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ABSTRACT
This experiment mainly focuses on the electrophilic aromatic substitution reactions and the factors which affect the relative
rates for the said reactions. For the first part of this experiment, reaction of benzene, chlorobenzene, aspirin, acetanilide, pnitrophenol, anisole, and phenol with bromine solution were observed. It shows that the compounds react faster than benzene
are most likely to have an activator substituent, and those that are slower have a deactivator substituent. For the second part
of the experiment, the solvent effect, using cyclohexane and acetic acid as reagents on the bromination of anisole was also
observed. The reaction favors using the more polar solvent was favored. And for the third part, the relative rate of reaction of
acetanilide in ethyl acetate is determined based on varying temperature. By plotting the results, it can be easily observed that
temperature is directly proportional to reactivity.
Keywords: electrophilic aromatic substitution, substituent effect, temperature effect, solvent effect, bromination of aromatic compounds
INTRODUCTION
Aromatic compounds are compounds that contain a
benzene ring, a six-membered ring with conjugated double
and single bonds. These compounds do not undergo
electrophilic addition reactions although they have multiple
double bonds, but undergoes electrophiilic aromatic
substitutions, where electrophilic substitutions replaces a
certain proton on benzene with another elecrtrophile. The
weak reactivity of the compound towards addition reaction
is due to complete pi () electron delocalization or simply
termed as resonance. Such reactions in the electrophilic
aromatic substitution reaction are halogenation, nitration,
sulfonation, Friedel-Crafts alkylation and acylation. For that
substitution, the reaction consists of an electrophile (E+) and
an electron-rich aromatic ring called nucleophile. The
electrophile would then be substituted to one of the H +
attached to the benzene ring.
This experiment was all about the reaction of aromatic
compounds with bromine. In each mechanism, the rate of
formation of electrophilic bromine was first determined.
One of the double bond of the aromatic ring attacked the
electrophilic bromine. A carbocation containing a bromine
substituent then formed. To be stable again, the hydrogen
sharing the carbon bond with bromine was removed.
Electrophiles can also be attacked by substituted aromatic
compounds or with functional groups. However, there is a
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Benzene, chlorobenzene, aspirin, acetanilide, pnitrophenol, anisole and phenol were subsequently reacted
with bromine. Because of the stabilizing property of
aromatic compounds, a catalyst is really needed in order to
complete a bromination reaction. However, the bromination
of aromatic compounds is not accompanied by a catalyst,
FeBr3. Thats why the reaction is not as fast as expected.
The time of reaction for each corresponding aromatic
compounds is tabulated below.
Table 1. Aromatic Compounds Structures
and Their Time of Reaction
Compound
Time of
Structure
Decolorizati
w/
on
classificati
on
Benzene
14 minutes
Chlorobenze
ne
16 minutes
Aspirin
22 minutes
Deactivator
ortho and
para
(-COOH)
Deactivator
meta
Acetanilide
17 minutes
pnitrophenol
15 minutes
(no reaction)
(-NO2)
Deactivator
Meta
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Anisole
15 minutes
Activator ortho and
para
Phenol
4 seconds
Aspirin
Activator ortho and
para
p-nitrophenol
Anisole
Phenol
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Most stable:
Ortho
Para
Meta
50%
50%
0%
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REFERENCES
1. Baluyut John Y. G., De Castro Kathlia A.,
Organic Chemistry Laboratory for Chemical Engineering
Students Part 2, 2004
2. http://ebookhome.org/home/fundamentals-oforganic-chemistry-6th-edition-157410.html
3. Solomon and Fryhle. Organic Chemistry. 8th
Edition. Prentice hall.
4. Klein, David. Organic Chemistry. John Wiley &
Sons, Inc., 111 River Street, Hoboken, NJ.
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