Downloaded from jeemain.

guru
AROMATIC COMPOUNDS Page # 3

AROMATIC COMPOUND

some important aromatic compounds with their common names.

Formula Name Formula Name

CH 3 CHO
Toluene Benzaldehyde
(bp 111 ºC) (bp 178 ºC)

OH COOH
Phenol Benzoic acid
(mp 43 ºC) (mp 122 ºC)

NH 2 CN
Aniline Benzonitrile
(bp 184 ºC) (bp 191 ºC)

O
CH3
C Acetophenone Ortho-xylene
CH3 (mp 21 ºC) (bp 144 ºC)
CH3
IUPAC Name of Substituted phenol and benzoic acid.
OH O
1
Br Br
Cl C
6 2
OH
5 3
4

2,6-Dibromophenol m-chlorobenzoic acid

Electrophilic Aromatic Substitution Reaction
H H H
H H H H H E
+ +
+ E E + H
H H H H H H

H H H
A reaction energy diagram for the electrophilic bromination of benzene. The reaction occurs in two
steps and releases energy.

H Br
H
Eact Br
H
Addition
Br (does NOT occur)

Br
+ Br2
+ HBr

Substitution

Reaction progress

394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482, 93527-21564
IVRS No. 0744-2439051, 0744-2439052, 0744-2439053, www.motioniitjee.com, email-info@motioniitjee.com
Downloaded from jeemain.guru
Page # 4 AROMATIC COMPOUNDS
Some Electrophilic Aromatic substitution reactions:

C
X R

NO2 R
Acylation
Halogenation
SO3H
Alkylation
Nitration

Sulfonation

(i) Ortho- and para-directing activators : Groups like –OH ad –NH2 present on a ring direct an electrophile,
E+, to ortho or para position and they react faster than benzene.
(ii) Ortho- and para-directing deactivators : Helogens present on a ring direct an electrophile, E+, to
ortho or para positions, and they react slower than benzene.
(iii) Meta-directing deactivators : Groups containing a carbonyl (C = O) or a –CN group direct an
electrophile, E+, to the meta positions, but they react slower than benzene.
No meta-directing activators are known. Figure 5.8 shows how the directing effects of the groups
correlate with their reactivities. All meta directing grops are deactivating and most ortho-and para-
directing groups are activating. The halogens are unique in being ortho and para directing and
deactivating.

O O
—NO2 —SO3H —COH —CH —Br —F —OCH3 —NH 2

Reactivity

—C N O O —I —Cl —H —CH3 —OH

—CCH3 —COCH3 (alkyl)

Meta-directing Ortho-and Ortho-and

deactivators para-directing para-directing
deactivators activators

Figure Substituent effects in electrophilic aromatic substitutions. All activating groups are ortho-and
para-directing, and all deactivating groups other than halogen are meta-directing. The halogens are
ortho and para-directing deactivators.

394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482, 93527-21564
IVRS No. 0744-2439051, 0744-2439052, 0744-2439053, www.motioniitjee.com, email-info@motioniitjee.com
Downloaded from jeemain.guru
AROMATIC COMPOUNDS Page # 5

CONCEPT MAP

Electrophilic Aromatic Substitution

involves reaction
between

An aromatic ring An electrophile

and
is is
can be

Activated towards Deactivated towards

+
electrophilic substitution electrophilic substitution X
+
NO 2
by by SO3
+
R
+
RCO
Electron-donating Electron-Withdrawing
groups groups

lower raise
the the

Energy of activation (Eact)

for arenium ion formation

Increase Decrease
reaction rate reaction rate

stabilize destabilize
An arenium ion

is a loses a proton to form the

Cyclohexadienyl cation Aromatic substitution product

394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482, 93527-21564
IVRS No. 0744-2439051, 0744-2439052, 0744-2439053, www.motioniitjee.com, email-info@motioniitjee.com