A.

Title of Experiment
Preparation of Cyclohexanone
B. The Aim of Experiment
1. The apprentice have skill for doing alcohol oxidation of cyclic secondary.
2. The apprentice can understand the oxidation reaction of cyclic secondary.
C. Literature Review
Organic Chemistry is the chemistry of carbon compounds that contain,
primarily, carbon, and hydrogen. The element carbon has a special role in chemistry
because it bonds with other carbon atoms to give a vast array of molecules. The
variety of molecules is so great that with find organic compounds in many common
products we use, such as a gasoline, medicine, shampoos, plastic bottles, and
perfumes. The food we eat is composed of different organic compounds that supply
us with fuel for energy and the carbon atoms needed to build and reapir the cells of
our bodies. Organic chemistry is the study of carbon compounds. Organic
compounds typically contain carbon and hydrogen and sometimes oxygen, sulfur,
nitrogen, or a halogen (F,Cl,Br,and I). the formulas of organic compounds are
written with carbon first, followed by hydrogen and then any other elements. Many
organic compounds are nonpolar molecules with weak attractions between
molecules. For example, vegetables oil which is a mixture of organic compounds,
does not dissolve inwater but floats on top. A very typical reaction of organic
compounds is that they burn vigorously in air (Timberlake. 2012: 354). Classes of
organic compounds can be distinguished according to functional groups they
contain. A functional group is a of atoms that is largely responsible for the chemical
behavior of the parent molecule.different molecules containing the same kind of
functional group or groups undergo similar reaction (Chang.2010 : 1026). Alcohols
may be considerd hydrocarbons to in which one or more hydrogen (H) atons are
replaced by hydroxyl (OH) groups. Their names are made up from the names of the
hydrocarbons to which they are related by giving these an-ol ending. In thisway,
CH4, methane, becomes CH3OH. Methanol (also called methyl alcohol): C2H6
ethane, becomes C2H5OH, ethanol (also known as ethyl or grain alcohol) and so on.

In for preparation of cyclohexanone is oxidation alcohol secondary cyclic becomes

ketones cyclic with be used chromat of potassium as oxidator in acid. (Brent. 1960:
88) . So, that can be conclude Organic Chemistry is the chemistry of carbon
compounds that contain, primarily, carbon, and hydrogen,such as Alcohol, ketones,
carboxylic Acids, etc.
Carbon can form more compounds than any other element because carbon
atoms are able not only to form singles, double, and triple carbon-carbon bonds, but
also to link up with each other inchains and ring structures. The branch of chemistry
that deals with carbon compounds is organic chemistry. Thus, by learning the
characteristic properties of many organic compounds. Most organic compounds are
derived from a group of compound known as hydrocarbons because they are made
up of only hydrogen and carbon (Chang.2010 : 1026). Alcohol a hydroxyl (-OH)
group a hydrogen atom in a hydrocarbon. The oxygen atom is shown in red the ball
and stick models. Aldehydes and ketones contain is a carbonyl group (C=O), which
cinsist if a carbon atom attached to an oxygen atom with a double bond. In a
aldehyde, the carbon ataom of carbonyl group is bonded to a hydrogen atom. Only
the simplest aldehyde, CH2O, has a carbonyl group attached to two hydrogen atoms.
In a ketone, the carbon atom of the carbonyl group is bonded to two other carbon
atoms (Timberlake. 2012: 373). Alcohols may be considerd hydrocarbons to in
which one or more hydrogen (H) atons are replaced by hydroxyl (OH) groups.
Their names are made up from the names of the hydrocarbons to which they are
related by giving these an-ol ending. In thisway, CH 4, methane, becomes CH3OH.
Methanol (also called methyl alcohol): C2H6 ethane, becomes C2H5OH, ethanol
(also known as ethyl or grain alcohol) and so on. In for preparation of
cyclohexanone is oxidation alcohol secondary cyclic becomes ketones cyclic with
be used chromat of potassium as oxidator in acid. (Brent. 1960: 88) . So, that be
concluded Carbon can form more compounds than any other element because
carbon atoms are able not only to form singles, double, and triple carbon-carbon
bonds.

