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Chapter 17

Aromatic Compounds

Aromatic Compounds: Overview
Aromatic Compounds: Overview
In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history ...
Nomenclature of Aromatic Compounds with a Single Substituent
Nomenclature of Aromatic Compounds with a Single Substituent
Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the ...
Nomenclature of Aromatic Compounds with Multiple Substituents
Nomenclature of Aromatic Compounds with Multiple Substituents
When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present. For disubstituted ...
Structure of Benzene: Kekulé Model
Structure of Benzene: Kekulé Model
In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three ...
Structure of Benzene: Molecular Orbital Model
Structure of Benzene: Molecular Orbital Model
According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, ...
Criteria for Aromaticity and the H&uuml;ckel 4<em>n</em> + 2 Rule
Criteria for Aromaticity and the Hückel 4n + 2 Rule
Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs ...
H&uuml;ckel's Rule Diagram of &pi; MOs: Frost Circle
Hückel's Rule Diagram of π MOs: Frost Circle
The Frost circle or the inscribed polygon method is a graphical method for determining the relative energies of π molecular orbitals (MOs) for ...
Frost Circles for Different Conjugated Systems
Frost Circles for Different Conjugated Systems
The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. ...
Aromatic Hydrocarbon Anions: Structural Overview
Aromatic Hydrocarbon Anions: Structural Overview
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene ...
Aromatic Hydrocarbon Cations: Structural Overview
Aromatic Hydrocarbon Cations: Structural Overview
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. ...
Five-Membered Heterocyclic Aromatic Compounds: Overview
Five-Membered Heterocyclic Aromatic Compounds: Overview
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. ...
NMR Spectroscopy of Aromatic Compounds
NMR Spectroscopy of Aromatic Compounds
Aromatic compounds can be identified or analyzed using proton NMR and carbon‐13 NMR. Typically, aromatic hydrogens or hydrogens directly bonded to ...
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