light

HBr

Alkanes are very unreactive, but they can be

brominated or chlorinated in the presence of
ultraviolet (UV) light. This is a substitution
reaction in which a hydrogen is removed from
the alkane and a halogen (Br) takes its place.(1)

Reaction for Alkenes, Alkynes and

Aromatic compound are similar with no.
2.

4. Tollens Test
O

(b) Alkene and Alkyne

NO REACTION

Since alkanes have only single CC bonds

present and with the absence of UV light , no
reaction with bromine is observed.

(a) Alkane:
Br2

Br2

AgO2
NH3H2O

OH

Ag

HBr

Metallic silver is deposited in a thin mirror

coating.

C. Follow-up
Application:

Questions

and

(a) Alkane from Alkene

An alkane from alkyne reaction can be
distinguish using Bromines Test. The reaction
between bromine and alkenes is an example of
a type of reaction called an addition reaction.
The bromine is decolourised because a
colourless
dibromo compound forms.
For
example:
ethene + bromine dibromoethane
C2H4 + Br2 C2H4Br2. (2)
(b) Alkene from Alkyne
An Alkene from Alkyne reaction can be
distinguish using Bayers test. The Baeyer test for
unsaturation is for determining the presence of
carbon-carbon double bonded compounds, called
alkenes
or
carbon-carbon
triple
bonded
compounds,
called
alkyne
bonds.
The Baeyer test uses dilute Pottasium
Permanganate to Oxidize the carbon-carbon
double or triple bond. It's called oxidation because
the double bond is replaced by a hydroxy group
(an OH group). The carbon's charge goes from
being +1 to +2, so it loses an electron (and is thus
oxidized).(3)

Reference/s:

(1) 5-Reactions of Hydrocarbons Laney College. (n.d.). Retrieved May

19, 2016, from
http://www.laney.edu/wp/chelifossum/files/2012/01/5-Reactions-ofHydrocarbons.pdf
(2) BBC Bitesize - GCSE Chemistry Alkanes and alkenes ... (n.d.).
Retrieved May 19, 2016, from
http://www.bbc.co.uk/education/guid
es/zvvwxnb/revision/5
(3) Alkene to Alkyne reaction. (n.d.).
Retrieved May 19, 2016, from
http://van.physics.illinois.edu/qa/listi
ng.php?id=21425
(4) Chapter 21: Hydrocarbons. (n.d.).
Retrieved from
http://chemtech.org/cn/cn1105/experi
ments/hydrocarbons.pdf/
(5) Lab # 1 "Organic Reactions" (n.d.).
Retrieved May 19, 2016, from
http://documents.mx/documents/adva
ncedtopicsinmasstransferpdf.html
(6) Reaction of Hydrocarbons. (n.d.).
Retrieved from
http://www.mcvts.net/cms/lib07/nj01
911694/centricity/domain/136/chap2
1.pdf
(7) ChemDraw Pro 8.0 (for chem structure)