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Chapter 17

Aromatic Compounds

Chapter 17

Aromatic Compounds

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
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
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
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
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 Hückel 4n + 2 Rule
Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs …
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
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
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
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
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
Aromatic compounds can be identified or analyzed using proton NMR and carbon‐13 NMR. Typically, aromatic hydrogens or hydrogens directly bonded to …
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Molecules bearing trifluoromethoxy (OCF3) group often show desired pharmacological and biological properties. However, facile synthesis of …
Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
The main purpose of this video is to show 6 reaction steps of a convergent synthesis and prepare a complex molecule containing up to three nonplanar …
Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
A synthetic process for the preparation of a variety of 1-aryl-1H-pyrazole-5-amines was developed. The microwave-mediated nature of this method makes it …