Reactive Intermediates

Explain the electronic structure and geometry of carbocations, carbanions, and free radicals.

Predict the relative stability of carbocations using hyperconjugation, resonance, and inductive effects.

Predict the relative stability of carbanions and free radicals using resonance, inductive effects, and orbital hybridization (s-character).

Analyze carbocation rearrangements, including 1,2-hydride/alkyl shifts and ring expansions.

Describe the stabilization mechanism in non-classical carbocations.

Distinguish between singlet and triplet carbenes and predict their characteristic reactivity patterns.

Given an intermediate, predict the most likely subsequent reaction pathway (e.g., rearrangement, substitution, elimination, addition).