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p. 445

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. The Walden Inversion Cycle (1896). (-)-Maleic Acid [ a ] D = -2.3. (+)-chlorosuccinic acid. (+)-Maleic Acid [ a ] D = +2.3.

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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. 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

  3. Fig. 12-5, p. 459

  4. http://www.chemtube3d.com/Main%20Page.html

  5. Characteristics of the SN2 reaction • Rate equation

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

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

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

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

  10. The sterics around the electrophilic carbon alters the SN2 rate by changing… • The ground state energy of the starting materials. • The energy of the transition state.

  11. Effect of ELECTROPHILIC CARBON on SN2 rate

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

  13. The leaving group alters the SN2 rate by changing… • The ground state energy of the starting materials. • The energy of the transition state.

  14. Effect of LEAVING GROUP on SN2 rate

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

  16. The nucleophile alters the SN2 rate by changing… • The ground state energy of the starting materials. • The energy of the transition state.

  17. Effect of NUCLEOPHILE on SN2 rate

  18. Effect of Solvent on SN2 rate p. 465

  19. Well solvated anion (reduced nucleophilicity) Poorly solvated anion (increased nucleophilicity)

  20. The solvent alters the SN2 rate by changing… • The ground state energy of the starting materials. • The energy of the transition state.

  21. Solvent effects on SN2 rate

  22. Fig. 12-8, p. 466

  23. Characteristics of the SN1 reaction • Rate equation

  24. Characteristics of the SN1 reaction • Rate equation • Molecular factors effecting SN1 reaction rate

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

  26. Stereochemical effects of the SN1 mechanism Fig. 12-11, p. 469

  27. Stereochemical effects of the SN1 mechanism Fig. 12-12, p. 470

  28. Effect of electrophilic carbon on SN1 rate:Carbocation Stability p. 472

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

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

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

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

  33. Effect of Solvent on SN1 rate p. 474

  34. SN2 vs. SN1

  35. What is the mechanism for the reaction below? • SN1 • SN2

  36. What is the mechanism for the reaction below? • SN1 • SN2

  37. What is the mechanism for the reaction below? • SN1 • SN2

  38. What is the mechanism for the reaction below? • SN1 • SN2

  39. Elimination Reactions • Intro: Eliminations vs. Substitutions • The E2 Mechanism • Rate • Molecular factors effecting the E2 mechanism •  Stereochemistry •  Zaitzev’s Rule •  Barton’s Experiments

  40. Stereochemistry of the E2 mechanism Fig. 12-19, p. 482

  41. Elimination Reactions : The E1 Mechanism • Rate • E1 and SN1 • Molecular factors effecting the E2 mechanism •  Stereochemistry •  Zaitzev’s Rule

  42. Summing it all up : SN1, SN2, E1 and E2 • Primary Alkyl Halides • Secondary Alkyl Halide • Tertiary Alkyl Halides

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

  44. Properties of Alkyl Halides p. 447

  45. The Grignard Reagent p. 453

  46. Synthesis of alkyl halides : review • Addition of HX to an alkene (section 7.6) • Obeys Markovnikov’s Rule (section 7.7) p. 227

  47. 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

  48. Synthesis of alkyl halides : review 2. Addition of X2 to an alkene (section 8.2) Anti addition p. 255

  49. Synthesis of alkyl halides : review 3. Radical Halogenation (section 6.3) Statistical p. 255

  50. Synthesis of alkyl halides : New • From alkynes • Allylic bromination with N-Bromo Succinimide • From Alcohols • Using strong acid • Via Tosylates • Using SOCl2 and PBr3

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