Chemistry, asked by berryberry, 1 year ago

why does the addition of Hcl to the folloeing olefin take place in the opposite manner as predicted by markonikov rule : CH2=CH-CO2Et + HCl -----> CH2Cl-CH2-CO2Et?

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Answered by Aayushkapoor
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because hydrogen break h bond or Cl are attched to addtional site

berryberry: can you explain more please?
Aayushkapoor: HCl and HI do not show peroxide effect. Radical chain reactions are successful when propagation steps are exothermic. An endothermic propagation step is reversible and would break the chain. With HI, the first propagation step is endothermic, because H-I bond is weak. Moreover, HI is oxidized by peroxide to I2 under reaction conditions.

With HCl, the second propagation step is endothermic, because the H-Cl bond is strong. 

With HBr, both the propagation steps are exothermic and HBr
Aayushkapoor: With HBr, both the propagation steps are exothermic and HBr adds to the double bond by  free- radical mechanism.
Aayushkapoor: ye phale wala h (HCl and HI do not show peroxide effect. Radical chain reactions are successful when propagation steps are exothermic. An endothermic propagation step is reversible and would break the chain. With HI, the first propagation step is endothermic, because H-I bond is weak. Moreover, HI is oxidized by peroxide to I2 under reaction conditions.)
Aayushkapoor: 2. With HCl, the second propagation step is endothermic, because the H-Cl bond is strong.
Aayushkapoor: 3. With HBr, both the propagation steps are exothermic and HBr adds to the double bond by  free- radical mechanism.
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