Name: Ma. Jessa A.

Dunting Experiment No: 8

Date Performed: March 12, 2019 Date completed: March 12, 2019

Experiment No. 8
HYDROCARBONS

I. DATA AND RESULTS

Table 1.1 Summary of Results for Different Tests on Hydrocarbons

Test Cyclohexane Cyclohexene Benzene
Physical Colorless with a Clear, colorless with a Colorless with a
Properties sweetish odor – pungent odor gasoline-like odor
chloroform like
Solubility Test Immiscible, colorless Immiscible, yellowish Immiscible,
upper layer, cloudy upper layer, colorless gelatinous white
white bottom layer bottom layer upper layer, colorless
bottom layer
Density Test Less dense than Less dense than Less sense than water
water water
Flammability Test Produced yellow Produced yellow- Produced yellow-
flame and no soot orange flame and orange flame and
when ignited amount of soot when presence of soot was
ignited observed
KMnO4 Test No color change, still Dark red solution, No color change, still
colored violet formation of brown colored violet
solution precipitate solution with bubble
suspension
Br2 Test Immiscible, Orange Colorless with residue Immiscible, Orange
upper layer, light present upper layer, light
yellow in color in yellow in color in
bottom layer bottom layer
Nitric Acid Test Colorless solution Orange solution with
with orange white precipitate
precipitate
Table 1.1 shows the different results and observations on different Hydrocarbons
(Cyclohexane, Cyclohexene, and Benzene) subjected to different tests.
 II. RESULTS AND DISCUSSION

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).
For this experiment, cyclohexane (member of cycloalkane family), cyclohexene (member of cycloalkene
family), and benzene (an aromatic hydrocarbon) are used for identification and determination of
hydrocarbon properties.
For the solubility and density test, four drops of each of the three hydrocarbons were placed in three different test tubes
and added with fifteen drops of water. It was then observed that the three hydrocarbons were immiscible with water since all
three liquids did not mix and instead formed two distinct layers, with the aqueous layer settling on the bottom and the organic
layer staying on top. The liquids did not mix because they are of different polarities. The general solubility rule is "like
dissolves like," meaning polar solvents dissolve polar solutes and nonpolar solvents dissolve nonpolar solutes
(Reference.com, 2019). For the aliphatic hydrocarbons, cyclohexane and cyclohexene, they do not generally dissolve
in water because they are nonpolar compounds and water is a polar solvent [PLQ 1]. Benzene, an aromatic hydrocarbon, is
also insoluble in water. Following the same law of solubility, benzene is insoluble in water since benzene is nonpolar and
water is highly polar. Adding benzene to water will only result to a mixture in which benzene will float on top of
the water with no apparent mixing. The attractive forces among the benzene molecules are relatively
weak London dispersion forces. The attractive forces among the water molecules are relatively strong hydrogen
bonds. The only attractive forces among the benzene and water molecules are London forces. Thus, a few
benzene molecules will enter the water layer, but the strong hydrogen bonds among the water molecules keeps
most of the benzene molecules out. Similarly, a few water molecules will enter the hexane layer because of the
water-hexane London forces. But, for the most part, water and benzene are immiscible. They do not dissolve in
each other [PLQ 4].
In the flammability test, two drops of each of the three hydrocarbons were placed on three different watch
glass and was then ignited with a matchstick. Cyclohexane, cyclohexene and benzene resulted in flame
production. This indicates that all of them are combustible, attributed to the presence of carbon atoms in each
compound. Cyclohexane produced yellow flame and no soot when ignited. In contrast, both cyclohexene and
benzene produced a yellow-orange flame and soot. Unsaturated compounds, thus, can be distinguished from
saturated compounds by virtue of soot production. Incomplete combustion that occurs in compounds with
multiple bonds such as cyclohexene and benzene results in soot due to formation of unburned carbon residues.

The Baeyer’s test for unsaturation is for determining the presence of carbon-carbon double bonded
compounds (alkenes) or carbon-carbon triple bonded compounds (alkyne). The Baeyer test uses dilute Potassium
permanganate to oxidize the carbon-carbon double or triple bond. It's called oxidation because the double bond
is replaced by a hydroxyl group (an OH group). The carbon's charge goes from being +1 to +2, so it loses an electron
(and is thus oxidized) [PLQ 7]. In Potassium permanganate test, a purple solution of the oxidizing agent KMnO4 is
added to an alkene, the alkene is oxidized to a diol and the KMnO4 is converted to brown MnO2. The diol
produced has two adjacent alcohol groups. The chemical equation is as follows:
𝑂𝐻 𝑂𝐻
𝐻3 𝐶 − 𝐶𝐻 = 𝐶 − 𝐶𝐻3 + 𝐾𝑀𝑛𝑂4(𝑎𝑞) → 𝐻3 𝐶 − − − 𝐶𝐻3 + 𝑀𝑛𝑂2(𝑠)
𝐶𝐻 𝐶𝐻
Alkanes and aromatic compounds did not react with potassium permanganate. Reactivity towards oxidation of
cyclohexene signifies that alkenes are predisposed to addition reactions. The presence of a double bond in an
alkene allows addition reactions to proceed. Pi electrons in a double bond are loosely held between atoms
accounting for alkene reactivity. Alkanes possess single bonds or σ electrons which are tightly bound to atoms and
hence, demonstrate no reactivity under normal conditions [PLQ 2]. Benzene, although comprised of double
bonds, displays stability or chemical unreactivity because of resonance present in its conjugated planar ring system.
Its pi electrons are not as reactive as the pi electrons of alkenes. Also, benzene have all six sp2 hybridized carbon
atoms forming a perfect hexagon. The stability is accounted for by the delocalization. As a general principle, the
more you can spread electrons around - in other words, the more they are delocalized - the more stable the
molecule becomes. The extra stability of benzene is often referred to as "delocalization energy" [PLQ 8]. More
rigorous conditions such as elevated temperature will be required to elicit a reaction from benzene or aromatic
compounds.

