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Related Concept Videos

Constitutional Isomers of Alkanes02:18

Constitutional Isomers of Alkanes

Organic compounds of the same molecular formula can have different structural formulas called constitutional isomers, and the phenomenon is known as constitutional isomerism. Alkanes with four or more carbons showing multiple structures with the same molecular formula thereby exhibit constitutional isomerism.
The linear isomer of an alkane is prefixed by the term “n”; hence a linear isomer of pentane is known as n-pentane. Based on the type of branching, some of the branched isomers are given...
Nomenclature of Alkynes02:39

Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
IUPAC Nomenclature of Aldehydes01:16

IUPAC Nomenclature of Aldehydes

Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although the aldehydic carbon’s locant...
Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides01:16

Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides

Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

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 benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
Characteristics and Nomenclature of Copolymers01:24

Characteristics and Nomenclature of Copolymers

Copolymers are the products obtained from the polymerization of multiple monomer species. So, in a polymer chain itself, there can be multiple repeating units that come from different monomers. The process of synthesizing a polymer from different monomer species is called copolymerization. When two monomers are involved, the polymer is known as a bipolymer. Polymers with three and four monomers are termed terpolymers and quaterpolymers, respectively. Figure 1 depicts the copolymerization of...

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Related Experiment Video

Updated: Jun 29, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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Octachloroazulene.

Yan Lou1, Joanne Chang, Jeffrey Jorgensen

  • 1Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA. david.m.lemal@dartmouth.edu

Journal of the American Chemical Society
|December 19, 2002
PubMed
Summary

Researchers synthesized the first perhaloazulene, a halogenated azulene compound. This novel synthesis opens new avenues for exploring halogenated aromatic compounds and their unique chemical properties.

Area of Science:

  • Organic Chemistry
  • Halogenated Compounds
  • Aromatic Systems

Background:

  • Azulene derivatives are known for their unique electronic and structural properties.
  • Perhalogenated aromatic compounds often exhibit distinct reactivity and stability.
  • Synthesis of novel halogenated azulenes remains an area of interest.

Purpose of the Study:

  • To synthesize the first perhaloazulene.
  • To investigate the chlorination behavior of hexachloroazulene.
  • To explore the reactivity of highly chlorinated azulene derivatives.

Main Methods:

  • Synthesis of 1,3,4,5,6,7-hexachloroazulene from hexachlorobutadiene and cyclopentadiene.
  • Electrophilic and free radical chlorination of hexachloroazulene.

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  • Chemical transformations of decachlorotetrahydroazulene using phosphazene bases, acid catalysis, and reduction with mercury.

    • Main Results:

    • Successful synthesis of the first perhaloazulene.
    • Chlorination of hexachloroazulene proceeds via addition, not substitution.
    • Radical chlorination yields decachlorotetrahydroazulene.
    • Decachlorotetrahydroazulene can be converted to nonachlorodihydroazulene, heptachloroazulene, or octachloroazulene depending on reaction conditions.
    • Octachloroazulene is sensitive and cannot be readily converted to its fluoro counterpart.

    Conclusions:

    • The synthesis of perhaloazulenes is achievable.
    • Highly chlorinated azulenes exhibit unique addition and elimination reactions.
    • The stability of octachloroazulene limits further halogen exchange reactions.