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BS Chemistry 4
6 September 2014
ELIMINATION
(27 August 2014)
I.
INTRODUCTION
For many alcohols, exchange of the hydroxyl group with solvent competes
with dehydration. This exchange indicates that the carbocation can undergo S N1
capture in competition with elimination. Under conditions where proton removal
is rate-determining, it would be expected that significant isotope effect would be
seen. This is, in fact, observed.
In connection to the facts stated this experiment aims to understand the
concept of elimination and synthesize an alkene from an alcohol and test it using
potassium permanganate test and bromine test.
II.
METHODOLOGY
6 September 2014
A. Materials
Tert-butyl alcohol
Conc. H2SO4
CaCl2
Acetone
1% Aqueous
KMnO4
Carbon
tetrachloride
2% bromine
250-mL round-bottomed
flask
Pipet
Aspirator
Thermometer
Reflux condenser (Relfux
set-up)
Iron stand
Thermometer holder
Alcohol lamp
Separatory funnel
Glass dropper
Wire gauze
Iron ring
B. Procedure
In a 250-mL round-bottomed flask, a 14-mL of water and conc. H 2SO4
was added. The acid was then cooled to about 50
and a 12.6-mL of
t-butyl alcohol was slowly added to the solution. The solution was then
subjected to reflux where it was ensured that no steam should be produce
or there will be lesser percentage yield.
The solution was then cooled at room temperature and then
transferred to a separatory funnel where the aqueous acid layer was
carefully drawn. The hydrocarbon layer was then washed with water in
order to remove traces of acid.
Due to limited resources, the experiment was cut to this part and the
hydrocarbon was then immediately subjected to the potassium
permanganate test and bromine test to check for the presence of alkene.
Potassium permanganate test was done by adding 3 drops of the
alkene solution in a 1-mL acetone and with vigorous shaking the 1%
Aqueous KMnO4 was added. The test would be positive if within 1 minute
the purple color will fade and there will be a formation of insoluble brown
hydrated oxides of manganese.
Bromine test was carried out in a hood. It was done by adding 3 drops
of the alkene solution to a 1-mL bromide in carbon tetrachloride. The test
would be positive if there will be a loss in the brown color of the solution.
6 September 2014
IV.
6 September 2014
is a better leaving group. The leaving group then cleaves out producing the
carbocation where it was attacked by the base. The base removes a beta-proton,
leaving behind its bonding electrons to form the new double bond.
Due to shortage of reagents the procedure was cut after the hydrocarbon was
isolated. The hydrocarbon was subjected to two confirmatory tests namely
potassium permanganate test and bromine test.
For bromide test, the brown solution became colorless which indicates a
positive test affirming the presence of alkene. The Bromine test for the alkene
crude product was positive because bromine is electron deficient and alkenes
have pi electrons forming a double bond that are open for attack. The reaction is:
(4)
Due to their C=C double bonds which can be broken, alkenes react readily
with bromine to produce saturated dibromoalkanes. In the presence of Br 2 or BrBr (which is red/brown), the Br-Br bond attacks the double bond forming C-Br
new bonds. Thus the red/brown color disappears.
In the potassium test, the violet solution turned into a brown insoluble
solution. Below is the reaction equation of the said test: (5)
V.
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Just as there were two mechanisms for nucleophilic substitution, there are
two elimination mechanisms. For this experiment, it followed the E1 mechanism.
The E1 mechanism is nearly identical to the SN1 mechanism, differing only in the
course of reaction taken by the carbocation intermediate.
VI.
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REFERENCES
Books:
Bruice, Paula Y. Organic Chemistry. 4th ed. Pearson Prentice Hall. 2004
Boyd, R. N. & Morrison, R.T. Organic Chemistry. 6th Ed. Prentice Hall.
1992
Carey, Francis A. Organic Chemistry. 4th ed. McGraw-Hill. 2000
Chang, Reymond. Chemistry. 10th ed. McGraw-Hill. 2010
McMury, John.Organic. Chemistry.8th ed. Brooks/Cole, Cengage Learning.
2012
Web:
E1 Reaction. ChemWiki. Retrieved on 3 August 2014, from
http://chemwiki.ucdavis.edu/Organic_Chemistry/Reactions/E1_Reaction
Elimination reactios. CHIME. Retrieved on 4 September 2014, from
http://www.mhhe.com/physsci/chemistry/carey/student/olc/graphics/carey0
4oc/ref/ch05eliminationreactions.html
EXPLAINING THE ELIMINATION REACTIONS PRODUCING ALKENES FROM
SIMPLE HALOGENOALKANES. ChemGuide. Retrieved on 4 September 2014,
from http://www.chemguide.co.uk/mechanisms/elim/elimtt.html
Introduction to Elimination Reactions. Master Organic Chemistry. Retrieved
on 3 September 2014, from
http://www.masterorganicchemistry.com/2011/10/10/introduction-toelimination-reactions/