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Names: Bryle Kristiann Camarote Date Performed: January 29, 2014

Nimrod Romelo Date Submitted: February 5, 2014


Sarah Jane Valdon

EXPERIMENT #6
Hydrocarbons

I. INTRODUCTION

Hydrocarbons are family of organic compounds composed entirely of carbon and


hydrogen. They are the organic compounds of simplest composition and may be considered the
parent substances from which all other organic compounds are derived.
Compounds in which the carbons are bonded to each other by only single bonds are
known as saturated compounds; examples include alkanes and cycloalkanes. Alkanes contain
only carbon and hydrogen atoms; they are considered saturated because they have only C-C
and C-H. Single bonds and thus contain the maximum possible number of hydrogen per carbon.
All carbons are sp3 hybridized and are connected by sigma bonds.
On the other hand, cycloalkanes are types of alkanes. One example is cyclohexane. It is a
colorless, volatile liquid with pungent odor and has the formula C6H12. It is produced by
hydrogenation of benzene and distillation of petroleum. It is used primarily as solvent for
paints, varnish and oils.

Unsaturated compounds are compounds that contain one or more double or triple
bonds between their carbon atoms. Several unsaturated compounds include alkenes, benzenes
and cyclohexenes. Alkenes are hydrocarbon that contain a carbon-carbon double bond, C=C.
They have the general formula CnH2n. Because of their double bond, alkenes have lesser
number of hydrogens per carbon than alkanes and are therefore referred to as unsaturated.
The double bond contains a pi bond while some single bonds have sigma bonds instead.
Alkenes include cyclohexene, benzene and toluene.
Ringed structures such as cyclohexenes, benzenes and toluenes are considered as
alicyclic compounds. Benzene is a colorless liquid with a characteristic odor and burning taste.
Its formula is C6H6. The benzene molecule is a closed ring of six carbon atoms connected by
bonds that resonate between single and double bonds.
It is insoluble in water but miscible in other elements or compounds. Toluene is a
colorless hydrocarbon occurring in coal tar. Toluene is sometimes called methylbenzene. It’s a
type of benzene with one methyl group attached. It is used as a solvent and as a source of
synthetic compounds.

Alkynes are hydrocarbons containing C= C. The carbon-carbon triple bond results from
the overlap of two sp-hybridized carbon atoms and consists of one sp-sp sigma bond and two p-
p pi bonds. Alkynes have the general formula: CnH2n-2. They are very actively chemically and are
not found free in nature.

Acetylene (C2H2) on the other hand, is a colorless, odorless, flammable gas having HC=
CH. It is also known as an ethyne. Acetylene gas is usually stored in metal tanks, under pressure,
dissolved in acetone. It burns in air with a hot and brilliant flame.
Hydrocarbon solubility follows the rule of like dissolves like. This means that polar compounds
like water and alcohols dissolve polar compounds. Nonpolar compounds dissolve other
nonpolar compounds but tend not to dissolve polar compounds.

Halogenation is the replacement of one or more hydrogen atoms in organic compounds


by a halogen. The halogenation of an alkane appears to be a simple substitution reaction in
which a C-H bond is broken and a new C-X bond is formed. The chlorination of methane
provides a simple example CH4 + Cl2 + hv and heat CH3Cl + HCl. Bromination of alkanes
occurs by similar mechanism, but is slower and more selective because a bromine atom is a less
reactive hydrogen abstraction agent than a chloride atom as reflected by the higher bond
energy of H-Cl than H-Br. Alkynes also undergo halogenation. Chlorine and bromine add easily
to a triple bond, the bromine test is able to determine the presence of unsaturation.

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.
The test with ammoniacal silver nitrate can be used to determine whether the carbon-
carbon triple bond is found in carbon chain’s end or not. The test involves the release of the
terminal proton of the alkyne so that the resulting acetylide ion can form an insoluble
precipitate with Ag+.

In this experiment, hydrocarbons were examined and investigated. Their solubilitie


behaviors were tested, their halogenation, oxidation and reactions with ammoniacal silver
nitrate were also observed.
II. RESULTS AND DISCUSSION

I. Investigation of Hydrocarbons

1. Solubility Behavior

This part of the experiment involves testing the miscibility of each sample to the CCl 4, H2O, 10%
NaOH, and H2SO4 solvents.

