CHEMISTRY UNIT TWO

Skill: ORR
PRACTICAL #

TITLE: Organic Functional Group (1)

AIM: To investigate some Physical and Chemical properties of Hexane,
Cyclohexene, and 2-Bromobutane.
THEORY:
Hydrocarbons are those organic molecules that have only hydrogen and carbon (no
other elements, especially not O, N, S, P). Some times when halogens (F, Cl, Br, I)
are attached the molecule is still put into the hydrocarbon category but even then it is
called a bromocarbon or halocarbon
Saturated hydrocarbons have only single bonds (alkanes, no double or triple bonds).
Unsaturated hydrocarbons, like alkenes and alkynes, not only burn, but also react by
an addition reaction at the double or triple bond. The addition product becomes
saturated, with fragments of the reagent becoming attached to the carbons of the
multiple bonds. Conjugated carbons are carbons that are part of an alternating
double-single-double-single-etc. connection.
Aromatic compounds are six membered rings that alternate 3 double and three
single bonds (every carbon is part of a double bond). They have a higher carbon to
hydrogen ratio than nonaromatic compounds, burn with a sooty flame as a result of
unburned carbon particles being present. Aromatic compounds are especially stable
and do not make addition reactions. They will not even do substitution unless there is
a catalyst present.
Aliphatic means not aromatic but is used most times to mean alkane like structures
Physical Properties of Hydrocarbons - The properties that we usually look at in
organic chemistry are density, solubility, colors, boiling point/melting point and acidity.
Density is the weight per volume of an object. When two objects to not mix, the
denser object sinks while the less dense object floats. In general organic compounds
are less dense than water and will float.
Solubility is the ability of a substance to dissolve and mix completely with a solvent.
The general principle is that like dissolves like. The two solvents we will use today
will be water and example of a very polar solvent and petroleum ether (it is not truly
ether) which is a mixture of C5 to C8 hydrocarbons and is an example of a nonpolar
solvent. Molecules that are mainly polar will dissolve in water but nonpolar chemicals
(all hydrocarbons) will dissolve only in nonpolar solvents. Remember the adage oil
and water do not mix.
Color - Most organic molecules are colorless (they are clear if a gas or liquid or white
if a solid). Color stems from conjugated carbons (14 or more carbons that alternate
double, single bonds) or from some metal attached.
MATERIALS: Test tubes, test tube racks, pipettes, watch glass, matches, mask,
goggles.
APPARATUS: Hexane, chloroform, Toluene (a double bond compound), Bromine
water, potassium permanganate, water, petroleum ether, 2-bromobutane, Silver
nitrate.

METHOD:

Solubility

(1). 1 cm3 of Hexane was placed into a test tube and 1cm 3 of water was added.
The test tube was shaken vigorously and observed after 1 minute.
(2). Step (1) was repeated using the solvents listed in the table and the table was
filled up with soluble or insoluble.
(3). Steps (1) and (2) above were repeated using Cyclohexene and 2Bromobutane respectively. The table was filled up and a conclusion about the
solubility of these compounds was made.
Solvent
Water

Hexane

Cyclohexene
Insoluble

2-Bromobutane
Insoluble

Chloroform
Soluble
Soluble
Soluble
Petroleum Ether
Soluble
Soluble
Soluble
Table displaying the results in terms of whether the organic compounds tested are
soluble or insoluble in the various solvents.

Combustion

10 drops of the Alkane was placed on a watch glass and was ignited. The
characteristics of the flame were observed. The watch glass was examined
afterwards.

Step 1 was repeated using an alkene.

Test solution
Hexane

Toluene

Observations
Burns with bright yellow/blue flame. Little amount of smoke.
The glass tube was clear after the flame.
Burns for a longer period than hexane. Burns with orange
flame and great amount of thick black soot. Watch glass had
a small dark cloudy ring in the center after the flame had
burnt out.

Table displaying the observation made from the combustion of an alkene and an
alkane.

Other tests

1 cm3 of the Hexane, Cyclohexene, and 2-Bromobutane were placed into

three separate test tubes and about 5 drops of acidified Potassium
permanganate was added into each and was shaken. Observations were
recorded in the table.

The above twice was repeated, one set was kept in the dark and observed
after one minute, using Bromine water.

Test reagent
KMnO4/H+

Bromine water(in light)

Bromine water(in dark)

Silver Nitrate sol.

Hexane
Two layers of liquid
formed. Yellow layer at
top and purple layer
beneath.
Two layers of liquid
formed. Yellow at top
and clear layer beneath.
Two layers of liquid
formed. Orange layer at
top and yellow layer
beneath.
Two layers of liquid
formed with small
fragments of precipitate.

Cyclohexene
Light purple solution.

2-Bromobutane

Two layers of clear

liquid formed.

Two layers of clear liquid

formed.

Two layers of liquid

formed. Yellow layer at
top and clear layer
beneath.
Two layers of clear
liquid formed.

Two layers of clear liquid

formed.
opaque/cloudy yellow
fragments of precipitate
with thin clear top layer
of liquid.

Table displaying the visible observations made from the tests performed.

Account for the differences observed in the combustion of the Alkane and the
Alkene

Draw the structure of the organic product formed by reaction of the Alkene
with KMnO4.

Account for any differences observed in the reactions of the Alkane and the
Alkene with Bromine in the dark.

