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Chell Ataiza 2C

April 20, 2017


SN1 Reaction: Preparation of Cyclohexyl Chloride

Chemical Equation:

4.80g 2.83g
% yield = 49.8%

Qualitative Test Results


Qualitative Test Observations Positive/Negative?
Alcoholic Silver Nitrate Test White-grey precipitate Positive
Baeyer Test No precipitate Negative
Chromic Acid Test No precipitate Negative

Data and Results


Physical and Chemical Properties
Mass Physical Appearance
Cyclohexanol 4.80g Colorless, clear (not cloudy)
Cyclohexyl Chloride/ 2.83g Light yellow in color, clear (not cloudy), thick
Chlorocyclohexane consistency/viscous

Discussion
The preparation of cyclohexyl chloride (chlorocyclohexane) from cyclohexanol is an S N1
reaction, in other words, it is a unimolecular nucleophilic substitution reaction. ZnCl2 (Zinc
Chloride) together with HCl is added to complex the OH substituent of the reactant, making
it a better leaving group. Cl-, being a weak conjugate base to the strong acid HCl that was
added, attaches itself to the carbocation instead of abstracting a proton (not strong enough).
The resulting product is a haloalkane, which in this experiment is cyclohexyl
chloride/chlorocyclohexane.
To be able to maximize the interaction of the reactants molecules with each other as well
as to maximize the experiments yield, a reflux set up was used to execute the procedure. The
reaction is accelerated by heating the set-up, thus producing more chlorocyclohexane in a
shorter period of time.
The qualitative test that were performed to verify the presence of the wanted product
(Chlorocyclohexane, a haloalkane) was an Alcoholic Silver Nitrate test. Insoluble silver
halides (precipitates) were formed because the confirmed haloalkane (Chlorocyclohexane)
reacted with the silver nitrate in ethanol through an SN1 mechanism:
-
A gN O 3
O
+
R X R O N + AgX
O
Post Lab Questions
Would you expect a 100% yield in the experiment? Explain.
For this experiment, a 100% yield is not expected due to technical reasons. The reflux
set-up used was not an enclosed set-up, thus the escape of some product due to overheating
(higher temperature = a different reactant is evaporated) cannot be completely avoided. A
perfect yield also cannot be expected due to the possibility of other side reactions occurring,
such as the reformation of cyclohexanol or the formation of cyclohexene (through a
competing E1 reaction).

What is the purity of the product based on the results of the qualitative tests? What factors
may affect the purity of the product obtained in the experiment?
Based on the results of the qualitative tests, the experimenters product produced has
the desired identity (Chlorocyclohexane) since it showed positive results for the Alcoholic
silver nitrate test. The said product is said to be pure since it indicated negative results for the
other qualitative tests that tests for the presence of alcohol (Chromic Acid test) and alkenes
(Baeyer test). The factors that may affect the purity of the product in the experiment is the
reformation of cyclohexanol and the formation of cyclohexene (through a competing E1
reaction).

Which among the tests for alcohols would give a conclusive result to attest the
presence/absence of cyclohexanol in the product? Explain. Why cant the other tests be used?
The qualitative test used to attest or verify the presence/absence of cyclohexanol is the
Chromic Acid test since cyclohexanol is known to be a primary alcohol. A primary alcohol is
an alcohol with a hydroxyl group connected to a primary carbon atom. A secondary alcohol is
an alcohol with a hydroxyl group connected to a carbon atom that is joined directly to two
other alkyl groups with other carbon atoms. Lastly, a tertiary alcohol is an alcohol with a
hydroxyl group connected to a carbon atom that is joined directly to three other alkyl groups
with other carbon atoms.
The other qualitative tests testing for alcohol (Iron III Chloride test for vinylic
alcohols and Lucas test for tertiary and secondary alcohols) cannot be used to verify the
presence of cyclohexanol because they do not test for the presence of primary alcohols.

What would you expect to find on the receiving flask if the organic layer were distilled
without drying it over sodium sulfate? Explain.
If the organic layer was not dried over sodium sulfate, then the by-products and
unreacted reagents would still be present in the layer. Once this particular layer is distilled,
then the reagent/reactant with the lowest boiling point would be transferred to the receiving
flask.

What changes on the experiment would you make if you want to prepare bromocyclohexane
instead? Explain.
To be able to prepare bromocyclohexane instead of chlorocyclehexane, HCl must be
substituted with Hydrobromic acid (HBr). The same mechanisms will still take place, HBr
will be added to complex the OH substituent of the reactant, making it a better leaving
group. Br, being a weak conjugate base to the strong acid HBr that was added, attaches itself
to the carbocation instead of abstracting a proton.

