ORGANIC CHEMISTRY FOR TECHNOLOGY

CHM 412
EXPERIMENT 8:
PREPARATION OF CYCLOHEXENE FROM CYCLOHEXANOL

NAME:

MARIAM HANANI ISMAIL

STUDENT ID:

2014827564

GROUP:

ED2604A

DATE OF EXPERIMENT:

10TH MAY 2016

DATE OF SUBMISSON:

17TH MAY 2016

INSTRUCTORS NAME:

MADAM FARIDAHANIM MOHD JAAFAR

EXPERIMENT 8
PREPARATION OF CYCLOHEXENE FROM CYCLOHEXANOL

Pre lab assignment

1. Find the density
reference(s).

for

cyclohexanol

and

cylohexene.

State

the

Density of cyclohexanol = 0.9624 g/ml

Obtained from https://en.wikipedia.org/wiki/Cyclohexanol
Density of cyclohexene = 0.7785 g/ml
Obtained from https://en.wikipedia.org/wiki/Cyclohexene
2. Show the calculation for the mass and moles for 20 ml of cyclohexanol.
(4 marks)
Mass of cyclohexanol = 0.9624 g/ml X 20 ml = 19.248 g
Molar mass = 6(12.01) + 12(1) + 16 = 100.158 g/mol
No. of mol = 19.248 g / 100.158 g/mol = 0.1922 mol

Apparatus
Thermometer -1
still head -1
condenser - 1
round bottom flask (50ml) - 1
receiving flask (50 ml) -1
rubber hoses - 2
conical flasks (150-250 ml) -2
adapters depending on the set available
retort stands - 2 pc
gravity funnel -1
water bath
separatory funnel and stopperv(150ml) -1 set
test tube - 1
Chemicals
Cyclohexanol
85% phosphoric acid
sodium chloride solid
10% sodium carbonate solution
anhydrous magnesium sulfate
boiling chips
ice cubes.
1-2% KMnO4 solution
Procedure
1.
2.
3.
4.
5.
6.
7.

8.

A simple distillation apparatus was set up.

Around 10.5ml of 85% phosphoric acid was added in a round bottom
flask.
20 ml of cyclohexanol and a few boiling chips was also added in.
The reaction mixture was distilled.
The receiving flask was immersed up to its neck in an ice bath to
avoid loss of any product (b.p. 83C).
The distillation flask was heated carefully so that a steady
distillation rate is obtained.
The temperature of the distilling vapors was not allowed to exceed
103C. The reaction mixture was stop heated when only a few ml of
liquid remain in the distilling flask or when the vapors exceed 103C.
The distillate was saturated by adding solid sodium chloride portion
wise with swirling. The salt was stop added when it is not dissolved
anymore. The excess sodium chloride was kept to a minimum.

9.

Any acid was neutralized by adding just enough 10% sodium

carbonate (Na2CO3(aq)) solution to the mixture with swirling to make
the aqueous layer basic (use blue litmus paper to the solution). Every a
few drops of Na2CO3(aq) added, the solution was tested by putting a
drop of the solution on a blue litmus paper until it the blue litmus paper
remained blue.
10. The mixture transfer to a separatory funnel and the aqueous layer
drained. The aqueous solution and the organic solution were
determined.
11. The organic layer was poured into an Erlenmeyer/conical flask and
dried it with just enough anhydrous magnesium sulfate.
12. The product was filtered into a clean, dry, round bottom flask via
gravity filtration.
13. The dried cyclohexene was redistilled.
14. The boiling point recorded and the volume of the product measured.
15. The product form was tested with a few drops of KMnO 4(aq), the
colour change observed.
Observations:
1. The clear phosphoric acid was inserted into the round bottom flask.
2. The distillate was combined with 1 and a half of solid sodium chloride until a
small amount of white precipitate was deposited at the bottom.
3. After 3 drops of sodium bicarbonate, the blue litmus paper remains
unchanged.
4. Two layer solutions were formed and when distilled water was added to
make sure which of the solution is organic solvent (top) or aqueous
solvent (bottom). The aqueous solvent increase in amount when
distilled water is added. The aqueous layer is distilled water and the
organic solvent is cyclohexene.
5. 2 and half spatula of anhydrous magnesium sulfate was added to the
cloudy cyclohexene until no more oily layer can be seen at the surface
of the cyclohexene solution.
6. The boiling point is 40oC and the volume of the clear solution of the
end product is 8.5 ml.
7. The cyclohexene solution decolorized the 2 drops of KMnO4(aq) solution.
Results:
Boiling point: 40oC
Volume of the product: 8.5 ml
The cyclohexene decolourized 2 drops of KMnO4(aq). This is an oxidation reaction which the
carbon-carbon double bonds (C=C) is substituted by the hydroxyl group (-OH).

