UNIVERSITI KEBANGSAAN MALAYSIA

LABORATORY REPORT
CHEMISTRY OF DRUGS
(NFNF 1813)

TITLE : REACTIONS OF HYDROCARBONS

NAME : NURUL BATRISYIA BINTI MOHAMAD A199887

AZRIN

GROUP : B2

LECTURER’S : ASSOC. PROF. DR KHAIRANA HUSAIN

NAME

DATE OF : 8/11/2023
EXPERIMENT

SEMESTER I, SESSION 2023-2024

FACULTY OF PHARMACY
TITLE

Reaction of hydrocarbons

AIM

1. To observe chemical property of hydrocarbons

2. To identify the solubility of each hydrocarbon.
3. To observe the reaction of hydrocarbons with iodine and bromine.
4. To observe the reaction of hydrocarbons with potassium permanganate.
5. To record the data of the reaction of each hydrocarbon.

INTRODUCTION

Hydrocarbons are compounds that contain only carbon and hydrogen. There are three main
classes of hydrocarbons, based on the types of carbon-carbon present. Saturated hydrocarbons
contain only carbon-carbon single bond. Unsaturated hydrocarbons contain carbon-carbon
multiple bonds as example, double bond, triple bond, or both. Saturated hydrocarbons are
known as alkanes if they are acyclic, or as cycloalkanes if they are cyclic. Unsaturated
hydrocarbons are known as alkenes (carbon-carbon double bonds) and alkynes (carbon-
carbon triple bonds) if they are acyclic or as cycloalkenes and cycloalkanes respectively if
they are cyclic.

APPARATUS AND CHEMICALS

- Apparatus

- Test tubes
- Test tube rack
- Beaker 250 mL
- Measuring cylinder 5 mL
- Dropper
 - Chemicals
- n-Hexane
- Pentane
- Cyclopentane
- Cyclohexene
- Sample A and B
- Bromine solution (1 %)
- Iodine solution (2 %)
- Potassium permanganate solution, KMnO4 (1 %)
- Sodium carbonate solution, Na2CO3 (1 M)

PROCEDURES

I. Solubility
1. 0.5 mL (5 drops) of n-Hexane is added into a clean and dried test tube.
2. Then, 3.0 mL of distilled water is added into the test tube.
3. The test tube shook vigorously and allowed the mixture to settle for a while. The
observation is recorded.
4. The procedures I (1-3) is repeated for pentane, cyclopentane, cyclohexene, sample A
and B.

II. Reaction with bromine

1. 1 mL of n-Hexane is added into a clean and dried test tube.
2. Then, 0.5 mL (5 drops) of bromine solution (1 %) is added into the test tube.
3. The test tube shook and allowed the reaction to occur for 5 minutes without light (the
test tube is placed in the dark). The observation is recorded.
4. Procedure II (1-3) is repeated with the presence of light. The observation is recorded.
5. Procedure II (1-4) is repeated for pentane, cyclopentane, cyclohexene, sample A and
B.

III. Reaction with iodine

1. 1 mL of n-Hexane is added into a clean and dried test tube.
2. Then, 0.5 mL (5 drops) of iodine solution (2 %) is added into the test tube.
3. The test tube shook and allowed the reaction to occur for 5 minutes without light
(the test tube is placed in the dark). The observation is recorded.
4. Procedure III (1-3) is repeated with the presence of light. The observation is
recorded.
5. Procedure III (1-4) is repeated for pentane, cyclopentane, cyclohexene, sample A
and B.

