Download Aromatic Substitution Orientation

Orientation in Electrophilic Aromatic Substitution
Ortho, para directors
O
CH3
O
CH3
O
CH3
O
CH3
O
CH3
Br+
H Br
H Br
O
H Br
Br
CH3
H Br
O
CH3
O
CH3
O
CH3
O
CH3
O
CH3
Br+
H
Br
H
Br
H
Br
Br
Ortho, para directing groups:
R
–NH 2, –NHR, –NR2
H
N
C O
Alcohols, ethers
Esters
Amines
Amides
R
Phenyl rings (aromatic compounds)
–CH3, –CH2CH3, –R
Alkyl groups
–F, –Cl, –Br, –I
Halides
Activating
–OH, –OCH3, –OR
O
C O
Orientation in Electrophilic Aromatic Substitution
Meta directors
O-
O
O-
O
O-
O
O-
O
O-
O
N+
N+
N+
N+
H Br
H Br
H Br
Br
N+
Br+
O-
O
N
O-
O
+
N
O-
O
+
N
+
O-
O
N
+
O
N
+
O-
Br+
H
Br
H
Br
H
Br
Br
Meta directing groups
O
N+
Nitro group, sulfonic acid
S
O
OH
O
O
C
C
OR
O
NH2
Aldehyde, ketone
C
H
CH3
CH 3
Carboxylic acid, ester, and amide
C
C
OH
O
N+
O
O
R
Quaternary ammonium
CH3
Deactivating
O-
Ortho, para director, activator:
H
Br +
Benzene
Meta
H
Br +
CH3
H
Br +
Ortho and
Para
CH3
CH3
E
42
2.5
58
Reaction Coordinate
Ortho, para director, deactivator:
H
Br +
Meta
Ortho and Para
Benzene
Cl
H
Br +
Cl
H
Br +
Cl
E
0.029
0.0009
0.137
Reaction Coordinate
Meta director, deactivator:
Ortho and Para
Meta
Benzene
E
H
Br +
H
Br +
H
Br +
CF3
CF3
CF3
0.00000 45
0.0000670
0.00000 45
Reaction Coordinate