Induced-dipole/induced-dipole forces are the only intermolecular attractive

forces available to nonpolar molecules such as alkanes. In addition to these forces,
polar molecules engage in dipoledipole and dipole/induced-dipole attractions. The
dipoledipole attractive force is easiest to visualize and is illustrated in two
molecules of a polar substance experience a mutual attraction between the
positively polarized region of one molecule and the negatively polarized region of
the other. As its name implies, the dipole/induced-dipole force combines features of
both the induced-dipole/induceddipole and dipoledipole attractive forces. A polar
region of one molecule alters the electron distribution in a nonpolar region of
another in a direction that produces an attractive force between them
(Carey.2000:130). Probably,a Keggin-type heteroatom is key to conversion of
cyclohexanol-cyclohexanone into adipic acid. therefore, activation of H2O2 needs a
more acidic heteroatom . As shown in Figure 10, at 9 h, up to 61% of
cyclohexanolcyclohexanone can be converted to adipic acid. Temperature is an
important factor in the catalytic conversion of cyclohexanol, cyclohexanone, and
cyclohexanol-cyclohexanone mixtures into adipic acid. All results indicated that the
1:1 mixture of cyclohexanol-cyclohexanone could form adipic acid with moderate
isolated yield. After optimization of the cyclohexanol-cyclohexanone mixture,
adipic acid was synthesized successfully at the yield of 68% at a reaction time of 9
h and a temperature of 90 C, using as the catalyst and with the melting point of
150-152 C (Lebani, dkk. 2015:87-89). The reaction between p-nitrobenzaldehid
and cyclohexanone occurs through Claisen condensation reaction Schmidt. This is
evident from the presence of hydrogen in the p-nitrobenzaldehid and
cyclohexanone. A carbonyl atom owned by cyclohexanone able to do tautometri,
namely in the form of tautomeric keto and tautomeric enol. Ability occurrence of
this tautomeric cause cyclohexanone is nucleophilic. The results showed the
occurrence multikondensasi aldo between p-nitobenzaldehid and cyclohexanone
form the compound 2- (4'-nitrobenzilidin) cyclohexanone and 2-sikloheksilidin-6 (4

'nitrobenzilidin) cyclohexanone with respective levels of 16.42% and 12:53%.

compound

produced

from

the

reaction

between

p-nitrobenzaldehid

and

cyclohexanone with concentrated hydrochloric acid catalyst is a compound of 2sikloheksilidin-6 (4'-nitrobenzilidin) cyclohexanone with molecular formula
C19H21NO3 and obtained levels of 12:53% and the compound 2- (4'nitrobenzilidin) cyclohexanone with molecular formula C13H12NO3 and levels of
16:42% (Pujdono, Mutiara, and Kurniawan. 2011:514-520). So, that be conclude .
In for preparation of cyclohexanone is oxidation alcohol secondary cyclic becomes
ketones cyclic with be used chromat of potassium as oxidator in acid.
D. Apparatus and Chemicals
1. Apparatus
a. Erlenmeyer
b. Destillation flask 500 ml
c. Condenser
d. Funnel
e. Round flask
f. Graduated cylinder 10 ml and 100 ml
g. Thermometer 100
h. Beaker glass 250 ml
i. Seaparating funnel 100 ml
j. Stir bar
k. Spray bottle
l. Stative
m. Rough Cloth
n. Smooth Cloth
2. Chemicals
a. Potassium dichromate (K2Cr2O7)
b. Sulfuric acid (H2SO4)
c. Cyclohexanol (C6H11OH)
d. Aluminium foil
E. Work Procedure
1. Dissolved potassium dichromate 20.5 grams in 100 ml water in a beaker.
2. Add the be careful 10 mL of concentrated sulfuric acid, then the mixture
and cooled 30 .

3. Put 10 ml of cyclohexane in a round bottom flask.

4. Added the into flask potassium dichromate little by little and shake until
well mixed
observe the temperature of the mixture.
5. If the temperature is from 55 , cooled the outside of flask with cold
water. cooled is done so that the mixture temperature of not less than 55
and not more than 60 .

