Ch_322a_7.07

Ch_322a_7.07 - Stereochemistry of the E2 Reaction Anti...

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Stereochemistry of the E2 Reaction Anti Relationship of Leaving Groups The results of many experiments indicate that there is an anti relationship between the leaving groups , and that the attacking base, the leaving groups, and the two carbon centers are all in a plane . C C H B: - L leaving groups are anti L H B: - anti-coplanar or anti-periplanar stereochemistry This requirement reflects the energetically favorable overlap of the developing p-orbitals that is possible in the transition state with this reacting conformation. C C H B L ! ! H L ! B ! developing p-orbitals overlap
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An Alternative Stereochemistry for the E2: Syn-Periplanar The E2 reaction also occurs by way of a syn-periplanar transition state in special situations, such as rigid structures incapable of achieving the more favorable anti-periplanar conformation. C C H L B: - syn-periplanar conformation The anti-periplanar mechanism is energetically favored over the syn-periplanar mechanism because of unfavorable torsional strain and electrostatic interactions in the latter. staggered
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Ch_322a_7.07 - Stereochemistry of the E2 Reaction Anti...

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