ELIMINATION REACTION OF CYCLOHEXANOL

By:
Ni Putu Wulan Romianingsih
Department of Chemistry Education, Faculty of Mathematics and Natural Sciences,
Ganesha University of Education
Jalan Udayana No. 11 Singaraja-Bali

This experiment aims to (1) understand the elimination reaction of cyclohexane and (2) identify
the product of reaction analyze. This experiment can be conducted by using fractional distillation
equipment. Cyclohexanol elimination reaction resulted in cyclohexanone. Then, identification of
products was done by comparing the physical and chemical properties of the products with
theory. Based on comparison, it is known that this experiment produced exactly the same
compound as in theory. The data show that cyclohexene is colorless solution and it was
produced as much as 5.8 mL or 4.708 gram with boiling point of 83 0C and the percentage of
yield is 59.06%.

Key words: Elimination reaction, cyclohexanol, cyclohexane

INTRODUCTION +
Elimination reaction is one of reactions H O H H H
occurred in organic compound. It is the +
inverse of addition reaction. This reaction is C C C C + O H
a way to synthesis alkenes.
Dehydration of alcohol to alkenes is an Step 3. Loss of a proton gives the alkane.
example of elimination reaction.
Dehydration requires an acidic catalyst to H2 O H
protonate the hydroxyl group of alcohol and +
converts it to a good leaving group. Loss of C C C C + H3O+
water, followed by loss of a proton, gives
the alkane. An equilibrium is established To drive this equilibrium to the right, it
between reactants and products. (Wade, is need to remove one or both of the
2010). Alcohol dehydration generally takes products as they form, either by distilling the
place through the E1 mechanism. The products out of the mixture or by adding a
mechanism is as follow: dehydrating agent to remove water. (Wade,
2010) In practice, combination of distillation
Step 1. Protonation converts the hydroxyl and a dehydrating agent is often used. The
group to a good leaving group. alcohol is mixed with dehydrating acid and
H the mixture is heated to boil. The alkne boils
+ at lower temperature than the alcohol
H O H H O H (because the alcohol is hydrogen bonded)
H+
C C C C and the alkene distills out of the mixture.
For example,

Step 2. Water leaves, forming a carbocation.

1

When more than one elimination
product can be formed, the major product is
the more substituted alkene-the one obtained
by removing a proton from the adjacent
carbon that has less hydrogen. The more
substituted alkene is the major product
because it is the more stable alkene, so it has
the more stable transition state leading to its
formation (Pahlavan, 2011).
Dehydration reaction sequence is a
primary alcohol> secondary alcohol>
tertiary alcohol. (Graham and Frhyle, 2000).
acid is a good oxidator, alcohol or a product
resulted can be oxidized as occur in alcohol
that is oxidized by chromic acid. Sulfuric
acid can make oxidation, therefore if it is
used will give effect to dehydration reaction
of cyclohexanol. (Frieda & Suja, 2004: 24)
In this experiment, cyclohexanol will
be conduct elimination reaction to produce
cyclohexene. The boiling point of
cyclohexanol is 1600C, boiling point of
posphate acid is 1580C, boiling point of
cyclohexene is 83oC- 85oC(ChemSpider:
Search and Share, 2013), and boiling point
of xilena for o-xilena is144,40C while for p-
xilena is 138.350C

Primary Alcohol METHODS

Al2 O3/ 400 o C The method of this experiment was
CH3 CH2 OH CH2 CH2
atau H S O 2 4
adopted from a book titled Praktikum Kimia
Ethyl-alcohol etil alkohol Ethylene etilena Organik developed by Frieda Nurlita and I
Wayan Suja (2004:24-25). It was conducted
Secondary Alcohol at Organic Chemistry Laboratory of
Chemistry Education Department, Faculty
H3C
Al O /
2 C
3 400
o
of Mathematics and Natural Sciences,
th
CH OH atau H S O CH 3 CH CH2 Ganesha Education University on 4 of
2 4
November 2013.
H3C
The experiment needed several
isopropil alkohol
Isopropyl alcohol Propenepropena material, namely 10.64 mL of cyclohexanol,
5 mL of phosphoric acid 85%, boiling stone,
Tertiary Alcohol distilled water (at sufficiently), ice , 10 mL
of xylene, and anhydrous substance
H3C (CuSO4).
o
Al O /
2 3 400 C
H3C CH OH atau H SO CH3 C CH2 The equipments used to conduct this
2 4
experiment are graduated cylinder 5 mL,
H3C graduated cylinder 10 mL, drop pipette,
CH3
spatula, watch glass, boiling flask, fraction
t - butil alkohol isobutana
t-butyl ( 2 - metil - 2 - Isobutene
alcohol propena ) (2-methyl-2-propene)
distillation, distillation adapter,
In the elimination process, alcohol will thermometer, heater, stirrer rod, pipe, beaker
be heate first with a strong acid which will glass 1000 mL, beaker glass 100 mL, beaker
produce alkene. Tertiary alcohol will glass 250 mL, separatory funnel, funnel,
undergo the formation of carbonium ion Erlenmeyer flask 100 mL, Erlenmeyer flask
which is relatively stable. While primary 50 mL, filter paper, porcelain crucible, statif,
alcohol is tend to be alkene product directly. clamp and ring.
If anion of an acid is a good nucleofile, such The procedure is like following steps.
as Br-, Cl-, so it possible to produce First, as much as 10.64 mL of cyclohexanol
substitution product. Then, if an anion of

