Beruflich Dokumente
Kultur Dokumente
chloride
Traya, Levie Grace M.
INTRODUCTION
Alkyl halides can be synthesized
when alcohols react with hydrogen
halides. An alkyl halide is a
hydrogen-substituted alkane, and a
hydrogen halide is a compound
consisting of hydrogen bonded to a
halogen. Alkyl halides are classified
as primary, secondary and tertiary
depending on the number of alkyl
substituents directly attached to
the carbon bearing the halogen
atom. The mechanism of acid
catalyzed substitution of alcohols
are termed SN1 and SN2, where S
stands
for
substitution
while
sub-N
stands for nucleophilic,
and the numbers 1 and 2 describes
the
first
and
second
order
respectively. The 1 and 2 also
represents whether the reaction is
unimolecular
or
bimolecular
reaction. The secondary alcohols
favor the react with hydrogen
halides by SN1 and SN2 mechanism.
For primary or methyl alcohol, both
molecules undergo SN2 mechanism
while tertiary alcohols undergo SN1
mechanism.
In SN1 reaction, the protonated
alcohol, or oxonium ion losses
water molecule and forms a
oxonium
ion
via
bimolecular
transition rate. The SN2 process is
expected to be especially slow and
is not observed in tertiary alcohols
due to the transition state being
crowded
as
the
degree
of
substitution decreases at the
reating
center,
SN2
reaction
becomes
dominant
over
SN1
reaction.
The
main
purpose
of
this
experiment is to prepare n-butyl
bromide from n-butyl alcohol via
SN2 and t-butyl chloride from tbutyl alcohol via SN1 reaction. Also
this experiment aims to understand
the SN1 and SN2 mechanism
involved in the reaction and to
determine the yielded percentage
of the experiment.
METHODOLOGY
anhydrous
calcium
chloride.
Stopper the flask and swirl the
contents until the liquid is clear.
Decant the clear liquid into a
drying distilling flask. Add boiling
stones and distill the crude n-butyl
bromide in a dry apparatus. Collect
the material that boils between 98
calculate
the
DISSCUSSION
Synthesis of t-butyl chloride
In
this
experiment,
n-butyl
alcohol, a primary alkyl halide, is
prepared by reacting the alkyl
halide with sodium bromide and
sulfuric acid. From the chemical
reaction presented below, the
reaction produces hydrogen halides
during the reflux when sodium
bromide reacted with sulfuric acid.
2 NaBr + H2SO4
Na2SO4
2 HBr +
Figure 2
solution.
The
drying
agent
anhydrous calcium chloride is
added in order to absorb water
droplets in and to purify the
organic layer. To ensure that all
water droplets are eliminated, an
excess anhydrous calcium chloride
should be added because if there is
any water droplets that remains in
the materials collected, it would
interfere with the analysis. After
the drying agent is filtered out, the
boiling stones are added to prevent
over boiling during distillation. The
distillation is done to purify the nbutyl bromide in the temperature
range of 98 and 102 .
Synthesis of n-butyl chloride
In this experiment, t-butyl alcohol
is converted to t-butyl chloride. In
order to synthesize t-butyl chloride
from t-butyl alcohol, hydrochloric
acid is used to react with t-butyl
alcohol. During the reaction, t-butyl
alcohol will undergo SN1 reaction.
The SN1 reaction is where the rate
of formation of t-butyl chloride is
dependent
only
on
the
concentration of the alcohol and is
independent to the amount of acid
used. A strong concentrated HCl is
added to t-butyl alcohol to provide
an acidic medium and to protonate
the electron rich hydroxyl group
allowing it to leave as a molecule
of H2O.