The addition of $\mathrm{HI}$ in the presence of peroxide catalyst does not follow anti-Markovnikov's rule…

The addition of $\mathrm{HI}$ in the presence of peroxide catalyst does not follow anti-Markovnikov's rule because :
  1. $\mathrm{HI}$ is a strong reducing agent.
  2. $\mathrm{H-I}$ bond is too strong to be broken homolytically.
  3. $\mathrm{I}$ atom combines with $\mathrm{H}$ atom to give back $\mathrm{HI}$.
  4. Iodine atom is not reactive enough to add across a double bond.

Solution

$\mathrm{HI}$ does not exhibit peroxide effect. $\mathrm{HI}$ bond although dissociates easily into iodine radicals, they being bigger in size are not much reactive but recombine together to form iodine molecule.

Asked in: JEE Main 2013 (09 Apr Online)

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