Lab CHM 457 Exp 2

EXPERIMENT 2: Preparation Of 4-Methylcyclohexene
OBJECTIVE
 To learn the distillation technique

 To understand the mechanism involved in the reaction
 To produce 4-methylcyclohexene through the acid-catalyzed elimination of water
from 4-methylcyclohexanol
INTRODUCTION
In this experiment, 4-methylcyclohexanol undergoes acid-catalyzed dehydration to give 4-

methylcyclohexene. The product is distilled from the reaction flask along with the water
generated. The distillate is washed with salt solution, dried and distilled.
The hydration of alcohols using strong mineral acids, such as sulphuric acid or phosphoric
acids, as a catalyst is a general laboratory method for preparing alkenes. The reaction is
conducted in a distillation apparatus. As the reaction mixture is heated, the lower boiling
products (cyclohexene with boiling point = 83 °C and water boiling point = 100 °C distilled
out and are collected out in the receiving flask. Any unreacted cyclohexanol (the starting
material ) and phosphoric acid ( the catalyst ) are left in the distilling flask because of their
high boiling points ( 161 and 213 ). However, a small amount of phosphoric acid still appears
in the receiving flask, the product is washed with aqueous sodium carbonate to neutralize the
acid. As we know, cyclohexene is insoluble in water and it is not lost during the crude
cyclohexene by drying the liquid over anhydrous sodium sulphate. Sodium sulphate is a salt
which forms a hydrate. Final purification is achieved by simple distillation.
MATERIALS
 7.5 mL of 4-methylcyclohexanol ( molecular weight = 114.2, boiling point = 171-

173 ), 2.0 mL of 85 % phosphoric acid, 30 drops ( 0.4 mL ) of concentrated sulphuric
acid, saturated sodium chloride solution, granular anhydrous sodium sulphate,
bromine test reagent, potassium permanganate test reagent
APPARATUS
 50 mL round bottom flask, 25 mL round bottom flask, Erlenmeyer flask, glass stirring
rod, Pasteur pipets, boiling stones, distillation apparatus, ice-water bath, heating
mantle, weighing balance
PROCEDURE
SAFETY CONSIDERATION
Phosphoric and sulphuric acids are very corrosive. We are not allowed to touch our skin. The
experiment have strong odours because have many of compound so that we used caution
when smelling them. In addition, the sample was kept away from the flames unless testing
small amounts for behaviour when heated. We were reminded all the times to place all
discarded in the waste bottle in fume hood
1) APPARATUS ASSEMBLY
 The apparatus for simple distillation was set up first. 50 mL round bottom flask was
used as distilling flask and a 25 mL round bottom flask as a receiver. An ice bath was
placed around the receiver to reduce the loss of product by evaporation. An empty 50
mL round bottom flask was weighed. 7.5 mL of 4-methylcyclohexanol was placed in
that round bottom flask using graduated pipets.
2) DEHYDARATION
 The distillation temperature was maintained below 100. We was continued until only
0.5-0.6 mL of the residue remains in the distillation flask or the mixture begins to
smoking or bumping.
3) ISOLATION AND DRYING OF THE PRODUCT

 The distillate was transferred to a separatory funnel with the aid of 3 mL saturated
sodium chloride solution. ( we don’t have to use centrifuge tube and Pasteur pipette )
4) DISTILLATION
 Drying agent was prevented before starting with distillation process. The 25 mL
round bottom flask was used as a receiver that should be pre-weighed. The
temperature range which is most of the product distill is the boiling point of our 4-
methylcyclohexene.
5) SPECTROSCOPY
 We are reminded to not do this part
6) UNSATURATION TEST
 This test must be done and our result was recorded and explained in discussion
 DATA AND RESULT
Weigh of 50 mL round bottom flask 66.117 g

( empty )
Empty 50 mL flask + 4-methylcyclohexanol 75.2591 g
25 mL round bottom flask ( empty + cap ) 67.6715 g
After second distillation 69.2814 g
 COLOUR CHANGES
4-Methylcyclohexanol + Bromine in CCl4 Colourless to yellow

4-Methylcyclohexanol + Potassium No changes in colour
Permanganate
4-Methylcyclohexene + Bromine in CCl4 Colourless to cloudy
4-Methylcyclohexene + Potassium Colourless and has brown precipitate
Permanganate
Observed boiling point of product: 68 °C
Literature boiling point of product: 83 °C

Calculation:
Percent Yield = 17.2755 %
From the reaction,
1 mol of 4-methylcyclohexanol = 1 mol of 4-methylcyclohexene
Molecular mass 4-methylcyclohexanol = 114.2 g mol-1
Molecular mass 4-methylcyclohexene = 96.2 g mol-1
n(mol) of 4-methylcyclohexanol = 6.2126 g / 114.2 g mol-1 = 0.0544 mol
Thus, 0.0544 mol of 4-methylcyclohexanol was produced.
Mass of cyclohexene = 0.0544 mol X 96.2 g mol-1 =5.23338 g
= 5.2334 g
Percent Yield (%) = (Experimental Yield/ Theoretical Yield) X 100
= (69.2814 g - 67.6715 g) / 5.2334 g X 100 %
=1.6099g/ 5.2334 g X 100 %
=30.7620 %
Discussion
In this experiment, we have done a preparation of 4-methylcyclohexene through

