1.

0 Title: Qualitative Analysis

2.0 Aim: To study the reaction of aliphatic and aromatic hydrocarbons.
3.0 Introduction:
Hydrocarbons are the simplest class of organic compounds and are composed solely of
hydrogen and carbon. This class can be further divided into two groups, which are aliphatic
hydrocarbons and aromatic hydrocarbons (Bruice, 2017). An aliphatic compound is a
hydrocarbon compound containing carbon and hydrogen joined together in straight chains and
branched trains. In addition to hydrogen, other elements may be bound to the carbon atoms in
the chain, including oxygen, nitrogen, chlorine, and sulfur. Aliphatic compounds could be
saturated or unsaturated, which are alkane, or alkene and alkyne (Rajesh Agarwal, 2019).
Whereas aromatic hydrocarbons are hydrocarbons containing sigma bonds and delocalized pi
electrons between carbon atoms in a ring (Berg, Stryer & Tymoczko, 2013). The first member of
aromatic hydrocarbon is benzene. A benzene ring is a ring of six carbons with alternating
double and single bonds. As a result, the benzene has six hydrogens and the formula for a
benzene molecule is C6H6. These compounds possess special properties due to the delocalized
electron density in benzene, including additional stabilization.

Diagram 1.0: Type of aliphatic alcohols

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 Diagram 2.0: Structural formula of phenol.
Alcohols are derivatives of hydrocarbons in which one or more of the hydrogen atoms in the
hydrocarbon have been replaced by a hydroxyl group (Tikhomirov, 2016). There are two types
of alcohol, which are aliphatic alcohol and aromatic alcohol. Aliphatic alcohols are derivatives of
an aliphatic hydrocarbon, whereas aromatic alcohols are derivatives of aromatic hydrocarbon
(Lundblad & Macdonald, 2018). Aliphatic alcohols can be classified according to the number of
R groups attached to the carbon with the hydroxyl group. If one R group is attached to that
carbon, the alcohol is a primary alcohol. If two R groups are attached, the alcohol is a
secondary alcohol. If three R groups are attached, the alcohol is a tertiary alcohol. The aromatic
alcohols are those compounds in which the hydroxyl group is not directly attached to the
nucleus but is linked to a carbon atom situated in a side-chain. Phenol is an example of
aromatic alcohol.

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4.0 Objective:
Identify whether KA1 and KA2 are aliphatic alcohol or aromatic alcohol.

5.0 Apparatus and material

5.1 Apparatus:
Test tube rack, test tubes, test tube holder, Bunsen burner, 250 cm3 beaker, distilled water,
tripod stand and dropper.

5.2 Materials:
10cm3 of KA1, concentrated ethanol, 10cm3 of KA2, concentrated phenol, 1mol
dm3 concentrated sulfuric acid, glacial ethanoic acid, 1mol dm -3 liquid sodium
hydroxide solution, 3mol dm  3 acidified potassium manganate (VII) solution, potassium iodide,
-

iron (III) chloride solution and ethanoic acid.

6.0 Procedure:
A. Reaction of KA1 
Test A
1. 1 cm3 of KA1 is poured into a test tube.
2. 1 cm3 of glacial ethanoic acid is added to the test tube.
3. 3 drops of concentrated sulfuric acid are added to the test tube.
4. The mixture is heated slowly in hot water.
5. The mixture is cooled and poured into a beaker containing distilled water. 
6. The observation is recorded.

Test B
1. 1 cm3 of KA1 is poured into a test tube.
2. 1 to 2 drops of potassium manganate (VII) solution is added into KA1 using a dropper.
3. The test tube is heated slowly using a Bunsen burner.
4. The observation is recorded.

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Test C
1. 5 drops of KA1 is added into the test tube using a dropper.
2. 2 cm3 of distilled water is added to the test tube.
3. The test tube is shaken until all the KA1 is soluble in distilled water.
4. 1 cm3 of 2.5 mol dm-3 sodium hydroxide solution is added to the test tube.
5. Potassium iodide is added to the mixture and shaken until the black colour of
iodine remains. 
6. Potassium iodide is added until the colour of iodine does not disappear for 2 minutes at
60 ⁰ C.
7. The observation is recorded.

