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I.

THEORETICAL BACKGROUND

Alkenes have a double bond between two carbon atoms comprising one sigma and one pi bond.
The pi bond is more reactive, whereas the sigma bond shares characteristics with alkanes. The sp2
hybridization of the carbon atoms in the double bond creates a planar structure. Alkenes can form
relatively stable isomers depending on whether substituents are positioned on the same (cis) or
opposite (trans) sides of the double bond since rotation around the double bond is not preferred.
Diastereoisomers Iis what they call these isomers (pressbooks.pub).

The molecular geometry of alkenes contains bond angles about each carbon in a double bond of
roughly 120 degrees, as predicted by the VSEPR model of electron pair repulsion. Steric strain
brought about by nonbonded interactions produced by functional groups connected to the double
bond's carbons may cause the angle to change. In propylene, for instance, the C-C-C bond angle is
123.9 degrees. With an average bond length of 133 picometres, the alkene double bond is both shorter
and stronger than a single covalent bond (Tamura et. al., 2013)

According to Salamova and Hites (2015), the polymerization of alkenes is an economically


significant process that produces polymers with high industrial value, such as the plastics
polyethylene and polypropylene. A free-radical process or an ionic mechanism can be used to carry
out polymerization.

The labels E and Z are used to denote the double bond geometry when an alkene has more than
one substituent. Alkenes with the higher priority groups on the same side of the double bond have
these groups together and are designated "Z." Alkenes with the higher priority groups on opposite
sides are designated "E." These labels derive from the German words "entgegen," which means
"opposite," and "zusammen," which means "together" (Morrison et. al., 2007).

One of the most practical groups of chemicals, alkenes can be used to create a variety of goods,
from polymers to medications. Nonetheless, the majority of alkenes that are sold in bulk come from
sources that use petroleum. Today, waste vegetable oil may be used as a starting material in a novel
process created by scientists at the Max Planck Institute for Coal Research to manufacture terminal
alkenes.

Using calculations from density functional theory and experimental data, Yu-Ming Li and his
team at Nankai University in China reported an intramolecular aminoboration reaction on
unfunctionalized olefins in 2015. They predicted a mechanism in which HCl elimination was the rate-
determining step and had an energy barrier of 37.6 kcal/mol.

Generally, the chemical activity of alkenes is driven by the type of bonding present, the
unsaturation, the double bond energy, and the presence of pi electrons. Alkenes go through further
processes. Alkenes react with electron-deficient entities because the double bond serves as a source of
electrons. These species, known as electrophiles, have the potential to add electrophiles. Alkene can
also go through polymerization and processes involving free radical addition.

II. TLO
TLO#9: Understand the reactivity, preparations, reactions of Alkenes. Discuss the basis for the
Baeyer's Test for unsaturation.

III. PROCEDURES
1. Observe the physical properties of the alkene (hexane or cyclohexene). Record your observations.
2. Place 2 ml of the alkene in a test tube. Add 3 drops of Br/CCl4 solution dropwise, observing the
solution after each drop. Add at least 10 drops and note the results carefully.
CAUTION!
Use bromine solution in the hood. Wear gloves when using this reagent.
3. Baeyer's Test for Unsaturation: Place 5 drops of the alkene into a test tube and add 2 drops of dilute
potassium permanganate solution. Shake the tube well, and record your observations.
4. Ignite (in hood) a few drops of the alkene in an evaporating dish.
5. Reaction with NaOH
To one test tube with 10 drops alkene, add 1-2 ml 3M NaOH. Observed for any sign of a reaction.
6. Reaction with HCI
To one test tube with 10 drops alkene, add 1-2 ml 3M HCl. Observed for any sign of a reaction.

IV. DATA & RESULTS


Physical Properties of Alkene: 
Observations

Physical state At room temperature, alkenes exist in all three phases, solid, liquids, and
gasses.

Color Alkenes are colorless

Solubility in water Alkenes are insoluble in water due to their non-polar characteristics.

Density compared to Alkenes are less dense than water with most densities in the range of 0.6
water to 0.7 g/mL.

