Scribd
Upload
50 views13 pages

Chapter 3

Chapter 3 discusses aromatic compounds, which were historically associated with fragrance but are now defined by their chemical behavior and electronic configuration. It covers the sources, naming conventions, and structural characteristics of benzene and its derivatives, including substitution reactions and resonance structures. The chapter also introduces polycyclic aromatic compounds like naphthalene, highlighting their fused ring structures.

Uploaded by

Apdalla Khayre
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPT, PDF, TXT or read online on Scribd
50 views13 pages

Chapter 3

Chapter 3 discusses aromatic compounds, which were historically associated with fragrance but are now defined by their chemical behavior and electronic configuration. It covers the sources, naming conventions, and structural characteristics of benzene and its derivatives, including substitution reactions and resonance structures. The chapter also introduces polycyclic aromatic compounds like naphthalene, highlighting their fused ring structures.

Uploaded by

Apdalla Khayre
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPT, PDF, TXT or read online on Scribd

Chapter 3.

Benzene and Aromaticity


Abdihakim Mohamed
BSc(MLT), MPH, MSc HSM
Aromatic Compounds
• Aromatic was used to described some fragrant compounds in
early 19th century
– Not correct: later they are grouped by chemical behavior
(unsaturated compounds that undergo substitution rather
than addition)
• Current: distinguished from aliphatic compounds by electronic
configuration

2
Sources of Aromatic Hydrocarbons

• From high temperature distillation of coal tar.


• Heating petroleum at high temperature.

3
Naming Aromatic Compounds
• Many common names (toluene = methylbenzene; aniline =
aminobenzene)
• Monosubstituted benzenes systematic names as hydrocarbons
with –benzene
– C6H5Br = bromobenzene
– C6H5NO2 = nitrobenzene, and C6H5CH2CH2CH3 is
propylbenzene

4
Common Names

5
6
Disubstituted Benzenes

• Relative positions on a benzene ring


– ortho- (o) on adjacent carbons (1,2)
– meta- (m) separated by one carbon (1,3)
– para- (p) separated by two carbons (1,4)
• Describes reaction patterns (“occurs at the para position”)

7
Naming Benzenes With More Than Two
Substituents
• Choose numbers to get lowest possible values
• List substituents alphabetically with hyphenated numbers
• Common names, such as “toluene” can serve as root name

8
Structure and Stability of Benzene
• Benzene reacts with slowly with Br2 to give bromobenzene
(where Br replaces H)
• This is substitution rather than the rapid addition reaction
common to compounds with C=C, suggesting that in benzene
there is a higher barrier

9
Drawing Benzene and Its Derivatives
• The two benzene resonance forms can be represented by a
single structure with a circle in the center to indicate the
equivalence of the carbon–carbon bonds
• This does indicate the number of  electrons in the ring but
reminds us of the delocalized structure
• We shall use one of the resonance structures to represent
benzene for ease in keeping track of bonding changes in
reactions

10
15.9 Polycyclic Aromatic Compounds:
Naphthalene
• Aromatic compounds can have rings that share a set of carbon
atoms (fused rings)
• Compounds from fused benzene or aromatic heterocycle rings
are themselves aromatic

11
Reactions of Benzene

12
Reactions of Benzene

13

You might also like