Organic Chemistry

Haloalkanes and Haloarenes – Organic Chemistry

Learn the nomenclature, preparation, and reactions of haloalkanes and haloarenes. All concepts are thoroughly explained as per JEE/NEET syllabus.

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Posted by Tushar Agarwal, 16/6/2021
Haloalkanes and Haloarenes – Organic Chemistry

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We can replace hydrogen atom(s) in an aliphatic or aromatic hydrocarbon by halogen atom(s). This results in the formation of alkyl halide (haloalkanes) and aryl halide (haloarenes), respectively. In this article, we will study the naming of haloalkanes and haloarenes, according to the IUPAC system of nomenclature.

Classification of Haloalkanes and Haloarenes

1. On the basis of the number of halogen atoms

We can classify them as mono, di, or polyhalogen compounds depending on whether they contain one, two, or more halogen atoms in their respective structures.

The different types of haloalkanes can be named as :-

  • Monohaloalkane (1 Halogen atom)
  • Dihaloalkane (2 Halogen atoms)
  • Trihaloalkane (3 Halogen atoms)

The different types of haloarenes can be named as :-

  • Monohaloarene (1 Halogen atom)
  • Dihaloarene (2 Halogen atoms)
  • Trihaloarene (3 Halogen atoms)

Monohalocompounds can further be classified. It is based on the hybridization of C atom to which the halogen atom is attached.

2. On the basis of the hybridization of the carbon atom

  1. Compounds Containing sp3 C—X

    (a) Alkyl Halides (or haloalkanes)
    They create a homologous series which is represented as CnH(2n+1)X. We can further classify them as primary, secondary, and tertiary based on the nature of Carbon to which the halogen atom is attached.

    (b) Allylic halides
    Here, the halogen atom is attached to a carbon atom which is adjacent to C=C double bond.

    (c) Benzylic halides
    The halogen atom in this type is attached to an sp3 hybridized carbon atom attached to an aromatic ring.

2. Compounds Containing sp2 C—X

(a) Vinylic Halides
These are the compounds in which the halogen atom is attached to an sp2 hybridized C atom of a carbon-carbon double bond.

(b) Aryl halides
The halogen atom in this type is attached to sp2 hybridized carbon atom present in an aromatic ring.

Nomenclature of Haloalkanes and Haloarenes

Alkyl halides have common names. We can derive them by naming the alkyl group followed by the name of halide. As per the IUPAC system of nomenclature, we name alkyl halides as halosubstituted hydrocarbons.

IUPAC Nomenclature

Nature of C-X bond in Haloalkanes and Haloarenes

We know that halogen atoms are more electronegative than a carbon atom. As a result, the C-X bond is polarized. Carbon carries a partial positive charge and the halogen atom bears a partial negative charge. As one goes down the periodic table, the size of the halogen atom increases. Consequently, the C-X bond length also increases.


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