Discussion:
1. The initial volume of cyclohexanol is 20ml and the end product, cyclohexene is 8.5 ml.
the expected volume is 15.79 ml. the percentage yield is 53.83 %.
2. There errors that could occur during distillation process are the presence of contaminants
in the fractionating column. If residual liquids have similar boiling point cyclohexene
used in this experiment, they could have contaminated either the distillate or the liquid in
the boiling flask, creating excess volume in the distillate.
3. Another possible error that could occur is loose sealed joints in glassware and residual
distillate left in the distillation apparatuses. Joints that were not tightly sealed could have
resulted in vapour loss, which would contribute to a lower volume of collected distillate.
Residual distillate condensation left stuck to the inside of the distillation apparatus also
contributes to distillate loss.
Conclusion:
The volume of cyclohexene produced is 8.5 ml. the expected volume is 15.79 ml. The percentage
yield is 53.83%.
References
Clark, J. (n.d.) Reactions of Alkenes with Potassium Manganate. Retrieved at 16th May 2016 at
http://chemwiki.ucdavis.edu/Core/Organic_Chemistry/Hydrocarbons/Alkenes/Reactivity_of_Alk
enes/Reactions_of_Alkenes_with_Potassium_Manganate
Deenik, P., Guerin, M, & Kiel, K. (n.d.) Lab 3: Distillation. Retrieved at 16th May 2016 at
https://ochemwonderstudents.wikispaces.com/DistillationLab
Georgia, N. (n.d.) Possible sources of error. Retrieved at 16th May 2016
https://www.coursehero.com/file/p1dknbu/Possible-sources-of-error-in-the-fractionaldistillation-method-could-include/

at

Questions:
1) Find the moles of cylohexene formed in the experiment.
H
OH

OH2

+ H2O

+ H2O

As the reaction only react with 1 mol of each molecule thus

1 mol of cyclohexanol = 1 mol of cyclohexene
0.1922 mol of cyclohexanol = 0.1922 mol of cyclohexene
2) Calculate the expected mass of pure product cyclohexene using the
number of moles cylohexanol used in the experiment based on the equation.
(2 marks)
Molar mass of Cyclohexene = 6(12.01) + 10(1.008) = 82.14 g/mol
Mass of expected Cyclohexene = 82.14 g/mol x 0.1922 mol = 15.79 g
2) Show the calculation for the percentage yield/conversion of cyclohexanol
to cyclohexene.
(2 marks)
Mass of cyclohexene obtained
Mass of cyclohexene theoretical

x 100 =

8.5
15.79 x 100 = 53.83 %

3) Suggestion another simple chemical test for the product instead of

KMnO4(aq) and state the observation. (2 marks)
Another simple chemical test for the product is using bromine water. If the
bromine water decolorizes, the double bond of alkene presence.
4) Draw the products that would be obtained by the dehydration of the
following molecules and state which are minor and major products. (4
marks)
(a)
2-heptanol

(b)

2-methyl-1-cyclohexanol

5) Why the amount of 85% phosphoric acid is not necessarily to be exact

amount as cyclohexanol? (1 mark)
The phosphoric acid is not necessarily to be exact amount as cyclohexanol
because phosphoric acid acts as a catalyst and as such increases the rate of
reaction but does not affect the overall stoichiometry. The phosphoric acid
also will stay in the round bottom flask and will not be distillate.