GRE Subject Test: Chemistry : Electrophilic Substitution
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Example Questions
Example Question #1 : Reaction Mechanisms
Of the aromatic compounds shown above, which would be meta-directing groups for subsequent electrophilic aromatic substitution reactions?
Nitrobenzene and anisole
Anisole
Bromobenzene
Nitrobenzene
Nitrobenzene
Only nitrobenzene would be a meta-directing group for additional electrophilic aromatic substitution (EAS) reactions. Although the bromine of bromobenzene is an electron-withdrawing group, halogens are not meta-directors; therefore, additional EAS reactions with bromobenzene would result in ortho or para attached substituents.
Remember that ortho additions are adjacent to the first substituent, meta additions are two carbons displaced from the first substituent, and para additions are opposite the first substituent.
(Note that these reactions would take place much more slowly than if there was an electron-donating group attached).
Example Question #1774 : Mcat Biological Sciences
Which of the aromatic compounds (shown above) would undergo electrophilic aromatic substitution most quickly?
Nitrobenzene
Anisole
Bromobenzene
Acetophenone
Anisole
Electrophilic aromatic substitution occurs most rapidly when the aromatic compound has electron-donating groups attached. Due to their electron affinity, halogens are electron-withdrawing groups. Acetophenone and nitrobenzene both bear partial positive charges on the substituent directly attached to the benzene ring, which pulls electron density out of the ring as well, causing the reaction not to occur.
Anisole is the only compound with an electron-donating group, and is the correct answer. The lone pairs on the oxygen atom can be used to initiate new bonds.
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