AROMATIC DISTRIBUTION

IN
BENZENE

DEPARTMENT OF CHEMISTRY
CAPITOL HILL COLLEGE
During the electrophilic substitution reaction of
monosubstituted benzene, the group already
present in the benzene ring decides the position of
new incoming group. This effect is called as
directive effect and the group already present in
the ring is known as directing groups. Directing
groups are of two types:
 Ortho and para directing groups
 Meta directing groups
1. Ortho and para directing group
 Either Single atom or group of atoms in which
central atom is bonded to other atoms by
single covalent bond
Increases the electron density around ortho
and para position, thereby directing the
incoming electrophile towards o/p position.
Eg: -OH, -Cl, -NH2 , alkyl groups( -CH3, -CH2CH3)
etc.
For example: The nitration of
chlorobenzene gives ortho and
para substituted chlorobenzene.
 From the resonance structure, it can be clearly seen
that in case of compounds having o/p- directors, the
electron density is relatively higher at ortho and para
position than at meta position. So electrophile prefers
to attack at o/p- position rather than m- position. For
example, -NH2 group acts as o/p- directing group as:
2. Meta directing group
 group of atoms in which central atom is
bonded with more electronegative atom by
multiple bonds
 decreases the electron density around ortho
and para position, thereby directing the
incoming group towards meta position.
 From the resonance structure, it can be clearly
seen that in case of compounds having meta-
directors, the electron density is relatively lower
at ortho and para position than at meta
position. So electrophile prefers to attack at
meta- position rather than ortho and para
position. For example, -NO2 group acts as meta-
directing group as:
Assignments:
1. Why –OH group is known as ortho/para
directing group? Explain with resonance
structure.
2. Why –COOH group acts as meta directing
group? Explain with the resonance structure.

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