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Compounds with Polar p Bonds

This article discusses compounds with polar p bonds and their reactions with nucleophiles, including nucleophilic addition-elimination reactions. It also covers the hydration rate, equilibrium constants, structural comparison, inductive effects, and reduction using LiAlH4 and NaBH4. Additionally, it explores the Grignard reaction and mechanism, synthesis using organometallics and direct/conjugate addition, as well as the advantages of Wittig reactions in synthesizing alkenes.

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Compounds with Polar p Bonds

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  1. Compounds with Polar p Bonds • In each of these species on the right, however, the C atom of the polar π bond possesses a leaving group. • The presence of a leaving group facilitates another type of reaction with nucleophiles, called nucleophilic addition–elimination reactions.

  2. Hydration Rate and Equilibrium Constants

  3. Structural Comparison

  4. Inductive Effects

  5. Reduction p. 617

  6. Reduction • Green Principles Addresses • Less Hazardous Reagents • Safer Solvent • Use of Renewable Feedstocks • Catalysis

  7. Selective Reduction

  8. LiAlH4 and NaBH4 Reactivity with a Proton Source

  9. Reduction of Other Functional Groups LiAlH4 must be used for both reductions

  10. Sodium Hydride

  11. Some Feasible Grignard Reagents • A Grignard reagent should not contain functional groups that react with strong bases or strong nucleophiles. • The Grignard reagents below are unfeasible.

  12. Grignard Reaction and Mechanism

  13. Grignard Reactions Can Be Used to Produce Carboxylic acids

  14. Wittig • Green Principles Addresses • Less Hazardous Reagents • Safer Solvent • Energy Efficiency

  15. Direct 1,2-Addition Mechanism

  16. Reversibility in Nucleophilic Addition

  17. Thermodynamic Product

  18. Thermodynamic or Kinetic Product?

  19. Organometallics in Synthesis

  20. Organometallics in Synthesis

  21. Synthesis and Direct/Conjugate Addition

  22. Synthesis and Direct/Conjugate Addition

  23. Synthesis and Direct/Conjugate Addition

  24. Synthesis and Direct/Conjugate Addition

  25. Synthesizing Alkenes: Wittig Reactions Are Better

  26. Synthesizing Alkenes: Wittig Reactions Are Better

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