12.

8 Aromatic Compounds

The space-filling model for

benzene consists of a six-carbon
ring with six hydrogen atoms.

Learning Goal:
Describe the bonding in benzene; and
name aromatic compounds.
General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 12.8 Aromatic Compounds

Complete the graphic organizer below.

Hydrocarbon

Aliphatic Aromatic

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Benzene, an Aromatic Compound

In 1825, Michael Faraday isolated a hydrocarbon

called benzene, which consists of a six-carbon ring
with alternating double bonds and the molecular
formula C6H6.

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Benzene, an Aromatic Compound
Benzene is
• an aromatic compound.
• a ring of six C atoms, each bonded to one H atom.
• a flat ring structure drawn with three alternating double
bonds.
• represented by two structures, because the electrons are
shared equally among all the C atoms.
• represented by a line-angle structural formula using a circle
in the center instead of the alternating double bonds.

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Aromatic Compounds

Some common examples of aromatic compounds that we use

for flavor are anisole from anise, estragole from tarragon, and
thymol from thyme.

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Benzene

• Each carbon atom uses three valence electrons to bond to

the hydrogen atom and two adjacent carbons. The fourth
valence electron was thought to be shared in a double bond
with an adjacent carbon.
• In 1865, August Kekulé proposed that the carbon atoms in
benzene were arranged in a flat ring with alternating single
and double bonds between the adjacent carbon atoms.

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Naming Aromatic Compounds

• Aromatic compounds containing a benzene ring and a

single substituent are named as benzene derivatives.
• Since the ring contains only one substituent, the ring is not
numbered.
• Some common names such as toluene, aniline, and phenol
are allowed by IUPAC rules.

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Naming Aromatic Compounds

1. Monosubstituted Benzenes
a. IUPAC name
CH 2CH 3 Cl CH 2
C(CH 3)3 NO 2

t-Butylbenzene Ethylbenzene Nitrobenzene Chlorobenzene Benzyl group

b. Common name
CH3 H HO
CH 2 Cl CH=CH 2 OH C O C O H2N

Benzyl chloride Toluene Styrene Phenol Benzaldehyde Benzoic acid Aniline

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Naming Aromatic Compounds

1. Monosubstituted Benzenes
b. Common name

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Naming Aromatic Compounds

2. Disubstituted Benzenes
A. All disubstituted benzenes, can give rise to three
possible isomers. The differentiate between the
isomers, the relative positions of the substituents are
designated by number or, more commonly, by the
prefixes ortho (o: 1,2), meta (m:1,3) or para (p:1,4).
Br
Br
Br
Br

Br
Br
1,2-Dibromobenzene 1,3-Dibromobenzene 1,4-Dibromobenzene
o-Dibromobenzene m-Dibromobenzene
General, Organic, and Biological Chemistry: Structures of Life, 5/e p-Dibromobenzene
© 2016 Pearson Education, Inc.
Karen C. Timberlake
 Naming Aromatic Compounds

2. Disubstituted Benzenes

B. When the substituents are different, they are

listed in alphabetical order
F
O 2N
C2H5
Cl

Br
I
1-Chloro-2-ethylbenzene 1-Bromo-3-nitrobenzene 1-Fluoro-4-iodobenzene
o-Chloroethylbenzene m-Bromonitrobenzene p-Fluoroiodobenzene

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Naming Aromatic Compounds

2. Disubstituted Benzenes
C. If one of the substituents is part of a parent
compound, then the disubstituted benzene is
named as a derivative of the parent compound.
O 2N COOH
OH
Cl

Br
H3C
2-Chlorophenol 4-Nitrotoluene 3-Bromobenzoic acid
o-Chlorophenol p-Nitrotoluene m-Bromobenzoic acid

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Naming Aromatic Compounds

2. Disubstituted Benzenes
D. Certain disubstituted benzenes are referred to by
their common names.
CH3
CH3 H3C
CH3

CH3
CH3
o-Xylene m-Xylene p-Xylene

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Naming Aromatic Compounds

2. Disubstituted Benzenes
E. If three or more substituents are attached to the
benzene ring, they are numbered in the direction to
give the lowest set of numbers and then named
alphabetically.

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Naming Aromatic Compounds

• When a benzene ring is a substituent, — C6H5,

it is named as a phenyl group.

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Chemistry Link to Health:
Common Aromatic Compounds

Toluene is used as a
reactant to make drugs,
dyes, and explosives
such as TNT
(trinitrotoluene).

The benzene ring is also

found in some amino
acids (the building blocks
of proteins).

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Chemistry Link to Health:
Common Aromatic Compounds

The benzene ring is found in pain relievers such as aspirin,

acetaminophen, and ibuprofen; and in flavorings such as
vanillin.

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Study Check

Select the correct name for each compound.

1. A. chlorocyclohexane
B. chlorobenzene
C. 1-chlorobenzene

2. A. 1,2-dimethylbenzene
B. 1,4-dimethylbenzene
C. 1,3-dimethylbenzene

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Solution

Select the correct name for each compound.

1. B. chlorobenzene

2. C. 1,3-dimethylbenzene

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Concept Map

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake