Eliminations and Summary_1perpg

Eliminations and Summary_1perpg - Eliminations Bimolecular:...

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Eliminations Bimolecular: E2
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What is going on? • The nucleophile, now behaving as a base, seeks out a proton on the adjacent carbon (that’s ß to you). The preferred conformation is anti-periplanar because that has a smooth transition to the aligned p-orbitals (the π -bond): OTos H O Anti-periplanar conformation + OTos + EtOH
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S N 2 vs E2 OTos H O Anti-periplanar conformation + OTos + EtOH E2 S N 2 HO E t (if S N 2, this is not a tertiary substrate)
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What happens in this elimination? OTos CH 3 Base ? 3 OTos OTos 3 H B
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The stereochemistry of elimination (E2):
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Eliminations and Summary_1perpg - Eliminations Bimolecular:...

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