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What is the mechanism of hydrohalogenation?

Hydrohalogenation = Addition of HX (HCl, HBr, HI) to an alkene.


Mechanism (Step by Step)

  1. Double bond attacks H⁺
    • The alkene has a π bond (electron rich).
    • This bond attacks the H⁺ from HX.
    • One carbon gets the hydrogen.
    • The other carbon becomes a carbocation (C⁺).
    • This step follows Markovnikov’s rule (H goes to carbon with more hydrogens).

  1. Carbocation formation
    • The more stable carbocation forms (tertiary > secondary > primary).
    • That’s why Markovnikov’s rule works.

  1. Nucleophile attack
    • The halide ion (X⁻, e.g., Cl⁻, Br⁻, I⁻) attacks the carbocation.
    • This makes the final product: an alkyl halide.

Example:

Propene + HBr →

  • Step 1: Double bond attacks H⁺ → carbocation forms on middle carbon.
  • Step 2: Br⁻ attacks carbocation → product is 2-bromopropane.

In short:

  1. Double bond grabs H.
  2. Carbocation forms (stable one).
  3. Halide attaches to carbocation.

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