CHAPTER 17
Benzene and Aromatic Compounds
17.1 Introduction
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Aromatic compounds are called
arenes
, with benzene being the parent arene.
•
The structure of benzene was first proposed by Kekulé.
•
The resonance description of benzene consists of 2 equivalent Lewis structures with
alternating single and double bonds.
•
The true structure of benzene is a resonance hybrid of the 2 Lewis structures, with a
circle representing 6π electrons delocalized over the 6 atoms of the ring.
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What is the hybridization and bond angle of each carbon atom in the benzene ring?
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Is benzene a nucleophile or an electrophile?
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Because of the extra stability of benzene, it only undergoes substitution reactions unlike
alkenes and alkynes which undergo addition reaction.
17.2 The Concept of Aromaticity (Hückel’s Rule)
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Four structural criteria must be satisfied for a compound to be aromatic.
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What are the 4 criteria for aromaticity?
Done by Dr. Felix N. Ngassa for Chemistry 242: Organic Chemistry for Life Sciences 2, GVSU, Spring/Summer 2011.
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An aromatic compound is more stable than a similar acyclic compound having the same
number of π electrons.
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- Spring '11
- Ngassa
- Benzene, Delocalized electron, GVSU, Dr. Felix N., Felix N. Ngassa
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