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FUNDAMENTAL OF ORGANIC
CHEMISTRYLABORATORY
REPORT
STUDENT ID : 2021126967
GROUP : A4AS1203C
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REACTIONS OF HYDROCARBONS AND ALKYL HALIDES
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INTRODUCTION
Hydrocarbons have been organic compounds that contain only carbon and hydrogen atoms.
They are primarily derived from natural sources such as petroleum, coal and natural gas.
Hydrocarbons are primarily used as fuels and solvents. The functional group is the primary
distinction between hydrocarbons which are alkene, alkyne, alkane and aromatic. They can be
either saturated or unsaturated. A saturated hydrocarbon has only one C-C bond (the sigma (σ)
bond). An unsaturated compound has at least two atoms connected by sigma (σ) and pi (π)
bonds.
Aromatic hydrocarbons were also cyclic compounds with a structure like benzene, containing
6- electrons in a 6-member ring. In general, -bond is significantly weaker than -bond. In many
cases, the -bond will be involved in a chemical reaction while remaining unaffected. In the
laboratory, widely used chemical exams for unsaturation hydrocarbons include bromine,
potassium permanganate, and sulfuric acid. As a result, the experiments that follow
demonstrate some of the basic reactions of unsaturated, and aromatic and saturated
hydrocarbons.
A compound including at least one halogen groups are attached to an alkyl group is known as
an alkyl halide. The halogen group includes bromide, iodide, fluorine, and chloride. Iodide ion
is really a strong nucleophile that dissolves in acetone. These properties, combined with
acetone's non-polar nature, favour the SN2 reaction. Because sodium chloride and sodium
bromide are insoluble in acetone and it will precipitate from solution, the reaction can be
followed. When an alkyl halide is exposed to an ethanolic solution of silver nitrate, the silver
ion coordinates with a pair of electrons on the halogen, weakening the carbon-halogen bond
and producing an insoluble silver halide. This reaction is carried out via an SN1 system.
OBJECTIVES
APPARATUS
CHEMICALS
1. Bromine water
2. Potassium permanganate
3. Heptane
4. Cyclohexane
5. Cyclohexene
6. Toluene
7. 1-bromobutane
8. 2-bromobutane
9. 2-bromo-2-methylpropane
10. Sodium iodide in acetone
11. Ethanolic silver nitrate
PROCEDURE/S
I. Combustion of Hydrocarbons
1. The Bunsen burner was ignited, and the flame was observed.
2. 2 drops of each hydrocarbon (cyclohexane, cyclohexene and toluene) were dropped on the
different spatula.
3. The hydrocarbon was ignited using a Bunsen burner and immediately removed from the
burner.
4. Observations based on the characteristics (colour and amount of smoke) of each flame along
with any residue left behind on the spatula (formation of soot) were recorded.
A. Aliphatic hydrocarbon
1. 1 ml of each hydrocarbon compound (cyclohexane, cyclohexene) were placed into three
different test tubes.
B. Aromatic hydrocarbon
1. 1 ml of toluene was placed in two different test tubes.
4. The test tubes were placed in a warm water bath for 15 minutes.
A. Aliphatic hydrocarbon
1. 1 mL of hydrocarbon compounds was placed (cyclohexane, cyclohexene) into three
different test tubes.
3. The test tube was shacked and let stand for 2 minutes.
2. 2 mL of dilute potassium permanganate solution was added into the test tube.
3. The test tube was shacked and let stand for 2 minutes.
Pre-caution steps:
1. Each test performed in a clean test-tube. The test tube was cleaned with ~0.25
mL ethanol or acetone after rinsed with water.
2. Do not contaminate reagents with samples or other reagents.
3. The results were examined to make sure that they make sense (for example, a
3° alkyl halide should not react via an SN2 mechanism faster than a 1° alkyl
halide).
