I.

Tittle of Experiment
Synthetic of Cyclohexene
II. Purpose
At the end of experiment, the student expected to understand about :
1. The general technique of liquid organic purification that consist of :
separation, drying, filterization, and distillation.
2. The general process of liquid organic compound purification that produce by
synthetic.
3. The principle of alcohol dehydration.
4. The principle of elephine unsaturated.
5. The reaction to show unsaturated elephine.
III. Preview of Literature
Historically called olephines (o-la-fins), alkenes are hydrocarbons that contain a
carbon-carylenebon double bond, C – C. Alkenes occur abundantly in nature, and
many have important biological roles. Ethylene, for example, is a plant hormone that
induces ripening in fruis, and a-pinene is the major constituent of turpentine.
Cycloalkenes are named in a similar way, but because there is no chain end to begin
fro,, we number the cycloalkane so that the double bond is between C1 and C2 and so
that the first subtituent has as low a number as possible. Note that it’s not necessary
to specify the position of double bond in the name because it’s always between C1
and C2.

(McMurry, Simanek, 2007: 73, 75)

Dehydration process is a separation process that is commonly used to illustrate

the formation and purification of a liquid product. Given the fact that the carbon
atoms joined in a ring structure, there will be no difference in the chemical
characteristics that formed after the reaction occurred. Cyclohexanol heated with
phosphoric acid (V) solid and liquid cyclohexene can be collected, filtered and
purified. Phosphoric acid (V) tend to be used in place of sulphuric acid because it is
safer and produces fewer side reactions. The reactions is :
(Clark, 2007)

A third important reaction of alcohols, both in the laboratory and in biological

pathways, is their dehydration to give alkenes. The C – O bond and a neighboring C –
H are broken, and alkene π bond is formed. A dehydration reaction :

Because of the usefulness of the reactions, a number of ways have been devised for
carrying out dehydrations. One method that work particularly. Well for tertiary
alcohols is the acid-catalyzed reaction. For example, treatment of 1-
methylcyclohexanol with waem aqueos sulfuric acid in a solvent such as
tetrahydrofuran results in loss of water and formation of 1-methylcyclohexene.

(McMurry, 2008 : 619-620).

The dehydration proceeds under acidic conditions and is a widley used olefin
forming reaction. In the laboratory phosphoric acid is the reagent of choice; sulphuric
acid, which is often used, can lead to extensive charring and oxidation and hence to
lower yields of alkene. Other reagents include potassium hydrogen sulphate and
anhydrous copper (II) sulphate. Passage over heated alumina is also effective.
Tertiary alcohols undergo elimination the more readly, and most certainly by an E1
process.

In the preparative example of the dehydration of 2-methylbutan-2-ol

[Me2C(OH)CH2Me]. The loss of Cl proton from the intermediate carbocation (2)
may take place from either of the two adjacent positions giving a mixture of
regioisomers, 2-methylbut-2-ene (3) and 2-methylbut-1-ene (1).

(Furniss B.S, 1989 : 487).

The circumvent the need for strong acid and allow the dehydration of
secondary alcohols, reagents have been developed that are effective under mild, basic
conditions. One such reagent, phosphorus oxychloride (POCL3) in the basic amine
solvent pyridine, is often able to effect the dehydration of secondary and tertiary
alcohols at 0˚C.

As note previously, biological dehydrations are also common and usually occur by an
E1cB mechanism on a substrate in which the –OH group is two carbons away from a
carbonyl group. An example occurs in the biosynthesis of the aromatic amino acid
tyrosine. A base first abstracts a proton from the carbon adjacent to the carbonyl
group, and the anion intermediate (McMurry, 2008 :621).

The dehydrations of primary or secondary alcohols when proceeding via a

secondary or primary carbocation respectively, may be preparatively less satisfactory
owing to intramolecular rearrengements involving a hydrogen or an alkyl group. The
driving force for such rearrangements is of course the relative thermodynamic
stability of the carbocations. This would give rise to agreater complexity of possible
products. With primary alcohols and shulphuric acid or phosphoric acid, the
corresponding intermediate esters are formed, from which ethers. One useful example
is the dehydration of the secondary alcohol 2-methyl-cyclohexanol, which yields a
mixture of two regioisomers in which the more highly substituted alkene
predominates; in this case the mixture may be separated by careful fractional
distillation (Furniss B.S, 1989 : 488).

