THEORY

The chemistry of organic compounds is primarily dictated by

its functional group. Some functional groups participate in acid base chemistry.
Amines are weak bases while carboxylic acids and phenol are weak acids. Some
alcohols are readily oxidized while aldehydes and ketones are readily reduced.in
substitution reaction n, some functional groups act as nucleophiles while others act
as electrophiles. Finally multiple bonds as in alkene and alkynes are required for
addition reaction.

1) HYDROCARBONS
a) Most halogens react readily with carbon-carbon multiple bonds that are not part
of an aromatic ring.

Bromine is typically chosen as the test reagent for alkanes and alkynes
because; if it reacts, its rich brown color will disappear.
b) Alkenes react readily with dilute aqueous potassium permanganate to
form a brown precipitate as a purple color of permanganate disappears.
Example:

c) Copper chloride test is useful for identification of terminal carbon-carbon triple

bond

2) ALCOHOLS
Alcohols are organic compounds that contain the hydroxyl group.
The simplest alcohol is methanol. Ethanol is found in alcoholic beverages and
preservatives and is used as a solvent. 2 propanol also known as rubbing alcohol is
found in astringents and perfumes
Alcohols are nucleophile
a) Iodoform test is the test specific for alcohols which have afree
methyl group and hydrogen attached to the carbon bearing the hydroxyl group such
ethanol and butanol
Example

3) PHENOLS
Benzene ring with a hydroxyl group is known as phenol.
Concentrated solutions of phenol are acoustic and cause burns
a) Phenols are weak acid compounds, so they are soluble weak
alkaline solutions only.
b) Most phenol reacts with FeCl 3to produce colored complexes. These
complexes may be red, purple, blue or green
Example

c) Phenol undergo substitution to aromatic ring, example bromination

or nitration reactions.

Resorcinol reduce potassium solution with oxidation +7 purple in color

to MnO2 with oxidation of +4 and undergo oxidation to Quinone

4: HALOGEN COMPOUNDS
Halogens containing compounds differ widely in reactivity depending upon their
structure.
a) Chlorobenzene can be hydrolyzed at atmospheric pressure if a siliconcatalyst is
used

b) Most halogens containing compounds react with silver nitrate to give an insoluble
silver halide

c)Ionic halide in which the halogen exist as negatively charged ions in both the
crystalline state as well as in solution ionic halides dissolve readily in water.

METHODOLOGY
1) MATERIAL USED
I) HYDROCARBONS
The hydrocarbons used in this experiment were;
a) Toluene
c) cyclohexene
b) Phenyl acetylene
d) n- heptane
The reagents on the test of hydrocarbons were;
a) Bromine
c) copper chloride
b) KMnO4
II) ALCOHOLS
The alcohols used in this experiment were;
a)1-butanol

c)1-butanol

b)2-butanol

d)t-butanol

The reagents used were;

a) Iodine

b) NaOCl solution

III) PHENOLS
The chemical compounds used were;
a) Phenol
b) Resorcinol
The reagents used in this experiment were;
a) Neutral FeCl3
c) KMnO 4
b) Bromine water
d) Ag (NH 3)2
IV)HALOGEN COMPOUNDS
The chemical compounds used were
a)t-butyl chloride
b)Chlorobenzene
The reagents used were;
a) Water
b) Hot NaOH

c) alcoholic silver nitrate

2: APPARATUS AND EQUIPMENT USED

i) Test tube
Used to carry out the mixture of compounds with a reagent test.

ii) Spatula
Used to transfer compounds to the test tube.
iii) Dropper
Used to transfer compounds which are in solution form from the container to
test tubes.
iv)Steam bath
Used to warm the mixture of compounds.
v) Test tube holder
Used to hold test tubes in position.
vi) Test tube brush.
Used for cleaning the test tubes.

EXPERIMENTAL
PROCEDURE
Every functional group had its own procedure in determination.
Hydrocarbons alcohols phenols and halogen compounds were determined in this
experiment. Here is every procedure in each group of organic compounds.

