A.

TITLE OF EXPERIMENT
Synthesis of Cyclohexene.
B. OBJECTIVE OF EXPERIMENT
At the las of experiment, the collegiant are expected to understand about:
1. Basic techniques segarding orgnic liquid purification involves the
separation, drying, filtration and destilation.
2. Basic processen in the sefining of organic liquid produced by a
synthesis.
3. Principle the dehydrate alcohol.
4. Principle unsaturated olefin.
5. Reaction to show unsaturated olefin.
C. LITERATURE REVIEW
According to (Dadari and dian, 2012: 71) Hydrocarbons are the simplest
organic compounds, composed of elements of carbon and hydrogen alone. Based
on the carbon chain shape, the hydrocarbons can be divided into aliphatic,
alicyclic, and aromatic compounds. The hydrocarbons in which all carbon-carbon
bonds are single covalent bonds are called saturated hydrocarbons. If there is one
double or triple carbon-carbon bond, it is classified as an unsaturated
hydrocarbon. A class of compounds of the same general formula and their similar
properties are called a homologous one.
According to (McMurry, 2011: 78) Alkenes, sometimes called olefins, are
hydrocarbons that contain a carbon–carbon double bond, C=C, and alkynes are
hydro carbons that contain a carbon–carbon triple bond, C≡C. Alkenes occur
abundantly in nature, but alkynes are much less common. Ethylene, for instance,
is a plant hormone that induces ripening in fruit, and -pinene is the major
component of turpentine. Life itself would be impossible without such compounds
as -carotene, a polyalkene that contains 11 double bonds. An orange pigment
responsible for the color of carrots, -carotene is a valuable dietary source of
vitamin A. It was once thought to offer some protection against some types of
cancer, but that has now been shown not to be true.
 Cycloalkanes are alkanes that are cyclic with the general formula CnH2n.
The simplest members of this class consist of a single, unsubstituted carbon
ring, and these form a homologous series similar to the unbranched alkanes. The
nomenclature of cycloalkanes is almost the same as that for alkanes,
with the exception that the prefix cyclo- is to be added to the name of the
alkane. When a substituent is present on the ring, the name of the substituent
is added as a prefix to the name of the cycloalkane. No number is required
for rings with only one substituent. Cycloalkenes are nonpolar molecules like
alkanes. As a result, they tend to have low melting and boiling points compared
with other functional groups. Cycloalkanes of ring sizes ranging from three to 30
are found in nature. Compounds containing five-membered rings (cyclopentane)
and sixmembered rings (cyclohexane) are especially common. Alkanes undergo
combustion reaction with oxygen at high temperatures to produce carbon dioxide
and water. This is why alkanes are good fuels. (Sarker, et al, 2007:66-68).
According to (Epstein, 1949: 379) For cyclopentene and cyclohexene, the
values of the heat-content function, free energy function, and heat capacity were
taken from reference. The resulting values of the thermodynamic function. Which
includes values of the following properties from 0o to 1500oK. Values of the
standard heat of formation at 25oC of gaseous cyclopentene and cyclohexene,
from carbon (solid, graphite) and hydrogen (gaseous).
Cyclopropane and cyclobutane are unstable due to their ring strain
compared with the larger cycloalkanes, e.g. cyclopentane and cyclohexane. The
two smaller cycloalkanes react with hydrogen, even though they are not alkenes.
In the presence of a nickel catalyst, the rings open up, and form corresponding
acyclic (open chain) alkanes. Cyclobutanes require higher temperature than
cyclopentane for ring opening. Alkyl halides have considerably higher melting
and boiling points compared with analogous alkanes. The boiling points also
increase with increasing atomic weight of the halogen atom. The alkyl halide
functional group consists of an sp3-hybridized carbon atom bonded to a halogen atom via
a strong s bond (Sarker, et al, 2007: 69-71).
In hydration, an alkene reacts with water A hydrogen atom (H) forms a
bond with one carbon atom in the double bond, and the oxygen atom in OH forms
a bond with the other carbon. The reaction is catalyzed by a strong acid such as
Hydration is used to prepare alcohols, which have the hydroxyl functional group.
In the general equation for hydration, the acid catalyst is represented by H+.

When water adds to a double bond in which the carbon atoms are attached to
different numbers of H atoms, the from HOH attaches to the carbon that has the
greater number of H atoms ( Timberlake, 2012: 397-398).
Organometallic compounds When a compound has a covalent bond between a
carbon and a metal, it is called an organometallic compound. Carbon–metal bonds vary
widely in character from covalent to ionic depending on the metal. Grignard reagents
These reagents are prepared by the reaction of organic halides with magnesium turnings,
usually in dry ether. An ether solvent is used, because it forms a complex with the
Grignard reagent, which stabilizes it. Organolithium reagents These reagents are prepared
by the reaction of alkyl halides with lithium metals in an ether solvent. Gilman reagents
or lithium organocuprates The most useful Gilman reagents are lithium organocuprates
(R2CuLi). They are easily prepared by the reaction of two equivalents of the
organolithium reagent with copper (I) iodide in ether. Alkyl halide reacts with
triphenylphospine to give a phosphonium salt, which is an important intermediate
for the preparation of phosphorus ylide (Sarker, et al, 2007: 71-72).
Alcohols undergo dehydration—the elimination of H2O—to give alkenes. A
method that works particularly well for secondary and tertiary alcohols is
treatment with a strong acid. For example, when 1-methylcyclohexanol is treated
with aqueous sulfuric acid, dehydration occurs to yield 1-methylcyclohexene.

