Expt.

13 Inferences
I. Properties of Cyclohexane
This experiment aims to differentiate alkanes, alkenes and alkynes. To do that, we must first
look at their physical properties. The alkane used here is cyclohexane. Looking at it, it is a clear
colorless liquid at room temperature with a petroleum-like odor. Regarding the solubility of
cyclohexane in water, it is immiscible thus, when mixed with water it formed layers. Since
cyclohexane has a density of 0.7781 g/mL, it is less dense than water making it float above
water.
Test for Unsaturation
a. Baeyer’s test
Baeyer’s reagent, named after the German organic chemist Adolf von Baeyer, is used as
a qualitative test for the presence of unsaturation such as double bonds. It is an alkaline
solution of potassium permanganate. Reaction with double or triple bonds in an organic
material causes the color to fade from purplish pink to brown. There is no reaction in
the solution as it remains purple in color, but 2 layers formed since cyclohexane and
aqueous KMnO4 are immiscible with cyclohexane settling at the bottom.
b. Bromine in Chloroform
(draw equation) C6H12 + Br2  C6H11Br + HBr
The test conducted in this experiment is bromine test. The test is been done by adding
bromine in chloroform to cyclohexane. The process that will take place is called
halogenation, a substitution reaction which needs the presence of ultraviolet light or
sunlight as it is a photochemical reaction that will produce bromocylohexane and
hydrogen bromide. When exposed to light, the solution turned yellow to colorless due
to the replacement of hydrogen atom with bromine atom producing bromocyclohexane
and hydrogen bromide. The blue litmus paper at the mouth of the vial turned pink since
hydrogen bromide is acidic.
c. Reaction with ammoniacal cuprous chloride
This test is done by adding cuprous chloride with cyclohexane. The solution formed 2
layers since cyclohexane is organic and immiscible with an inorganic cuprous chloride.
Since cyclohexane is less dense, it floated to the top while cuprous chloride settled at
the bottom.
d. Reaction with concentrated sulfuric acid
The last test is done by adding concentrated sulfuric acid to cyclohexane. Cyclohexane is
not reactive as this reaction is an addition reaction. Hence, the solution remained colorless, but
there is a double layer that formed on the surface of the solution.

Overall, most of the tests done on cyclohexane had no reaction except for bromine which
halogenated cyclohexane through substitution but aside from that every test yielded a negative
result. This means that there is no unsaturation present in cyclohexane which is true since
alkanes and cycloalkanes are saturated hydrocarbons meaning all the carbon atoms have the
maximum amount of hydrogen in them.

II. Properties of Cyclohexene

 Just like cyclohexane, cyclohexane is a colorless liquid that is insoluble in water and
less dense than water (0.811 g/mL). Thus, when it was added with water, the 2
formed layers with cyclohexene floating at the top.
Test for Unsaturation
a. Baeyer’s test
(draw structure) 3 C6H10 +KMnO4 + 2H2O  3 C6H10OH + MnO2 + KOH
Baeyer's reagent is an alkaline solution of cold potassium permanganate, which is a
powerful oxidant making this a redox reaction. Reaction with double or triple bonds (-
C=C- or - C≡C-) in an organic material causes the color to fade from purplish-pink to
brown. Decolorization of a purple solution and formation of a brown precipitate (MnO2)
is a positive result for this kind of test. Bayer’s test involves a redox reaction were in
Mn7+ is reduced to Mn4+ and alkene is oxidized to a diol. Alkenes react with KMnO4 to
give a diol and MnO2. Thus, cyclohexene yielded a positive result
b. Bromine in chloroform
(draw structure) C6H10 + Br2  C6H10Br2
In this test, the double bond of cyclohexene breaks down and becomes single bonds due
to the bromine atoms bonded to each of the carbon atoms that shared the double
bond. Thus, the solution turned colorless as it formed dibromocyclohexane.
c. Reaction with concentrated sulfuric acid
In this reaction, the solution turns cloudy and there is heat released. Cyclohexene reacts with
concentrated sulphuric acid to produce alkyl hydrogen sulphates. There is heat released due to
the breaking down of the carbon-carbon double bond in cyclohexene which releases energy
that produces a net evolution of heat energy.