2
and 5 mL of posphate acid were poured into
boiling flask and then shaked until mixed.
Fractionation colomn was setted on the
boiling flask and then it was connected with
distillation adapter, cooler, and thermometer
as the following figure:
Figure 1. Distillation equipment
The distillation was conducted until
the residue are about 2.5 mL – 5 mL. The
reaction result was cooled by using ice bath
to decrease the evaporation. The flask was
let to be cold and then mixed with 10 mL of
xylene. The height of the top layer of
mixture was observed. The distillation was
continued until the top layer was half of it.
Distilates were collected in separatory
funnel and then washed by 10 mL of water.
After that, the distilate was entered into the
erlenmeyer flask and then dried with
anhydrous CuSO4. When the distilate dried,
it was entered into boiling flask and it was
concucted fractional distillation again. The
boiling point was observed , it was weigt
and it was checked the refractive index.
RESULT
Elimination reaction of Cyclohexanol
produces colorless solution which has
boiling point of 83oC as much as 5.8 mL.
Theoretically, the elimination reaction of
cyclohexanol that is secondary alcohol
produces an alkene namely cyclohexene.
The elimination reaction of cyclohexanol are
included in one order elimination reaction
(E1). The reaction mechanism are as follow:
Step 1. Protonation of the hydroxyl group
Step 2. Ionization to a carbocation and
deprotonation to give the alkenes
Based on the mechanism of the
elimination reaction above the product
resulted is cyclohexene. Cyclohexene has
boiling point of 83-85oC (ChemSpider
Search and Share, 2013). Cyclohexene is
colorless liquid. The boiling point between
experiment result and the theory are
identical. Thus, the product of this
experiment is definitely cyclohexane.
Theoretically, the volume of product
should be 9.83mL or 7.9712 gram according
to following equation:
C6H11OH → C6H10 + H2O
V cyclohexanol used = 10.6 mL
Mass cyclohexanol = V x 
=10.6 mLx 0.94 g/mL
= 9.964 g
mass
n cyclohexanol =
Mr
9.964 g
= 100 g/mol
= 0.09964mol
n cyclohexanol = n cyclohexene =
0.09964mol
Mass cyclohexene = n x Mr
= 0.09964mol x 80 g/mol
= 7.9712 g
V cyclohexene = Mass / ρ
= 7.9712 g / (0.811 g/ml)
= 9.83 mL
Experimentally, the volume of product
obtained in this experiment is 5.8 mL or
4.708 gram as following calculation.
Mass cyclohexene = ρ x V
= 0.811 g/mL x 5.8 mL
= 4.708 gram
3
 So the percent yield of the Solomons, Graham and Craig Fryhle. 2000.
cyclohexene from experiment can be Organic Chemistry Seventh Edition.
calculated as follow: United State: John Wiley and Sons,
experimental mass Inc.
% yield  x 100%
theoritical mass Pahlavan. 2011. Chem Lab Manual.
4,708 gram Accessed on 9th of November 2013 from
 x 100%  59.06 %
7,9712 gram http://swc2.hccs.edu/pahlavan/2423L9.p
The mass obatined is so much less than df.
theory because during distillation, the vapor
leaked.

CONCLUSION
Based on the result and data analysis,
it can be concluded that 1) elimination
reaction of cyclohexanol produce
cyclohexene; (2) the Cyclohexene produced
as much as 5.8 mL or 4.866 gram with
percentage of yield of 59.06%

ACKNOWLEDGMENT
Thanks to God the Almighty for
blessing the author during experiment and
writing the article. I would like to say big
thanks to Dr. I Nyoman Tika, M.Si and
organic laboratory assistance for guidance
and supports during experiment.

REFERENCES
(2013). Retrieved November 10, 2013, from
ChemSpider: Search and Share:
http://www.chemspider.com/Chemical
-Structure.10054.html
Anwar, C., Purwono, B., Pranowo, H. D., &
Wahyuningsih, T. D. (1994).
Pengantar Praktikmu Organik.
Yogyakarta: Departement Pendidikan
dan Kebudayaan.
L.G. Wade, J. (2010). Organic Chemistry.
Upper Saddle River: Pearson
Eduation, Inc.
Nurlita, F., & Suja, I. W. (2004). Buku Ajar:
Praktikum Kimia Organic. Singaraja:
IKIP Negeri Singaraja.

4
 Assessment Rubric of Practicum Report

Organic S1

Name : Ni Putu Wulan Romianingsih

ID : 1113031073
Date : 11th of November 2013
Name of practicum : Elimination Reaction of Cyclohexanol

No. Aspek yang dinilai Bobot Skor Bobo x skor

(%) (0-100)

1 Format 5

2 Abstract 10

3. Introduction 20
Materials and Methods
4. 10

5. Result and discussion 30

Conclusion
6. 10
Acknowledgment
7. 5
References
8. 5
Clear
9.- 5

Total score 100

Singaraja, 11th of November 2013

Lecturer,

Dr. I Nyoman Tika, M.Si.