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Out CH(3)-underset(CH(3))underset(|)(CH)...

Out `CH_(3)-underset(CH_(3))underset(|)(CH)-CH_(2)-Cl` and `CH_(3)-CH_(2)-underset(CH_(3))underset(|)(CH)-Cl` , which is more reactive towards `S_(N)1` reaction and why?

Text Solution

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`CH_(3) –CH_(2)-underset(CH_(3))underset(|)CH_(2)-Cl` is more reactive.
The `S_(N)1`reaction proceeds through the formation of carbocation. The compound which forms more stable carbocation will be more reactive.
`underset(" 1-Chloro-2-methylpropane")(CH_(3)-underset(CH_(3))underset(|)CH-CH_(2)-Cl) overset(-Cl,^(-))to underset(1^(@) "Carbocation")(CH_(3)-underset(CH_(3))underset(|)CH-overset(+)CH_(2))`
`underset("2- Chlorobutane")(CH_(3) –CH_(2)-underset(CH_(3))underset(|)CH-Cl) overset(-Cl^(-))to underset(2^(@) "Carbocation")(CH_(3)-CH_(2)-underset(CH_(3))underset(|)overset(+)CH)`
Since `2^(@)` carbocation is more stable than `1^(@)` carbocation, 2-Chlorobutane will be more reactive towards `S_(N)1` reaction.
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Knowledge Check

  • CH_(2)CH_(2)CH_(2)-Cl and CH_(3)-underset(CH)underset(|)(CH)-CH_(3) shows which type isomerism

    A
    Chain isomers
    B
    position isomers
    C
    Functional isomers
    D
    Metamers

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