This dehydration can do with warm alcohol with an acid at rather high
temperature. The reaction result is out and distillation. The reaction result still dirty is
azeotrop from cyclohexene, water, and a little matter with high boiling point.
Sulphate acid that get in distillation result loss by wash with water and NaHCO3
solution. At the washed, water and organic compounds matter isn’t mixed so that the
organic layer can separate with separation funnel. Cyclohexene that haven’t get yet
react to form complex like anhydrate. The solid compound separated with filtering it,
then the recidu from cyclohexene that without water but mixed with a little
cyclohexene that doesn’t separate with CaCl2 and a little dycyclohexyl eter. So that
cyclohexene purifying by distillation on its boiling point (Team of Organic Chemistry
Lecturer, 2012 : 37).

Cyclohexene is a hydrocarbon with the formula C6H10. This cycloalkane is a

colorless liquid with a sharp smell. It is an intermediate in various industrial
processes. Cyclohexene isn’t very stable upon long term storage with exposure to
light and air because it form peroxides. A common experiments for beginning organic
chemistry students is the acid catalyzed dehydration of cylohexanol with distillative
removal of the resulting cyclohexene froom the reaction mixture :

(Anonymous, 2012)
IV. Apparaturs and Chemicals
1. Apparaturs
a. Condensor
b. Thermometer 110˚C
c. Erlenmeyer 25 ml and 50 ml
d. Separation Funnel
e. Distillation Flask
f. Beaker Glass
g. Volumetric glass
h. Pump
i. Hase
j. Cork
k. Scotch tape
l. Bunsen burner
m. Asbes gauze, tripod
n. Matches
o. Boling rocks
p. Dropper
q. Razor blade
r. Filtering paper
s. Common funnel
t. Stative and clamp
u. Stir bar
2. Chemicals
a. Cyclohexanol (C6H11OH)
b. Concentrated Sulphate acid (H2SO4)
c. NaHCO3 solution 10% (Sodium bicarbonate)
d. CaCl2 anhydrate (Calcium Chloride)
e. KMnO4 1% Solution (Pottasium permanganate)
f. Aquades
g. Ice Block
h. Tissue
V. Work Procedure
1. Entered 21 ml of cyclohexanol into distillation flask 200 ml and added
carefully H2SO4 (Concentrated) as much 2 ml and shaked well.
2. Added 2-3 pieces of boiling rocks and set up the condenser of the flask.
 3. Heated the flask with little five with used micro burner (as substitute can be
used oil steamer that heated at 130-140˚C) so that the temperature will not
over 95˚C.
4. Continued the distillation until recidu that rest little. The recidue will produce
white smoked.
5. Moved the distillate into separation funnel, made the layer separated.
6. Put out the layer below
7. Washed the organic layer in the separation funnel with 10 ml water, 10 ml
NaHCO3 10% and once with water as much 10 ml.
8. Poured the hydrocarbon via funnels mouth into Erlenmeyer (dried), added 3-
4 gram CaCl2 anhydrate shaked during 2-3 minutes, made it silent for 15
minutes, shaked once.
9. Poured the dry hydrocarbon into separation funnel that completed by filtering
paper that “Fluted”
10. Collected the boiling fraction at 80-85˚C on the flask that height known
11. Calculated the mass of cyclohexene.
VI. Result
No Experiment Observation
1 21 ml cyclohexanol + 2 ml H2SO4 Brown color solution, Hot
(Concentrated) ----- shaked well

2 2-3 pieces of boiling rocks --- Produce white smoke recidue, while
distillation (not over 95˚C) (first color solution (2 layers form above
distillate at 76˚C) White color and below colorless)

