FOUNDATION IN MEDICAL STUDIES (JULY 2013 INTAKE) CHM1024 LABORATORY REPORT

PRACTICAL 3 : IDENTIFICATION OF HYDROCARBONS

NAME MATRIX ID GROUP SEMESTER DATE LECTURER

: : : : : :

AKMAL ADIB BIN FADZIL CPM0018_2013C A TWO 17th DECEMBER 2013 MR. MOHD YUSOFF
HUSSAIN
OBJECTIVE The objective of this experiment is to identify hydrocarbons and
determine their properties.

INTRODUCTION Hydrocarbons are organic compounds that contain only carbon and
hydrogen. Hydrocarbons can be classified into two main types which are aliphatic
hydrocarbons and aromatic hydrocarbons. Aliphatic hydrocarbons are further divided
into three major groups which are alkanes, alkenes and alkynes. Aromatic
hydrocarbons are hydrocarbons that have at least one aromatic ring. They are known
as arenes. Some examples of aromatic hydrocarbons include benzene (C6H6) and
methylbenzene (C6H5CH3). These hydrocarbons can also be classified into saturated
and unsaturated hydrocarbons. If a hydrocarbon contains only carbon-carbon single
bonds (C C) and has no multiple bonds (double or triple bonds), it is said to be
saturated because it has the maximum number of bonded hydrogen atoms. If a
hydrocarbon contains multiple bonds, it is said to be unsaturated. That means that
alkanes and cycloalkanes are classified as saturated hydrocarbons while alkenes,
alkynes and aromatic hydrocarbons are known as unsaturated hydrocarbons.

Alkanes are the simplest family of hydrocarbons that contain carbon hydrogen
bonds and carbon carbon single bonds. The general formula for alkane is CnH2n+1
where n can be either 1, 2, 3 and so on. The carbon hydrogen bonds are only very
slightly polar and so there are no parts of the molecules which carry any
significant amount of positive or negative charge that makes other things gets
attracted. Alkanes have a fairly restricted set of reactions that in which are
combustion, halogenations and cracking process. Alkanes are not very reactive and
have little biological activity.

Cycloalkanes or cyclic alkanes are a type of hydrocarbon just like alkanes but
contain one or more rings. Cycloalkanes with a single ring are named analogously to
their normal alkane counterpart of the same carbon count such as cyclopropane,
cyclobutane, cyclopentane cyclohexane and so on. The larger cycloalkanes with
greater than 20 carbon atoms are typically called paraffins. Cycloalkanes have the
same general formula as alkenes (CnH2n). Therefore, cycloalkanes are isomeric with
alkenes. Cycloalkanes are similar to alkanes in their general physical properties,
but they have higher boiling points, melting points, and densities than alkanes. 2
Alkenes are unsaturated hydrocarbons containing a carbon carbon double bond. The
general formula for alkene is CnH2n where n can be either 2, 3, 4 and so on. The
first member of the alkene family is ethene with a formula of C2H4. Alkenes are
relatively stable compounds but are more reactive than alkanes because of the
presence of a carbon carbon double bond. The majority of the reactions of alkenes
involves the break of this double bond into single bonds. The main reaction of
alkene is addition such as hydrogenation, halogenation and oxidation.

Cycloalkenes or cyclic alkenes are a type of hydrocarbon related to alkenes but

have one or more rings. Cycloalkenes are named in a similar way as cycloalkanes but
since there is no chain end to begin from, the cycloalkenes are numbered so that
the carbon atoms in the double bond are designated as C1 and C2. Alkenes contain
double bonds by definition, and cycloalkenes benefit from enhanced stability if the
double bonds are conjugated. Cyclohexene is one such case, where if it contains a
total of three double bonds it is no longer called cyclohexene. A six-carbon ring
with three alternating (and therefore conjugated) double bonds is called benzene,
and benzene is such a stable molecule that it displays completely different
chemistry than other non-aromatic cycloalkenes. Cycloalkenes are perhaps among the
most important organic substances for biological and industrial purposes because
they are used in the production of molecules essential to a broad spectrum of
applications. Understanding cycloalkenes is a critical part of understanding
organic chemistry and its applications to biology, medicine, industry and every
other relevant field.

For this experiment, cyclohexane (member of cycloalkane family) and cyclohexene

(member of cycloalkene family) are to be used for identification and determination
of hydrocarbon properties.

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APPARATUS AND MATERIALS 1. 10 test tubes. 2. Test tube rack. 3. 100 ml beaker. 4.
Test tube holder (clamp). 5. Cyclohexane (C6H12). 6. Cyclohexene (C6H10). 7.
Concentrated sulphuric acid (H2SO4). 8. 2 % bromine in tetrachloromethane
(Br2/CCl4). 9. Dilute potassium permanganate solution (0.5 % KMnO4 solution) 10.
Dilute sodium hydroxide solution (10 % NaOH solution). 11. Dilute sodium carbonate
solution (10 % Na2CO3 solution). 12. Distilled water. 13. Blue litmus paper.