IV. Reaction with potassium permanganate

1. 2 mL of distilled water is added into a clean and dried test tube.
2. Then, 2 drops of potassium permanganate solution (1 %) and 1 drop of sodium
carbonate solution are added into the test tube.
3. The test tube is shaken until the solution becomes homogenous.
4. 3-4 drops of n-Hexane are added into the test tube. The test tube is shaken again, and
the observation is recorded.
5. The procedures IV (1-4) are repeated for pentane, cyclopentane, cyclohexene, sample
A and B.
RESULTS

I. Solubility

HYDROCARBON OBSERVATION EXPLAINATION REACTION

EQUATION
n-Hexane Two layers are n-Hexane is No reaction
formed insoluble in water equation
because n-Hexane
are nonpolar
substance.
Pentane Two layers are Pentane is insoluble No reaction
formed in water because equation
pentane is nonpolar
substance.
Cyclopentane Two layers are Cyclopentane is No reaction
formed insoluble in water equation
because
cyclopentane is
nonpolar substance.
Cyclohexene Two layers are Cyclohexene is No reaction
formed insoluble in water equation
because
cyclohexene is
nonpolar substance.
Sample A Two layers are Sample A is No reaction
formed insoluble in water equation
because they are
nonpolar substance.
Sample B Two layers are Sample B is No reaction
formed insoluble in water equation
because sample B is
nonpolar substance.
 II. Reaction with bromine
i) In the presence of light

HYDROCARBON OBSERVATION EXPLAINATION REACTION EQUATION

n-Hexane Reddish brown n-Hexane is an alkane
of bromine that will undergo free
solution become radical substitution with
yellowish bromine in the presence
of UV light to produce
haloalkane. The
observation of bromine
is slightly decolorized.

Pentane Reddish brown Pentane is an alkane

of bromine that will undergo free
solution become radical substitution with
yellowish bromine in the presence
of UV light to produce
haloalkane. The
observation of bromine
is slightly decolorized.

Cyclopentane Reddish brown Cyclopentane is an

of bromine alkane that will
solution become undergo free radical
yellowish substitution with
bromine in the presence
of UV light to produce
haloalkane. The
observation of bromine
is slightly decolorized.
Cyclohexene Reddish brown Cyclohexene is an
of bromine alkene that will
solution undergo electrophilic
decolourised addition reaction with
bromine in the presence
of UV light to produce
haloalkene. The colour
of bromine is
decolourized
Sample A Reddish brown Sample A is an alkane
of bromine that will undergo free
solution become radical substitution with
yellowish bromine in the presence
of UV light to produce
haloalkane. The
observation of bromine
is slightly decolorized.

Sample B Reddish brown Sample B is an alkene

of bromine that undergoes
solution electrophilic addition
decolourised reaction with bromine
in the presence of UV
light to produce
haloalkene. The colour
of bromine is
decolourized.
 ii) In the dark

HYDROCARBON OBSERVATION EXPLAINATION REACTION EQUATION

n-Hexane No changes n-Hexane is an
alkane. Alkane will
not react with
bromine without the
presence of UV light.
Pentane No changes Pentane is an alkane.
Alkane will not react
with bromine without
the presence of UV
light.
Cyclopentane No changes Cyclopentane is an
alkane. Alkane will
not react with
bromine without the
presence of UV light.

Cyclohexene Reddish brown Cyclohexene is an

of bromine alkene that undergoes
solution electrophilic addition
decolourised reaction with bromine
to produce haloalkene
because it has double
bond. The bromine
colour decolourised.
Sample A No changes Sample A is an
alkane. Alkane will
not react with
bromine without the
presence of UV light.
Sample B Reddish brown Sample B is an alkene
of bromine that undergoes
solution electrophilic addition
decolourised reaction with bromine
to produce haloalkene
because it has double
bond. The bromine
colour decolourised

III. Reaction with iodines

i) In the presence of light

HYDROCARBON OBSERVATION EXPLAINATION REACTION

EQUATION
n-Hexane No changes n-Hexane is an alkane that
cannot undergo free radical
substitution with iodine in the
presence of UV light to produce
haloalkane because iodine is less
reactive that bromine so the
single bond of alkane cannot be
broken down.

Pentane No changes Pentane is an alkane that cannot

undergo free radical substitution
with iodine in the presence of
UV light to produce haloalkane
because iodine is less reactive
than bromine so the single bond
of alkane cannot be broken
down.
Cyclopentane No changes Cyclopentane is an alkane that
cannot undergo free radical
substitution with iodine in the No reaction

presence of UV light to produce

equation
haloalkane because iodine is less
reactive that bromine so the
single bond of alkane cannot be
broken down.

