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Carbocations in general are stabilized by hyperconjugative interactions where po

ID: 935819 • Letter: C

Question

Carbocations in general are stabilized by hyperconjugative interactions where possible. The standard picture of this stabilization is illustrated below left (structure 1), with the empty p orbital mixing with an aligned sp3 hybrid C-H bond. The vinyl carbocation 2 presents a variant of this hyperconjugative interaction. Now, an sp2 hybrid is mixing with the empty p orbital. Hyperconjugative interaction 2 differs fro the standard model 1 in two important aspects: (1) The hybrid orbital used by the carbon of the C-H bond is different (sp3 in 1 vs. sp2 in 2), and (2) the angle between the C-H bond and the p orbital is different (~ 109 in 1 vs. ~ 120 in 2).

Explanation / Answer

option A