Académique Documents
Professionnel Documents
Culture Documents
Abstract
Alkyl halides consist of an alkyl group linked to a halogen atom (X) by a single bond. It can
be prepared by reacting it with a hydrohalogen (HX). In this experiment, tert-butyl chloride was
synthesized through the reaction of tert-butyl alcohol and concentrated hydrochloric acid
following SN1 mechanism. It was then separated from its aqueous solution using a separatory
funnel given the knowledge that is insoluble in water. A simple distillation set-up was equipped to
purify the obtained compound. The experiment was successfully able to synthesize an alkyl
halide as the end product tert-butylchloride obtained was found to be colorless, having a boiling
point of 51 C, which agrees with the theoretical boiling point of tert-butyl chloride. However, due
to some errors, only 5.26 grams of the product was obtained, giving a percent yield of 53.93 %,
suggesting a more careful execution of the procedures.
I. Introduction
Alkyl halides, also called haloalkanes,
simply have a halogen atom bonded to one
of the sp3 hybrid carbon atoms of an alkyl
group. The halogen is more electronegative
than carbon, and the C X bond is polarized
with a partial positive charge on carbon and
a partial negative charge on the halogen. A
generic formula of R-X where X = fluorine,
chlorine, bromine or iodine would be suitable
for these compounds. These are classified
according to the nature of the carbon atom
bonded to the halogen. If the halogen
bearing carbon is bonded to one carbon, it is
called primary halide (1). If there are two
carbons bonded to the halogen-bearing
solid
NaHCO3
and
then swirled. This was decanted into another
dry flask. The collected filtrate was dried
using a small amount of anhydrous CaCl2. A
small amount of anhydrous CaCl 2 is still
added until it clumped together.
II. Methodology
Figure
2a.
Draining the
Lower
Layer
[8]
and
Venting
on
the
[4]
.
I.
Figure
4.
Reaction[4].
Nucleophilic
Substitution
II.
III.
5.26 g
92.57 g/mol
0.84 g/cm3
105.36 g
Color
clear/ colorless
Solubility in water
insoluble
Boiling point
51 C
Table 3. Summary of Experimental Results
Mass
of
tert-butyl 7.809 g
alcohol
Mass
of
tert-butyl 5.26 g
chloride
Theoretical yield
9.75 g
Percent yield
53.93 %
Boiling point
51 C
By the end of the experiment, the desired
product was gathered and it was found that
it has a percent yield of 53.93 % and a
boiling point of 51 C, which is almost similar
with its theoretical boiling point.
IV. Conclusion
With a percent recovery of 53.93 %
and with a boiling point of 51 C, the
experiment is reckoned a success as it was
able to obtain the desired product tert-butyl
chloride via SN1 reaction of tert-butyl alcohol
and concentrated hydrochloric acid.
Improvement in the experimental
procedures such as carefully separating the
layers may help to increase the yield of the
desired product because it is possible that
some amount of the organic layer were
discarded together with the aqueous layer.
This experiments errors could be further
minimized by ensuring the completeness of
the distillation process because it is also
possible that not all of the sample compound
was converted to tert-butyl chloride.
All in all, it is always best to follow the
experimental procedures with caution to
improve the results.
V. References:
=(weight
of
vial+tert-butyl
chloride)-weight of vial
=27.52 g 22.26g
= 5.26 g
Millimole of tert-butyl chloride
The equation (CH3)3COH + HCl
(CH3)3CCl + H20 gives us a 1:1 ratio:
=
0.7809
1 mol
1000 mmol
g
10 ml
ml
105.36
mmol
1000 mmol
1 mol
)
1 mol
7.809 g (
)
74.12 g
alcohol
)
92.57 g
)
1mol
tert-butyl