1: HYDROCARBONS
a) Action of bromine
Each compound given which were toluene, phenylacetylene, cyclohexene and
n-heptane, each was dissolved in carbon tetrachloride on different test tubes.
Solution of bromine was added in carbon tetrachloride to the compounds in
test tubes.
A blank test was run simultaneously with solvent (CCl 4) alone to determine
decolourization.
The solution where no decolourization took place was exposed to strong light
(sunlight) for few minutes.
b) KMnO4 Test
Each compound given was dissolved in 1 ml of acetone in different test tubes.
1-2 drops of dilute KMnO4 was added to solution of acetone and
hydrocarbons.
A blank test was run simultaneously with solvent alone to determine which
compound decolorize the colour of MnO4
c) Action of copper chloride
To prepare a reagent, 1-2 ml of 10% copper sulfate solution in 5 ml dilute
ammonia until the initial precipitate and just a clear solution is obtained.
A solution of hydroxylamine hydrochloride was added drop wise with shaking
until the solution became first green then completely colorless.
A portion of the reagent was added to alcoholic solution of each hydrocarbon
and shaken, in order to determine precipitation.

2: ALCOHOL
a) Iodoform test

 The mixture of alcohol (about 10 drops) (i.e. 1-propanol, 1-butanol, t-butanol

and cyclohexanol and 1 ml 10% KI were warm together.
The solution of NaOCl was added to the warm mixture drop by drop.
The same test was performed by acetone to find out how Iodoform smells.

3: PHENOL
a)Neutral FeCl3 test
An aqueous solution of 1ml FeCl3 solution was treated dropwise with a dilute
0.1M sodium hydroxide solution until a faint precipitate was obtained.
Few drops of neutral FeCl3 solution were added to a neutral aqueous solution
of phenol.
b) Bromine water test
1 ml of bromine water was added to a few drops of the phenol and shaken.
c) KMnO4 test
The compound (phenol) was dissolved in 1 ml acetone.
1-2 drops of dilute KMnO4 was added to the solution.
Blank test was simultaneously run with a solvent alone (acetone and KMno 4)
to observe which compounds decolorize MnO 4.
d) Ag (NH3)2 test
To prepare tollens reagent,6 drops of dilute NaOH was added to 1 ml
aqueous AgNO3 followed by dilute ammonia solution drop wise until the
precipitate Ag2O is just dissolved.
The suspension or solution of phenol was tested with litmus paper.
If acidic,NaHCO3 solution was added drop wise with shaking until a solution is
just alkaline.
The resulting solution was tested with few drops of tollens reagent and
shaken thoroughly.
The formation of precipitation indicates that the compound has been
oxidized.

4: HALOGEN COMPOUNDS
a) Action of water
Few drops about 100mg of the compound was added to 1 ml of water in test
tube and shaken.
The compound was observed if soluble, and for any sign of reaction. The
solution was tested with blue litmus paper.

b) Action of hot NaOH

About 10 drops each of the compound B and C in separate test tubes were
dissolved in 1 ml mixture of 1:1 ethanol/2M NaOH solution.
The solution was boiled for about 1 minute and cool.
1 ml of dilute nitric acid acidified the solution and aqueous AgNO 3 was added.
c) Alcoholic silver nitrate
About 10 drops each compound was dissolved in 1 ml of ethanol in separate
test tubes and into each about 0.5 ml of alcoholic AgNO 3 solution was added.
It was allowed to stand and observe the rate of development if any of
precipitate of AgCl

RESULTS AND
CONCLUSION
1: HYDROCARBONS
REAGENT

HYDROCARBON

Action of bromine water

Toluene

Phenyl acetylene

OBSERVATION AND
REACTION
-It forms two layers, top
layer is colourless and
bottom is brown colour
initially
-It formed yellow colour
when exposed to sunlight
i.e.
-On standing it formed two
separate layers brown at
top(bromine) and
colourless at the bottom
(toluene)
NEGATIVE TEST
-It decolorized the colour
of bromine when added.
-It formed yellow
precipitate of phenyl
acetylene on sunlight.
-The litmus paper changed
from blue to red
POSITIVE TEST.

Blank test(Bromine)

Cyclohexene

-It formed two clear layers

with bromine.
-It decolorized bromine
-It had no effects on litmus
paper.
POSITIVE TEST

n-heptane

-It does not decolorize

bromine
-Two layers were formed
colorless layer at the top
and brown layer at the
bottom
NEGATIVE TEST.