For cyclohexane, mixing it into the CCl4 solvent resulted in a clear solution. The same
goes for the benzene and the toluene. The results signify that each sample is miscible to the
carbon tetrachloride solvent. This is due to the principle “like dissolves like”. Our solvent is a
nonpolar molecule (with zero dipole moment) because of the four chloride atoms arranged in a
tetrahedral arrangement around the carbon, cancelling their electronegative forces which can
cause polarity.
And each organic sample (cyclohexane, benzene, and toluene) only contain C-H bonds,
they are generally nonpolar. Because both components are nonpolar, we can therefore say that
they are soluble in the solvent.

When water was added to cyclohexane, benzene, and toluene, a clear and colorless
solution gave rise. The resulting solution is heterogeneous with two layers which imply that
hydrocarbons are immiscible and thus insoluble with water.

Furthermore, water is a polar compound due to very polar O-H bonds. In addition,
nonpolar hydrocarbons, on the other hand, don’t dissolve in polar water. The same goes for the
10% NaOH solvent. Cyclohexane formed a separation layer when mixed with the solvent
indicating that both are immiscible with each other, benzene formed a clumpy layer with the
solvent showing minute emulsions, and toluene also formed a separation layer with the solvent
but with bubble suspension showing the evolution of gas molecules. We can clearly conclude
that each compound is insoluble with the sodium hydroxide solvent. The solvent is polar due to
the dipole moment of the –OH while the samples are nonpolar. The same principle applies
which is “like dissolves like”.

Lastly, we used sulfuric acid H2SO4 as the solvent. Mixing with cyclohexane produced an
immiscible mixture with the upper layer clearer than the lower layer which may be due to the
gases evolved from the agitation of the concentrated acid. The same result was obtained for
the benzene and toluene which formed a translucent upper layer. All samples were immiscible
with the solvent because H2SO4 is polar while the samples are nonpolar. Moreover, all were
exothermic.
Table 6.1 below summarizes all the remarks being observed in the solubility behavior of the
given solvents.

PHYSICAL
SOLVENT SAMPLE COLOR OBSERVATIONS MISCIBILITY
STATE
Cyclohexane Colorless Very clear Miscible Liquid
CCl4
Benzene Colorless clear Miscible Liquid
(nonpolar)
Toluene Colorless clear Miscible Liquid
Unequal Liquid with
Cyclohexane Colorless Immiscible
Separation two layers
More curved
H20 Liquid with
Benzene Colorless separation Immiscible
(polar) two layers
layer
Bent separation Liquid with
Toluene Colorless Immiscible
layer two layers
Equal Liquid with
Cyclohexane Colorless Immiscible
Separation two layers
Liquid with
Clumpy,
Benzene Colorless Immiscible two layers
10 % NaOH separated layer
Clearer upper
layer, bubble Liquid with
Toluene Colorless Immiscible
suspension at two layers
lower layer
Upper layer
more clear,
Liquid with 2
Cyclohexane Colorless unequal Immiscible
layers
separation,
exothermic
Translucent
Concentrated
upper layer,
H2SO4
Benzene Colorless unequal Immiscible Liquid 2 layers
separation,
exothermic
Translucent
Liquid with 2
Toluene Colorless upper layer, Immiscible
layers
exothermic
Table 6.1 Solubility Behavior of the different Hydrocarbons
2. Halogenation

In this part of the experiment involves testing the reactivity of the organic compound
with bromine or specifically, determining whether a particular compound have double bonds or
triple bonds. A positive result shows the loss of the red-orange colour of the bromine solution.
Bromine test involves electrophilic addition reaction were in alkenes react with Br2 to form a trans-
dibromoalkane. For saturated hydrocarbons (alkanes), they undergo substitution reactions with
halogens when exposed to ultraviolet light while unsaturated hydrocarbons (alkenes and alkynes)
readily undergo addition reactions with halogens.

In the experiment, 0.05 M Br2ICCl4 was added to the wrapped and unwrapped test
tubes of cyclohexane, benzene and toluene. The tubes were allowed to stand for 10 minutes
and later examined. The set of unwrapped samples were found to have changed colour from
red-orange to whitish clear: Cyclohexane appeared clearer than toluene and benzene, while
both toluene and benzene showed to be translucent white. For the set of wrapped samples, all
displayed a translucent light orange colour with the cyclohexane clearer than toluene and
benzene.
Benzene and toluene are aromatic hydrocarbons. Though benzene and toluene have
C=C, they don’t react like alkenes or alkynes. The result showed a negative test as the yellow-
orange remained. Aromatic rings are less reactive toward electrophiles like bromine than
alkenes or alkynes are. For bromination of aromatic hydrocarbons to take place, a catalyst is
needed. And this bromination occurs as electrophilic aromatic substitution. Electrophilic
addition is not favored by aromatic rings because the stabilities will be lost. Instead, they
undergo substitution for stability. Pi-bonds in benzene and toluene contain localised electrons
sited above and below the two carbon atoms in the double bonds. This produces a region of
high electron density.

