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SAMONTE, Gianella Bianca C.

22B
October 26, 2016
Experiment No. 7: Preparation of Chlorocyclohexane

Data and Results


HCl
OH

Z n C l2

Cl

Chlorocyclohexane
2.93 g/5.40 g = 54.26%

Cyclohexanol
4.56 g
Qualitative Test
Result

Chromic Acid test

Alcoholic Silver Nitrate Test

(-) , reddish brown

(+) , cloudy white solution

Table 1. Qualitative tests

Figure 1. Chromic Acid Test result (left) and


Alcoholic Silver Nitrate Test (right)
Discussion

ThisexperimentmakesuseoftheSN1reactionwhichreferstonucleophilicreactions
wheretheratedeterminingstepinvolvesonlyonesubstrate,makingitunimolecular.
Therearetwoparts:thelossofaleavinggrouptoformacarbocationandtheattackof
anucleophiletogivethefinalproduct.2.93gofchlorocyclohexanewasyieldedfrom
theexperimentwhichmakesfora54.26%percentyieldatleastmorethanhalf.A
reflux setup was used for this experiment which means that a cause for the low
percentyieldcouldbebecauseofthefactthatasignificantamountofproducthad
escapedasvaporthroughthealuminumfoil.Chromicacidtestandalcoholicsilver
nitratetestwereusedforthisexperimentandbothtestsresultedintheexpectedand
preferredresults:areddishbrownsolutionforchromicacidtestandacloudywhite
solution for alcoholic silver nitrate test. This meant that the product was pure
chlorocyclohexaneandnotracesofcyclohexaneremaininthesolution.Asaresult,

theobjectivesoftheexperimentweremetanditwasproventhattheSN1reaction
mechanismmaybeusedtoformchlorocyclohexanefromcyclohexanol.
Answers to postlab questions
1. A 100% yield is not expected for this experiment because other side reactions may
occur aside from the S N 1 reaction. These side reactions include the reformation of
cyclohexanol and the formation of cyclohexene which may occur when there is
presence of water or when elimination occurs. These may happen via the following
mechanisms:

2.

3.
4.
5.

Aside from this, the solution undergoes three washes in the separatory funnel and so it
is possible that some of the product in the organic layer may have been drained
together with the aqueous layer due to inevitable human error.
The qualitative tests performed for this experiment were chromic acid test and
alcoholic silver nitrate test. The chromic acid test resulted in a reddish brown solution
which confirms for the presence of chlorocyclohexane. On the other hand, the
alcoholic silver nitrate test resulted in a slightly cloudy white solution which indicated
for the absence of cyclohexanol. Based on these results, the product was found to be
pure chlorocyclohexane. Factors that may affect the purity of the product may again
include the presence of water that may have reverted the product back to
cyclohexanol and elimination that may have formed cyclohexene.
Cyclohexanol has a secondary alcohol present and so the qualitative tests that may
give conclusive results for the presence of cyclohexanol would be chromic acid test
and Lucas test.
Sodium sulfate acts as a drying agent and as such absorbs the remaining water that
may cause the final product to be impure due to the stated reasons in the previous
questions.
If bromocylohexane is to be prepared from cyclohexanol, hydrobromic acid is to be
used instead of hydrochloric acid. The hydroxyl group bonds to the zinc chloride and
will then convert to a better leaving group by protonation via hydrobromic acid. A
carbocation is then formed and is attacked by bromide ions instead of chloride ions
which finally results to bromocyclohexane.

Sample calculation
Theoretical yield = Molecular weight of chlorocyclohexane
Molecular weight of cyclohexanol
= 118.60 g/mol
100.16 g/mol

x 4.56g = 5.40 g

Theoretical weight = 5.40 g


Actual weight = 2.93 g
Percent recovery = 2.93 g x 100 = 54.26%
5.40 g
References

x Mass of cyclohexanol

Guidote AM, del Rosario DR, Abuzo AL. 06a E1 and SN1 Reactions. 2005.
Guidote AM, del Rosario DR, Abuzo AL. 07e Preparation of Chlorocyclohexane. 2005.