Tetrachloride (CCl4)

-Two layers were formed

colorless layer(CCl4) at the
top and brown
layer(bromine) at the
bottom
NO REACTION

DISSCUSION ON HYDROCARBON WITH ACTION OF BROMINE:

Hydrocarbon compounds are primarily made up carbon and
hydrogen atoms. In this experiment, our given hydrocarbons were toluene, phenyl
acetylene, cyclohexene and n-heptane. Their chemical structures are drawn below;

Apart from n-heptane (saturated hydrocarbon), the rest of the given compounds
were unsaturated hydrocarbons. The presence of either double or triple bond in
unsaturated compounds, make the compound to be reactive toward bromine
solution and eventually decolorize the bromine reagents.
n-heptane is unreactive in nature and failed to decolorize the
bromine solution during the observation of the reaction when exposed to sunlight.
The decolourization of bromine indicates the presence of unsaturated hydrocarbons.

For phenyl acetylene;

REAGENT

HYDROCARBON

OBSERVATION AND
REACTION

KMnO4

Toluene

-Two layers were formed,

colourless (toluene) at the
top and purple
(permanganate) at the
bottom.
NEGATIVE TEST

Phenyl acetylene

-It decolorized the KMnO4

to brown.
-It formed precipitate at
the bottom
POSITIVE TEST

Cyclohexene

-It dissolved and

decolorized KMnO4 to
brown.
-Only dissolved but has no
reaction
NEGATIVE TEST.

n-heptane

-It formed two different

layers KMnO4 at the
bottom and colourless at
the top.
-It doesnt decolorize
permanganate layer.

Acetone

-The solution formed two

Blank test(KMnO4)

layers purple at the

bottom and colourless at
the bottom.

DISSCUSION ON HYDROCARBON WITH KMnO4 TEST

Potassium permanganate is a very good oxidizing agent. During a chemical reaction

with alkyl benzene, it oxidizes the alkyl benzene side chains to yield benzoic acids

For phenyl acetylene;

For cyclohexene;

For n-heptane;

REAGENT

HYDROCARBON

Action of copper chloride

toluene

OBSERVATION AND
RESULTS
-Two layers were formed,
both colorless.
-No precipitation
NEGATIVE TEST
-Yellow ppt was formed.

phenyl acetyne
POSITIVE TEST

Cyclohexene

-Two colourless layers

were formed.
-No ppt was formed.
NEGATIVE TEST.
-Two colourless layers
were formed.
-No ppt was formed.
NEGATIVE TEST.

nheptane

DISSCUSION ON HYDROCARBON WITH ACTION OF CuCl:

Copper chloride test had effect on identification of hydrocarbons
with triple bonds and terminal carbon-carbon triple bond. After the reagent was
prepared and added on each test tube that contain separate hydrocarbon
compounds, many compounds did not dissolve or if they did it was small extent of
dissolution. Toluene, cyclohexene and n-heptane did not react with copper chloride
but phenyl acetylene did react with CuCl 2 to form yellow precipitates as seen below;

For toluene;

For cyclohexene;

For n-heptane;

2 : ALCOHOLS
REAGENT

ALCOHOL

OBSERVATION AND
REACTION

Iodoform test

1-propanol

-It formed a clear solution

at room temperature and
when warmed.
-Negative smell test
-NEGATIVE TEST
-It formed two colourless
solution at room
temperature and when
warmed.
-on addition of NaOCl it
formed two layer, top
being yellowish and
bottom colourless
-NEGATIVE TEST
-when KI was added, it
became yellowish
-at room temperature and
warm conditions, formed
yellowish at top and
colourless layer at the
bottom.
-POSITIVE TEST

1-butanol

2-butanol

t-butanol

Cyclohexanol

-it formed a clear solution

at room and warm
temperature.
-no change of its smell.
-POSITIVE TEST

-at room temperature and

when warmed there was a
suspension.
-no smell was detected.
NEGATIVE TEST.

DISSCUSION ON ALCOHOL:
Iodoform test is the test specific for alcohols which have a free
methyl group and a hydrogen attached to carbon bearing the hydroxyl group such
as 2-butanol.
Alcohols are generally classified into primary, secondary or
tertiary depending on number of carbon atoms surrounding the carbon attached to
the functional group (-OH). During the experiment, only 2-butanol and t-butanol
tested positively when compared to the blank test that involved acetone in 10% KI.
The smells resembled. Other alcohols did not match the smell of the blank test.
Both 2-butanol and t-butanol contains a methyl group as a terminal group which is
easier to be substituted during the Iodoform test with KI solution.
When NaOCl was added, the reaction became;

for t-butanol;

3: PHENOL;
REAGENT

PHENOLS

OBSERVATION

Phenol

-it changes the greenish colour of

ferric chloride into brownish.

