Student name : Experiment name :
Abdullh Nasser Alharbi. Preparation of cyclohexene from cyclohexanol.
15/11/2020
ID: 2200000216
Objective:
prepare cyclohexene from cyclohexanol and determine the e ciency of this conversion.
Introduction:
During an E1 reaction, alcohols undergo dehydration to form an alkene when heated with a
strong acid. The acid-catalyzed dehydration of an alcohol is an important method for the
preparation of an alkene. It is also an example of an elimination reaction, which proceeds by a
rst order mechanism via an intermediate carbocation. In this experiment, cyclohexanol is
dehydrated to cyclohexene in the presence of phosphoric acid: Distillation is employed in this
experiment to synthesize and purify cyclohexene.
Materials:
1-bottom aks
2-Cyclohexanol
3-phosphoric acid
4-graduated cylinder
5-separatory funnel
6-Clamp
7-sodium carbonate solution
8-test-tube
9-conical aks
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Method:
In a 10 mL round-bottom ask, weight out 3 mL of cyclohexanol.
Add 4 mL of 85% H3PO4
and 5 drops of concentrated H2SO4
while swirling the solution.
Attach ask distillation head, thermometer/adapter, condenser, vacuum adapter, and
receiving ask.
Turn on the heating mantle, distill the reaction mixture, and collect the distillate until no
more liquid distills or the temperature rises above 85 . ℃
Remove receiving asks and transfer distillate to centrifuge tube.
As the temperature cools, two layers should form. Using a Pasteur pipette, remove the
bottom layer and place in a container labeled “Recovered Acid Layer.”
Dry the top organic layer by adding anhydrous CaCl2
With a Pasteur pipette, remove the liquid and transfer to a tarred ask.
Weight and determine the percent yield of the product
Following the synthesis of cyclohexene from cyclohexanol, you should determine whether the
product cyclohexene was or was not formed during the procedure.
Take 5-6 drops of the product formed in a small test tube.
Add 1-2 drops of potassium permanganate (KMnO4) to the product.
Solution turns colorless
Take 5-6 drops of the starting product.
Add 1-2 drops of potassium permanganate (KMnO4) to the starting product.
Solution retains the color.
Result :
Tabel of observation:
Calculation Cyclohexanol H3PO4 (85%) Cyclohexene
Molecular weight g/mol 100.185 g/mol 97.995 g/mol 82.143 g/mol
Amount in mL 3 mL 4 mL ——
Amount in (g) 2.89 g 6.74 g 0.709 g
Density in (g/mL ) 0.9624 g/mL 1.685 g/mL 0.81 g/mL
Moles 0.028 moles 0.068 moles ——
% yield = mass of product (experimental)/ theoretical yield of product (g) x100
0.709 g of cyclohexene/2.30 g of cyclohexanol x100 = 30.8% recovery.
The mechanism of reaction is shown below :
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Discussion :
This experiment was all about observing the laboratory procedure in the preparation of
cyclohexene from cyclohexanol. As has already been established in the introductory portion of
this laboratory report, this conversion comes about from the catalytic dehydration of the alcohol
to introduce the unsaturation into the structure. As a preliminary, this dehydration falls under the
mechanisms of Elimination reactions, speci cally one of the E1 (Unimolecular Elimination) nature.
Basically speaking, the E1 mechanism is similar in pattern with the SN1 mechanism and in the
sense that it is also a two step process. Though they are fundamentally di erent in terms of their
fast second step, the two mechanisms share the same rst rate detemining step, which is the loss
of a leaving group and the formation of a carbocation.
Source:
[Link] manuals/[Link]
[Link] ganic_Chemistry_II_Experiment_No_2
_Preparation_of_Cyclohexene
https: /[Link]
[Link]
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