Understand the physical properties, sources

and main uses of the aromatic

hydrocarbons.
 Relate the physical properties of benzene to its
molecular structure.
 Name benzene derivatives using the IUPAC system of
nomenclature and by common names.
 Derive the structural formula of a benzene derivative
from its IUPAC and common names.
 State the major sources of benzene and its derivatives.
 Elaborate on the importance of benzene and its
derivatives in industry and daily life
Aromatic Compounds
 Aromatic compounds contain benzene.
 Benzene C6H6 has 6 C atoms and 6 H Atoms
 Two possible ring structures show benzene.
H H
H H H H

H H H H

H H

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Benzene Structure
The structures for benzene are also written as one
formula with a circle within the ring to represented
the alternating double bonds.

Benzene
structure

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Aromatic Compounds in Nature and Health
Many aromatic compounds are common in nature
and in medicine.

CHO
COOH
COOCH3 CH3 CH3
CH3CHCH2 CHCOOH
OCH3

OH

Aspirin Vanillin Ibuprofen

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Naming Aromatic Compounds
Monosubstituted Benzenes
 Systematically named in same manner as other
hydrocarbons
 – Benzene used as parent name
 C6H5Br is bromobenzene
 C6H5NO2 is nitrobenzene
 C6H5CH2CH2CH3 is propylbenzene
Naming Aromatic Compounds
Aromatic compounds are named with benzene as
the parent chain. One side group is named in front
of the name benzene.

CH3 Cl

methylbenzene chlorobenzene

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Naming Aromatic Compounds
Disubstituted benzenes
 Named using one of the prefixes
1. ortho- (o-)
 Ortho-disubstituted benzene
has two substituents in a 1,2
relationship
2. meta- (m-)
 Meta-disubstituted benzene
has its substituents in a 1,3
relationship
3. para- (p-)
 Para-disubstituted benzene
has its substituents in a 1,4
relationship
 Naming Aromatic Compounds
When two groups are attached to benzene, the ring
is numbered to give the lower numbers to the side
groups. The prefixes ortho (1,2), meta (1,3-) and para
(1,4-) are also used.
Cl
CH3 Cl
CH3

Cl CH3

1,2-dimethylbenzene 1,3-dichlorobenzene 1-chloro-4-methylbenzene

(ortho-dimethylbenzene) (meta-dichlorobenzene) (para-chloromethylbenzene)

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Some Common Names
Some substituted benzene rings also use a common
name. Then naming with additional more side groups
uses the ortho-, meta-, para- system.
CH3 CH3 OH

Cl
Toluene meta-chlorotoluene phenol
(Methylbenzene) (meta-chloromethylbenzene) (hydroxybenzene)

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Learning Check
Select the names for each structure:
Cl
1. Chlorocyclohexane
2. Chlorobenzene
3. 1-chlorobenzene
CH 3
1. Meta-methyltoluene
2. Meta-dimethylbenzene
3. 1,3-dimethylbenzene
CH 3
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Solution
Select the names for each structure:
Cl
2. Chlorobenzene

CH 3 1. meta-methyltoluene
2. meta-dimethylbenzene
3. 1,3-dimethylbenzene
CH 3
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Learning Check
Write the structural formulas for each of the
following:
A. 1,3-dichlorobenzene

B. Ortho-chlorotoluene

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Solution
Write the structural formulas for each of the
following: Cl

A. 1,3-dichlorobenzene
Cl

B. Ortho-chlorotoluene CH3
Cl

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Learning Check
Identify the organic family for each:

A. CH3CH2CH3

B.

C.
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Solution
Identify the organic family for each:

A. CH3CH2CH3alkane

B. cycloalkane

aromatic
C.
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Fused Benzene Rings

Naphthalene

3,4-Benzpyrene
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Carcinogens
 Fused ring of benzene cause cancer
 Contain four or more fused rings
 Present in tobacco smoke, auto exhaust, and
burned food
 The more a person smokes, the greater the
risk of developing cancer

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