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The Complete Report of Organic Chemistry I with title “Preparation of

Cyclohexene” Was made by:
name : Hasrilia Beskara
ID : 1713441008
group : V (five)
class : ICP of Chemistry Education
After checked and consulted by assistant and assistant coordinator, so this report was
accepted
Makassar, April 2018
Assistant Coordinator, Assistant,

Imranah, S.Pd Dwi Kurniawan

ID 1413041006

Known by
Reaponsibility Lecturer,

Hardin S.Si, S.Pd, M.Pd

ID 19870807 2015 04 1 004
A. TITLE OF EXPERIMENT
Preparation of cyclohexene.
B. OBJECTIVE OF EXPERIMENT
1. Basic technique of purification liquid organic compound such as separation
drying, filtration, and distillation.
2. Basic process on the purification liquid organic compound that produce by
sintesys.
3. Dehydration alcohol foundation.
4. Unsaturated olefyne foundation.
5. The reaction unsaturated olefyne.
C. REVIEW OF LITERATURE
Alkenes, sometimes called olefins, are hydrocarbons that contain a carbon double
bond, C=C, and alkynes are hydro carbons that contain a 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
B-carotene, a polyalkene that contains 11 double bonds. Carbon–carbon double
bonds are present in most organic and biological molecules, so a good understanding
of their behavior is needed. We’ll look at some consequences of alkene
stereoisomerism and then focus in detail on the broadest and most general class of
alkene reactions, the electrophilic addition reaction (McMurry, 2011: 78).
Double bonds are accommodated by rings of all sizes. The simplest
cycloalkene, cyclopropene, was first synthesized in 1922. A cyclopropene ring is
present in sterculic acid, a substance derived from one of the components of the oil
present in the seeds of a tree (Sterculia foelida). As we saw, cyclopropane is
destabilized by angle strain because its 60° bond angles are much smaller than the
normal 109.5° angles associated with sp3hybridized carbon. Cyclopropene is even
more strained because the deviation of the bond angles at its doubly bonded carbons
from the normal sp2 hybridization value of 120° is greater still. Cyclobutene has, of
course, less angle strain than cyclopropene, and the angle strain of cyclopentene,
cyclohexene, and higher cycloalkenes is negligible. So far we have represented
cycloalkenes by structural formulas in which the double bonds are of the cis
configuration. If the ring is large enough, however, a trans stereoisomer is also
possible (Carey, 2011: 180).
 Cyclohexane itself, in which only hydrogens are attached to the carbon
atoms, is not only free of angle strain and torsional strain, but free of van der Waals
strain as well. Hydrogens on adjacent carbons are the same distance apart as in
(staggered) ethane and, if anything, feel mild van der Waals attraction for each other.
We notice that the three axial hydrogens on the same side of the molecule are thrown
rather closely together, despite the fact that they are attached to alternate carbon
atoms; as it happens, however, they are the same favorable distance apart as the other
hydrogens are (Marrison, 2002: 299).
According to Marrison (2002: 492) alcohols are compounds of the general
formula ROH, where R is any alkyl or substituted alkyl group. The group may be
primery, secondary, or tertiary, it may be open-chan or cyclic, it may contain a
double bond, a halogen atom, or an aromatic ring. All alcohol contain the hydroxyl (-
OH) group, which, as the functional group, determines the properties characteristic
of this family. Variations in structure of the R group may affect the rate at which the
alcohol undergoes certain reactions, and even, in a few cases, may affect the kind of
reaction. Compounds in which the hydroxyl group is attached directlyto an aromatic
ring are not alcohol, they are phenols, and differ so markedly from the alcohols that
we shall consider them in a separate chapter. For example

Much of the background needed to understand organic reactions has been

covered, and it’s now time to begin a systematic description of the major functional
groups. We’ll start in this chapter with a study of the alkene and alkyne families of
compounds, and we’ll see that the most important reaction of these two functional
groups is the addition to the C=C and C=C multiple bonds of various reagents X–Y
to yield saturated products. In fact, all the reactions we’ll discuss in this chapter
follow the same pattern (McMurry, 2011: 112).
Alkene formation in elimination react is requires that X and Y be substituents
on adjacent carbon atoms. By making X the reference atom and identifying the
carbon attached to it as the carbon, we see that atom Y is a substituent on the ἀ
carbon. Carbons succeedingly more remote from the reference atom are designated.
Only ẞ elimination reactions. (Beta (ẞ) elimination reactions are also known as 1,2
eliminations (Carey: 2011: 181).