Overall, all the tests for unsaturation done on cyclohexene yielded positive results which is true
since a cycloalkene has a double which means that 2 carbon atoms do not have the maximum
number of hydrogen atoms making it unsaturated.
III. Preparation and Properties of Acetylene
Preparation of acetylene
The chemical reaction for the preparation of acetylene is:
(draw structure) CaC2(s) + 2H2O (l) → Ca(OH)2(s) + C2H2 (g)
With the use of separatory funnel, water is added to calcium carbide placed inside
the distilling flask. When in contact with water, calcium carbide produces acetylene
gas that will pass through the side arm of the distilling flask through the glass tip
guided by the rubber tubing. To check if acetylene gas is produced, the rubber
tubing with glass tip is dipped into the water trough with water, and if bubbles
formed, there is acetylene gas produced. This method is called water displacement
method and this method is used to prepare acetylene. Also, when the tip of the
rubber tubing was ignited with a lit matchstick, acetylene gas which is flammable,
reacted and produced a flame.

Properties of acetylene
Acetylene is a colorless gas with garlic-like odor. It is soluble in water only slightly
because acetylene is nonpolar and water is polar. When a nonpolar molecule
approaches a polar molecule, the latter induces polarity in the former momentarily.
This induction arises due to interaction between the electronic clouds of the two
molecules. During this short lived polarity, the gas molecule is attracted by water
molecule thereby causing solubility. Acetylene’s density is around 0.8988-0.92 g/mL
making it less dense than water.
Test for unsaturation
a. Baeyer’s test
3 C2H2 + KMnO4 + 2H2O → 3 C2H2OH + MnO2 + KOH
Just like cyclohexene, the solution had brown precipitate since Baeyer's reagent
is an alkaline solution of cold potassium permanganate, which is a powerful
oxidant making this a redox reaction. The reagent reacting with the triple bond
caused the color to fade from purplish-pink to brown. Decolorization of solution
and formation of brown precipitate (MnO2) are positive results for this test.
Bayer’s test involves a redox reaction were in Mn7+ is reduced to Mn4+ and
alkyne is oxidized to a diol. Alkynes react with KMnO4 to give a diol and MnO2.
b. Bromine in chloroform
C2H2 + Br2 → BrHC=CHBr
BrHC=CHBr + Br2 → CHBr2CHBr2
Just like cyclohexene, acetylene reacted with bromine through addition. The
bromine atoms bonded to each of the carbon atoms that shared the triple bond.
Thus, the solution turned colorless.
c. Reaction with ammoniacal cuprous chloride
C2H2 + 2CuCl → Cu2C2 + 2HCl
Cuprous chloride in a basic solution reacts with acetylene to form copper(I)
acetylide. The copper ions replaced the hydrogen atoms thus this reaction is a
substitution reaction. The solution had a brown precipitate which is the copper(I)
acetylide. This is done to test the presence of acetylene and based on the results,
there is acetylene gas present.
d. Reaction with concentrated sulfuric acid
Just like cyclohexene, the solution turns cloudy and there is heat released.
Acetylene reacts with concentrated sulfuric acid to produce alkyl hydrogen
sulphates. There is heat released due to the breaking down of the carbon-carbon
triple bond in acetylene which releases energy that produces a net evolution of
heat energy.

Overall, acetylene which contains one triple bond also yields positive results for
all the tests for unsaturation since two carbon atoms do not have the maximum
number of hydrogens making it unsaturated.

The test that will differentiate saturated from unsaturated hydrocarbons is the
Baeyer’s test. If an alkane which is a saturated hydrocarbon is tested with
KMnO4, there is no reaction since saturated hydrocarbons are less reactive with
an addition reaction. On the other hand, unsaturated hydrocarbons in Baeyer’s
test will undergo an addition reaction wherein there is brown precipitate (MnO 2)
 formed due to the reduction of Mn7+ to Mn4+ and the double or triple bond is
then turned into a diol.
(draw structure) alkene/alkyne +KMnO4 + 2H2O  diol + MnO2 + KOH

Bromine test is also used to test for unsaturation so this test differentiates saturated
from unsaturated hydrocarbons. Saturated hydrocarbons do not change colors when
tested with bromine while unsaturated hydrocarbons changes color from yellow to
colorless when added with bromine.
C6H10 + Br2  C6H10Br2

C2H2 + Br2 → BrHC=CHBr

BrHC=CHBr + Br2 → CHBr2CHBr2

These tests can also be used to differentiate cyclohexane from cyclohexene, and
cyclohexane from acetylene since cyclohexane is a saturated hydrocarbon and both
cyclohexene and acetylene are unsaturated hydrocarbons.

Lastly, to differentiate cyclohexene from acetylene, we need to the (???) test