Organic Chemistry
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Unlike the addition of Cl2, HCl addition is not stereospecific. Explain why this is so.
Both H+ and Cl− can be added to any part of the molecule since all parts are susceptible to attack.
The reagent HCl is much less potent than Cl2 so it gives a lot of side products.
The addition of HCl involves a cyclic chloronium ion intermediate which was formed from a concerted step. This allows for carbocation formation and variability in the site of addition of both H+ and Cl−.
There is variability in both the first and second steps of HCl addition. Both H+ and Cl− could be added to the top or the bottom or to the front face or the back face, leading to syn- and anti-addition products.