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Predict the major product formed when HC...

Predict the major product formed when HCl is added to iso-butylene. Explain the mechanism involved.

Text Solution

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Reaction between iso-butylene and HCl are as follows:
`underset("Iso-butylene")(H_(3)C-undersetunderset(CH_(3))(|)(C)=CH_(2))+HCloverset("Markownikoff.s rule")rarrunderset("2-chloro-2-methylpropane")(H_(3)C-undersetunderset(CH_(3))(|)oversetoverset(Cl)(|)(C)-CH_(3))`
Electrophilic addition reaction takes place in accordance with Markownikoff.s rule.
Mechanism
(i) `HClrarrH^(+)+Cl^(-)`
(ii)
We know that `3^(@)` carbocation is more stable than `1^(@)` carbocation, hence `3^(@)` carbocation proceed to react with `Cl^(-)` ion.
`H_(3)C-undersetunderset(CH_(3))(|)oversetoverset(CH_(3))(|)(C^(+))+Cl^(-)rarrunderset("2-chloro-2-methylpropane")(H_(3)C-undersetunderset(CH_(3))(|)oversetoverset(CH_(3))(|)(C)-Cl)`
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