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Chemistry · Ch 6 — Haloalkanes and Haloarenes

Compounds Containing sp² C—X Bond

6.1.3

Compounds Containing sp² C—X Bond

When the halogen atom is bonded to an sp2sp^2-hybridised carbon instead of an sp3sp^3 one, the monohalo compound falls into one of two classes.

(a) Vinylic Halides

A vinylic halide has the halogen bonded directly to an sp2sp^2-hybridised carbon that is itself part of a carbon–carbon double bond:

C=C−X\mathrm{C=C-X}

The halogen sits right on one of the doubly-bonded carbons — not on a carbon next to the double bond (that would make it allylic instead). This holds whether the double bond is part of an open chain or part of a ring.

Open-chain vinylic halide
Open-chain vinylic halide

Drawn by us to help you understand the concept clearly, and verified to make sure it's accurate. For exams, practice from your NCERT textbook's own diagram.

CH2=CH-X, the simplest vinylic halide: the halogen is bonded directly to the sp2 carbon that is itself part of the C=C double bond, not to a carbon next to it (that neighbouring-carbon case is allylic instead). This direct C(sp2)-X bond is why vinylic and aryl halid …

Cyclic vinylic halide
Cyclic vinylic halide

Drawn by us to help you understand the concept clearly, and verified to make sure it's accurate. For exams, practice from your NCERT textbook's own diagram.

The ring form of a vinylic halide: X sits directly on the sp2 ring carbon that is itself part of the ring's own C=C double bond, not on a carbon next to it -- the cyclic counterpart to the open-chain …

(b) Aryl Halides

An aryl halide has the halogen bonded directly to an sp2sp^2-hybridised carbon of an aromatic ring — the halogen is attached straight to a ring carbon, unlike a benzylic halide where the halogen-bearing carbon sits just outside the ring. Substituted aromatic rings, such as one carrying both a methyl group and the halogen at different ring positions, are also grouped under aryl halides as long as X is bonded directly to a ring carbon.

Aryl halides (plain and substituted)
Aryl halides (plain and substituted)

Drawn by us to help you understand the concept clearly, and verified to make sure it's accurate. For exams, practice from your NCERT textbook's own diagram.

X bonded directly to an aromatic-ring carbon: a plain aryl halide (Ph-X) and a substituted example carrying an extra methyl group on the ring, showing that any halogen-on-ring-carbon compound counts as an aryl halide re …

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