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EXPERIMENT 3: OXIDATION OF CYCLOHEXANOL WITH PCC ON A SILICA

GEL SUBSTRATE

OBJECTIVE

To investigate the oxidation of cyclohexanol to cyclohexanone with PCC on a

silica gel substrate


To investigate test of TLC
To determine the IR spectrum of cyclohexanone

INTRODUCTION
Oxidation reactions of alcohols greatly increase the synthetic usefulness of these
compounds. Only primary and secondary alcohols can be easily easily oxidized with the
former converted to aldehydes or carboxylic acids and the latter to the corresponding
ketones. The strength and selectivity of oxidizing agents varies widely, the use of
oxochromium(IV) amine reagents is fundamental for a number of organic oxidative
transformations. Pyridinium chlorochromate (PCC) is the most commonly used of these
reagents, due to its availability, stability and versatility. Oxidation with PCC generally
proceeds through a simple, one step reaction :
EQUIPMENTS AND INSTRUMENTS
1. Pestle and mortar
2. Magnetic stirrer
3. Rotatory evaporator
4. IR

MATERIALS

Cyclohexanol (FW 100.16) ( 0.95 g/ml)


0.10 g (1.00 mmol)
Pyridinium chlorochromate (FW 215.56)
0.43 g (2.00 mmol)
Silica gel (230 400 mesh)
0.43 g (for synthesis)
Dichloromethane
Celite
Saturated NaCl
Anhydrous Na2SO4
Ethyl acetate
Petroleum ether
Silica gel (30- 70 mesh)
for filtering
Silica gel (230- 400 mesh)
for column chromatograpy

PROCEDURE
1. PCC and silica gel (23o=4oo mesh was combined and grind with a pestle and mortar
and a light orange powder was formed.
2. The powder was added to 25ml round bottom flask along with 6ml dichloromethane.
3. Then the cyclohexanol was added and stirred for 2o=3o minutes.
4. The solution was tested with TLC for every five minutes.
5. After the reaction was completed, the reaction solution was diluted with 1oml of ether
and the solution was filtered through a pipet containing a cotton plug, 1cm Celite, 3cm
silica gel (35=7o mesh.
6. The solution was extracted with 2x5ml of water and saturated NaCl solution.
7. The solution was dried over anhydrous Na2SO4 and the solvent was evaporated under
vacuum.
8. The crude product was purified using column chromatography (ethyl\acetate petroleum
ether as the solvent system.
9. TLC was performed to identify the suitable solvent system.

DATA AND RESULT


Cyclohexanone Spectra
Assign
A
B

Shift (ppm)
2.35
2.07 to 1.55

CALCULATION
C6H11OH (cyclohexanol) C6H10O (cyclohexanone)
0.1 g C6H11OH x x x

11molC
molC
986.615
HH11
g10OH
O
100
11molC
.molC
16 gC
66H
6HH
11
10
11
OH
O
OH

Mass of C6H1O = 0.098g


Rf value
Rf =
5 minute
=
= 0.002
10 minute

dis tan cetravelbysub tan ce


dis tan cedtravelbysolventfront
1.0
8.3

=
= 0.36

3.0
8.3

15 minute
=
= 0.22

1.8
8.3

20 minute
=
= 0.19

1.6
8.3

25 minute
=
= 0.31

2.6
8.3

30 minute
=
= 0.29

2.4
8.3

DISCUSSION
This experiment is run to produce cyclohexanone from cyclohexanol using the method of
oxidation with PCC on a silica gel substrate. Unfortunately, the experiment was failed
due to certain errors occurred during the experiment. The final product of cyclohexanone
is not been obtained. Only the result for testing with TLC is obtained as it has been test at
the beginning of the experiment after the cyclohexanol react with PCC. The result of TLC
has been reported on calculation part. The TLC test should be conducted by using two
solvent to compare with each other and to determine the suitable solvent. However, in
this experiment it was been conducted by using only one solvent which is ethyl acetate
and the comparison cannot be held.

The final product of the experiment is not been obtained due to some errors. The error
might come at the beginning of the experiment which is when the process of transferred
the light orange powder from the mortar into another container. Students not take into
account the remaining powder that are stick on the mortar which is it may affect the yield
of the final product. Next, the using of cotton wool in the pipette is too much and made
the solution been absorbed by the cotton wool result in decreasing the volume of the
product. The process to remove the solvent using rotatory evaporator showed the final
product is not been transferred to the other round bottom flask proved the experiment was
failed.
The literature melting point of cyclohexanone is -47oC in range. In IR spectrum, C=O
functional group for ketone supposed to have IR absorption at range of 1680-1750 cm-1.
Aromatic hydrocarbons show absorptions in the regions 1600-1585 cm-1 and 1500-1400
cm-1 due to carbon-carbon stretching vibrations in the aromatic ring.

CONCLUSION
The experiment failed. Cyclohexanone is not obtained from the experiment.
PROBLEMS
1. Would the final product been any if you had used strong oxidizing agents such as
chromic acid?
Yes. The final product has different when used a stronger oxidizing agent.
What would your products have been if you had been oxidizing the following compound
with
A. PCC
For secondary alcohol converted to ketones, while for primary alcohol
convert to aldehyde.
B. b.chromic acid?
For secondary alcohol converted to ketones, while for primary alcohol

convert to carboxylic acids.

2. Given that PCC is only sparingly soluble in CH2Cl2 while cyclohexanol is miscible in
CH2Cl2, suggest a reason for the importance of grinding the PCC and silica gel to form
powder.
The chromium byproduct deposits with pyridine as a sticky black tar, which can
complete workup. Addition of an inert adsorbent that is silica gel to allows the sticky
byproduct to absorb to the surface and makes workup easier.

REFERENCES
1. http://www.nvcc.edu/alexandria/stb/chm/246/46_oxidation.pdf
2. T.W.Graham Solomons and Craig B. Fryhle (2011). Organic chemistry (10th ed.). John
Wiley & Sons, INC. 691 pp.