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Jiara Laine Montano

25 & 27 October 2016

Chem 26AA

03 November 2016
Experiment no. 7: Preparation of Chlorocyclohexane
Experiment no. 8: Dehydration of Cyclohexanol

Data and Results


Product
Chlorocyclohexane
Cyclohexene

Weight
2.54 grams
3.75 grams

Theoretical Yield
5.70 grams
6.56 grams

Percent Yield
44.60%
57.16%

Table 1. Weights of products from the Sn1 and E1 reactions

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

Table 2. Qualitative Test Results

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

dehydrohalogenation reaction, the strong base removes a slightly acidic hydrogen


proton from the alkyl halide. This leaves the electrons from the cleaved bond to move
towards the carbocation wherein a halogen is attached. When these electrons approach
the adjacent carbon the halogen breaks free, allowing these two carbons two form a
double bond. In an alcohol dehydration reaction, the acid protonates the alcohol for the
hydroxyl ion to dissociate and thus produce a carbocation. The carbocation will then be
deprotonated and will form a double bond thus producing an alkene.
In the preparation of cyclohexanol, the SN1 reaction of cyclohexanol in the presence
of hydrochloric acid and zinc chloride proceeds in a reflux so as to increase the yield. After
the reflux reaction, two layers were formed from the initial peach solution in the round
bottom flask. The upper layer was clear dull orange while the bottom layer was a cloudy
white aqueous layer. The organic layer (i.e. the orange layer) was washed with distilled water,
sodium bisulfite to neutralize excess zinc chloride in a redox reaction (ZnCl 2 is an oxidizing
agent, NaHSO3 is a reducing agent) and sodium sulfate to any presence of the aqueous
layer with traces of HCl and ZnCl2 that might constitute as an impurity. If the product
was distilled without drying drops of the aqueous layer and water will be present in the
receiving flask as they have boiling points below that of chlorocyclohexane.
Based on the qualitative tests done the product was relatively pure as the
presence of chlorocyclohexane was confirmed (positive alcoholic silver nitrate test) while
the absence of cyclohexanol was verified (negative chromic acid test). These tests were
utilized as the alcoholic silver nitrate test confirms for the presence of a halogen through
the formation of a precipitate (a white precipitate was observed in the test) while the
chromic acid test detects the presence of a secondary or primary alcohol. The Lucas
Test which detects the presence of a tertiary alcohol was not used as cyclohexanol is a
secondary alcohol. A secondary alcohol will not react with the Lucas reagent. Thus it
will not be able to ascertain the presence of cyclohexanol.
If this experiment aimed to synthesize bromocyclohexane instead of
chlorocyclohexane, HBr and KBr would have been used instead of HCl and ZnCl 2. This
is so that a bromide ion will act as a nucleophile and substitute the alcoholic hydroxyl
group instead of a chloride ion.
In both experiments, the purity of the substance may not only be affected by the
kind of reaction but also from contaminated glass wares and spatula, chemical quality
(e.g. it may have been contaminated by another spatula) and low or high boiling
impurities in the reagents. Also both experiments are not expected to have a 100 percent
yield because of the incomplete transfer of liquids. The organic layer may leave residue
in the round bottom and receiving flasks, separatory funnel and other glass wares
causing product loss. Furthermore, during distillation we do not allow the round bottom
flask to be boiled to dryness and that also reduces the yield.
Conclusion
The objectives of these two experiments were to synthesize chlorocyclohexane and
cyclohexene and ascertain their presence through qualitative tests. These experiments also
allowed one to directly observe SN1 and E1 reactions.
Based on the data and results of the experiment, the objects were successfully
accomplished with a percent yield of 45% for chlorocyclohexane and 57.16% for
cyclohexene albeit an impure cyclohexene product due to the presence of cyclohexanol.

To improve the results of the experiment it is suggested that distillation be done to


ensure the purity of the products and standardized movements to be more time efficient and
avoid spillages.
References
G., D., & A. (2014). Extraction RCS [PDF]. Department of Chemistry, Ateneo de Manila
University.
"Organic Chemistry Reactions: Speed Study Guides." Google Books. Speedy Publishing
LLC, 3 Sept. 2014. Web. 29 Sept. 2016.
Appendix
*All this data was computed assuming 100 percent purity
Theoretical Yield :

8 grams cyclohexanol

1 mole cyclohexanol 1 mole cyclohexene


82.143 grams

=6.56107 grams=
100.158 grams
1 mole cyclohexanol 1mole cyclohexene

Percent Yield :
3.75 grams
100=57.16
6.56 grams