Sample Calculations
Percent Recovery (%) = actual yield of chlorocyclohexane/theoretical yield of chlorocyclohexane
= (2.83g /5.68401126g) x 100
= 49.7887824% or 49.8%
Computing for Theoretical yield:
Theoretical grams of benzyl acetate = grams of cyclohexanol used x (molecular weight of
chlorocyclohexane / molecular weight of cyclohexanol)
= 4.80g x (118.604g/mol / 100.158/mol)
= 5.68401126g or 5.68g

References
(1) Introducing Alcohols [Internet]. Synthesizing an ester from an alcohol and acyl chloride
[Internet]. [Place unknown] [Publisher unknown]; [Date unknown] [cited 2017 April 19].
Available from: http://www.chemguide.co.uk/organicprops/alcohols/background.html
(2) Guidote AM, del Rosario DR, Abuzo AL. Experiencing Organic Chemistry. Quezon City:
Office of Research and Publications, Ateneo de Manila University; 2005.
Chell Ataiza 2C
April 20, 2017
Fischer Esterification: Synthesis of Benzyl Acetate

Chemical Equation:
O
OH
O
+ O
OH H 2S O 4

4.52g 5.48g 1.92g


%yield = 30.59%

Qualitative Test Results


Qualitative Test Observations Positive/Negative?
Hydroxamic Acid Test Violet solution Positive
Chromic Acid Test No precipitate Negative

Data and Results


Physical and Chemical Properties
Mass Physical Appearance
Benzyl Alcohol 4.52g Colorless, clear (not cloudy)
Acetic Acid 5.48g Colorless, clear (not cloudy)
Benzyl Acetate 1.92g Light yellow in color, clear (not cloudy)
(product)

Discussion
The preparation of benzyl acetate is an acid-catalyzed condensation of a carboxylic
acid and an alcohol, called Fischer Esterification.

Post Lab Questions


Would you expect a 100% yield in the experiment? Explain.
A 100% yield cannot be expect from this experiment because being an equilibrium
reaction, the products may revert back to their initial reactants in the presence of water. In
addition to this, some of the organic layer may have been left in the aqueous layer for every
washing of the liquid-liquid extraction. Furthermore, some of the organic layer may have
been left in the initial container after decantation.

What is the purity of the product based on the results of the qualitative tests? What factors
may affect the purity of the product obtained in the experiment?
Based on the results of the qualitative tests, the product purely contains Benzyl
Acetate and does not contain the initial reactant. A Hydroxamic Acid test was performed to
verify the presence of an ester (Benzyl Acetate), while the Chromic Acid test was performed
to verify the presence/absence of a primary/secondary alcohol (Benzyl alcohol). The
Hydroxamic Acid test yielded positive results (formation of violet solution) thus confirming
the presence of Benzyl Acetate, the negative results were yielded from the Chromic Acid test
(no precipirate was formed) thus signifying the absence of an alcohol.
A factor that may affect the purity of the product in this experiment may be due to
erroneous washing in the separatory funnel. Since the different reagents used to wash the
organic layer differed in how their molecules interacted with the molecules of the organic
layer, the densities of the layers begin to change, and their order of appearance was changed.
Although the organic layer was made to settle at the bottom of the separatory funnel before
draining, it cannot be assured that all of the organic layer was completely separated due to the
mixing of the products. Some organic particles may still be present in the aqueous layer. The
same can be said regarding the presence of aqueous particles. Some aqueous particles may be
present in the organic layer. An error may also occur if the experimenters cannot identify
which of the present layers in the separatory funnel is the organic layer. They may collect the
impure aqueous layer instead.
Improper drying using sodium sulfate can also cause impurities in the product. If the
benzyl acetate was not properly separated from water, the reaction will reverse and benzyl
alcohol will reform.

Why is benzyl acetate extracted first using liquid-liquid extraction prior to distillation and
not the other way around? What would you expect in the receiving flask if the reaction
mixture is distilled immediately after the reaction?
In this experiment, if distillation was performed before the liquid-liquid extraction,
separation of compounds in the solution would be unsuccessful. The receiving flask of the
distillation set-up would contain the original contents of the organic layer instead of
separating benzyl acetate because benzyl acetate has the highest boiling point (210oC) among
all the compounds in the solution. This means that benzyl acetate would be the last to leave
the RBF.

What other derivatives of acetic acid readily reacts with benzyl alcohol to form benzyl
acetate? Why arent these synthetic routes used in the synthesis of benzyl acetate and Fischer
esterification is used instead?
Carboxylic acid derivatives such as acid anhydride and acid chloride readily reacts
with benzyl alcohol to form benzyl acetate. This is because the rate of the reaction depends
on the nucleophiles ability to attack the acyl carbon. This ability (or rate of attack) increases
when the said acyl carbon is more positive. Acid anhydride and acid chloride readily reacts
with benzyl alcohol because their acyl carbons are more positive due to their electronegative
substituents. Despite their fast rate of reactivity, acid anhydrides are not used for the synthesis
of benzyl acetate because it is more expensive than acetic acid and acid chlorides arent used
because it is moisture sensitive and when it reacts with water, it will convert to other acids
which are not responsive to esterification.

Sample Calculations
Percent Recovery (%) = actual yield of benzyl acetate/ theoretical yield of benzyl acetate
= (1.92g / 6.27717403g) x 100
= 30.5870124% or 30.59%
Computing for Theoretical yield:
Theoretical grams of benzyl acetate = grams of benzyl alcohol used x (molecular weight of
benzyl acetate / molecular weight of benzyl alcohol)
= 4.52g x (150.18g/mol / 108.14g/mol)
= 6.27717403g or 6.28g
References
(1) Synthesizing an ester from an alcohol and acyl chloride [Internet] [Place unknown]
[Publisher unknown]; [date unknown] [cited 2017 April 19]. Available from:
http://www.researchgate.net/post/Synthesizing_an_ester_from_an_alcohol_and_acyl_chlorid
e-what_solvent_to_use
(2) Guidote AM, del Rosario DR, Abuzo AL. Experiencing Organic Chemistry. Quezon City:
Office of Research and Publications, Ateneo de Manila University; 2005.