Discussion:
Part A

Organic solvents are only soluble in organic solvents. Water is a polar compound
while organic compounds are nonpolar. Organic compounds are immiscible in
water. Like dissolves like. Therefore polar compounds only dissolves polar
compounds and nonpolar compounds only dissolve nonpolar compounds.
Part B

The combustion of hexane yielded a bright yellow with slight blue flame. A blue flame will
indicate that a larger amount of heat is produced while the yellow flame will indicate
that a lesser amount of heat is produced. However, the combustion of hexane was
complete since there was no smoke and no residue left on the watchglass. Therefore
during this combustion reaction, there was enough oxygen to convert the carbon
atoms of hexane to carbon dioxide and the hydrogen atoms to water. The equation is
as follows:
2C6H14(l) + 19O2 (g) 12CO2(g) + 14H2O(g) + Heat
C6H5CH3(l) + O2(g) C6H5CH2(s)+ H2O(g) + Heat
Concentration is a factor which affects the rate of a chemical reaction. Therefore, the
combustion of hexane occurred faster than the combustion of toluene since the
concentration of oxygen adequate or in proportion with the concentration of C - H
atoms. Hence the reaction of hexane with oxygen was much faster.

Part C
Reactions with Bromine
Hexane
Bromine reacts with hexane in a substitution reaction. UV light was needed for the
reaction. Bromine will react with C - C single bonds in hexane by replacing a H with a
Br. The equation is as follows:
C6H14(l) + Br2 (aq) C6H13Br(l) + HBr(g)
Hence the colourless Hexane reacted with the orange Br water to form yellow 1Bromohexane and hydrogen bromide.
The orange bromine when first placed into the test tube with the hexane became the
bottom layer because water is denser than hexane. When the test tube was shaken,
a bromine atom was substituted for a hydrogen and hence the organic compound
adopted the orange colour of the Br and became the top layer (to the naked eye, the
orange colour kind of upturned). This indicated that substitution had occurred. The
organic compounds are always less dense than that of water.
Alkenes - Toluene
Toluene consists of a double C - C bond like alkenes and therefore they share the same
chemical properties with respect to their double bond. Toluene react rapidly with
bromine to add a Br2 molecule across the C=C double bond.
(cyclohexene) C6H12 (l) + Br2(aq) C6H12BrOH(l) + HBr(g)
The bromine decolourizes in when added to the alkene. Hydrogen bromide (HBr) adds
across a C=C double bond to form the corresponding alkyl bromide, in which the
hydrogen ends up on the carbon atom that had more hydrogen atoms to begin with.

Markovnikov's rule states that the hydrogen atom adds to the carbon atom that
already has the larger number of hydrogen atoms when HX adds to an alkene. This
rule is only applicable to unsymmetrical alkene like toluene.
The reaction of bromine in the dark with the alkane did not occur because this
hydrocarbon is saturated and bonds are harder to break. So, the catalyst of light was
needed to commence the reaction. Since there was no light, no reaction occurred. There
was no colour change in this reaction. However, reaction between bromine in the dark
and the alkene (toluene), addition of bromide ion to the hydrocarbon occurred.
Therefore, according to visual observation the orange color moved to the less dense
area (the hydrocarbon area). Light was not needed to initiate the reaction because of the
presence of a double bond.
2-Bromobutane
In the reaction of 2-bromobutane and bromine, substitution occurred but in a whole new
mechanism because it has a polar bond. The polarity in the haloalkane 2bromobutane is due to the fact that the halogen atom, bromine in this case, is more
electronegative than the carbon atom. And so, it exerts a stronger pull on the shared
electron in the C - Br bond. Nucleophilic substitution occured. The equation is as
follows:
C2H5Br(l) + Br2(aq) CH2BrCH2Br(l) + HBr(g)

Acidified Potassium Permanganate

Hexane
Alkanes are relatively inert to chemical oxidizing agents such as acidified potassium
permanganate, where alkenes are readily oxidized at room temperature. Acidified
potassium permanganate only reacts in the presence of a double bond i.e with
unsaturated hydrocarbons. Therefore, no reaction occurred between KMnO4 and
hexane. This is why the purple colour remained as the bottom layer.
Alkene - Toluene
Acidified potassium permanganate oxidizes unsaturated compounds. The oxygen in the
MnO4 reacts with a carbon from the double bond. The purple color is lost to
becoming clear i.e. from purple MnO4 to colourless Mn2+ ion. The reaction is n
oxidation addition reacrion and it did not require heat.
alkene + KMnO4/H+ alkanediol + Mn2+

2-Bromobutane

2-Bromobutane is an unsaturated compound therefore; acidified potassium

permanganate was unable to oxidize this compound. Therefore, the purple colour
was still evident.

Silver Nitrate
Hexane and Alkene (Toluene)
Both hexane and the alkene did not react with silver nitrate because they do not have a
halogen atom of which the Ag atom can readily react ionically. There was no
precipitate formed and the liquids remained clear.

2-Bromobutane
Silver nitrate reacted very well with the haloalkane when compared to the alkene and
alkene. Silver nitrate and 2-bromobutane produce a slight precipitate of a pale yellow
color which thickened up with time. 2-bromobutane being a secondary haloalkene
reacted to produce such a precipitate. Ag2+(aq) + Br-(aq) AgBr(s)
Conclusion:

Organic compounds are only soluble in nonpolar solvents.

Alkanes undergo complete combustion while alkenes undergo incomplete

combustion.