Chemical Properties of an Alkene


Observations

Addition of Br2/CCl4 The solution is immiscible, and the bromine just sink and
settled at the bottom of the test tube

Dil. KMnO4 The solution is slightly immiscible and its color changes from
Equation: violet to brown (precipitate).
C6H12(1HEl) + KMnO4 + H2O =
C6H12O2(a) + KOH + MnO2 +
0.5H2(g)

Combustion There flame was yellow-orange colored that produced a black


Equation: smoke.
C6H12 + 9 O2 = 6 CO2 + 6 H2O

Reaction with NaOH The solution is not immiscible and there is an evident presence
of separation layers between the two solvents
Reaction with HCl  Similar with NaOH, the solution is not immiscible and there is
an evident presence of separation layers between the two
solvents
Is the alkene an acid, base, or neutral solution?
Alkenes are neutral compounds.
V. DISCUSSION
Compared with alkanes, alkenes are more reactive. An addition reaction occurs between alkenes
and halogens, such as bromine. While there were no notable color changes in the experiment, the
mixture of bromine reagent, whose color is reddish, should make the red color disappear and turn
colorless. The disappearance of the red color indicates that the sample contains an alkene; this
happens because the double bond breaks, and the bromine atom attaches to each carbon.
On the other hand, Baeyer's unsaturation test is employed to determine the existence of double-
bonded compounds known as alkenes or triple-bonded compounds known as alkyne linkages. A diol
substitutes an alkene (a compound with two hydroxy groups). In the experiment conducted, when
potassium permanganate is mixed with an unsaturated hydrocarbon or hexene in particular, the violet
color vanishes. The disappearance of the violet color took place with the formation of a brown
precipitate of manganese oxide.
For the flame test, when the alkene was ignited, it resulted in a yellow flame with soot. Alkenes
burn with a luminous sooty flame because the double bond reduces the amount of hydrogen and
indicates incomplete combustion. Incomplete combustion occurs because of limited oxygen due to
the higher proportion of carbon in the compound.
The alkene was reactive to the initial reagents, but for NaOH and HCl, the alkene didn't react with
them, leading to the separation of layers. They were found to be immiscible to each other, and this is
because basic laboratory reagents such as sodium hydroxide do not usually react with double bonds.
VI. QUESTIONS
1. Briefly discuss at least 3 methods of preparing alkenes.
Preparation of alkenes include the following: the presence of palladised charcoal, alkynes are
reduced with hydrogen; can be produced by heating alkyl halides in the presence of alcoholic
potash; lastly, Alcohols reacting with concentrated sulfuric acid, resulting in the creation of
alkenes. 

2. What is the basis for the Baeyer's test for unsaturation?


If the pink color of the solution lasts, the test is negative, indicating that it isn't a double bond
there and that the compound is saturated. If the pink hue vanishes, the test is affirmative and
indicates that a double bond is present, indicating that the organic compound is unsaturated.

3. Write the mechanism for the bromination of ethane.


The overall reaction of photochemical bromination of ethane includes 2 separate categories
called initiation and propagation. 
4. What simple chemical tests may be used to differentiate the alkene from an alkane? Describe the
test.
Bromine water test is used to differentiate and determine between alkane and alkene, When
bromine water is combined with an alkane, there is no change, however, when mixed with an
alkene, it becomes colorless.

VII. CONCLUSION
The obtained results could sufficiently aid the students in meeting the experiment's objectives to
understand the reactivity, preparations, and reactions of Alkenes and discuss the basis for the Baeyer's
Test for unsaturation. The students can therefore conclude that Alkenes are often synthesized by
elimination processes in which two atoms on neighboring carbon atoms are withdrawn, creating a
double bond. Wherein dehydration of alcohols, dehydrohalogenation of alkyl halides, and
dehalogenation of alkanes are examples of preparations. In addition, alkenes are relatively stable
compounds but are more reactive than alkanes because of the reactivity of the carbon–carbon π-bond.
VIII. REFERENCES

F Liu and Y Liang, Org. Biomol. Chem., 2019, 17, 2776 (DOI: 10.1039/c9ob00264b)

https://www.chemistryworld.com/news/new-hydroamination-reactions-discovered-after-

revisiting-old-mechanism/3010291.article

Marta V, Salamova A and Hites RA. Halogenated flame retardants in the Great Lakes environment

(2015) Acc Chem Res 48: 1853-1861.  https://edelweisspublications.com/edelweiss/article/trade-

off-fire-retardant-solar-cell-materials-environmental-issues-ecs-18-105.pdf

Morrison, Robert T., and Boyd, Robert N. Organic Chemistry. 6th ed. Englewood Cliffs, NJ: Prentice

Hall. 1992. ISBN 0-13-643669-2 https://www.newworldencyclopedia.org/entry/Alkene

Takahashi K, Tanaka S, Yamaguchi M, Tsunoda Y, Akitsu T, et al. Dual purpose Br-containing Schiff

base Cu(II) complexes for DSSC dyes and polymer flame retardants (2017) J Korean Chem Soc

61: 129-131 https://edelweisspublications.com/edelweiss/article/trade-off-fire-retardant-solar-

cell-materials-environmental-issues-ecs-18-105.pdf

X Sun, J Chen and T Ritter, Nat. Chem., 2018, DOI: 10.1038/s41557-018-0142-4

https://www.chemistryworld.com/news/waste-vegetable-oils-turned-into-chemicals-for-drugs-

and-plastics/3009650.article

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