Test D
1. 1 cm3 of KA1 is poured into a test tube.
2. A few drops of iron (III) chloride is added to the test tube using a dropper.
3. The observation is recorded.

B. Reaction of KA2 
Test A
1. 1 cm3 of KA2 is poured into a test tube.
2. A few drops of iron (III) chloride is added into KA2 using a dropper.
3. The observation is recorded.

Test B
1. 1 cm3 of KA2 is poured into a test tube.
2. A few drops of sodium hydroxide solution is added into KA2 using a dropper.
3. The observation is recorded.

Test C

1. 1 cm3 of KA2 is poured into a test tube.

2. A small amount of ethanoic acid and concentrated sulphuric acid is added into KA2.
3. The observation is recorded.

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7.0 Result:

A. Reaction of KA1 

Test Observation Conclusion

A  No change in the colour of the  Ester is produced.
(Ester test) solution.  KA1 is an alcohol.
 No precipitate is formed.
 A fruity odour is produced
B  The purple colour mixture  Manganese(IV) oxide is
(Oxidation test) turned colourless produced.
 The brown precipitate is  KA1 is not an aromatic alcohol.
formed
C  Mixture turned colourless  Triiodomethane is produced.
(Iodoform test)  The yellow precipitate is  KA1 either is ethanol or a
formed secondary alcohol.
D  No changes in the colour of  No reaction is take placed.
(Ferric chloride the mixture  KA1 is not an aromatic alcohol.
test)  No precipitate is formed.

B. Reaction of KA2 

Test Observation Conclusion

A  The yellow colour mixture  [C6H5O-]3 Fe3+ complex is
(Ferric chloride turned to purple colour formed.
test)  KA2 is an aromatic alcohol.
B  No changes in the colour of  Sodium phenoxide is formed.
(Reaction with the mixture  KA2 is phenol.
NaOH)  No precipitate is formed
C  No changes in the colour of  Ester is produced.

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 (Ester test) the mixture  KA2 is an alcohol.
 No precipitate is formed
 A fruity odour is produced.
8.0 Discussion:

A. Reaction of KA1 

When KA1 reacts with glacial ethanoic acid and concentrated sulfuric acid, there is no
change in the colour of mixture; no formation of the precipitate; and a fruity odour is produced.
Based on Kohli Nitin (2008), the fruity odour indicates the formation of an ester in this reaction
because all esters have a fruity odour. Since the reaction of KA1 with a carboxylic acid and
concentrated sulfuric acid produce ester, KA1 should be alcohol. Hence, KA1 is alcohol.

Diagram 3.0 : Reaction of alcohol with carboxylic acid.

When KA1 reacts with acidified potassium manganate (VII) solution, the purple colour
mixture turned to colourless and brown precipitate is formed. Based on Moeller (2012),
decolourisation of the mixture and the formation of brown precipitate shows that acidified
potassium manganate (VII) has undergone reduction. Reduction of acidified potassium
manganate (VII) produces manganese(IV) oxide which is brown in colour and hydroxide ion.
Hence, this shows that the alcohol has undergone oxidation either to form carboxylic acid or
ketone in this reaction. Therefore, KA1 is not tertiary alcohol nor aromatic alcohol because
these alcohols are resistant to oxidation. This is because tertiary alcohol and aromatic do not
have any hydrogen atom attached directly to the carbon atom carrying hydroxyl group for the
oxidation to take place (Yip, 2016). Therefore, can be concluded that KA1 is not an aromatic
alcohol.

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 Diagram 4.0: Reduction of acidified potassium manganate (VII).

When potassium iodide and sodium hydroxide are added to KA1, the mixture turned
colourless and yellow precipitate is formed. Based on Yip (2016), the yellow precipitate shows
that triiodomethane is formed in the mixture. Only ethanol and secondary alcohols can produce
triiodomethane when reacts with potassium iodide and sodium hydroxide (Briggs, 2002). This is
because only ethanol and secondary alcohols have a methyl group in the alpha position for the
formation of triiodomethane. While tertiary alcohol and aromatic do not even have any hydrogen
atom attached directly to the carbon atom carrying hydroxyl group for the reaction to take place.
Hence, KA1 either is ethanol or secondary alcohol.