4. The chemical tests were repeated for confirmation.
I. Effect of structure of alkyl halides on the rates of SN2 and SN1 reactions
A. SN2 reaction
1. 2 drops of each alkyl halide (1-bromobutane, 2-bromobutane and 2- bromo-2-
methylpropane) were placed into three clean test tubes.
2. 2 mL of sodium iodide was added in acetone into each test tube and the content mixed
thoroughly and note the time.
3. If no reaction within 5 minutes, place the test tube in water bath (~50 °C).
4. Observations and the time of the first appearance of any cloudiness or precipitate formed
were recorded.
B. SN1 reaction
1. 2 drops of each alkyl halide (1-bromobutane, 2-bromobutane and 2- bromo-2-
methylpropane) were placed into three clean test tubes.
2. 2 mL of ethanolic silver nitrate was added into each test tube and the content mixed
thoroughly and note the time.
3. If no reaction within 10 minutes, place the test tube in water bath (~50 °C).
4. Observations and the time of the first appearance of any cloudiness or precipitate formed
were recorded.
4. Observations and the time of the first appearance of any cloudiness or precipitate formed
were recorded.
RESULTS
I. Combustion of Hydrocarbons
without Remain
iron unchanged 𝐶6 𝐻5 𝐶𝐻3 + 𝐵𝑟2
filling → 𝐶6 𝐻5 𝐶𝐻3 𝐵𝑟2
I. Effect of structure of alkyl halides on the rates of SN2 and SN1 reactions
SN1 Solution turned Solution turned very Solution turned very cloudy
(Ethanolic slightly cloudy cloudy
silver nitrate)
DISCUSSION
There are three objectives of carrying out this experiment; the first is to investigate the
solubility of hydrocarbon compounds, the second is to compare the chemical reactivity of
aliphatic hydrocarbon and aromatic hydrocarbon compounds, and the third is to assess the
reactivity of alkyl halides compounds. This experiment was separated into three parts: part a,
part b, and part c.
After experiment were conducted, we can summaries all the results that we obtained. Based on
the observation and data obtained on the data sheet, Part a of this experiment was conducted to
determine the solution of hydrocarbon in heptane and water. This objective was meeted, and
the experiment was successful. Cyclohexane, cyclohexene, and toluene were found to form a
layer on the surface of the solution in every test tube and all of these hydrocarbons were found
to be immiscible in water. This can happen because water is a polar solvent while hydrocarbons
are a non-polar solvent, and hydrocarbons and water cannot combine or mix because water has
a strong polar hydrogen bond while hydrocarbons have a week force dispersion. (James
Ashenhurst, 2020). In heptane, on the other hand, hydrocarbons (cyclohexane, cyclohexene,
and toluene) did not create a form layer when mixed. This clearly has shown that hydrocarbons
are miscible in heptane and could even mix, due to the fact that water and hydrocarbon are both
non-polar solvents with weak dispersion forces and organic solvents, so both can be mixed well
and apply "like dissolves like" principle because both have similarity in characteristics (Matt ,
2011).
This experiment was done for part b to identify the chemicals properties of hydrocarbons
compounds. This experiment had been split into three minor parts. Part a, the first step is to
decide whether hydrocarbon compounds go through an incomplete or complete combustion.
The amount of soot and black smoke produced, as well as the color of flames, are the three
elements observed in this experiment. Cyclohexane, cyclohexene, and toluene were used and
underwent a complete combustion due to a sufficient supply of oxygen in the experiment room.