Cyclohexene Yellow iodine Cyclohexene is an alkene that

solution has double bond. Iodine is less
decolourised reactive than bromine. However, *

Chio (12)2
CHio+2Ic
iodine still can be broken down
by the electrophilic addition
reaction. So, yellow colour of
iodine solution decolourised.
Sample A No changes Sample A is an alkane that
cannot undergo free radical
substitution with iodine in the No reaction

presence of UV light to produce

equation
haloalkane because iodine is less
reactive than bromine so the
single bond of alkane cannot be
broken down.

Sample B Yellow iodine Sample B is an alkene that has

solution double bond. Iodine is less
decolourised reactive than bromine. However,
sample
B+I2 In

iodine still can be broken down

by the electrophilic addition
reaction. So, yellow colour of
iodine solution decolourised.
 ii) In the dark

HYDROCARBON OBSERVATION EXPLAINATION REACTION

EQUATION
n-Hexane No changes n-Hexane is an alkane that
cannot undergo free radical
substitution with iodine to
produce haloalkane because
iodine is less reactive than
bromine so the single bond of
alkane cannot be broken down.

Pentane No changes Pentane is an alkane that cannot

undergo free radical substitution
with iodine to produce
haloalkane because iodine is less
reactive than bromine so the
single bond of alkane cannot be
broken down.

Cyclopentane No changes Cyclopentane is an alkane that

cannot undergo free radical
substitution with iodine to
produce haloalkane because
iodine is less reactive than
bromine so the single bond of
alkane cannot be broken down.

Cyclohexene Yellow iodine Cyclohexene is an alkene that

solution has double bond. Iodine is less
decolourised reactive than bromine. However,
iodine still can be broken down
 by the electrophilic addition
reaction. So, yellow colour of
iodine solution decolourised.
Sample A No changes Sample A is an alkane that
cannot undergo free radical
substitution with iodine to
produce haloalkane because
iodine is less reactive than
bromine so the single bond of
alkane cannot be broken down.

Sample B Yellow iodine Sample B is an alkene that has

solution double bond. Iodine is less
decolourised reactive than bromine. However,
iodine still can be broken down
by the electrophilic addition
reaction. So, yellow colour of
iodine solution decolourised.

IV. Reaction with Potassium Permanganate

HYDROCARBON OBSERVATION EXPLAINATION REACTION EQUATION

n-Hexane No changes n-Hexane is an alkane
that doesn’t have double
bond to oxidize with
potassium permanganate
that act as oxidizer. The
reaction between n-
 Hexane and KMnO4
doesn’t occur.
Pentane No changes Pentane is an alkane that
doesn’t have double
bond to oxidize with
potassium permanganate
that act as oxidizer. The
reaction between pentane
and KMnO4 doesn’t
occur.
Cyclopentane No changes Cyclopentane is an
alkane that doesn’t have
double bond to oxidize
with potassium
permanganate that act as
oxidizer. The reaction
between cyclopentane
and KMnO4 doesn’t
occur.
Cyclohexene The purple Cyclohexene is an alkene
colour KMnO4 that has double bonds
decolourised and that can allow oxidation
brown precipitate to occur between
formed cyclohexene and
KMnO4. The oxidation
produced brown
precipitate, MnO2.
Sample A No changes Sample A is an alkane
that doesn’t have double
bond to oxidize with
potassium permanganate
that act as oxidizer. The
reaction between sample
 A and KMnO4 doesn’t
occur.
Sample B The purple Sample B is an alkene
colour KMnO4 that has double bonds
decolourised and that can allow oxidation
brown precipitate to occur between sample
formed B and KMnO4. The
oxidation produced
brown precipitate,
MnO2.

