Organic Chemistry

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8. Elimination Reactions

E2 Mechanism

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Time to discuss the most complicated mechanism of the bunch, E2. It’s an awesome reaction, but there are a few extra details we’re gonna have to keep track of!

1

concept

Drawing the E2 Mechanism.

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Summary: A negatively charged nucleophile reacts with an inaccessible leaving group to produce beta-elimination in one-step.

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2

concept

Understanding the properties of E2.

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Properties of E2 reactions:

  • Nucleophile =  Strong
  • Leaving Group =  Substituted
  • Reaction coordinate = Transition State
  • Reaction = Concerted
  • Rate =  Bimolecular
  • Rate =  k[Nu][RX]
  • Stereochemistry = Anti-Coplanar
3

example

Rank reactivity toward E2

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