Alcohols are compounds of the general formula ROH, where R is any alkyl
or substituted alkyl group. The group may be primary, secondary, or tertiary; it may
be open-chain or cyclic; it may contain a double bond, a halogen atom, or an
aromatic ring. All alcohols- contain the hydroxyl (-OH) group, which, as the
functional group, determines the properties characteristic of this family. Variations in
structure of the R group may affect the rate at which the alcohol undergoes certain
reactions, and even, in a few cases, may affect the kind of reaction. Compounds in
which the hydroxyl group is attached directly to an aromatic ring are not alcohols;
they are phenols, and differ so markedly from the alcohols that we shall consider
them in a separate chapter (Morrisson, 2002: 492).
In the dehydration of alcohols, the H and OH are lost from adjacent carbons.
An acid catalyst is necessary. Before dehydrogenation of ethane became the
dominant method, ethylene was prepared by heating ethyl alcohol with sulfuric acid.
Other alcohols behave similarly. Secondary alcohols undergo elimination at lower
temperatures than primary alcohols, and tertiary alcohols at lower temperatures than
secondary alcohols. For example cyclohxanol with H2SO4 in 140⁰C will form
cyclohexene and water. H2SO4 and phosphoric acid (H3PO4) are the acids most
frequently used in alcohol dehydrations. Potassium hydrogen sulfate (KHSO4) is also
often used (Carey, 2011: 182).
The dehydration of alcohols and the conversion of alcohols to alkyl halides
by treatment with hydrogen halides are similar in two important ways:
1. Both reactions are promoted by acids.
2. The relative reactivity of alcohols decreases in the order tertiary
secondary primary.
These common features suggest that carbocations are key intermediates in alcohol
dehydration, just as they are in the conversion of alcohols to alkyl halides. A three-
step mechanism for the sulfuric acid-catalyzed dehydration of tert-butyl alcohol.
Steps 1 and 2 describe the generation of tert-butyl cation by a process similar to that
which led to its formation as an intermediate in the reaction of tert-butyl alcohol with
hydrogen chloride. Step 3 is new to us and is the step in which the double bond is
formed. Step 3 is an acid-base reaction in which the carbocation acts as a Brønsted
acid, transferring a proton to a Brønsted base (water). This is the property of
carbocations that is of the most significance to elimination reactions. Carbocations
are strong acids; they are the conjugate acids of alkenes and readily lose a proton to
form alkenes. Even weak bases such as water are sufficiently basic to abstract a
proton from a carbocation. As noted earlier primary carbocations are too high in
energy to be intermediates in most chemical reactions (Carey, 2011: 185).
Dehydration-dehydrogenation of cyclohexanol was carried out using a down-
flow, fixed bed reactor of 8 mm internal diameter at atmospheric pressure. The
catalyst (0.1 g) was pretreated in the reactor at 300°C for 2 hrs. Oxygen was then
passed through the catalytic bed and followed by feeding of the reactant at the flow
rate of 6 mL hr-1. The reaction was carried out at 300°C for 1 hr. The product in
liquid form was collected at the bottom of the reactor and analyzed by a Hewlett
Packard Model 5880A gas chromatography with Flame Ionization Detector (FID).
Analysis was carried out from 40-200°C at the heating rate of 10°/ min by using
Phase AT-WAX capillary column (Man, 2005: 45).
According to Marrison (2002: 523) alcohols react readily with hydrogen
halides to yield alkyl halides and water. The reaction is carried out either by passing
the dry hydrogen halide gas into the alcohol, or by heating the alcohol with the
concentrated aqueous acid. The least reactive of the hydrogen halides, HC1, requires
the presence of zinc chloride for reaction with primary and secondary alcohols; on
the other hand, the very reactive ter-butyl alcohol is converted to the chloride by
simply being shaken with concentrated hydrochloric acid at room temperature. For
example:

The direct release of the hydroxy group produces benzene along with H2O
and the double bond hydrogenation of the aromatic ring produces a cyclohexanol
intermediate, and then cyclohexene is formed. The hydrogenation reaction continues
to form cyclohexane (Putri, 2016: 170).
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 then turn off the water bath and wait until
stop produce distilate.
6. Pour the deitilate 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). 2 drops of cyclohexene added 2 ml of H2SO4 dilute (shake)
F. OBSERVATION RESULT