alcohol dehydration. The dehydration reaction of alcohols to generate alkene proceeds by
heating the alcohols in the presence of a strong acid, such as sulfuric or phosphoric acid, at
high temperatures. The acid protonates the alcoholic hydroxyl group, permitting it to
dissociate as water. Loss of a proton from the intermediate (elimination) brings about an
alkene. Sulfuric acid produces messy results.not only it is an acid, but it is also a strong
oxidising agent.
When we distill the product from the reaction mixture as it is formed, the equilibrium
of this reaction will also being achieved. The 4-Methylcyclohexene (boiling point = 101 –
102) will be formed the distilled water that is also formed. By continuously removing the
products, we have managed to yield more product of 4-Methylcyclohexene. Because the 4-
Methylcyclohexanol has low boiling point. So we have done the experiment carefully.
To remove the catalyst (acid) , the distillate mixture with a saturated sodium chloride
solution. This step also partially removes the water from the 4-Methylcyclohexene layer, the
drying process will be completed by allowing the product to stand over anhydrous sodium
sulphate.
From the results that we have got, the reaction 4-Methylcyclohexanol + Bromine in
CCl4 indicates color changes from colourless to yellow and the reaction of 4-
Methylcyclohexanol + Potassium Permanganate indicates no colour changes. For 4-
Methylcyclohexene + Bromine in CCl4, the reaction indicates colour changes from colourless
to cloudy and for the reaction of 4-Methylcyclohexene + Potassium Permanganate it appears
as colourless and has brown precipitate.
Conclusion
The percentage of 4-Methylcyclohexene yielded is 30.7620 % with 1.6099g produced

experimentally. We have managed to produce 4-methylcyclohexene from the starting
material, 4-methylcyclohexane through the acid-catalyzed elimination of water.
Question
1. Utilizing structural formula, write a chemical equation for the preparation of 4-

methylcyclohexene from 4-methylcyclohexanol.
2. The preparation of cyclohexene from cyclohexanol is what basic type of reaction?

What is the name of this reaction?
- Elimination Reaction
3. Why is the receiving flask supposed to be kept on ice during the preparation of
cyclohexene?
-An ice bath to cool the receiving flask is recommended so as to keep the vapors of
cyclohexene to a minimum in the laboratory
4. If 2-methylcyclohexanol is dehydrated, two possible alkene product is obtained.

Draw the structure of these two product and predict which of the two products is the
major product.
-The more stable (major) alkene product is 1-methylcyclohexene and the minor
product is 3-methylcyclohexene.
5. Show the complete acid-catalyzed mechanism for the dehydration of 2-
methylcyclohexanol
References
1. 36 Dehydration of Alcohols. (2016). Efficiently Studying Organic Chemistry. doi:

10.1055/b-0036-135234
2. Martin S. Sillberberg, Patricia G. Amateis, “ CHEMISTRY: THE MOLECULAR

NATURE OF MATTER AND CHANGE”, 7TH edition, McGraw-Hill Education, Inc. N.Y
2015, page 617-658
3.Griesbeck, A. G. (2006). Acid-Catalyzed Dehydration of 4-Methoxyphenyl-Substituted
Alcohols. Quinones and Heteroatom Analogues, 1.

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EXPERIMENT 2: Preparation Of 4-Methylcyclohexene

 To learn the distillation technique

In this experiment, 4-methylcyclohexanol undergoes acid-catalyzed dehydration to give 4-

 7.5 mL of 4-methylcyclohexanol ( molecular weight = 114.2, boiling point = 171-

3) ISOLATION AND DRYING OF THE PRODUCT

Weigh of 50 mL round bottom flask 66.117 g

4-Methylcyclohexanol + Bromine in CCl4 Colourless to yellow

Observed boiling point of product: 68 °C

Literature boiling point of product: 83 °C

Percent Yield = 17.2755 %

From the reaction,

1 mol of 4-methylcyclohexanol = 1 mol of 4-methylcyclohexene

Molecular mass 4-methylcyclohexanol = 114.2 g mol-1

Molecular mass 4-methylcyclohexene = 96.2 g mol-1

n(mol) of 4-methylcyclohexanol = 6.2126 g / 114.2 g mol-1 = 0.0544 mol

Thus, 0.0544 mol of 4-methylcyclohexanol was produced.

Mass of cyclohexene = 0.0544 mol X 96.2 g mol-1 =5.23338 g

Percent Yield (%) = (Experimental Yield/ Theoretical Yield) X 100

= (69.2814 g - 67.6715 g) / 5.2334 g X 100 %

=1.6099g/ 5.2334 g X 100 %

In this experiment, we have done a preparation of 4-methylcyclohexene through

The percentage of 4-Methylcyclohexene yielded is 30.7620 % with 1.6099g produced

1. Utilizing structural formula, write a chemical equation for the preparation of 4-

2. The preparation of cyclohexene from cyclohexanol is what basic type of reaction?

4. If 2-methylcyclohexanol is dehydrated, two possible alkene product is obtained.

1. 36 Dehydration of Alcohols. (2016). Efficiently Studying Organic Chemistry. doi:

2. Martin S. Sillberberg, Patricia G. Amateis, “ CHEMISTRY: THE MOLECULAR

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