Consider the relative thermodynamic stabilities of the following carbanions: , , , and . What specif — GOC and Organic Chemistry Basics Chemistry Question

💡 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.