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Question 63

Given below are two statements:
Statement I: On the basis of inductive effect, the order of stability of alkyl carbanions is $$CH_3^- > CH_3CH_2^- > (CH_3)_2CH^- > (CH_3)_3C^-$$.
Statement II: Allyl and benzyl carbanions are more stabilised by inductive effect and not by resonance effect.
In the light of the above statements, choose the correct answer from the options given below

Statement I: On the basis of inductive effect, the order of stability of alkyl carbanions is 

$$CH_3^- > CH_3CH_2^- > (CH_3)_2CH^- > (CH_3)_3C^-$$.

Correct,

Carbanions are destabilized by electron-releasing $$+I$$ alkyl groups.

  • More alkyl groups → more electron density → less stable carbanion.
  • Hence stability order is: $$CH_3^->1^{\circ\ }>2^{\circ\ }>3^{\circ\ }$$

  • Statement II: 

    Incorrect,

    Allyl and benzyl carbanions are more stabilised by inductive effect and not by resonance effect. 

    The Priority order to check the stability of any compound is: 

    Aromaticity $$>$$ Resonance $$>$$ Hyperconjugation $$>$$ Inductive Effect 

    Allyl and benzyl carbanions are highly stable mainly due to resonance delocalization of negative charge.                                                                                                         

    Examples:

    • Allyl carbanion → charge delocalized over allylic system.
    • Benzyl carbanion → charge delocalized into benzene ring.

    Therefore, Option C is correct $$i.e$$ Statement I is correct but Statement II is incorrect.

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