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Synthesis of an Alkyl Halide

Frances Abegail G. Quezon and Felipe D. Garcia Jr.


Institute of Chemistry, University of the Philippines, Diliman, Quezon City 1101 Philippines
Date/s Performed: July 12, 2013; Date Submitted: July 19, 2013
Introduction
The aim of the experiment was to
synthesize an alkyl halide and to purify it by
distillation. This experiment made use of the
different boiling points of the starting reagent,
tert-butyl alcohol, and the product, tert-butyl
chloride. A tertiary alcohol was used because
it reacts more readily with HX compounds
compared to other alcohols.[1]
The reaction involved was
OH
Cl
(1)
+ HCl
This reaction is a substitution reaction,
particularly an SN1 reaction.
The yield from distillation was
measured with a graduated cylinder. After
converting the volume of the initial reagent
and the final product to grams using their
corresponding densities, the percent yield was
calculated using the formula below:
tert butylchloride(exp)
% yield
x100
tert butylchloride(theo)
(1)
Experimental Details
In the first part of the experiment, 10
mL tert-butyl alcohol was made to react with
20 mL cold concentrated HCl in a separatory
funnel. Tert-butyl alcohol was used because
tertiary alcohols react more readily with HX
compounds such as HCl, compared to other
alcohols.[1]
The type of reaction was a substitution
reaction, type SN1. This type occurs in less
reactions than the other type, S N2. SN1
reactions occur only in tertiary substrates,
provided that the solvent is hydroxylic, such
as water or alcohol, and the that the reaction
happens under neutral or acidic conditions.[1]

This was the rationale behind the


choice of reagents in this experiment. Also,
SN1 reactions depends on the concentration of
the substrate and not on the nucleophile. The
substrate is tert-butyl alcohol while the
nucleophile is the Cl- ion. Therefore, the
nucleophile should be added in excess since
the substrate was the limiting reagent in the
experiment.
The reaction involved in the
experiment, reaction (1), yielded a volatile
product. The boiling point of this being
50.7C. Because of its nature, tert-butyl
chloride needed to be kept chilled and tightly
covered[2] so HCl should be reacted cold in
order to avoid loss of yield due to premature
volatilization.
After these, the mixture was gently
swirled and the internal pressure was relieved
from time to time to avoid pressure build up. It
was then allowed to stand for 20 minutes to
allow the layers to separate. NaCl or any other
inorganic salt solution may be added to
facilitate layer separation. This technique is
called salting out. It reduces the solubility of
the organic compound in the aqueous layer so
that it preferentially dissolves in the non polar
layer.[3]
After separation, the bottom layer was
released in a receiving flask. This layer was
the aqueous layer, the layer to be discarded.
However, if unsure of which is the aqueous
layer and which is the non polar layer, a few
drops of water may be added. The water is
immiscible in the non polar layer and would
form two layers.

Figure 1. separatory funnel set-up[4]

References
(1) McMurry, J. Fundamentals of
Organic Chemistry, 7th ed; Brooks/Cole: USA,
2011; pp 222-245.
(2) Organic Chemistry Group
Organic Chemistry Laboratory Manual 2008,
34-37.
(3)
Chulalongkorn
University
Department of Chemistry Separation by
Solvent Extraction http://www.chemistry.sc.

chula.ac.th/home.htm (accessed July 15,


2013).
(4) Universtiy of Sydney, School
of Chemistry E28 Extraction of Organic
Compounds http://firstyear.chem.usyd.edu.
au/prelab/e28.shtm (accessed July 15,
2013).

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