File:5.13 Final- wiki image.jpg

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Resonance-stabilized carbocations require proper orbital overlap

Summary

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Description
English: 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
Date
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Author Kaden167

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current00:20, 7 December 2020Thumbnail for version as of 00:20, 7 December 20201,018 × 462 (45 KB)Kaden167 (talk | contribs)Uploaded own work with UploadWizard

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