DISCUSSION

I) Solubility

From this experiment, it is shown that all 6 hydrocarbons are insoluble in water.
All hydrocarbons are nonpolar since hydrocarbons contain only carbon and
hydrogen. One property of being a nonpolar molecule is that it’s not soluble in
water since it is hydrophobic, but it is soluble in nonpolar organic solvent. Water is
polar, which means there is a difference in electronegativity and a dipole moment
(2 lone pairs). However, alkane containing C-H bond is nonpolar. Polar substances
tend to dissolve in polar solvent and hence, alkanes being nonpolar, will not
dissolve in polar solvent. Therefore, the reaction in this experiment shows that all
hydrocarbons are insoluble in water as it forms two layers when it reacts with
water.

II) Reaction with Bromine

Alkenes and alkynes, known as unsaturated carbon, are much more reactive than
the parent alkanes. They react rapidly with bromine, for example, adding Br2
molecules across the C=C double bond.
In the presence of light, bromine reacts with both saturated and unsaturated
hydrocarbons. In this reaction, the hydrogen atoms in the hydrocarbon are
substituted by the bromine atoms. However, in this experiment, we can see that n-
Hexane, pentane and sample A do not react completely with bromine solution as
the reddish brown of bromine solution are slightly decolourised by the process
called free radical substitution. The solution was supposed to be colourless but
maybe some error that happen during experiments like our solution might be not
shaken well due to not having cock stopper for the test tube and the solution does
not expose to UV light long enough for it to react completely. But, in alkenes
which is cyclohexene and sample B they still can undergo reaction called
electrophilic addition reaction.
In the dark, alkane which is n-hexane, pentane, cyclopentane and sample A don’t
undergo any reaction because in the absence of light bromine molecules in
bromine water become intact and do not dissociate into reactive bromine atoms.
So, they cannot break the bond through homolytic cleavage. However, in the
alkene the pi bond in the alkene’s double bond act as a nucleophile, attacking the
bromine molecule. So, in this reaction bromine molecules are added across the
double bond resulting in the formation of dihalide compound. It is shown in
cyclohexene and sample B reaction, the reddish colour of bromine water become
colourless indicates the occurrence reaction.
III) Reaction with iodine

Alkanes being relatively unreactive compounds, do not typically react with iodine
under normal conditions. Iodine is a less reactive compound compared to bromine.
While bromine readily undergoes addition reaction with alkenes, iodine is less
reactive and does not react with alkanes in a similar manner and alkanes generally
require more reactive conditions or catalyst to undergo reactions with iodine. No
matter how, in cyclohexene and sample B a halogen addition reaction known as
iodination occurs. The pi electrons in the alkene double bond act as a nucleophile,
attacking the iodine molecule. One of the iodine atoms in the iodine molecule
forms a bond with one of the carbon atoms in the double bond, breaking the pi
bond. Then, the other iodide atom becomes a negatively charged iodide ion (I-)
due to loss of electrons. This iodide ion is attracted to a proton (H+) from the
solvent or another reactant to maintain charge neutrality. Similar to bromination,
the iodination reaction is also stereospecific, with the iodine atoms adding to the
carbon atoms of the double bond in an anti-addition manner. The results obtained
from the presence of light and in the dark are the same. Cyclohexene and sample
are the only hydrocarbons that react with iodine that they became colourless.

- T -

+ I -

I -> t
I-
t

I -

.
I

t
I -

t -
I
IV) Reaction with potassium permanganate

Potassium permanganate is an oxidizing agent that reacts with unsaturated

aliphatic hydrocarbons but does not react with alkanes or aromatic hydrocarbons.
It can be seen in this experiment where a brown precipitate, MnO2 formed from a
deep purple colour, KMnO4 when it reacts with cyclohexene and sample B, but
nothing has change in n-Hexane, pentane, cyclopentane and sample A. In the
presence of an alkane, potassium permanganate will not undergo any noticeable
reaction. Alkanes lack functional groups that are easily oxidizable, such as carbon-
carbon double or triple bonds. As a result, the oxidizing power of potassium
permanganate is not effectively harnessed in the presence of alkanes. Potassium
permanganate (KMnO4) is commonly used to oxidize alkenes. The reaction
between an alkene and potassium permanganate is known as oxidative cleavage or
ozonolysis, depending on the reaction conditions. Under basic conditions,
potassium permanganate can oxidize alkenes by breaking the carbon-carbon
double bond and forming two carbonyl (C=O) groups.

