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MHT-CET Chemistry · Alkynes

Alkynes: Haloalkynes and Hybridisation

An alkyne has a C≡C triple bond whose two carbons are sp hybridised; a haloalkyne has its halogen on one of those triple-bond carbons.

Why this matters

3 PYQs. Two ask which structure is a haloalkyne, set twice in 2024; one counts sp² carbons in a diyne. One card.

Concept 1 of 1: Haloalkynes and the Hybridisation of Carbon

The name follows where the halogen sits. On a triple-bond carbon it is a haloalkyne; one carbon away it is propargylic; on a double-bond carbon it is a haloalkene. The hybridisation follows the bond: triple bond sp, double bond sp², single bonds only sp³.

Definition

  • Haloalkyne: X bonded to an sp carbon of C≡C — CH₃CH₂C≡C–X, chloroethyne HC≡C–Cl.
  • X on the carbon next to C≡C (CH₃C≡C–CH₂X, 3-chlorobut-1-yne) is propargylic, not a haloalkyne.
  • Hybridisation: C≡C carbons sp; C=C carbons sp²; saturated carbons sp³.
  • Hexa-1,4-diyne HC≡C–CH₂–C≡C–CH₃ has no sp² carbon.
StructureClass
CH₃CH₂C≡C–XHaloalkyneQ
Chloroethyne, HC≡C–ClHaloalkyneQ
CH₃C≡C–CH₂XPropargylic halideQ
CH₃CH₂CH=CH–XHaloalkene (vinylic)
sp² carbons in hexa-1,4-diyneZeroQ
Practice this conceptself-check

The same idea in a real exam question:

MHT-CET · 2024 · 12th May Shift 2 · Q58Moderate

Example 1 · Alkynes · Nomenclature and Identification of Alkynes

Which among the following is haloalkyne?

Any halogen in an alkyne

A halogen anywhere in the molecule does not make a haloalkyne. It must sit on the C≡C carbon itself.

Summary — formulas & gotchas at a glance

A revision cheat-sheet for the formulas and gotchas above. Click any concept name to jump back to its full explanation.

Reference tables (1)

Haloalkynes and the Hybridisation of Carbon5 rows
StructureClass
CH₃CH₂C≡C–XHaloalkyneQ
Chloroethyne, HC≡C–ClHaloalkyneQ
CH₃C≡C–CH₂XPropargylic halideQ
CH₃CH₂CH=CH–XHaloalkene (vinylic)
sp² carbons in hexa-1,4-diyneZeroQ

Watch out for (1)

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