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Question 41

In which of the following pairs is A more stable than B?

Option A: B is more stable than A because B is a tertiary ($$3^\circ$$) radical stabilized by more hyperconjugation, whereas A is only a secondary ($$2^\circ$$) radical.

Option B: B is more stable than A because the cyclopropyl radical (A) suffers from high angle strain and has greater s-character in its radical orbital, making it highly unstable compared to the standard cyclohexyl radical (B).

Option C: B is more stable than A because B is an allylic radical stabilized by resonance, whereas A is a vinylic radical where the unpaired electron sits directly on a $$sp^2$$ carbon, making it exceptionally unstable.

Option D: A is more stable than B because the triphenylmethyl radical ($$\text{Ph}_3\text{C}^\bullet$$) is extensively stabilized by resonance across three aromatic rings, which vastly outperforms the simple hyperconjugation stabilizing the tert-butyl radical ($$(\text{CH}_3)_3\text{C}^\bullet$$).

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