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METHOD A. Bromine Test. 1. 1 ml of cyclohexane is added to 5 10 drops of 2 %
bromine in tetrachloromethane (Br2/CCl4) in a clean test tube. The test tube is
shaken well and after two or three minutes, any changes are observed. 2. A second
similar test tube is prepared. The first test tube is placed in the laboratory
locker and the second one is placed in a bright sunlight. 3. Both test tubes are
allowed to stand for 10 15 minutes and are compared after that. 4. The colour of
the solution in each test tube is observed. 5. A blue litmus paper is placed into
each test tube to test whether hydrogen bromide was evolved or not. 6. Steps 1 5
are repeated with cyclohexene with just one test tube of sample. (Sunlight reaction
is not needed)
Apparatus set-up for Experiment A

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B. Aqueous Potassium Permanganate Test (Baeyers Test). 1. 1 ml of cyclohexane is
added to a mixture of 5 10 drops of dilute potassium permanganate solution (0.5 %
KMnO4 solution) and 3 drops of dilute sodium carbonate solution (10 % Na2CO3
solution) in a clean test tube. 2. The test tubes are shaken for 1 2 minutes and
the results are noted.

Apparatus set-up for Experiment B

3. Steps 1 2 are repeated with cyclohexene and the results are noted.

C. Sulphuric Acid Test. 1. 1 ml of cyclohexane is added into a clean test tube.

With gentle shaking, 5 drops of concentrated sulphuric acid are added very
cautiously. 2. The test tubes are shaken well and the results are noted. 3. Several
aspects are observed which includes whether heat is evolved or not and whether the
hydrocarbon dissolves or not. 4. The contents are discarded by pouring them into a
beaker containing at least 50 ml of water. 5. Steps 1 4 are repeated with
cyclohexene and the results are noted.
Apparatus set-up for Experiment C

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D. Sodium Hydroxide Test. 1. 1 ml of cyclohexane is added to 5 drops of dilute
sodium hydroxide solution (10 % NaOH solution). The test tube is shaken well. 2.
Any changes are observed and the results are noted. 3. Steps 1 2 are repeated
with cyclohexene and the results are noted.
Apparatus set-up for Experiment D

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RESULTS Observation Reagent Used Cyclohexane The yellowish-brown solution remains 2
% Br2 in CCl4 (in the dark) unchanged. The colour of the blue litmus paper remains
unchanged. The yellowish-brown solution turns colourless. 2 % Br2 in CCl4 (in
sunlight) The colour of the blue litmus paper changes from blue to red. The
solution contains The solution contains 0.5 % KMnO4 + 10 % Na2CO3 double layers.
The colour of the solution remains purple. double layers. The colour of the
solution changes from purple to brown. There are presence of brown precipitates in
the solution. The solution contains double layers. The colour of Concentrated H2SO4
the solution remains colourless. No heat is evolved. The colour of the solution 10
% NaOH remains colourless. The solution contains double layers. The solution
contains double layers. The colour of the solution changes from colourless to
cloudy. Heat is evolved. The colour of the solution changes from colourless to
yellow. The solution contains double layers. Cyclohexene The yellowish-brown
solution turns colourless. The colour of the blue litmus paper changes from blue to
red.

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DISCUSSIONS Molecular and Structural Formula of Cyclohexane and Cyclohexene. As
mentioned in the introduction, cyclohexane is a member of the cycloalkane family.
Cyclohexane is produced by reaction between benzene and hydrogen. Cyclohexane has a
distinctive detergent-like odor, reminiscent of cleaning products. Its molecular
formula is C6H12. Its structural formula is shown below :
Expanded structural formula Skeletal structural formula

Cyclohexene is a member of the cycloalkene family. It is produced by partial

hydrogenation of benzene. It is a ccolourless liquid with a sharp smell. It is also
not very stable for prolonged storage with exposure to light and air because it
will form peroxides. Cyclohexene has a molecular formula of C6H10. Its structural
formula is shown below :
Expanded structural formula Skeletal structural formula