When bromine approaches benzene/toluene, electrons in pi-bond repel electrons in


Br-Br bond, inducing a dipole in the Br2 molecule, it is now polar. Pi-electron pair from the
double bond is now attracted to the slightly positive bromine atom, causing the double bond to
break, forming a new bond between one carbon atom and one bromine atom, forming a
positively charged carbocation. The bond between the two Br atoms breaks by heterolytic
fission, forming a bromide ion. The Br- ion is attracted towards the intermediate carbocation,
forming a covalent bond.

Furthermore, the function of CCl4 is to be the solvent for bromine. Since bromine is
immiscible with nonpolar hydrocarbon compounds, carbon tetrachloride aids by allowing the
two compounds easily react. Moreover, by dissolving the Br2, the reactant energy is lowered,
lowering the activation energy, and thereby making the reaction go more readily. While for
cyclohexane, the ultraviolet light acts as a catalyst in order for the reaction to occur. The energy
from the UV light is absorbed by the Bromine gas and breaking it into two bromine radicals. The
bromine would then remove and replace one hydrogen from the cyclic ring forming a cyclic
halide. HBr is produced as a by-product.
Benzene and toluene comprise of double bonds and bromine readily reacts with them even
without the prescence of catalysts. Via electrophilic substitution, the Br2 replaces one of the
hydrogen singly bonded to the benzene/toluene ring with HBr produced as a by-product.

Table 6.2 below summarizes all the results and observation in halogenation.

Sample Unwrapped RESULT Wrapped RESULT


Lighter translucent
Cyclohexane Less translucent white POSITIVE NEGATIVE
orange
Light translucent
Benzene Translucent white POSITIVE NEGATIVE
orange
Light translucent
Toluene Translucent white POSITIVE NEGATIVE
orange

Table 6.2 Halogenation

3. Oxidation: Reaction with Baeyer’s Reagent

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.

In the experiment, when cyclohexane reacted with Baeyer’s reagent, there was no
color change observed, the solution still remains purple, and no layers were formed. This
confirms that potassium permanganate does not react with alkanes because they are saturated
(single bonds which are taken and have more amount of hydrogen bonded). For benzene,
bubble suspension at the top of the light purple layer was perceived. The same remark also
goes with toluene but only has an exception, this time it is only lighter than what we have
observed in benzene.

Despite the unsaturation of aromatic rings, they do not usually react with strong
oxidizing agent such as KMnO4. They are inert to oxidation. Table 6.3 below summarizes the
results of this part of the experiment.

Table 6.3 Oxidation: Reduction with Baeyer’s Reagent


SAMPLE OBSERVATION RESULTS
Color change is unobservable
Hexane NEGATIVE
(Purple color)
Benzene Color change is unobservable NEGATIVE
(Purple color), Bubble
suspension showed
Color change is unobservable
Toluene NEGATIVE
(Purple color)
Cyclohexene Brown POSITIVE

4. Reaction with Ammoniacal Silver Nitrate

Ammoniacal silver nitrate serves as a test to determine the presence of a triple bond
(alkyne). The reaction includes the release of terminal proton of the alkyne so that the acetylide
ion can form an insoluble precipitate with Ag+. For example, acetylene reacts with ammoniacal
solution of AgNO3 forming acetylide of silver.

H-C C-H + 2 AgNO3 + 2 NH4OH AgC CAg + 2NH4NO3 + 2H20


(white precipitate)
When ammoniacal AgNO3 was added to cyclohexane, the solution formed two
immiscible layers in which bubble suspensions were present. Since the reaction with
ammoniacal AgNO3 is exclusive to alkynes, the cyclohexane resulted in a negative test in which
there is no reaction.
Table 6.4 below summarizes all the observations and results of the experiment.