Diagram 5.0: Reaction of secondary alcohol with iodine and sodium hydroxide.

When KA1 is tested with iron (III) chloride, no changes in the colour of the mixture and
no precipitation. This shows that there is no reaction between these two solutions. Iron (III)
chloride only reacts with aromatic alcohol to produce a complex with ferric ion (Yip, 2016). This
occurs when the chlorine atoms are replaced by the aromatic alcohol, changing the coordination
property of the central iron atom. Hence, this changes the colour of the solution to purple. Since
there is no reaction between KA1 and iron (III) chloride, KA1 is not an aromatic alcohol.

Diagram 6.0: Reaction of phenol with iron (III) chloride.

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B. Reaction of KA2

When KA2 is tested with iron (III) chloride, the iron chloride compound gives the mixture a
yellow appearance. Later, the mixture turned to a purple colour. The purple colour shows the
presence of complex with ferric ion which is [C6H5O-]3 Fe3+ in the mixture (Yip, 2016). This is
formed by the replacement of chlorine atoms by the aromatic alcohol. Since this reaction only
occurs between iron (III) chloride and aromatic alcohol, can be concluded that KA2 is an
aromatic alcohol.

Diagram 7.0: Reaction of aromatic alcohol with iron (III) chloride.

When KA2 is tested with sodium hydroxide solution, there are no changes in the colour of
the mixture and no precipitation. This shows that sodium phenoxide is produced during this
reaction. Even though the formation of sodium phenoxide is quite tricky to identify since the
initial colour of the mixture and the colour of sodium phenoxide is colourless, the presence of
sodium phenoxide is still acceptable since the observation is colourless. Sodium hydroxide
solution only reacts with phenol to produce sodium phenoxide (Yip, 2016). Therefore, can be
concluded that KA2 is phenol.

Diagram 8.0: Reaction between aromatic alcohol and sodium hydroxide.

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 When KA2 reacts with glacial ethanoic acid and concentrated sulfuric acid, there is no
change in the colour of mixture; no formation of the precipitate; and a fruity odour is produced.
The fruity odour indicates the formation of an ester in this reaction because all esters have a
fruity odour. Since the reaction of KA2 with a carboxylic acid and concentrated sulfuric acid
produce ester, it is verified that KA2 is an alcohol.

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9.0 Conclusion:

In conclusion, KA1 is an aliphatic alcohol, whereas KA2 is an aromatic alcohol. This is because
KA1 produce ester when reacts with glacial ethanoic acid and concentrated sulfuric acid; KA1
undergo oxidation when reacts with acidified potassium manganate (VII); KA1 produce
triiodomethane when reacts with potassium iodide and sodium hydroxide; and KA1 does not
react with iron (III) chloride. Besides, KA2 produce complex with ferric ion when reacts with iron
(III) chloride; KA2 produce sodium phenoxide when reacts with sodium hydroxide solution; KA2
produce ester when reacts with glacial ethanoic acid and concentrated sulfuric acid.

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10.0 References

Berg, J. M., Stryer, L. & Tymoczko, J. L. (2013). Biochemistry: A Short Course. New York:

Macmillan Education.

Briggs, J. G. R. (2002). Level Course in Chemistry. Singapore: Pearson Education South Asia.

Bruice, P. Y. (2017). Organic Chemistry (8th edition). London: Pearson Education.

Kohli Nitin. (2008). Longman Science Chemistry 10. India: Pearson Education.

Lundblad, R. L. & Macdonald, F. M. (2018). Handbook of Biochemistry and Molecular Biology.

Boca Raton: CRC Press.

Moeller, T. (2012). Chemistry: With Inorganic Qualitative Analysis. New York: Elsevier

Rajesh Agarwal. (2019). Chemistry Module IV Organic Chemistry I for IIT JEE main and

advanced. Chennai: McGraw Hill Education.

Tikhomirov, V. V. (2016). Hydrogeochemistry Fundamentals and Advances, Groundwater

Composition and Chemistry Volume 1. Beverly: John Wiley & Sons.

Yip, P. (2016). PRE-U STPM Text Chemistry Term 3. Selangor Darul Ehsan: Penerbitan
Pelangi.

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