Image: 5.13 final- resonance-stabalized carbocation

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Description: The sp2 lone pair of molecule A is oriented such that it forms sufficient orbital overlap with the empty p orbital of the carbonation to allow form the formation of a pi bond, sequestering the carbonation in a contributing resonance structure. The lone pair of molecule B is rotated 90º with respect to the empty p orbital of the carbonation, demonstrated by the Newman projection (bottom right). Without proper orbital overlap, the nitrogen lone pair cannot donate into the carbocation's empty p orbital. Thus, the carbocation of molecule B is not resonance-stabilized.
Title: 5.13 final- resonance-stabalized carbocation
Credit: Own work
Author: Kaden167
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Carbocation

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