Acid-catalyzed dehydrations usually follow Zaitsev’s rule and yield the more
highly substituted alkene as the major product (Mc Murry, 2012: 268).
A polymer is a large molecule that consists of small repeating units called
monomers. In the past hundred years, the plastics industry has made synthetic
polymers that are in many of the materials we use every day, such as carpeting,
plastic wrap, nonstick pans, plastic cups, and rain gear. In medicine, synthetic
polymers are used to replace diseased or damaged body parts such as hip joints,
teeth, heart valves, and blood vessels. Many of the synthetic polymers are made
by addition reactions of small alkenes (Timberlake, 2012: 399).
Accorring to (Mc Murry, 2012: 237-238) Zaitsev’s rule, a predictive
guideline formulated in 1875 by the Russian chemist Alexander Zaitsev, base-
induced elimination reactions generally give the more highly substituted alkene
product—that is, the alkene with the larger number of alkyl substituents on the
double bond. Treatment of 2-bromobutane with KOH in ethanol, for instance,
gives primarily but-2-ene (disubstituted; two alkyl group substituents on the
double-bond carbons) rather than but-1-ene (monosubstituted; one alkyl group
substituent on the double-bond carbons).

Alkyl chlorides are also obtained by the reaction of alcohols with SOCl2 in
pyridine or Et3N. Alkenes are obtained by dehydration of alcohols via elimination
reactions, and esters are prepared conveniently by the acid-catalysed reaction of
alcohols and carboxylic acids. Symmetrical ethers are obtained from the
dehydration of two molecules of alcohol ( Sarker, et al, 2007: 78).
D. APPARATUS AND CHEMICALS
1. Apparatus
a. Distillation flask (1 piece)
b. Condensor reflux (1 piece)
c. Funnel 70 mm (1 piece)
d. Round flask 250 mL (1 piece)
e. Erlenmeyer 250 mL (1 piece)
f. Erlenmeyer 500 mL (1 piece)
g. Drop Pipette (3 pieces)
h. Graduated cylinder 25mL (1 piece)
i. Graduated cylinder 50mL (1 piece)
j. Thermometer 110℃ (1 piece)
k. Beaker 250 mL (1 piece)
l. Separate Funnel 250 mL (1 piece)
m. Spray Bottle (1 piece)
n. Test Tube (2 pieces)
o. Watch Glasses (1 piece)
p. Stative and Clamp (1 piece)
2. Chemicals
a. Sulfuric acid concentrated (H2SO4)
b. Cyclohexanol (C6H12O)
c. Sodium Bicarbonate (NaHCO3)
d. Magnecium Oxide (MgO)
e. Aquades (H2O)
f. Aluminium foil (Al2O3)
g. Filter paper
h. Boiling Stone
E. WORK PROCEDURES
1. Measure 21 ml of cyclohexanol in graduated cylinder 25 ml and add into
distillation flask.
2. Measure again 2 ml of H2SO4 concentrated in graduated cylinder in cupboard
acid, and add into distillation flask.
3. Mix well the mixture, and add some of boilin stone.
4. Place the distillation flask in water bath, and connect it with condenser and
use thermometer 110℃.
5. Do distillation until the temperature near reach 70 ℃ then turn off the water
bath and wait until stop produce destilate.
6. Pour the destilate in beaker into separate funnel.
7. Separate cyclohexene and wash with water, 10 ml of NaHCO3 and water
again.
8. Dry with MgO, mix until 2-3 minutes then filter the solution use filter paper.
9. Then do Unsaturated test with 2 drops of cyclohexene added 2 ml of KmnO4
(shake).
F. OBSERVATION RESULT
G. DATA ANALYSIS
H. DISCUSSION
I. CONCLUSION AND SUGGESTION
BIBLIOGRAPHY

Dadari, Dian Wulan and Dian Novita. 2012. ANALYSIS OF TEST RESULTS
ON BLOG MEDIA LEARNING IN THE MATTER ALKANES,
ALKENES, AND ALKYNES. Journal of Chemical Education. (1), 2252-
9454.
Epstein, M.B, Kenneth, S.P., and Fredrick, D.R. Heats. 1949. Equilibrium
Constants, and Free Energies of Formation of Cyclopentene and
Cyclohexene. Journal of Resarch of The National Bureau of Standars, (42),
379-382.
McMurry, J. 2011. Fundamentals of Organic Chemis try, Seventh Edition. USA:
Cengage Learning.
Sarker, D.s., and Lutfun,N.2007.Chemistry For Pharmacy Students. British: John
Willey and Sons.
Timberlake, Karen C. 2012. Chemistry : an introduction to general, organic, and
biological chemistry. United State: Prentice Hall.