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Experiment 1 : Bromine Test. For this experiment, 1 ml of cyclohexane is added to 5
10 drops of 2 % bromine in tetrachloromethane in a test tube and shaken well. A
similar one is prepared. One of them is placed in a laboratory locker to represent
reaction in dark. The other one is placed under sunlight. This experiment is
conducted to detect halogenation of hydrocarbons which is one of the substitution
reaction that requires a presence of ultraviolet (UV) light for halogenation to
takes place. For the test tube placed in the dark, there are no changes detected.
This is because there are no presence of UV light. For the test tube placed under
sunlight, it is observed that the yellowish-brown solution turns colourless. This
is because the presence of UV light from the Sun causes a hydrogen atom from the
cyclohexane to be replaced by a bromine atom from the bromine via the free radical
substitution mechanism. The brownish-yellow colour of the bromine fades and the
solution becomes colourless. The product of the halogenation reaction is
bromocyclohexane and hydrogen bromide. The chemical equation is as follows : C6H12
+ Br2 C6H11Br + HBr Besides that, the colour of the blue litmus paper changes to
red. This is because hydrogen bromide has acidic properties that causes a change in
colour of the blue litmus paper from blue to red. The experiment is repeated but
this time, cyclohexane is changed with cyclohexene. Unlike cyclohexane, cyclohexene
react with bromine in both light and dark conditions. That is why reaction in the
dark for cyclohexene is not done as the result will be the same as the reaction
under sunlight. For the test tube placed under sunlight, it is observed that the
colour of the yellowish-brown solution turns colourless. This is because bromine
reacts with cyclohexene to form the product of addition reaction which is
dibromocyclohexane. The reaction between them is called an electrophilic addition
reaction because the bromine molecule is an electrophilic reagent and it is added
to the double bond of cyclohexene during reaction. The yellowish-brown colour of
the bromine fades and the solution becomes colourless. The chemical equation is as
follows : C6H10 + Br2 C6H10Br2 Besides that, it is observed that the blue litmus
paper changes colour from blue to red. This is because the dibromocyclohexane is
acidic.

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Experiment 2 : Aqueous Potassium Permanganate Test (Baeyers Test). For this
experiment, 1 ml of cyclohexane is added to a mixture of 5 10 drops of dilute
potassium permanganate solution (0.5 % KMnO4 solution) and 3 drops of dilute sodium
carbonate solution (10 % Na2CO3 solution) in a clean test tube. The test tube is
shaken well for 1 2 minutes. There is no reaction or changes occurred except for
the presence of double layer forming on the surface of the solution. It is formed
because of the presence of oil in the benzene ring of cyclohexane. The experiment
is repeated but this time, the cyclohexane is replaced with cyclohexene. It is
observed that the colour of the solution changes from purple to brown. It is also
observed that there are presence of brown precipitates in the solution. This is
because the cycloalkene is oxidised by the dilute alkaline KMnO4 solution at room
temperature. The purple colour of the KMnO4 solution disappears and a cloudy brown
colour appears is caused by the precipitation of manganese (IV) oxide, MnO2. The
decolourisation of the purple solution of MnO4- ions at room temperature is a test
for carbon carbon double or triple bonds. The presence of double layer on the
surface of the solution has the same reason as in cyclohexane. The chemical
equation for the oxidation reaction is as follows :

3C6H10 + KMnO4 + 2H2O 3C6H10OH + MnO2 + KOH

Experiment 3 : Sulphuric Acid Test. For this experiment, 1 ml of cyclohexane is

added to a clean test tube. With gentle shaking, 5 drops of concentrated sulphuric
acid are added into the test tube very cautiously. The test tube is shaken well.
The test tube is quickly then placed onto the palm to detect whether heat is
evolved from the reaction. It is observed that there are no changes and no heat is
evolved. This is because cycloalkanes cannot undergo addition reaction with
concentrated sulphuric acid as cycloalkanes are not reactive. The experiment is
repeated with cyclohexene instead of cyclohexane. It is observed that the colour of
the solution changes from colourless to cloudy. This is because cyclohexene reacts
with concentrated sulphuric aid to produce alkyl hydrogensulphate which causes the
solution to turn cloudy. Besides that, heat is evolved. It is because of the
breaking of the carbon carbon double bond in cyclohexene which causes energy to
be released in the form of heat energy. For both experiments, double layer is
formed on the surface of the solution. It is caused by the presence of oil on the
benzene ring of cyclohexane and cyclohexene. 11
Experiment 4 : Sodium Hydroxide Test For this experiment, 1 ml of cyclohexane is
added to 5 drops of dilute sodium hydroxide solution in a clean test tube. The test
tube is shaken well. For cyclohexane, there are no changes happens. The experiment
is then repeated with cyclohexene. It is observed that the colour of the solution
changes from colourless to yellow. The presence of double layer in both test tubes
are caused by the presence of oil on the benzene ring of cyclohexane and
cyclohexene.

