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Chem 26AA
03 November 2016
Experiment no. 7: Preparation of Chlorocyclohexane
Experiment no. 8: Dehydration of Cyclohexanol
Weight
2.54 grams
3.75 grams
Theoretical Yield
5.70 grams
6.56 grams
Percent Yield
44.60%
57.16%
Experiment 7
Qualitative Test
Chromic Acid Test
Alcoholic silver nitrate
Result
Negative
Positive
Experiment 8
Qualitative Test
Chromic Acid Test
Baeyers Test
Result
Positive
Positive
Discussion
The two experiments conducted produced chlorocyclohexane and cyclohexene.
Chlorocyclohexane was produced through an SN1 reaction of Cyclohexanol in the presence of
hydrochloric acid and zinc chloride as catalyst while cyclohexene was produced through an
E1 dehydration of Cyclohexanol using phosphoric acid as catalyst respectively.
In the dehydration of cyclohexanol, E1 the reaction proceeds in a distillation set-up
with cyclohexanol in the round bottom flask and cyclohexene in the receiving flask.
Phosphoric acid was added and heat was applied so as to catalyze the rate of reaction in
dehydration without affecting the particular chemical reaction. Since the it was difficult to
reach the desired temperature during distillation (cyclohexanol boiling point range, 80-95 oC)
using a water bath, a direct flame distillation set-up was used after refluxing the roundbottom flask for 30 minutes to increase product yield. A high temperature helps maximize
the yield as it provides more kinetic energy for the reactants to collide. It is important
that the temperature be maintained so as to push the product through the set up and
not hold up in the apparatus. Some of the product will be lost if it is hold up in the
apparatus and thus will reduce the product yield. Due to the long distillation process
due to the holding up of the product it is also possible that low and high boiling
impurities be pushed through the condenser and ended up in the receiving flask.
After the distillation process the receiving flask should contain cyclohexene, water
and small amount of the impurities (i.e. acid carried over). It is important to remove the
impurities by drying it as it can react with cyclohexene and revert back to cyclohexanol.
Based on the results of the qualitative test the cyclohexene product was not pure and
was actually a mixture of both cyclohexene (indicated by a positive Baeyers test) and
cyclohexanol (indicated by a positive chromic acid test). Based on these, the product
needed to be distilled once again but the amount produced was insufficient to have
another distillation.
Cyclohexene can also be synthesized not only dehydration but also through
dehydrohalogenation of alkyl halides. The difference between the two is that
dehydrohalogenation is a base-promoted reaction (i.e. strong bases aid in the
elimination process) while the dehydration of alcohols is an acid-catalyzed reaction. In a
8 grams cyclohexanol
=6.56107 grams=
100.158 grams
1 mole cyclohexanol 1mole cyclohexene
Percent Yield :
3.75 grams
100=57.16
6.56 grams