Table 6.4 Reaction with Ammoniacal Silver Nitrate


Ammoniacal Silver Nitrate
Sample
Pre-observation Color Clarity Physical Sate
Colorless with Clear with
Clear and
Cyclohexane formation of bubble Liquid
soluble
two layers suspensions

B. Preparation and Testing of Acetylene Gas

The acetylene gas was prepared by reacting water to calcium carbide. The slowly addition of
water to calcium carbide resulted to the release of acetylene gas.
The chemical reaction for the preparation of acetylene is:
CaC2(s) + 2H2O (l) → Ca(OH)2(s) + C2H2 (g)

Acetylene gas was then released upon the slow addition of water. Afterwards, the collected
gas was then tested for its solubility behaviour with cyclohexane, toluene, and benzene. For
cyclohexane, it mixed well with no sign of layer formation. The same goes for toluene and
benzene. Acetylene was next tested with halogenation using 0.05 M Br2ICCl4.
The unwrapped mixture appeared less clear or slightly foggy than the wrapped mixture. For
oxidation using Baeyer’s reagent, acetylene caused the solution to change in color with bubble
formation. And lastly, acetylene was tested with its reaction with ammoniacal silver nitrate and
resulted in the formation of precipitates.

Table 6.5 below summarizes the results of this part of the experiment.

Solvent Observation
Change in color of the solution with bubble
Baeyer’s reagent (violet)
formation
Ammonium silver Precipitate formed
Wrapped Unwrapped
Br2 in CCl4 (red orange) Less clear, slightly
Clearer
foggy

Table 6.5 Preparation and Testing of Acetylene Gas

Terminal alkynes are acidic because of its sp hybridization. In sp hybridized orbitals, the
electron pair is nearest to the nucleus. This causes the alkyne to lose its Hydrogen and form an
H+ ion. Since the electron pair is near the nucleus, the anionic compound becomes stable. And
a stable conjugate base means that it is an acidic compound. But they acidity is still greatly less
than water.

Given below are the reagents and the reaction conditions that would distinguish between
the following compounds. Written also are the equations for the reactions involved:

a). Benzene and Ethylbenzene

Baeyer’s Reagent
 Benzene does not get oxidation with baeyer’s reagent, but when ethyl benzene is
oxidised with baeyer’s reagent (alkaline KMnO4) it gives Benzoic acid which gives
effervescence of CO2 with bicarbonate

b.) 1-butyne and 2-butyne

Reaction with ammoniacal AgNO3


 With the reaction of Ammoniacal AgNO3, it’s possible to determine whether the C≡C is
found at the end of the carbon chain or not. Upon reaction, the terminal end of 1-
butyne releases a proton so that the resulting acetylide ion can form an insoluble
precipitate with Ag+. The reaction for 2-butyne is different.
c. 2-methylpentane and 2-methyl-2-pentene

Reaction with bromine


 2-methylpentane is an alkane and 2-methyl-2pentene is an alkene, to distinguish one
from the other, bromine test can be used. 2-methylpentane react with bromine to
produce H-Br gas as a by product, while 2-methyl-2pentene does not produce H-Br.

d. toluene and 1-methylcyclohexene


 Baeyer’s Test

III. CONCLUSION

Hydrocarbons are compounds that contain only hydrogen and carbon atoms and
because of the cancellation of C-H, they become a non-polar compound. Since they are non-
polar compounds they will be only dissolves in non-polar compounds like CCl4 as the rule of
solubility states that like dissolves like. Hydrocarbons are immiscible in a polar compound such
as water, NaOH , and H2SO4. If Br2 is used as a halogen, the reaction 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. The Baeyer’s test is a test 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). 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. Different errors can be encountered in this experiment like the calibration of
equipment, the personal biases of the individual especially on the color change of the
compound and the describing the compound in the looks, physical state, miscibility etc. Errors
can be eradicated by the proper calibration of the equipment and by the and by taking care of
what is being noted.
Various test in determining the specific functional groups by observing its behaviour
when it reacts with certain reagent. These chemical reactions such as halogenation and
oxidation help us predict what type of hydrocarbon is being tested (saturated or unsaturated).
In the experiment, halogenation and oxidation reaction more likely took place for unsaturated
hydrocarbon due to electron dense areas making substitution of the hydrogen by a halogen
easier. We also observed that most of the chemical reactions accompany change in color,
change in temperature of the given solution and formation of precipitates which signals that
reaction really happened. Careful handling of the solutions should be done during the
experiment to prevent skin irritation and burns.

IV. REFERENCES

McMurry, Foundations of Organic chemistry, Philippine Edition, 2004.


Cadwell, William. College Chemistry, 1977.
Voldhardt, Organic Chemistry, 2001.
Morrison, Organic Chemistry 2nd Edition, 2004.

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