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Lecture 1 Aromatic Chemistry

The document is a lecture on Basic Organic Chemistry focusing on Aromaticity, specifically discussing the chemistry of arenes and polycyclic aromatic hydrocarbons for second-year students at Cairo University. It covers the structure and stability of benzene, including Kekule's structure, resonance theory, and molecular orbital theory, explaining the unique properties of aromatic compounds. Additionally, it introduces antiaromatic compounds and the criteria for classifying compounds as aromatic, antiaromatic, or non-aromatic.

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Nourhan Ibrahim
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17 views20 pages

Lecture 1 Aromatic Chemistry

The document is a lecture on Basic Organic Chemistry focusing on Aromaticity, specifically discussing the chemistry of arenes and polycyclic aromatic hydrocarbons for second-year students at Cairo University. It covers the structure and stability of benzene, including Kekule's structure, resonance theory, and molecular orbital theory, explaining the unique properties of aromatic compounds. Additionally, it introduces antiaromatic compounds and the criteria for classifying compounds as aromatic, antiaromatic, or non-aromatic.

Uploaded by

Nourhan Ibrahim
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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Cairo University

Faculty of Science
Chemistry Department

Basic Organic Chemistry:


Chemistry of Arenes and Polycyclic
Aromatic Hydrocarbons

Chem. 242
For Second Year Students

1
Chapter One
Lecture One
Aromaticity

2
Introduction

3
The classification of organic compounds is based on the
structure of molecules.

4
Aromatic Compounds
Unsaturated cyclic molecules which have additional stability due to the
arrangement of π-electrons

5
Chemistry of Benzene
• Stable and fragrant organic compound with molecular formula of
C6H6.
• The actual structure of benzene remains a mystery for a long time.

How to explain the chemical structure of benzene?


A) Kekule's structure:
• Kekule assumed that the structure of benzene is a cyclic hexagonal
with alternating single and double bonds.
• Benzene can be considered as 1,3,5-cyclohexatriene.

6
Shortcoming of Kekule’s approach
• In view of the proposed structure of benzene, there should be
two ortho-disubstituted isomers, but only one isomer is actually
observed.

• Unlike other olefins, benzene reacted by substitution reactions rather


than by addition reactions.
• Later, it had been confirmed that benzene is a planar hexagon with
identical bond lengths (all bonds in benzene equals 1.40 Ǻ).
7
B) The Resonance Theory:
• In chemistry, theory by which the actual normal state of a molecule is
represented not by a single valence-bond structure but by a
combination of several alternative distinct structures. The molecule is
then said to resonate among the several valence-bond structures or
to have a structure that is a resonance hybrid of these structures.
• In light of this theory, benzene ring can be represented by two
equivalent resonating structures and the truly structure is the hybrid
one.

8
• The hybrid structure can explain the formation of single ortho-
disubstituted isomer.
• The resonance theory also explained why the six carbon-carbon bond
lengths are equivalent; the value of each (C-C) bond is shorter than
normal single bond (C-C) and longer than the double bond (C=C).

9
 The resonance theory also explained the high stability of benzene ring
due to the delocalization of π-electrons.

10
C) The Molecular Orbital Theory:
• Each carbon atom in benzene has sp2 hybridization. These hybrid
orbitals form three covalent bonds (2 C-C and one C-H) with bond
angle of 120o. Thus, benzene has a planar structure.
• Each carbon atom in benzene has an unhybridized p-orbital, above
and below the plane of benzene ring, that contains one electron
(Figure a).

11
• The p-orbitals overlap around the ring, (Figure b), to form a bonding
molecular orbital with electron density above and below the plane of
the ring (Figure c).

• There are six p molecular orbitals for benzene.

12
13
14
15
16
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The features of Antiaromatic compounds
1) Cyclic, planar, and contain conjugated system of π-electrons (double,
single, double, ....).
2) The antiaromatic compounds must contain 4n p-electrons (n is an
integer number 1, 2, 3, ....).

Annulenes: Monocyclic hydrocarbons with conjugated system. A prefix


in brackets indicates the number of carbons in the ring. 18
Important Note
If the compounds did not fulfill the requirements of aromatic or
antiaromatic characters it will be Non-aromatic compounds

Examples:

19
Examples of aromatic and non-aromatic systems:

20

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