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Lab Report CHM456

1) The experiment aimed to synthesize 4-methylcyclohexene from 4-methylcyclohexanol through a dehydration reaction and determine the percentage yield. 2) 4-Methylcyclohexanol was dehydrated through heating to form 4-methylcyclohexene, eliminating a water molecule. Various tests confirmed the product was the alkene 4-methylcyclohexene. 3) The percentage yield of 4-methylcyclohexene was calculated to be 7.2% based on the theoretical and actual yields obtained.

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900 views6 pages

Lab Report CHM456

1) The experiment aimed to synthesize 4-methylcyclohexene from 4-methylcyclohexanol through a dehydration reaction and determine the percentage yield. 2) 4-Methylcyclohexanol was dehydrated through heating to form 4-methylcyclohexene, eliminating a water molecule. Various tests confirmed the product was the alkene 4-methylcyclohexene. 3) The percentage yield of 4-methylcyclohexene was calculated to be 7.2% based on the theoretical and actual yields obtained.

Uploaded by

Johan Daniyal
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© © All Rights Reserved
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Experiment 2 : PREPARATION OF 4 METHYLCYCLOHEXENE FROM

DEHYDRATION OF 4 METHYLCYCLOHEXANOL

OBJECTIVE
1. To classify alkanes and alkenes using chemical reaction test.
2. To able to synthesize 4 - methylcyclohexene from 4 methycyclohexanol by
distillation.
3. To determine the percentage yield of 4-methylcyclohexene.
INTRODUCTION
In this experiment some properties of hydrocarbons will be studied, where 4methylcyclohexanol will be hydrated to form 4-methlcyclohexene by elimination
reactions. The substrate is 4-methylcyclohexanol (R-OH). The hydroxyl group in ROH is a poor leaving group because it would have to leave as a hydroxide ion (

OH . By adding a strong acid will help hydroxide to be eliminate as water (


H 2 O . As the water leaves the substrate material, a proton also lost in an
elimination process. The end is the alkene product.

The 4-methylcyclohexene product will be distillate again with the water that also
forms. A wash with saturated sodium chloride solution will help remove the most
residue water from the distillate product.
Cyclohexene is an unsaturated hydrocarbon. In chemistry, a hydrocarbon is any
chemical compound that consists only of the elements carbon (C) and hydrogen (H).
The major classes of hydrocarbons are alkanes, alkenes, alkynes and aromatic
hydrocarbons. The alkanes are the least reactive class, because they contain only
carbon and hydrogen and they have no reactive functional groups. There are a
number of simple tests that may be used to differentiate alkanes from alkenes.
These tests are based upon the reactivity of alkenes with a variety of reagents to
which the alkanes are insensitive. In this experiment, we can distinguish between
cyclohexene (alkene) and cyclohexane (alkane) using chemical reaction tests, which
is bromine and permanganate tests.

DATA AND RESULT

7.5ml of 4-methylcyclohexanol is used.


Boiling point for 4-methylcyclohexanol : 80 celcius
3ml of NACI was added.
Boiling point of 4-methylcyclohexene : 82 celcius.

TEST TO DETERMINE THE END PRODUCT (Alkane/Alkene)

Result for

BROMINE TEST

Unknown

end

product

BAEYERS TEST

Colour of

Br2 (light

(potassium permanganate)
Colour of potassium

yellow

disappear

permanganate (dark

is

slowly.
Result : Positive with

purple

was

changed

to

light

alkenes

purple

and

brown

precipitate of MnO2

is form.
Result : Positive with
alkenes.

CALCULATION
Mass of empty conical flask was recorded for 3 times to get the average.

74.447g
74.467g
74.464g

The average mass is 74.459g.


The mass of conical flask with 4-methylcyclohexene is

81.3783g.

1. THE THEORITICAL YIELD :


The mass of 4-methylcyclohexene :
81.3783g 74.459g
= 6.92g.

Theoritical Yield =

mass of 4methylcyclohexene (g)


relative molar mass(gmol1)

6.92 ( g )
( 7 x 12 )+ (1 x 12 ) gmol1

6.92 ( g )
96 gmol1

= 0.07208
2. PERCENTAGE YIELD OF 4-METHYLCYCLOHEXENE
=

theoretical yield( g)
X 100
relative molecular mass (gmol1)

= 7.2%

DISCUSSION

In

this

experiment,

all

the

process

conducted

is

success.

Thus,

4-

methylcyclohexanol was converted completely to form 4-methylcyclohexene by


elimination process. The water has been eliminated with the product of alkene. The
result from the data show amount of 4-methycyclohexanol solution before distillate to
form 4-metyhlcyclohexene, and also the calculation of theoretical yield.
The elimination reaction involves the loss of an OH from one carbon and an H from
an adjacent carbon. Overall, this amounts to the elimination of a molecule of water,
resulting in a pi-bond formation of an alkene or alkyne. The loss of water from a
molecule is called dehydration. In this experiment, 4-methylcyclohexanol is
dehydrated to 4-methylcyclohexene according to the following reaction:

Starting the experiment with 7.5ml of 4-methylcyclohexanol is used, and the


temperature (boiling point) during the distillation process is 80 celcius, where is
under 100 celcius as stated in lab manual. Next for the second distillation of 4methylcyclohexene, the boiling point is 82 celcius. This second distillation is for the
elimination of excess water ( H 2 O .

Several test was carried out to determine the

obtained end product is alkene or alkane, which is bromine test and potassium
permanganate, or known as Baeyers test. The end product was separated into two

test tube, one for bromine test, and another one for Baeyers test (potassium
permanganate).
For the bromine test, few drops of bromine was added into the first test tube. When
the bromine is mixed with the end product, the colour of bromine (yellowish), will
change to colourless. As the result, it proved that the end product was an alkene. If
the product have presence of alkane, no change of colour was initially observed.
Next for the Baeyers test (potassium permanganate), few drops of potassium
permanganate is added to the second test tube. The disappearance of the purple
colour of potassium permanganate and the appearance of brown precipitate (MnO2)
is a positive test for the presence of alkene. Because alkane will not react with
potassium permanganate.

CONCLUSION
In this experiment, preparation of 4-methylcyclohexene from dehydration of 4methylcyclohexanol is successfully done. The proving of end product either its
alkene or alkane has be done with two chemical test, that is bromine test and
baeyers test (potassium permanganate). Both result for the chemical test is positive
that the end product is 4-methylcyclohexene.

REFFERENCES
Chemistry 11th Edition by Goldsby Chang
General Chemistry by Fordham
Introduction of Organic Chemistry by Elias James Crey

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