In the reactivity of bromine with the three hydrocarbons, it was found out that only cyclohexene reacts
with bromine. Cyclohexene react spontaneously with bromine water due to their unsaturated nature. It was
observed that the color of the yellowish-brown solution turns colorless. 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 color of the bromine fades and the solution becomes colorless. The chemical
equation is as follows:
𝐶6 𝐻10 + 𝐵𝑟2 → 𝐶6 𝐻10 𝐵𝑟2
On the other hand, cyclohexane and benzene did not react with bromine as there was no reaction
that was observed during the experiment. Alkanes do not react spontaneously with bromine
water due to their saturated nature. Bromine is non-polar and therefore dissolves more readily
in a non-polar alkane than in polar water. Therefore, when alkanes come into contact with
bromine water, they cause it to decolorize, while they adopt the color. Cyclohexane has no pi-
unsaturation and is therefore not nucleophilic. It does not react with bromine unless energy in
the form of light or heat is applied. While in benzene, the increased stability of benzene makes
addition reactions difficult, thus reactions such as decolonization of bromine water do not occur
with benzene. This is because addition reactions would require the delocalized ring structure to
be broken, reducing the stability of the molecule. Substitution reactions are therefore more
favorable. And also, Benzene has delocalized electrons spread over 6 carbon atoms, whereas
alkenes have localized electrons above and below the 2 carbon atoms in the double bond and
benzene has a lower π electron density resulting in an insufficient electron density to polarize
the Br2 molecule. This results in the requirement of a halogen carrier.
To determine for the aromaticity of a compound, Nitration test was accomplished. The
samples were reacted with HNO3 and H2SO4. The general mechanism in this kind of reaction is an
electrophilic aromatic substitution. When tested with benzene, it was found out that benzene is
an aromatic compound due to the reaction during the test. Concentrated sulfuric acid acts as a
catalyst. The source of the nitronium ion is through the protonation of nitric acid by sulfuric acid,
which causes the loss of a water molecule and formation of a nitronium ion. In the nitration of
benzene, nitric acid is activated with sulfuric acid to produce a stronger electrophile, the
nitronium ion and because the nitronium ion is a good electrophile, it is attacked by benzene to
produce nitrobenzene [PLQ 5]. The mechanism of the reaction of nitration of benzene is as
follows [PLQ 11]:
Cyclohexane, on the other hand, were not reactive to the nitronium ion since no benzene ring
was present in their structures. The difference in reactivity of benzene and cyclohexane is due to
them being saturated or unsaturated. Since Benzene contains double bonds in which they are
referred to as unsaturated, atoms are easily attached to it. On the other hand, cyclohexane is a
saturated compound in which it contains single bonds making them more less reactive than
benzene. Unsaturated hydrocarbons are more reactive when compared to saturated
hydrocarbons since in unsaturated compounds it consists of double bonds (pi bonds) which are
weak and can be easily cleaved by incoming group therefore increasing the reactivity. In
saturated hydrocarbons only sigma bonds are present and these bonds are very strong and stable
[PLQ 6].
Aniline is an ortho/para director. For example, when aniline is chlorinated, the product
obtained is ortho and para. The –NH2 group directs the incoming group –CL to ortho and para
positions on the ring. Therefore, -NH2 group is an ortho-para director. While Nitrobenzene is a
meta director. The group which directs the second incoming group to the meta position, is called
a meta director. For example, alkylation of nitro benzene gives m-alkylnitro benzene as major
product. Therefore, –NO2 group is a meta director. The nitro group in nitrobenzene is a meta
director, while Amino group in aniline is ortho and para directing because a lone pair of electrons
is present on N which releases the electron density to the benzene ring and hence activates the
benzene ring towards electrophilic substitution reactions at ortho/para positions [PLQ 9 & 10].
 The fourth hydrocarbon that was supposed to be also tested was acetylene but since it
was unavailable, experiment was not conducted. However, some safety precautions when
preparing acetylene in the lab are needed since acetylene gas is highly flammable and can be
potentially explosive. Toxic gas, fumes, and vapors are emitted during operation, thus, atomic
absorption equipment must be properly vented. Avoid contact of chemicals with eyes and skin
and follow all laboratory safety guidelines. Additional safety tips include: wearing safety glasses
for mechanical protection, chemical-resistant gloves, and a chemical-resistant apron [PLQ 3].

III. CONCLUSION
Hydrocarbons are compounds that consist only of hydrogen and carbon atoms. Due to
the cancellation of C-H, they become a non-polar compound. To determine the solubility of
hydrocarbons, the general rule, “like dissolves like” is applied. The flammability test concluded
that all of them are flammable (due to the presence of carbon and hydrogen atoms) but only
cyclohexene and benzene produced soot, which differentiates saturated and unsaturated
compounds when burned. The Baeyer’s test is used for double bonds or alkenes. For positive
results using KMnO4 it must show decolorization of a purple solution and formation of a brown
precipitate (MnO2). In the reaction with bromine water, the reaction with bromine is said to be
positive to the free radical substitution if it loses red-orange color of the molecular bromine and
the evolution of gas, hydrogen bromine has occurred. To determine for the aromaticity of a
compound, nitration test was accomplished.
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