EXPERIMENT 9

RELATIVE RATES OF ELECTROPHILIC AROMATIC SUBSTITUTION

QUESTIONS:
1. Arrange the compounds used in the experiment in order of increasing
reactivity towards Br2 in CH3COOH. Explain.
2. Do your experimental results agree with the theoretical data? If not, what
are the possible sources of error?
3. Predict the order of reactivity of the following compounds towards
chlorination from the least reactive to the most reactive:
A. Toluene, nitrobenzene, anisole, and methylbenzoate
B. benzene, acetophenone, bromobenzene, and benzyl alcohol
C. styrene, benzaldehyde, aniline, and iodobenzene
4. Explain the effect of solvent in the reaction of acetanilide and Br 2 in Part B.
ANSWERS TO QUESTIONS:
1. The arrangement will be:
nitrophenol < chlorobenzene < benzene < acetanilide< phenol < aniline
because the compound having stronger EDGs (electron-donating groups)
react faster while compounds with EWGs (electron-withdrawing groups) react
slower.
2. The results do not agree with the theoretical data. Some possible sources of
error may include inconsistent proportion of amounts of the reactants in the
test tubes in the experiment.
3. a. methyl benzoate < bromobenzene < benzene < anisole
b. acetophenone < iodobenzene < benzene < benzyl alcohol
c. benzaldehyde < iodobenzene < styrene < aniline
4. Both Bromine and acetanilide are more soluble in the solvent acetic acid than
in cyclohexane because compounds with more similar IMFA tend to have
faster reaction rates as it has a better collision rate between the particles.
Therefore, acetic acid is a better solvent in the reaction of acetanilide and Br 2.