6. If the mixture temperature does not exceed 60 more chill in the air
for approximately 30 minutes while occasionally shaken.
7. Mixture was transferred into a distillation flask of 500 mL and added 100
mL of water, then mounted cooler for distillation
8. The mixture obtained by distillation to approximately 65 mL of distillate,
consisting of two layers, the water layer and a layer of cyclohexanone.
9. Saturated reaction mixture to clean as much as 12 grams NaCl, then
separate the layers of cyclohexanone.
10. Cyclohexanone separation layer, layer air then with 12 ml in the extraction
of petroleum ether.
11. Mixtured extract with a layer of cyclohexanon (C6H12O)
12. Dry with 3 grams of magnesium sulfate anhydrate.
F. Observation Result

Activity
20.5 gr of K2Cr2O7 (orange) + 100 ml
H2O (colorles)
K2Cr2O7 (orange) + 10 ml H2SO4
(colorelss)
10 ml of C6H12O (colorless) + K2Cr2O7
of solution (orange) the cooled
Mixed 100 ml of H2O (colorless) + the
mixture indestillation flask 250 ml, next
destillation

Observation
Produce of solution K2Cr2O7 (orange)
and there is crustal precipitate
Produce red brick
Black color and hot, temperature is 73

Produce 50 ml distillate H2O (water)

and C6H12O (oil)

Separation between cyclohexanone (oil)

an water with funnel destillation
Add ether to cyclohexanone in funnel
separation 12 ml and separation the
cyclohexanone and ether
Add the cyclohexanone 12 ml with
MgSO4

Produce 1 ml cyclohexanone of color

yellow (oil)
Produce 12 ml cyclohexanone

Produce 6 ml cyclohexanone

G. Data Analysis
If known : Mass of Potassium dichromate

= 20.5 gram

Mass of cyclohexanol

= 9.47 gram

Mr K2Cr2O7

= 294 gram/mol

Mr C6H11OH

= 130 gram/mol

Density of K2Cr2O7

= 0.95 gram/ml

Volume of C6H11OH

= 10 ml

Volume of K2Cr2O7

= 10 mL

Asked : % rendemen

= .... ?

Solution : n C6H11OH

n K2Cr2O7

C6H11OH

gram 20.5 gram

=
=0.06 mol
Mr
gram
294
mol

K2Cr2O7

C6H10 +

Initial : 0.07 mol

0.06 mol

React : 0.06 mol

0.06 mol

0.06 mol

mol

gram 9.47 gram

=
=0.07 mol
Mr
gram
130
mol

H2O
0.06

Eq

0.01

0.06 mol

mol
Mass of C6H10 (theory)

= mol C6H10 x Mr C6H10

= 0.06 Mol x 112 gram/Mol
= 6.72 gram

Mass of C6H10 (practicum)

= C6H10 X Volume C6H10

= 0.949 gram/ml X 6 ml
= 5.694 gram

% Rendemen

mass of practic
100
mass of theory

5.694 gram
100
6.72 gram

= 0.84 X 100 %
= 84%

practicum

mass of practicum
volume of practicum

5.694 gram
6 ml

= 0.949 gram / ml

0.06

H. Discussion
Berdasarkan prosedur kerja yang telah dilakukan, oksidator yang digunakan
untuk mengoksidasi sikloheksanol menjadi sikloheksanon adalah larutan K 2Cr2O7
dalam asam yang merupakan oksidator kuat. Pada reaksi oksidasi ini, sikloheksanol
dioksidasi dengan pengurangan atom H menjadi sikloheksanon, dan krom
mengalami reduksi dari +6 menjadi +4 yang tidak stabil kemudian berubah menjadi
+3. Pembuatan sikloheksanon menggunakan kalium bikromat dan sikloheksanol,
dan juga air sehingga akan terjadi reaksi oksidasi. Kalium bikromat berfungsi
sebagai oksidator. Air ditambahkan terlebih dahulu ke dalam gelas kimia agar
ketika kalium bikromat dimasukkan ke dalam gelas tidak akan terjadi letupan,
karena kalium bikromat adalah oksidator kuat. Kemudian ditambahkan asam sulfat
pekat yang berfungsi sebagai katalis yaitu untuk mempercepat terjadinya reaksi,
dan juga asam sulfat pekat inilah yang dapat bereaksi dengan alcohol
(sikloheksanol). Kemudian campuran didinginkan sampai