Then, after complete combustion, water and carbon dioxide were identified. As a result,
compounds that do not undergo complete combustion (incomplete combustion) still produce
water as a byproduct of the reaction, but also carbon and carbon monoxide. Cyclohexane, an
alkane, produces yellowish-orange, flame burned vigorously, makes a small amount of smoke
and soot because it has a single bond and a smaller carbon percentage, makes the flame difficult
to sustain longer after strong combustion. Apart from that, cyclohexene manage to produce
black smoke and a lot of soot, produce yellow flame, and burnt moderately strong because
it has a higher percentage of carbon and a double bond, which makes it an unsaturated
hydrocarbon than cyclohexane (saturated carbon, alkane), and this also makes cyclohexene
burns more than cyclohexane. After that, toluene, which is the combustion of aromatic
hydrocarbons, was stronger than cyclohexene and cyclohexane because it consists of the
highest ratio carbon atoms to hydrogen atoms, producing the blackest smoke and soot among
those hydrocarbon compounds. (Aliphatic Hydrocarbons, 2021)
Bromine was involved in the next minor part of experiment b (part b). Cyclohexane managed
to preserve the yellowish-orange color of bromine solution due to the fact that cyclohexane had
no response toward the bromine because it was a saturated hydrocarbon, it causes no reaction.
But the reaction will only take place under UV light. Cyclohexene manages to change or
decolorize the color of bromine into a clear solution while creating a lot of air bubbles. A
colourless upper layer and lower dark reddish brown colour produced were made in a toluene
and iron fillings test tube because it can only react in the presence of a catalyst (iron fillings)
in electrophile substitution reactions. Toluene test tube without iron fillings or catalyst, remain
unchanged because toluene become low reactive to bromine.
Potassium permanganate was involved in the last part of experiment b (part b). The potassium
permanganate color was preserved in cyclohexane, showing that there is no reaction between
cyclohexane and potassium permanganate because cyclohexane is saturated hydrocarbon.
Cyclohexene then produced dark brown solutions from the purple solution of potassium
permanganate because it oxidized to diol. Toluene, on the other hand, has no reaction to
potassium permanganate because all its carbon atoms have been handed out, which leaves
potassium permanganate's color unchanged (purple).
Finally, in this experiment (part c), this experiment was conducted to explain the reactions of
alkyl halide involves 1-bromobutane, 2-bromobutane and 2-bromo-2-methylpropane. After the
observation, it was determined that 2-bromo-2-methylpropane is more reactive in SN1 reagents
than SN2 when the rates of the reaction involving SN1 and SN2 are considered. While 1-
bromobutane and 2-bromobutane has the same rate in SN1 and SN2. SN1 is an ethanolic silver
nitrate meanwhile SN2 is sodium iodide in acetone, and both are nucleophilic substitution
reactions. Still, SN2 has higher reaction rates than SN1 because SN2 is bimolecular but instead
SN1 is unimolecular. (James Ashenhurst, 2021). White precipitate was formed at the bottom
of the second test tube, and the solution become very cloudy because of solvent polarity in
SN1. When SN2 was added, it catalyzes cations instead of anions when polar aprotic solvent
is used. Water used in SN1 acts as a protic solvent, which balances the intermediate
carbonation. No changes in the rate of reaction were found as the nucleophilic was solvated by
concentration in alkyl halides. The fact that the solution in all test tubes became very cloudy
indicated that the concentration of alkyl halides remained constant.
QUESTIONS
ANSWER: Because of their uneven charge distribution, hydrocarbons are insoluble in polar
solvents. According to the solubility rule, "like dissolves like," which indicates that polar
solvents dissolve polar solutes or non-polar solvents dissolve non-polar solutes.
Hydrocarbons, on the other hand, are soluble in non-polar solvents because they are non-
polar molecules with the same intermolecular forces which allow Hydrocarbons and the non-
polar solvent to interact.
ANSWER: There really are two types of combustion: complete & incomplete combustion, and
it can go through either of them based on the quantity of oxygen available. If there is enough
oxygen, complete combustion occurs. The hydrocarbon fuel's oxygen and carbon atoms will
combine with oxygen in an exothermic reaction, using up all of the reactant. Incomplete
combustion when there is insufficient oxygen, and it results in the production of carbon
monoxide as well as water at the end of the process.
UV LIGHT
ANSWER: 𝐶6 𝐻12 + 12𝐵𝑟2 → 𝐶6 𝐵𝑟12 + 12 𝐻𝐵𝑟
8. What would be the effect of carrying out the sodium iodide in acetone
reaction with the alkyl halides using an iodide solution half as
concentrated?
