Consider the relative thermodynamic stabilities of the following carbanions: , , , and . What specif — GOC and Organic Chemistry Basics Chemistry Question
Question
Consider the relative thermodynamic stabilities of the following carbanions: $CH_3^-$, $CH_3CH_2^-$, $(CH_3)_2CH^-$, and $(CH_3)_3C^-$. What specific stabilizing role does hyperconjugation play in this series?
Answer: C
💡 Solution & Explanation
Hyperconjugation ($\sigma \rightarrow p$ overlap) fundamentally requires an empty or half-filled orbital to accept electron density. Carbanions have a completely filled non-bonding orbital (holding a lone pair). Therefore, they cannot accept electrons from $\alpha$ -C-H bonds. The decreasing stability from methyl to tertiary is driven by destabilizing $+I$ inductive effects.
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