Neutral FeCl3 test

Resorcinol

POSITIVE TEST
-dark green colour was observed

`
POSITIVE TEST
Phenol
KMnO4 Test

-It dissolved on reagent

-The grey color of the solution
was observed.

POSITIVE TEST
Resorcinol

-it dissolved on the reagent.

-black ppt was formed at bottom

Phenol

POSITIVE TEST
- Was acidic for litmus paper
On addition of NaHCO3 became

AgNO3 test

alkaline and precipitate were

formed.

Resorcinol

POSITIVE TEST
-no acids
-No reaction
NEGATIVE TEST

DISSCUSION ON PHENOL:
A) Action of KMnO2
-phenols reduce potassium permanganate solution and undergo
oxidation to quinines.
-the manganese is reduced from +7 which give a purple colour to
+
4 which is brown.

B) Action of bromine water

POSITIVE TEST: Decolourization of bromine;
This test is good for water soluble phenols.
C) ferric chloride test
POSITIVE TEST: production of blue, violet, purple, green or red brown
colour.
-the positive results are for all types of Ar-OH
-the test must be done in the hood.

4: HALOGENS
REAGENT

COMPOUND

OBSERVATION

t-butyl chloride
Action of water

Chlorobenzene

t-butyl chloride
Alcoholic silver nitrate
AgNO3

Chlorobenzene

Action of hot NaOH

Chlorobenzene

-formation of two layers

upper layer was cloudy
and bottom was clear
-litmus paper changed
from blue to red

POSITIVE TEST
- formation of two layers
bottom layer was
Chlorobenzene and top
layer was water
-litmus paper changed
from blue to red.

POSITIVE TEST
-it dissolved in ethanol.
-ppt was formed after
addition of alcoholic
AgNO3

POSITIVE TEST
-It dissolved in ethanol.
-Two colourless layers
were formed.
-No formation of ppt.
NEGATIVE TEST
-after addition of ethanol
of 2n NaOH, two layers
were formed.
-On boiling two layers
separated completely
-After cooling the colour
changed and it was
cloudy.

-Purple (brown precipitate

was formed after addition
of AgNO3.)

DISSCUSION ON ACTION OF SILVER NITRATE:

t-butyl chloride dissolved in ethanol. Addition of AgNO 3 (alcoholic) causes
the formation of white precipitates, which indicates that the reaction occurred.

Chlorobenzene dissolved in ethanol but when alcoholic AgNO 3 solution was added, 2
separate layers were formed. This is an indication that this reaction was negative
for Chlorobenzene.

CONCLUSION
Generally, from the results, most of the unsaturated
hydrocarbon, alkene and alkyne functional groups which are double and triple bond
respectively showed positive test with most of the reagents because they are non
stable, hence more reactive. For Iodoform test, from the results, it indicated that is
the specific for alcohols which have free methyl group and hydrogen attached to the
carbon bearing the hydroxyl group such as 2-butanol
In additional, for phenol most of the phenols are in acidic form,
that is why positive test had on litmus paper. On reaction with ferric chloride
solution colored complex compound was formed. Not only that but also phenol
decolourise the brown colour of bromine or halogens compounds from results, most
of halogens react with silver nitrate to give insoluble silver halide(AgX) which is
white ppt.

RECOMMENDATIONS
In this experiment, there are some recommendations which can be
put forward in order in order to improve on the coming experiments and also help
the future chemists who will carry on this experiment.
Firstly, every test should be carried twice or more times in order
to improve on the results. On doing so it is important to cap your unknown vial
tightly after removing the required amount for the test as these compounds may
have stronger smells and will evaporate very quickly.
Also, in bromine test, only small amount of bromine should be
used. If too much bromine is used to a solution to a solution a false negative result
may be generated as all of the alkene/alkyne is consumed before the bromine.
Lastly, before any chemist goes to the lab should understand the
properties and chemical structure of given compounds so that they can know
whether they should give a positive or negative result for each test. This will
improve on the results.