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V.
There are multiple ways to
produce alkyl halides (e.g. through radical
halogenation
of
alkanes,
allylic
bromination of alkenes, using Grignard
reagents, etc.) but the most generally
used method of preparation is to make
them from alcohols (McMurry, 2010). The
general mechanism is as follows, where X
is a halogen (i.e. F, Cl, Br, or I):
VI.
VII.
|
|
VIII.
COH + HX
CX + HOH
IX.
|
|
X.
XI.
The mechanism involves the
substitution of one nucleophile by another
(McMurry, 2011). First, the hydroxyl group
detaches from the alkane (thus leaving
the alkane with a carbocation) and
attacks the hydrogen group of a hydrogen
halide, forming water and a halogen ion.
This nucleophilic halogen ion then attacks
the electrophilic alkane group (by virtue
of its carbocation), forming the alkyl
halide.
XII.
Based on current literature, the
experimenters performed the synthesis of
an alkyl halide from an alcohol in order to
supplement their knowledge of alkyl
XXIX.
XXX. The
mixture
was
left
undisturbed for 20 minutes. Layers
XXXVIII.
XLVIII.
LI.
color
LIV.
solubil
ity
LVII. boiling
point
XLIX. t
ert-butyl
alcohol
LII.
c
olorless
LV.
m
iscible
LVIII. 8
3C
L.
tertbutyl chloride
LIII.
colorles
s
LVI.
slightly
miscible
LIX. 51C
LXI.
The balanced equation
for the reaction is the following:
LXII.
LXIII.
XXXIX. Figure 3. Simple Distillation Apparatus
Nimitz
XL.
The crude tert-butyl chloride
previously decanted inside a flask was
then installed to the distillation set-up.
The water pump was turned on.
XLI. The sample in the flask was
heated to a gentle boil. The temperature
reading on the thermometer rose rapidly
and when the reading remained constant
the boiling point was recorded. The
recorded boiling point was 80C.
XLII. The vapors and condensate
passed through the side arm and into the
condenser (where most of the vapor
condensed into liquid). The experimenters
made sure that when the mixture started
boiling, the heat source was adjusted
accordingly.
The
condensate
then
eventually poured into the receiving flask.
The experimenters watched for drops
disregarding the first five drops.
XLIII. The experimenters determined
the collected fraction by using a Pasteur
pipette. The total number of drops was
then converted into milliliters, garnering a
7.2 mL yield of tert-butyl chloride.
XLIV. The wastes were disposed into
the appropriate waste containers: the
aqueous solutions diluted and poured into
the sink, and the organic compounds
disposed in appropriate organic waste
jars.
XLV.
XLVI. Results and Discussion
XLVII. To complement the results, the
following table (Figure 4) shows a
summary of the properties of tert-butyl
alcohol and tert-butyl chloride:
LXIV.
LXV. This implies that 1 mmol of
(CH3)3COH is equivalent to 1 mmol of
(CH3)3CCl.
In
the
experiment,
ten
milliliters of tert-butyl alcohol was
prepared. This is equivalent to 7.90 g
which is equal to 106.58 mmol, as shown
in the following equation:
LXVI.
10 mL
0.79 g
=7.90 g
mL
LXVII.
mol
1000 mmol
7.9 g
=106.58 mmol
74.12 g
mol
LXVIII.
LXIX. The yield of the tert-butyl
chloride was 7.20 mL. This is equivalent
to 6.05g, and thus 65.36 mmol produced,
as calculated in the following equation:
LXX.
7.20 mL
0.84 g
=6.05 g
mL
LXXI.
LXXII.
6.05 g
mol
1000 mmol
=65.36 mmol
92.57 g
mol
LXXIII.
LXXIV. A summary of the reaction
scheme is shown below (Figure 5), along
with the experimental results:
LXXV.
LXXVI. (CH3)3COH 1)HCl; 2)NaHCO3>
(CH3)3CCl
LXXVII.
LXXVIII.
LXXIX.tert- LXXX. ter
butyl
t-butyl
alcohol
chloride
LXXXI.Mass
LXXXIV.
m
olecular
weight
LXXXVII.
d
ensity
XC.
mmol
XCIII.
LXXXII.
7.90g
LXXXV.
74.12g/mo
l
LXXXVIII.
0.79g/mL
XCI. 106.
58 mmol
LXXXIII.
6.05g
LXXXVI.
92.57g/m
ol
LXXXIX.
0.84g/mL
XCII. 65.
36 mmol
106.58 mmol
mol
92.57 g
=9.87 g
1000 mmol
mol
CIV.
CV.
Another possible reaction is 2methylpropene,
as
shown
in
the
illustration below:
CVI.
XCVI.
XCVII.
The percent yield is
therefore 61.30%, as calculated below:
XCVIII.
6.05 g (obtained)
100=61.30
9.87 g (theoretical)
C.
CI.
CII.
The yield was only 61.30%. It is
possible that this number was caused by
CVII.
CXX.
Clark, J. n.d. Properties of Alkyl
Halides. Retrieved March 7, 2015 from
http://chemwiki.ucdavis.
edu/Organic_Chemistry/Alkyl_Halides/P
roperties_of_Alkyl_Halides.
Licensed
under CC BY-NC-SA 3.0 US.
CXXI.
El-Fellah, M. 2012. Laboratory
Course in Organic Chemistry. Organic
Chemistry Lab I 5332. Accessed March
6,
2015.
http://www.elfellah.com/Organic Chemistry Lab. I
5332.htm.
CXXII.
Hollingworth,
RM.
1976.
Chemistry, biological activity, and uses
of
formamidine
pesticides.
Environmental Health Perspectives.
14, 57-69.
CXXIII.
King, C. n.d. Preparation of TButyl Chloride. Accessed March 6,
2015.
http://christopherking
.name/Organic%20I
%20Labs/Preparation%20of%20t-butyl
chloride.htm.
CXXIV.
McMurry,
JE.
2011.
Fundamentals of Organic Chemistry
7th ed. Brooks-Cole, New York.
CXXV.
McMurry, JE. 2010. Organic
Chemistry 8th ed. Brooks-Cole, New
York.
CXXVI.
Nimitz, JS. 1991. Experiments
in Organic Chemistry. Prentice Hall:
New Jersey.
CXXVII. Rowland,
FS.
2006.
Stratospheric
ozone
depletion.
Philosophical Transactions of the Royal
Society
B:
Biological
Sciences.
361(1469), 769-790.
CXXVIII. Tang, S & Zhao, H. 2014.
Glymes as versatile solvents for
chemical reactions and processes:
From the laboratory to industry. RSC
Advances. 4(22), 11251-87.
CXXIX.
Watrous, RM. 1947 Health
hazards
of
the
pharmaceutical
industry. British Journal of Industrial
Medicine. 4 (2), 111-125.
CXXX.
CXXXI. Appendices
CXXXII. Attached is the data sheet for
this experiment.