Why Cyclic Hydrocarbons Are Used Instead Of Chain Hydrocarbons? Cyclic hydrocarbons
(cycloalkanes and cycloalkenes) are similar to chain hydrocarbons (alkanes and
alkenes) in their general physical property but cyclic hydrocarbons have higher
boiling points, melting points and densities than chain hydrocarbons. This is due
to the stronger London forces as the ring shape allows for a larger area of
contact. Containing only C C and C H bonds, unreactivity of cyclic hydrocarbons
with little or no ring strain makes it preferable for use in the experiment instead
of the chain hydrocarbons. when used in the experiments, the results shown have a
larger, clearer reaction and easier to detect changes rather than chain
hydrocarbons because the chain hydrocarbons reactions are too fast for detection
in the lab.

Cyclohexane VS Cyclohexene. Based from all of the experiments, it can be seen that
cyclohexene is more reactive compared to cyclohexane. Cyclohexene participates in
many reactions such as, oxidation and addition reactions mainly due to its C C
double bond presence. Cyclohexane does not participate in any addition reaction due
to its C C single bond. Cyclohexane undergoes halogenation in the first
experiment but remain unreactive for the other experiments.

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Precautions. Throughout the experiment, there a few precautions that are taken and
noted. One of them is that all of the chemical wastes used during the experiments
are disposed in the waste container prepared by the lab instructor. This is to
because some of them are too dangerous to be disposed normally. Some of the wastes
are also hard to be cleaned if it is disposed normally into the sink. Besides that,
all of test tubes used in the experiment needs to be rinsed and cleaned with
distilled water before use. This is to avoid any chemical substances that may still
contained inside the test tubes to interfere with the results. Another one is that
cyclohexane, cyclohexene and potassium permanganate solution are handled in a fume
chamber and the ventilation of the lab must be in good condition. This is to avoid
or at least minimise the inhalation of these substances among the students.

CONCLUSION In this experiment, the properties and difference between alkanes and
alkenes are identified. In can be seen from the experiments that alkenes
(represented by cyclohexene) are more reactive than alkanes (represented by
cyclohexane). It is mainly due to the difference of C C bonds between alkanes and
alkenes. Alkenes shows a lot of reactions including, addition reaction and
oxidation reaction. Alkanes shows only substitution reaction in this experiment.
Therefore, alkenes are more reactive hydrocarbon than alkanes.

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QUESTIONS 1. Why is there a difference in reaction when the bromine test is done in
the dark and in the presence of sunlight? Explain your answer. The difference is
clear when cyclohexane is used. Cyclohexane requires presence of UV light so that
halogenation reaction can takes place. Cyclohexane reacts with bromine when the
test is done in the presence of sunlight because sunlight contains UV light that is
used for the halogenation reaction. Cyclohexane does not reacts with bromine when
the test is done in the dark because there are no presence of UV light for the
halogenations reaction to take place. 2. Write the equation for the reaction
between cyclohexane and sodium hydroxide. Based from the experiment, there is no
equation for the reaction between cyclohexane and sodium hydroxide because the
cyclohexane did not react with sodium hydroxide.

3. Explain why the hydrocarbons dissolve in one solvent but not the other.
Hydrocarbons are covalent compounds and does not dissolve in ionic solvents. It
tends to dissolve in a solvent that has similar properties main in polarity aspect.
Hydrocarbons are non-polar. Thus, it cannot dissolve in water which is a polar
solvent. 4. Explain why alkenes are more reactive compared to alkanes. Alkenes are
unsaturated hydrocarbons that consist C C double bond. These double bonds have a
high tendency to break and combine with other elements to form single bonds which
are more stable. Alkanes are saturated compounds that consist of C C single bonds
which are stable. Therefore, alkenes are more reactive than alkanes.

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REFERENCES 1. CHEMISTRY FOR MATRICULATION SEMESTER 2 FOURTH EDITION, Tan Yin Toon,
Oxford Fajar Sdn. Bhd. 2013. 2. http://www.phar.kufauniv.com/staff/asri/iemg/1.pdf
3. http://spot.pcc.edu/~mdeming/102/Labs/CH102_Lab_3_Hydrocarbon_Rxns.pdf 4.
http://global.britannica.com/EBchecked/topic/278321/hydrocarbon 5.
http://chemed.chem.purdue.edu/genchem/topicreview/bp/1organic/hydro.html 6.
http://en.wikipedia.org/wiki/Hydrocarbon#General_properties 7.
http://en.wikipedia.org/wiki/Cycloalkane#Properties 8.
http://chemwiki.ucdavis.edu/Organic_Chemistry/Hydrocarbons/Alkanes 9.
http://chemwiki.ucdavis.edu/Organic_Chemistry/Hydrocarbons/Alkenes 10.
http://chemwiki.ucdavis.edu/Organic_Chemistry/Hydrocarbons/Alkenes/Reactions_of
_Alkenes 11. http://en.wikibooks.org/wiki/Organic_Chemistry/Alkenes/Cycloalkenes
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