3 Put the layer below, add 10 ml 2 layers form : - white color

water ----- shaked 2 minutes - colorless

4 Put out the layer below, add 2 layers form : - white color
NaHCO3 10 ml ----- shaked 2 - colorless
minutes

5 Put out the layer below, add 10 ml 2 layers form : - white color
of water --- shaked 2 minutes, put - colorless
out the layer below

6 Add Cacl2 anhydrate White sediment below

7 Filter the solution White color solution

 8 Distillate the solution Produce 6,3 gram of cyclohexene
(colorless)
9 Dropped 5 drops of KMnO4 1% Produce brown color solution

VII. Data Analyze

Known : V C6H11OH : 21 ml
Mr C6H11OH : 100 gr/mol
ρ C6H11OH : 0,95 gr/ml
Mr C6H10 : 82 gr/mol . Mass C6H10 = 6,3 gram
Asked : % Rendement : ….?

Mass C6H11OH = ρ.V

= 0,95 gr/ml . 21 ml
= 20 gr
𝑀𝑎𝑠𝑠
n C6H11OH = 𝑀𝑟
20 𝑔𝑟
= 100 𝑔𝑟/𝑚𝑜𝑙
= 0,2 mol
C6H11OH H2SO4 C6H10 + H2O
Mass C6H10 = n . Mr
= 0.2 mol. 82 gr/mol
= 16,4 gr
BP (Mass Practicum)
% rendemen = x 100 %
BT (Mass Theory)
6,3 𝑔𝑟𝑎𝑚
= 16,4 𝑔𝑟𝑎𝑚 x 100 %
= 0,38 x 100 %
= 38,41
VIII. Discussion
The experimental of synthetic cyclohexene did with added cyclohexanol into
distillation flask and added concentrated H2SO4 then shaked well so that mixing
perfectly and produce brown color solution. H2SO4 on this trial as catalyst to make
fast the reaction occurred. Then distillated the solution and added 3 pieces of boiling
stones on flask as function to reduce the popping on flask while heated. When it
distillated, the temperature restored so that more than 95˚C because the cyclohexene
have boiling point 92,98˚C. so that, when the temperature over, cyclohexene didn’t
form. When the temperature over, the Bunsen burner off or the cyclohexanol stopped
then heated until the temperature back to normal. Drops of first distillate achieved at
temperature 76˚C. then achieved full of distillate, the result moved into separation
funnel. Formed 2 layers that are white color cyclohexene above and water that
colorless in under. It caused because difference both of density which water 1 gr/ml
than cyclohexene have 0,811 gr/ml. the other things affected is polarity of substances
whish cyclohexene is non-polar and water is polar so that cannot be mixing. The
water layer is under layer throw away. Then cyclohexene washed with water by
shaked for 2 minutes to reduce the dirty substances like azeotrop mixture (the liquid
mixture that cannot be separate with boiled because the vapor phase composition
from liquid identic), water and a little material that have high boiling point. Then
formed 2 layer such as cyclohexene (white color) above and water layer and dirty
substances rest below. The under layer is throw away and the cyclohexene washed
with NaHCO3 10% with shaked for 2 minutes to lost and neutralized the sulphate acid
that still on cyclohexene. Formed 2 layer that are cyclohexene (white color) above
and acid rest below and water below. The under layer throw away. Cyclohexene
produce dryed with CaCl2 anhydrate that function as bonded water on cyclohexene.
Then filtered with used filtering paper to separate with CaCl2. The result of filtering
is cyclohexene that water free and a little dicyclohexyl ether. So that cyclohexene
purified with distillated on its boiling point, 82,98˚C and got colorless cyclohexene as
much 6,3 gram that was little if compared with weight of theory as much 16,4 gram.
This caused of the little distillated produced on first distillated result so that second
distillate result didn’t get weight theory that needed so that after rendement
calculation got 38,41%.
1. Decompose of catalyst to be ions
H2SO4 (aq) H+(aq) + HSO-4 (aq)
2. Reversible reaction, that concerned protonation of hydroxyl group
CH2 CH2
CH2 CH – O – H CH2 CH2

