Araniador, Glaicyl Dame Ann B.

17, 2016

Date Performed:

Bronzal, Lucile A.
2016

Date Submitted:

March

March 22,

Mameloco, Neri May G.

EXPERIMENT NO. 9
RELATIVE RATES OF ELECTROPHILIC AROMATIC SUBSTITUTION
I. INTRODUCTION
Electrophilic Aromatic Substitution is an organic reaction in which an electrophile
substitutes a hydrogen in an aromatic compound. Aromaticity is
Benzene rings are very stable, aromatic molecules. Therefore, the electrophile must be
VERY strong in order to disrupt aromaticity.
II. RESULTS AND DISCUSSION
A. Relative rates of Bromination
Test Solutions

0.05 M Br2 in 90% CH3COOH (away from

sunlight for 30 mins)
Ethyl acetate of benzene
Dark yellow
Ethyl acetate of chlorobenzene
Yellow
Ethyl acetate of phenol
Dirty White
Ethyl acetate of nitrophenol
Light Yellow
Ethyl acetate of aniline
Pale Yellow
Ethyl acetate of acetanilide
Peach
The first one that becomes pale yellow is phenol followed by nitrophenol, aniline,
acetanilide, chlorobenzene and ethyl acetate of benzene respectively.
B. Effects of Solvents on Reaction Rates
Reagent
0.05 M Br2 in Cyclohexane

Acetanilide
Orange
Clear
0.05 M Br2 in 90% CH3COOH
Yellow
Clear
Polar protic solvents speed up the rate of the unimolecular substitution reaction
because the large dipole moment of the solvent helps to stabilize the transition state. The
highly positive and highly negative parts interact with the substrate to lower the energy of
the transition state. Since the carbocation is unstable, anything that can stabilize this even
a little will speed up the reaction.
In the experiment, acetic acid is a polar solvent, it only takes 2 seconds of
decolorization or the reaction to happen and produce a yellow solution whereas in
cyclohexane, a nonpolar solvent, it takes 3 seconds to obtain decolorization and produce
an orange solution.
III. CONCLUSION AND RECOMMENDATIONS
Bromine is highly corrosive and causes severe burns. Wear gloves and handle reagents
with care. 90% Acetic Acid is a high concentrated acid, be careful to not allow skin contact. If any
skin contact is made, rinse affected area immediately with running water and soap.

All of the organic aromatic molecules possess toxic properties. Phenol, particularly, is toxic
and may be absorbed by the body through skin. Handle with care and keep away from mouth
and eyes. Report immediately to the instructor if spilled.

IV. REFERENCES/ BIBLIOGRAPHY

(n.d.) Comparative Rates of Electrophilic Aromatic Substitution Reactions. Retrieved March
20, 2016 from http://www.xula.edu/chemistry/documents/orgleclab/EASprocedure
Chem 33.1 Laboratory Manual
Chem 33.1 Course Syllabus