30 , karena asam

sulfat hanya akan dapat bereaksi dengan sikloheksanol pada suhu dingin. Kemudian
ditambahkan sikloheksanol yang merupakan bahan pereaksi untuk menghasilkan
sikloheksanon. Campuran dikocok dengan kuat agar dapat bercampur dengan kuat.
Campuran menjadi berwarna hijau kehitaman dan menghasilkan panas/kalor.
Reaksi ini merupakan reaksi eksoterm karena terjadi perpindahan panas dari system
ke lingkungan. Campuran ditutup dalam labu Erlenmeyer bertutup kasa agar tidak
meletup dan suhunya tidak melebihi

50 . Jika suhunya melebihi

maka dinginkan campuran di dalam air es. Jika suhunya kurang dari
bukan sikloheksanon yang akan terbentuk dan jika melebihi

50

50 maka
60

maka

sikloheksanon akan rusak.

Jika suhu campuran telah konstan, maka campuran didestilasi yang bertujuan
untuk memisahkan sikloheksanon dari senyawa-senyawa lain agar diperoleh

sikloheksanon yang murni. Hasil destilasi diperoleh destilat sebanyak 65 mL dan

terbentuk dua lapisan, lapisan atas adalah sikloheksanon, dan lapisan bawah adalah
air dan campuran zat-zat lain. Kemudian dijenuhkan dengan garam NaCl sedikit
demi sedikit agar tidak terlewat jenuh. Fungsi penjenuhan dengan NaCl adalah
untuk memisahkan air yang masih bercampur dengan sikloheksanon. Kemudian
terbentuk

dua

lapisan,

lapisan

atas

berwarna

kuning

seperti

minyak

(sikloheksanon), dan lapisan bawah berwarna bening (air). Hal ini terjadi karena
massa jenis sikloheksanon (0,95 g/mL) lebih kecil dari massa jenis air (1,00 g/mL).
Dan sikloheksanon bersifat non polar sedangkan air bersifat polar. Lalu, lapisan air
diekstraksi dengan petroleum eter yang berfungsi untuk mengikat sikloheksanon
yang masih bercampur dengan air. Dan terbentuk dua lapisan, lapisan air dibuang
dan lapisan sikloheksanon disatukan dengan lapisan sikloheksanon hasil
penjenuhan lalu ditambahkan magnesium sulfat yang berfungsi untuk mengikat
sisa-sisa air. Reaksinya:
MgSO4 + H2O MgSO4.xH2O
Kemudian larutan disaring dengan kertas saring dan diperoleh sikloheksanon
sebanyak 6 ml dengan % rendemen 84 %. Sikloheksanon yang diperoleh berwarna
bening kekuning-kuningan. Persen rendemen tersebut menunjukkan bahwa tingkat
keberhasilan percobaan cukup rendah, maksudnya sikloheksanon yang diperoleh
hanya 84 % dari massa teori (6.72 gr). massa hasil percobaan hanya 5.694 gr.
Larutan tidak didestilasi lagi karena volumenya tidak mencukupi untuk didestilasi.

BIBLIOGRAPHY
Brent, Robert. 1960. The Golden Book of Chemistry experiments. New York:
Golden press.
Carey, francis. 2000. Organic chemistry Fourth Edition. USA: Mc.Graw Hill

Chang, Raymond. 2010. Chemistry 10th Edition. USA: Mc.Graw Hill

Lesbani, dkk. 2015. Production of Adipic Acid from Mixtures of CyclohexanilCyclohexanone using Polyoxometalate Catalylts. Vol19 No.2.
Pujdono, Mutiara, Verdia Erlita, Kurniawan, Indra. 2011. Reaksi Multisep
Kondensasi Aldol dalam Sintetis Turunan Benzilidin Ketin daei pNitrobenzaldehid dan Sikloheksanon. Vol 5. No1.
Timberlake, C. Karen. 2012. Chemistry An Introduction to General, Organic, and
Biological Chemistry. USA: Mc.Graw Hill