CH2 CH2 + H+ CH2 CH2 + H2O

CH2 CH2
3. Released the (OH) group produce kation sec-cyclohexyl

CH2 H CH2
CH2 CH – O – H CH2 CH2

CH2 CH2 -H2O CH2 CH2 + H2O

CH2 CH2

4. Released of proton from carbon atom that beside of positive carbon to made
perfect this reaction

CH2 CH2
CH2 CH CH2 CH

CH2 CH2 -H+ CH2 CH + H+

CH2 CH2
Dehydration reaction is number of phase

CH2 CH2
CH2 CH -OH CH2 CH

CH2 CH2 - H CH2 CH + H+

CH2 CH2

Tested of unsaturated on cyclohexene with added KMnO4 that purple color as

function tested substance of unsaturated of solution indicated with changer of
solution. Cyclohexene is hydrocarbon compound that unsaturated (Olephine
compound) proved with changes color to be brown color (reaction occurred).

OH
+ KMnO4 H2O + MnO2 + KOH

OH
IX. Conclusions and suggestions
1. Conclusion
Based on the experiment, can be concluded that
a. The synthetic of cyclohexene did by purifying technique, such as
separation process, filtering, drying, and distillation.
b. The synthetic of cyclohexene forming from dehydration reaction of
alcohol (cyclohexanol) with sulphuric acid (H2SO4).
c. The principle of dehydration alcohol is always initiate by protonation of
the hydroxyl group.
d. Cyclohexene reaction show elephine unsaturated proved by changes color
when reaction with KMnO4 to brown color.
e. Cyclohexene produce is 6,3 gram with rendement percentage as much
38,41 %.
2. Suggestions
a. Expected to apprentice do the experiment well and carefully so that can
get the best result
b. Expected to laborant give good apparatus.
 BIBLIOGRAPHY

Anonymous. 2012. Cyclohexene. http://en.wikipedia.org/w.index.php?title=

cyclohexene&olddid=486014752 . Accessed on May 10th 2012.

Clark, Jim. 2007. Dehidrasi Alkohol. http://chem-is-try.org/dehidrasi20%-

alkohol20%chem20%-is%20%-try20%20-htm-htm. Accesed on May 10th
2012

Furniss, B.S. 1989. Textbook of Practical Organic Chemistry 5th edition. USA: John
Wiley and Sons.Inc

McMurry, John and Eric Simanek. 2007. Fundamentals of Organic Chemistry. USA:
Thomson Learning.Inc

McMurry, John. 2008. Organic Chemistry. USA: Thomson Learning.Inc

Team of Organic Chemistry Lecturer. 2012. Reference of Organic Chemistry

Practical. Makassar: Chemistry Departement FMIPA UNM.
Answer Of Question

1. Recorded % rendement, color, and bias index of cyclohexene!

2. Write down the equation reaction of test unsaturated reaction result above!
3. Based on the work procedure above, where the phase of separation dirty from
cyclohexene? a). Cyclohexanol b). Suplhate acid c). Water
4. Write down the mechanism reaction of cyclohexene! where the reaction that part
of mechanism that’s chemical equilibrium process. Why the process can occurs
perfectly?

Answer :
𝑀𝑎𝑠𝑠
1. n C6H11OH = 𝑀𝑟
20 𝑔𝑟
= 100 𝑔𝑟/𝑚𝑜𝑙
= 0,2 mol

Mass C6H10 = n . Mr
= 0.2 mol. 82 gr/mol
= 16,4 gr
BP (Mass Practicum)
% rendemen = x 100 %
BT (Mass Theory)
6,3 𝑔𝑟𝑎𝑚
= 16,4 𝑔𝑟𝑎𝑚 x 100 %
= 0,38 x 100 %
= 38,41

2. OH
+ 2KMnO4 H2O + 2MnO2 + 2 KOH

OH

3. a) Cyclohexanol separated with distillation technique

b) Sulphate and separated with washed use NaHCO3
c) Water separated with separation funnel and dryed with CaCl2 anhydrate
4. Phase I. H2SO4 (aq) H+ (aq) + HSO4-(aq)
Phase II. OH H
O–H
+ H+
Phase III. H
O–H + + H2O

Phase IV.
+
+ H+