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  • In the presence of peroxide addition of HBr to propene takes place according to anti Markovnikov’s rule but peroxide effect is not seen in the case of HCl and HI. Explain.

In the presence of peroxide addition of HBr to propene takes place according to anti Markovnikov’s rule but peroxide effect is not seen in the case of HCl and HI. Explain.

Answers (1)

(i) 

(ii) ^.C_{6}H_{5}+H-Br\overset{homolysis}{\rightarrow}C_{6}H_{6}+Br^.

(iii) 

(iv) CH_{3}+\dot{C}H-CH_{2}Br+H-Br\overset{Homolysis}{\rightarrow}CH_{3}-CH_{2}-CH_{2}Br+\dot{B}r

Since the H-Cl bond is stronger than the H-Br bond, the peroxide effect is observed only in the case of HBr. It is not observed in the case of HI as well.

H-Br has lesser bond energy than H-Cl; thus, the H-Cl bond is not cleaved by the free radical, whereas the H-I bond is weaker and iodine free radicals combine to form dimer iodine molecules.

Markovnikov's rule is an organic chemistry generalization that predicts the regioselectivity of electrophilic addition reactions to unsymmetrical alkenes and alkynes:

  • The electron-rich component of the reagent adds to the carbon atom with fewer hydrogen atoms.
  • The electron-deficient component adds to the carbon atom with more hydrogen atoms.
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