CHM143L Organic Chemistry 2 Laboratory

3rd Quarter SY 2014-2015

Factors Affecting the Relative Rates of Electrophilic Aromatic Substitution Reactions

Tagalog, Christian, Tolentino, Aika Cecille, I. Terrado, Rence, Valencia, Ifame

Prof. Oliver, School of Chemical Engineering, Mapua Institute of Technology; Aika Tolentino, CHM143L/A31, School of Chemical Engineering and Chemistry, Chemical
Engineering, Mapua Institute of Technology

ABSTRACT
The experiment named Melting Point and Boiling Point of Organic Compounds aims to show the
factors that affects the physical properties of Organic Compounds such as the Boiling point and
the Melting point. Certain techniques are used to further help the people who conducts the
experiment to achieve more accurate and prcised results. In this paper contains certain
information on boiling point and melting point and what affects them to change. The methods
done are also used in other fields to determine the boiling point and melting point of the
compound. The group was assigned to determine the range of the boiling point and the melting
point and to compare their work to the true value of the physical property constant. Some ranges
are not in the scope of the true value because of impurities of apparatus and also due to improper
focus on the experiment therefore conducting minimal errors. Brief discussions and explanations
were gathered for more understanding of this experiment.

Keywords: Boiling point, Melting point, Organic Compounds, Intermolecular forces, Impurity, Branching

INTRODUCTION
Electrophilic aromatic substitution is an organic reaction
in which an electrophile replaces an atom attached to an
aromatic system. Some of the most important
electrophilic aromatic substitutions are aromatic nitration,
aromatic halogenation, aromatic sulfonation, and
acylation and alkylating Friedel-Crafts reactions.
However, in this experiment, only aromatic halogenation
was shown. Here, phenol, chlorobenzene, p-nitrophenol,
aspirin, benzene, anisole and acetanilide will undergo
bromination reactions and the products from these
reactions will be isolated, purified and analysed. Here,
the substituted benzenes react differently in depending
on the nature of the substituent attached to the
compound. The substituent could make the ring more
reactive than benzene if it functions as an activator. If not,
it makes the ring less reactive than benzene.
Substituents are also classified according to their
orientations. They are classified as ortho-para if they
function as activators and meta if it functions as
deactivator. Aside from the nature of the substituent,
other factors like temperature and solvent affect the rate
of reactions. The purposes of this experiment are: to
visualise the effect of substituents in the relative rates of
electrophilic aromatic substitution, to know the effect of
solvent on the reaction rates, and to know the effect of
temperature on the rates of reaction.
MATERIALS AND METHODS
A proper attire was strictly followed to minimize the
impact of accidents that might occur during the
experiments. Especially, protective goggles and mask
was worn to avoid injury.
The reagents used for this experiment were 0.2M solution
in ethyl acetate of benzene, chlorobenzene, aspirin,
acetanilide, p-nitrophenol, anisole; a bromine solution; a
0.05 bromine in cyclohexane, and bromine in acetic acid.
As for apparatus, micro test tubes with cork stopper, hot
water bath, dropper, hot plate, test tube rack, and
thermometer were used. These apparatus were cleaned
before performing the experiment to avoid possible
source of error in the process.
For the first part of the experiment, a 0.2M solutions in
ethyl acetate of benzene, chlorobenzene, aspirin,
acetanilide, p-nitrophenol, anisole and phenol are the
organic compounds mix properly. It was occasionally
observed for any evident reaction.
that were tested for any substituent effect. Twenty drops
of each solution was transferred in separated test tubes.

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 CHM143L Organic Chemistry 2 Laboratory
3rd Quarter SY 2014-2015

Then twenty drops of bromine solution was added to COMPOUND REACTIONS INVOLVED
each test tubes. The time of addition was noted and the
time of reaction was recorded. The test tubes were Benzene
shaken to have the solutions to As for the second part of
this experiment which is the solvent effect, 0.2M solutions
in ethyl acetate of anisole was tested. A twenty drops of Chlorobenzene
anisole solution was transferred in a test tube and a 20
drops of freshly prepared 0.05M bromine in cyclohexane Aspirin
was added to it. Then on another test tube, 20 drops of
Acetanilide
anisole solution and 20 drops of bromine in acetic acid
was transferred on the test tube. The reactivity of the P-nitrophenol
anisole solution in two solvents were compared.
Anisole
Phenol
Lastly, as for the third part of this experiment which is the
temperature effect, a 0.2M acetanilide in ethyl acetate
was tested. A 20 drops of 0.2M acetanilide in ethyl II. Solvent Effect
acetate was transferred in three different test tubes and
another 20 drops of bromine in acetic acid was added to Table 2.1. (Time of Decolorization of Solvent Effect)
it each test tubes. The test tubes were heated in 50C,
COMPOUND TIME OF REMARKS
70C and 90C respectively in water bath prepared by
preheating a 400mL beaker containing 300mL of water. DECOLORIZATION
The time of decolorization was observed. Anisole + 23 minutes ( turned Cloudy upon
Bromine in pale yellow) addition of
RESULTS and DISCUSSIONS cyclohexane 30 minutes (turned cyclohexane
clear)
I. Substituent Effect
Anisole + 55 minutes Slower reaction
Table 1.1 (Time of Decolorization of Substituent Effect) Bromine in
acetic acid
COMPOUND TIME OF REMARKS
DECOLORIZATION
III. Temperature Effect
Benzene Dark red
Table 3.1. (Time of Decolorization of Solvent Effect)
Chlorobenzene Dark red
Aspirin 17 minutes Dark red (but COMPOUND TIME OF REMARKS
lighter than DECOLORIZATION
benzene and 90C 52 seconds Turned pale
chlorobenzene) yellow
Acetanilide 1 second orange 70C 71 seconds Turned pale
P-nitrophenol 3 minutes Dark orange yellow

Anisole 8 minutes Light orange 50C 90 seconds Turned pale

yellow
Phenol 19 minutes orange
Graph 1.1 (Temperature Effect)
Table 1.2 (Reaction involved)

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 CHM143L Organic Chemistry 2 Laboratory
3rd Quarter SY 2014-2015

CONCLUSIONS AND RECOMMENDATIONS

REFERENCES

1. Klein, D. (2012) Organic Chemistry. John Wiley

&Sons, Inc. NY, America.

2. Cruz, K. and Miranda M. Oragnic Laboratory

Manual,

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