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MCAT Question A Day - 4/19/13 - Answer!

The resonance structures of aniline account for the

A.  lower basicity compared with aliphatic amines.
B.  increase in reactivity of the aromatic ring toward electrophilic attack.
C.  increase in negative charge on the ortho and para positions.
D.  All of the above

The correct answer is (D). Resonance structures show how the lone-pair electrons are distributed around the aromatic ring. The increased negative charge on the ortho and para positions accounts for the increased reactivity of the molecule to electrophilic attack as well as the preferred attack at these positions.