ANSWER: The reaction would be slower because SN2 reactions favour a high
concentration of the nucleophile.
ANSWER: 𝑪𝟒 𝑯𝟗 𝑩𝒓 + 𝑵𝒂𝑰 → 𝑪𝟒 𝑯𝟗 𝑰 + 𝑵𝒂 𝑩𝒓
ANSWER: When 1-bromobutane was mixed with sodium iodide in acetone, it reacted faster
than 1-chlorobutane. The reason for this is that 1-bromobutane is a better leaving group than
1-chlorobutane because it has a weaker base.
CONCLUSION
In conclusion, the experiment's objectives were met and exceeded. We were able to
successfully meet all the adjectives, as evidenced by the data sheet from the experiment. This
experiment was conducted to investigate the solubility of hydrocarbon compounds, the second
is to compare the chemical reactivity of aliphatic hydrocarbon and aromatic hydrocarbon
compounds, and the third is to assess the reactivity of alkyl halides compounds. We can
conclude from this experiment that hydrocarbons like cyclohexane, cyclohexene, and toluene
are miscible with non-polar solvents like heptane but immiscible with polar solvents like water.
This goal was accomplished.
Next, to work out whether organic compound compounds bear incomplete or complete
combustion. we tend to complete from this experiment that cyclohexane, cyclohexene, and
resolvent were fully burned, which when complete combustion, water and carbon dioxide were
distinguished. Compounds that undergo incomplete combustion manufacture not solely water
as a by-product, however it additionally carbon and monoxide. Toluene, as associate
hydrocarbon, has the best carbon-to-hydrogen atom quantitative relation, formed the darkest
smoke and soot amongst organic compounds. Cyclohexane managed to preserve the yellowish-
orange colour of bromine as a result of cyclohexane had no reaction with atomic bromine, but
the reaction can solely turn up or react underneath UV light. Cyclohexenes discolour the colour
of atomic bromine into a transparent or clear colour and generate plenty of air bubbles. In our
experiment, a colourless solution and dark reddish brown in iron fillings tube because it will
solely react within the presence of a catalyst, that is iron fillings in electrophile substitution
reactions. Test tube that does not have iron fillings or catalyst remain unchanged as resolvent
became less reactive to atomic number 35, bromine. The colour of permanganate was preserved
in cyclohexane as a result of there was no reaction among cyclohexane and permanganate due
to cyclohexane being a saturated organic compound. Because of it oxidised to dihydric alcohol,
cyclohexene generated dark brown resolutions from the purple solution of permanganate.
The final part of this experiment was done to understand the reactions of alkyl halide. 2-
bromobutane is clearly quite reactive in sn1 reagents than sn2. Due to the effect of solvent
polarity in sn1, white precipitate formed from the solution at the bottom of the second test tube
and became cloudy. When sn2 is introduced, it catalyzes cations in polar aprotic solvents.
Because the nucleophilic has been solvated by concentration in alkyl halides, no changes in
reaction rate were observed the solution in all test tubes became extremely cloudy indicates
that concentration of alkyl halides stayed constant. Overall, this experiment was successful in
determining the solubility of hydrocarbon compounds, to compare the chemical reactivity of
aliphatic hydrocarbon and aromatic hydrocarbon compounds and to assess the reactivity of
alkyl halide compounds.
REFERENCES
James Ashenhurst. (2020, February 12). Polar Protic? Polar Aprotic? Nonpolar? All About
Solvents. Retrieved from Master Organic Chemistry :
https://www.masterorganicchemistry.com/2012/04/27/polar-protic-polar-aprotic-
nonpolar-all-about-solvents/
James Ashenhurst. (2021, february 6). Comparing the SN1 and SN2 Reactions. Retrieved from
master organic chemistry:
https://www.masterorganicchemistry.com/2012/08/08/comparing-the-sn1-and-sn2-
reactions/