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Explain why (CH3)3C^(oplus) is more stab...

Explain why `(CH_3)_3C^(oplus)` is more stable than `CH_3 overset (oplus) C H_2` and `overset (oplus) C H_3` is less stable.

Text Solution

Verified by Experts

Hyperconjugation interaction in `(CH_3)_3 C^(oplus) (I)` is greater than that of `C` in `CH_3 overset (oplus) CH_2 (II)`, as `(I)` has nine `(C - H)` bonds and `(II)` has three `(C - H)` bonds.
In `overset (oplus) CH_3`, the vacant `p` orbital is perpendicular to the plane in which `(C- H)` bonds lies , hence cannot overlap with it.
Thus, `overset (oplus) CH_3` lacks hyperconjugative stability.
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Knowledge Check

  • overset(Theta)(C)H_(3) is less stable than

    A
    `CH_(3)-overset(Theta)(C)H_(2)`
    B
    `CH_(3)-overset(Theta)(C)H-CH_(3)`
    C
    `overset(Theta)(C)H_(2)-NO_(2)`
    D
    `CH_(3)-overset(Theta)(C)H-C_(2)H_(5)`

  • Identify the carbocations lesser stable than CH_(3)-overset(oplus)(C)H_(2) :

    A
    `.^(oplus)CH_(3)` :
    B
    `underset(("Vinyl Carbocation"))(CH_(2)=overset(oplus)(CH))`
    C
    D

  • The species CH_(3)overset(+)CHCH_(3) is less stable than :

    A
    `(CH_(3))_(3)C^(+)`
    B
    `CH_(3)CH_(2)overset(+)CH_(2)`
    C
    `CH_(3)overset(+)CH_(2)`
    D
    `CH_(3)^(+)`

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