- 0Ano of
t 0 = Mn =8 - - t MnOz
II

8
Ig OH
From this experiment, we can determine the group of hydrocarbons in sample A is alkane
while in sample B is alkenes. It can be seen in when sample A took longer time to
decolourised bromine in light, does not react with iodine in both light and dark and does not
react with potassium permanganate as it remains purple. On the other hand, sample B become
colourless with bromine in the presence of light and dark, does react with iodine by
decolourised the colour of iodine and formed brown precipitated when react with potassium
permanganate.

CONCLUSIONS

In conclusion, the hydrocarbon reaction can help determine the characteristic and properties
of hydrocarbon. In the solubility test we can conclude that hydrocarbons are insoluble in
water. The reason is because hydrocarbons contain only carbon and hydrogen, so make it
nonpolar. Therefore, it does not react with polar molecules which is water. Then, for bromine
test, only alkene react with bromine in the dark while alkane does not react with bromine
unless in presence light. This reaction involving electrophilic addition can help in distinguish
between alkane and alkene. In the iodine test, alkenes are the only hydrocarbon that can react
with iodine while others remain the same. Next, in potassium manganate test we can say that
only alkene reacted with potassium permanganate, which is a strong oxidizing agent thus
undergo oxidation process and produces diol. Lastly, all these tests help to differentiate
hydrocarbons between alkane and alkene as sample A and B that unknown hydrocarbons but
after the experiment we can classified sample A as alkane while sample B is an alkene.
REFERENCES

Dewick, P. M. 2008. Essential of Organic Chemistry. West Sussex: John Wiley &

Sons, Ltd. (latest edition)

Dewick, P.M. 2009. Medicinal Natural Products: A Biosynthetic Approach. Ed. Ke3.

England: John Wiley & Sons, Ltd. (latest edition)

McMurry, J. 2016. Organic Chemistry. Ed. Ke-9. Pacific Grove: Brooks/Cole. (latest

edition)

Sarker, S. & Nahar, L. 2007. Chemistry for Pharmacy Student: General, Organic

and Natural Product Chemistry. New York: John Wiley & Son. (latest

edition)

Solomons, T.W.G. & Fryhle, C.B. 2016. Organic Chemistry. Ed. Ke-11. New York:

John Wiley & Sons, Inc. (latest edition)

Liu, X. (2021). 9.2 halogenation reaction of alkanes. Retrieved from

https://kpu.pressbooks.pub/organicchemistry/chapter/9-2-halogenation-reaction-of-
alkanes/

Libretexts. (2023). Retrieved from

https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(O
rganic_Chemistry)/Reactions/Addition_Reactions/Electrophilic_Addition_Reactions/Re
actions_of_Alkenes_with_Bromine
QUESTION

1. Explain the function of light in the reactions II and III.

To provide energy required for both of it to undergo homolytic cleavage during
initiation step of the mechanism.

2. Explain why the sodium carbonate solution is added into the potassium
permanganate solution in reaction IV.
Help the potassium permanganate to become slightly alkaline since halogenation need
to be in alkaline environment. This will make potassium permanganate first become
dark green then produce dark brown precipitate.

3. Determine the most reactive hydrocarbon for each reaction (II-IV).

In reaction II, the most reactive hydrocarbon is cyclohexene. In reaction III, is
cyclohexene. Lastly, reaction IV is cyclohexene.

4. Determine the class of hydrocarbon for sample A and B. Explain your answers.
Sample A is alkane because sample A took longer time to decolourised bromine in
light, does not react with iodine in both light and dark and does not react with
potassium permanganate as it remains purple. Sample B is alkene as it decolourised
when added to bromine and iodine indicating that it is a reactive substance and able to
react with halogen without the presence of light. Besides, when sample A added into
potassium permanganate, it decolourised and turn to brownish. This is because only
alkene undergo oxidation by using potassium permanganate as agent.