No. Activity Result

1. 21 mL cyclohexene (colorless) + 2 Black solution
mL H2SO4 concentrated (colorless)
then shaked. Added three piece of
boling stone thes distillation
2. Distillate filled into separation funnel. Turbidity solution in upper layer and
Throw the bottom layer. The layer on colorless solution in bottom layer
top washed with 10 mL H2O + 10 Formed two layers, white solution in
mL NaHCO3 + 1m mL H2O than upper layer and colorless solution in
throw the bottom layer. bottom layer
3. Upper layer + 3 g MgO, shaked in 3 Colorless
minute. Leave it along 15 minute
while shake it occasionally
4. Filtered 7 mL of cyclohexene
5. Testing:
2 drops cyclohexene + 2 mL KMnO4 Brown and there is precipitate
1% (purple)
2 drops cyclohexene + 2 mL KMnO4 Colorless
1% (purple)
G. ANALISYS DATA
Known :
Mr C6H11OH = 100 gr/mole
𝜌C6H11OH = 0,962 gr/mL
V C6H11OH = 21 mL
Mr C6H10 = 82 gr/mole
𝜌 C6H10 = 0,811 gr/mL
V C6H10 = 2,1 mL
Asked : % Rendement ….. ?
Solution :
H2SO4
C6H11OH C6H10 + H2O
 Mass of C6H11OH = 𝜌 . V
= 0,962 gr/mL . 21 mL
= 20,202 gr

𝑚
 Mole of C6H11OH = 𝑀𝑟
20,202 𝑔𝑟
= 100 𝑔𝑟/𝑚𝑜𝑙𝑒

= 0.202 mole
C6H11OH → C6H10 + H2O
nC6H11OH ~ n C6H10
0,202 mole ~0,202 mole
 Mass Theory = Mole . Mr
= 0.202 mole . 82 gr/mole
= 16,564 gr
 Mass Experiment = V .𝜌
= 7 mL . 0,811 gr/mL
= 5,677 gr
𝑀𝑎𝑠𝑠 𝐸𝑥𝑝𝑒𝑟𝑖𝑚𝑒𝑛𝑡
 % Rendement = × 100 %
𝑀𝑎𝑠𝑠 𝑇ℎ𝑒𝑜𝑟𝑦
5,677 𝑔𝑟
= 16,564 𝑔𝑟 × 100 %

= 34,27 %

H. DISCUSSION
Alkena, atau biasa disebut olefin, adalah hidrokarbon yang mengandung ikatan
rangkap karbon C = C. Secara detail pada reaksi alkena yang paling luas dan paling
umum, reaksi adisi elektrofilik (McMurry, 2011: 78). Pada percobaan ini
sikloheksanol dehidrasi menjadi sikloheksena. Sikloheksena ini dibuat dengan
menggunakan H2SO4 sebagai katalis. Larutan sikloheksanol yang tidak berwarna lalu
ditambhakan H2SO4 yang juga tidak berwarna. Setelah penambahan H2SO4 larutan
dikocok agar homogen dan kemudian larutan berubah menjadi warna hitam. Setelah
itu larutan kemudian didestilasi dengan menambahkan batu didih sebelumnya pada
larutan, batu didih berfungsi untuk mengurangi letupan pada saat pemanasan.
Adapun tujuan dari destilasi ini ialah untuk memisahan zat cair dari campurannya
berdasarkan perbedaan titik didih atau berdasarkan kemapuan zat untuk menguap.
Sikloheksena memiliki titik didih yang paling kecil, sehingga sikloheksena pertama
kali menetes sebagai destilat. Sedangkan selain sikloheksena seperti air dan
sikloheksanol yang titik didihnya lebih besar akan menguap. Destilasi dilakukan
pada suhu diatas 1000C hingga hasil destilasi atau destilat tertampung. Kemudian
destilat dimasukkan ke dalam corong pisah untuk memisahkan dua komponan
larutan. Pada corong pisah akan terbentuk dua lapisan, dimana lapisan atas
merupakan sikloheksena dan lapisan bawah adalah air, hal ini disebabkan karena
larutan memiliki massa jenis yang berbeda, diaman sikloheksena memiliki massa
jenis lebih rendah dari air yaitu 0,811 g/mL sedangkan air memiliki massa jenis 1
g/mL kemudian lapisan bawah dibuang. Setelah corong tinggal berisi larutan
sikloheksena, larutan tersebut ditambahkan dengan aquades untuk menetralkan
larutan dan lapisan bawah. Setelah itu sikloheksena ditambahkan natrium bikarbonat
yang berbentuk kemudian dikocok, hal ini bertujuan untuk menetralkan sisa-sisa
asam dari katalis H2SO4 lalu kembali dimasukkan air untuk memisahkan sisa-sisa air
dari campuran lalu lapisan bawah dibuang.
Larutan sikoheksena kemudian dipindahkan pada Erlenmeyer dan ditambahkan
dengan MgO, adapun fungsi MgO ini untuk menyerap sisa-sisa air karena sifatnya
yang anhidrat. Larutan kemudia dikocok dan disaring menggunakan corong biasa
yang telah dilapisi dengan kertas saring agar larutan sikoheksena terbentuk
sepenuhnya dan dari percobaan larutan sikloheksena yang dihasilkan ialah 7 mL. dan
dilakukan perhitungan % rendamen. Perhitungan rendamen beetujuan unutk
menghitung kuantitas sikloheksena yang diperoleh dengan membandingkan dengan
teori. Persen rendamen yang dihasilkan ialah 34,7% yang berarti hanya 34,7%
larutan sikloheksena yang dihasilkan dari teori. Untuk menguji ketidakjenuhan dari
sikloheksena dilakukan dua uji, yaitu uji dengan KMnO4 dan H2SO4. Pada
penambahan H2SO4 larutan tetap tidak berwarna. Pada penambahan KMnO4 yang
awalnya berwarna uangu kemudian ditambah dengan larutan sikloheksena terbentuk
larutan yang berwarna coklat dan terdapat endapan yang berarti sikloheksena
teroksidasi dengan adapun reaksinya sebagai berikut:

OH

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

(sikloheksena) (1,2 heksadiol) (mangan dioksida)

I. CONCLUSSION AND SUGGESTION

1. Conclussion:
Based on the practicum we have done, we can conclude that:
1. The basic technique of organic compound’s purification of liquid such as

distillation, separation, drying, and filtering .

2. Dehydration of cyclohexene will take off molecule of H2O and formed

cyclohexene with using H2SO4 as a catalys.
3. Usaturated test can be known with react with KMnO4 and the result is brown
solution with precipitate.
4. Rendamen percent that we get form this practiocum is 34,7%
2. Suggestion
Practitioner have to know the work procedure and the basic theory that occur on
the practicum and becarefully to added the solution into the other solution.
 JAWABAN PERTANYAAN
1. % rendemen hasil dan warna sikloheksena

Known :
Mr C6H11OH = 100 gr/mole
𝜌C6H11OH = 0,962 gr/mL
V C6H11OH = 21 mL
Mr C6H10 = 82 gr/mole
𝜌 C6H10 = 0,811 gr/mL
V C6H10 = 2,1 mL
Asked : % Rendement ….. ?
Solution :
H2SO4
C6H11OH C6H10 + H2O
 Mass of C6H11OH = 𝜌 . V
= 0,962 gr/mL . 21 mL
= 20,202 gr
𝑚
 Mole of C6H11OH = 𝑀𝑟
20,202 𝑔𝑟
= 100 𝑔𝑟/𝑚𝑜𝑙𝑒

= 0.202 mole
C6H11OH → C6H10 + H2O
nC6H11OH ~ n C6H10
0,202 mole ~0,202 mole
 Mass Theory = Mole . Mr
= 0.202 mole . 82 gr/mole
= 16,564 gr
 Mass Experiment = V .𝜌
= 7 mL . 0,811 gr/mL
= 5,677 gr
𝑀𝑎𝑠𝑠 𝐸𝑥𝑝𝑒𝑟𝑖𝑚𝑒𝑛𝑡
 % Rendement = × 100 %
𝑀𝑎𝑠𝑠 𝑇ℎ𝑒𝑜𝑟𝑦
5,677 𝑔𝑟
= 16,564 𝑔𝑟 × 100 %

= 34,27 %

Sikloheksena berwarna putih keruh

2. Hasil reaksi pengujian ketidakjenuhan
a. Reaksi dengan KMnO4
OH

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

b. Reaksi dengan H2SO4

3. Berdasarkan cara kerja, tahap-tahap pengotoran dipisahkan dari sikloheksena:

a. Sikloheksanol dihilangkan pada waktu proses destilasi

b. Asam sulfat dihilangkan pada waktu penambahan air dan NaHCO3

c. Air dihilangkan pada waktu penambahan MgO

4. Mekanismenya yaitu:
Tahap 1: Penguraian katalis menjadi ion-ionnya
H2SO4 H+ + HSO4-
Tahap 2: Protonasi
OH +
O H
+ H+ H
H
H
Tahap 3: Melepaskan gugus H2O

+
O H
H
-H2O + + H2O
H H
isochery cation

Tahap 4

+
+ H+ + HSO4-
H
 BIBLIOGRAPHY

Carey A. Francis. 2011. OrganicChemistry 4th Edition. United States: The McGraw-
Hill.
Man Wonh Kah, et al. 2005. Jurnal Teknologi: Effect of Loaded Alkali Metals on this
Structural, Basicity and Catalytic Activity of Zeolite Beta.Malaysia:
Universiti Teknologi Malaysia.
Marrioson Robert Thornton and Boyd Robert Neilson. 2002. Organic Chemistry 6th
Edition. New Dehli: Prentice-Hall of India Private Limited.

McMurry John. 2011. Fundamental of Organic Chemistry. United States: Prentice

Hall.

Putri Irma Fadhila, et al. 2016. Kajian Aktivitas Katalitik CoMo/Al2O3 pada Reaksi
Hidrodeoksigenasi Anisol dan Guaiacol. ISSN 2503-4146. Solo: Universitas
Sebelas Maret.