Objective

1. To learn distillation technique

2. To understand the mechanism involved in the reaction
3. To produce 4-methylcyclohexene through the acid-catalyzed elimination of
water from 4-methylcyclohexanol

Introduction

In this experiment, 4-methylcyclohexene is formed through the acid-catalyzed

dehydration of 4-methylcyclohexanol. The product which is
4-methylcyclohexene is distilled from the reaction flask along with the water
generated. The distillate is washed with salt solution, dried and distilled.

For dehydration to be possible,the OH group on 4-methylcyclohexanol must

be converted into H2O through acid-catalyzed dehydration using a strong acid
catalyst such as phosphoric acid and sulfuric acid. The reaction is conducted in
a distillation apparatus. The H2O molecule will then become the favored
leaving group and leave on its own resulting in the formation of a carbocation
in excess water. The water will remove the acidic hydrogen on the carbocation
producing the desired alkene as well as regenerating the acid catalyst. The time
effective way to collect th 4-methylcyclohexene is to heat the reaction to reflux
as it is taking place. This allows the product to be separated from the starting
materials by means the boiling point discrepancy between the isolated alkene
(101-102℃) and the starting alcohol (171-173℃).Any unreacted cyclohexanol
(the starting material) and phosphoric acid (catalyst) are left in the distilling
flask because of their high boiling points (161℃ and 213℃ ). However, a
small amount of catalyst stil appears in the receiving flask, the product is then
washed with saturated sodium chloride to neutralize the acid.After the distillate
is collected any impurities of water and phosphoric acid can be extracted by
adding anhydrous sodium sulfate.Sodium sulfate is a salt which forms a
hydrate. Final purification is achieved by simple distillation. The product
formed is then identified using unsaturation test which is using bromine test
and Baeyer’s test.
Procedure

An apparatus for simple distillation was set up. 100 ml round-bottom flask and 50
ml round-bottom flask was used as the distilling flask and receiving flask. An ice
bath was placed around the receiver to lessen the loss of product by evaporation.
Then, an empty 100 ml round-bottom flask was weighed. 7.5 ml of
4-methylcyclohexanol was placed using graduated pipets and the flask was
reweighed again to get the mass of alcohol. 2.0 ml of 85% phosphoric acid and 30
drops of concentrated H2SO4 along 2 boiling chips was added in the distillation
flask and mix thoroughly. The mixture was heated with a heating mantle and
distilled slowly with maintain the distillation temperature below 100℃.
Distillation was continued untill only 0.5-0.6 ml of residue remains in the flask or
the mixture began to smoke or bump. Next, the distillate was mixed with 3ml of
saturated NaCl and the mixture was transfered into a test tube. The test tube was
closed with the cork tightly and the layers was mixed by swirling and shaking.
This step was repeated to allow the layers to separate. The bottom aqueous layer
was drawn off with a Pasteur pipet and discarded. The crude of
4-methylcyclohexene was transfered using pasteur pipet to an Erlenmeyer flask. A
small amount of anhydrous Na2SO4 was added and a stopper was placed. The
liquid was dried for at least 15 minutes while gentle swirling. The simple
distillation was cleaned,dried and reassambled with acetone during drying interval.
A receiver of 50 ml round-bottom flask was weighed and transfered the dried
cyclohexene with pasteur pipet into 100 ml round-bottom flask. 2 boiling chips
was added and distilled and repeated the step as above for distillation process.after
that,the flask was reweighed and calculate the percentage yield of
4-methylcyclohexene.

Unstaturation test using Br2 in CCl4 and KMnO4

3 drops of 4-methylcyclohexanol was placed into 2 separate tset tubes. 6 drops of

Br2 in CCl4 in one of the test tube and 4 drops of KMnO4 was added in other test
tubes. Any colour changes was observed. Next, 3 drops of 4-methylcyclohexene
that was obtained was placed in 2 separate test tubes. 6 drops of Br2 in CCl4 was
added in one of the test tube and 4 drops of KMnO4 was added in other test tubes.
Any colour changes was observed.