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Mastering Organohalides: Substitution and Elimination Reactions

Explore the synthesis and properties of alkyl halides, from Grignard reagents to radical halogenation. Dive into SN2 and SN1 reactions, mechanisms, and influencing factors for reaction rates.

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Mastering Organohalides: Substitution and Elimination Reactions

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  1. Chapter 12: Organohalides 12.5 – 12.15 : Substitution and Elimination Reactions 12.4 : The Grignard Reagent 12.1-12.3 : Preparation of Alkyl Halides p. 445

  2. Properties of Alkyl Halides Table 12-1, p. 446

  3. Properties of Alkyl Halides p. 447

  4. Synthesis of alkyl halides : review • Addition of HX to an alkene (section 7.6) p. 227

  5. Synthesis of alkyl halides : review • Addition of HX to an alkene (section 7.6) • Obeys Markovnikov’s Rule (section 7.7) • Carbocations that can rearrange, will rearrange (section 7.10) p. 239

  6. Synthesis of alkyl halides : review 2. Addition of X2 to an alkene (section 8.2)

  7. Synthesis of alkyl halides : review 3. Radical Halogenation (section 6.3)

  8. Synthesis of alkyl halides : New • From alkenes • Allylicbromination with N-BromoSuccinimide • From Alcohols • Using strong acid • Via Tosylates • Using SOCl2 and PBr3

  9. The Allyl Radical

  10. Synthesis of alkyl halides : New • From alkynes • Allylicbromination with N-BromoSuccinimide • From Alcohols • Using strong acid • Via Tosylates • Using SOCl2 and PBr3

  11. Synthesis of alkyl halides : New • From alkynes • Allylicbromination with N-BromoSuccinimide • From Alcohols • Using strong acid • Via Tosylates • Using SOCl2 and PBr3

  12. Synthesis of alkyl halides : New • From alkynes • Allylicbromination with N-BromoSuccinimide • From Alcohols • Using strong acid • Via Tosylates • Using SOCl2 and PBr3

  13. Organometallics

  14. The Grignard Reagent

  15. The Gilman Reagent

  16. The Suzuzi – Miyaura Cross Coupling The Nobel Prize in Chemistry 2010 "for palladium-catalyzed cross couplings in organic synthesis" Richard F. Heck Ei-ichiNegishi Akira Suzuki

  17. Substitution and Elimination Reactions

  18. Characteristics of the SN2 reaction • Rate equation

  19. Characteristics of the SN2 reaction • Rate equation • Mechanism

  20. Fig. 12-5, p. 459

  21. The Walden Inversion Cycle (1896) (-)-Maleic Acid [a]D = -2.3 (+)-chlorosuccinic acid (+)-Maleic Acid [a]D = +2.3 (-)-chlorosuccinic acid Fig. 12-2, p. 455

  22. SN2

  23. Characteristics of the SN2 reaction • Rate equation • Mechanism • Molecular factors effecting SN2 reaction rate

  24. The Effect of Reactant and Transition Structure Energies on Reaction Rate Fig. 12-6, p. 460

  25. Effect of ELECTROPHILIC CARBON on SN2 rate p. 461

  26. Effect of ELECTROPHILIC CARBON on SN2 rate Fig. 12-7, p. 461

  27. Effect of ELECTROPHILIC CARBON on SN2 rate

  28. Effect of LEAVING GROUP on SN2 rate p. 463

  29. Effect of LEAVING GROUP on SN2 rate

  30. Effect of NUCLEOPHILE on SN2 rate Table 12-2, p. 462

  31. Effect of NUCLEOPHILE on SN2 rate

  32. Effect of Solvent on SN2 rate

  33. Effect of Solvent on SN2 rate

  34. Solvent effects on SN2 rate

  35. Characteristics of the SN1 reaction • Rate equation

  36. Characteristics of the SN1 reaction • Rate equation • 2. Mechanism of SN1 reaction

  37. Stereochemical effects of the SN1 mechanism

  38. Stereochemical effects of the SN1 mechanism

  39. Characteristics of the SN1 reaction • Rate equation • 2. Mechanism of SN1 reaction • 3. Molecular factors effecting SN1 reaction rate

  40. Effect of electrophilic carbon on SN1 rate p. 467

  41. Effect of electrophilic carbon on SN1 rate:Carbocation Stability

  42. Effect of electrophilic carbon on SN1 rate: Resonance in Carbocations Fig. 12-13, p. 471

  43. Bond Disassociation Energies and Carbocation Stability p. 472

  44. Bond Disassociation Energies and Carbocation Stability <  p. 472

  45. Effect of LEAVING GROUP on SN1 rate p. 472

  46. Effect of LEAVING GROUP on SN1 rate Effect of LEAVING GROUP on SN2 rate p. 472

  47. Effect of Solvent on SN1 rate Fig. 12-15, p. 474

  48. Effect of Solvent on SN1 rate p. 474

  49. Predict mechanism for the reactions below.

  50. Predict mechanism for the reactions below.

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