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Competition among S N 2, S N 1, E2, and E1 Reactions

Competition among S N 2, S N 1, E2, and E1 Reactions. S N 2. S N 1. Competition among S N 2, S N 1, E2, and E1 Reactions. E2. E1. Rate-Determining Steps Revisited. S N 2. S N 1. E2. E1. Nucleophile Strength. The Free Energy Diagram. Hammond Postulate.

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Competition among S N 2, S N 1, E2, and E1 Reactions

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  1. Competition among SN2, SN1, E2, and E1 Reactions SN2 SN1

  2. Competition among SN2, SN1, E2, and E1 Reactions E2 E1

  3. Rate-Determining Steps Revisited SN2 SN1 E2 E1

  4. Nucleophile Strength

  5. The Free Energy Diagram

  6. Hammond Postulate

  7. Hammond Postulate Applied to SN2 Reactions

  8. Nucleophile Strength Revisited

  9. Effective Electronegativity

  10. The Base Strength in E2 and E1 Reactions

  11. The Base Strength in E2 and E1 Reactions

  12. Steric Hindrance in SN2 Reactions

  13. Concentration of the Attacking Species

  14. Leaving Group and pKa

  15. Leaving Groups and SN2 Rates

  16. Leaving Groups and SN1 Rates

  17. Leaving Group Ability and SN2/SN1/E2/E1 Reactions • SN1 reactions are more sensitive to leaving group ability than SN2 reactions are. • Excellent leaving groups favor SN1 and E1 reactions over corresponding SN2 and E2 reactions.

  18. SN2 Reactions and the Hybridization

  19. Effect of Alkyl Groups on the C Bonded to the L

  20. Rate of SN2 and Steric Hindrance

  21. E2 and Steric Hindrance

  22. Rate of SN1 and E1 versus Carbocation Stability

  23. Hyperconjugation secondary can do 2x, tertiary can do 3x

  24. Summary of the Influence of the Number of Alkyl Groups on the Carbon

  25. Solvent Effects

  26. Solvation

  27. Solvent Effects

  28. polar solvents especially good for SN1 (OK for some SN2) aprotic solvents (no H on O or N) cannot H-bond to Nu especially good for SN2

  29. Leaving Group Ability

  30. Regioselectivity in EliminationReactions: Zaitsev’s Rule

  31. Another Example of Zaitsev’s Rule

  32. Exception to Zaitsev’s Rule

  33. Inter- vs Intra- molecular Reaction

  34. Inter- vs Intra- molecular Reaction forms ring

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