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p. 251

p. 251. Alkenes & Alkynes. Prepapration of alkenes 1. Dehydrohalogenation 2. Dehydration. Alkenes & Alkynes. Reactions of alkenes & alkynes A. Electrophilic Additions to Alkenes Hydrohalogenation 2. Halogenation Halohydrins 4. Hydration. Alkenes & Alkynes.

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p. 251

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  1. p. 251

  2. Alkenes & Alkynes • Prepapration of alkenes • 1. Dehydrohalogenation • 2. Dehydration

  3. Alkenes & Alkynes • Reactions of alkenes & alkynes • A. Electrophilic Additions to Alkenes • Hydrohalogenation • 2. Halogenation • Halohydrins • 4. Hydration

  4. Alkenes & Alkynes • Reactions of alkenes & alkynes • A. Electrophilic Additions to Alkenes • Hydrohalogenation (Chapter 7)

  5. Alkenes & Alkynes • Reactions of alkenes & alkynes • A. Electrophilic Additions to Alkenes • 2. Halogenation

  6. Electrophilic addition of Br2 to an alkene

  7. p. 217

  8. p. 218

  9. Alkenes & Alkynes • Reactions of alkenes & alkynes • A. Electrophilic Additions to Alkenes • 2. Halogenation (working backwards)

  10. Alkenes & Alkynes • Reactions of alkenes & alkynes • A. Electrophilic Additions to Alkenes • Halohydrins

  11. Alkenes & Alkynes • Reactions of alkenes & alkynes • A. Electrophilic Additions to Alkenes • 4. Hydration • i. acid catalyzed

  12. Alkenes & Alkynes • Reactions of alkenes & alkynes • A. Electrophilic Additions to Alkenes • 4. Hydration • ii. oxymercurication

  13. Alkenes & Alkynes • Reactions of alkenes & alkynes • A. Electrophilic Additions to Alkenes • 4. Hydration • iii. Hydroboration & oxidation

  14. p. 223

  15. + + - - d d d d Fig. 7-4, p. 225

  16. Jmol

  17. Alkenes & Alkynes • Reactions of alkenes & alkynes • B. Electrophilic Additions to Alkynes • Hydrohalogenation (Chapter 7) • 2. Halogenation • Halohydrins • 4. Hydration

  18. Alkenes & Alkynes • Reactions of alkenes & alkynes • B. Electrophilic Additions to Alkynes • 3. Halohydrins

  19. Alkenes & Alkynes • Reactions of alkenes & alkynes • B. Electrophilic Additions to Alkynes • 4. Hydration • i. acid catalyzed

  20. Alkenes & Alkynes • Reactions of alkenes & alkynes • B. Electrophilic Additions to Alkynes • 4. Hydration • ii. oxymercuration

  21. Alkenes & Alkynes • Reactions of alkenes & alkynes • B. Electrophilic Additions to Alkynes • 4. Hydration • ii. Hydroboratoin & oxidation

  22. Alkenes & Alkynes • Reactions of alkenes & alkynes • C. Reductions • 1. Alkenes • i. Catalytic hydrogenation

  23. Alkenes & Alkynes • Reactions of alkenes & alkynes • C. Reductions • 2. Alkynes • i. Catalytic hydrogenation • a. Complete reduction

  24. Alkenes & Alkynes • Reactions of alkenes & alkynes • C. Reductions • 2. Alkynes • Catalytic hydrogenation • ii. Lindlar’s catalyst (partial reduction)

  25. Alkenes & Alkynes • Reactions of alkenes & alkynes • C. Reductions • 2. Alkynes • iii. Dissolving metal reduction (partial reduction)

  26. epep !

  27. Alkenes & Alkynes • Reactions of alkenes & alkynes • D. Alkyne alkylation

  28. Fig. 8-19, p. 292

  29. Alkenes & Alkynes • Reactions of alkenes & alkynes • E. Carbene addition

  30. Fig. 7-6, p. 228

  31. Carbenes

  32. Alkenes & Alkynes • Reactions of alkenes & alkynes • F. Oxidations • Introduction

  33. Alkenes & Alkynes • Reactions of alkenes & alkynes • E. Oxidations • 1. epoxidation • Peracids (RCO3H)

  34. Epoxide formation through reaction of peracids

  35. Alkenes & Alkynes • Reactions of alkenes & alkynes • F. Oxidations • 1. epoxidation • ii. via halohydrins

  36. The Nobel Prize in Chemistry 2001 "for their work on chirally catalysed hydrogenation reactions" "for his work on chirally catalysed oxidation reactions" William S. Knowles Ryoji Noyori K. Barry Sharpless

  37. Thalidomide • Racemic thalidomide prescribed for morning sickness (1956 – 1961) • (R)-enantiomer is an antiemetic • (S)-enantiomer is a teratogen

  38. Sharpless epoxidation (CH3)3COOH

  39. Knowles Asymmetric Reduction

  40. Alkenes & Alkynes • Reactions of alkenes & alkynes • F. Oxidations • 2. dihydroxylation • i. osmium tetraoxide

  41. Alkenes & Alkynes • Reactions of alkenes & alkynes • E. Oxidations • 2. dihydroxylation • ii. from epoxides

  42. Alkenes & Alkynes • Reactions of alkenes & alkynes • F. Oxidations • 2. Dihydroxylation • Application : Synthesis

  43. Alkenes & Alkynes • Reactions of alkenes & alkynes • E. Oxidations • 3. oxidative cleavage • i. ozonolysis

  44. p. 237

  45. Alkenes & Alkynes • Reactions of alkenes & alkynes • E. Oxidations • 3. oxidative cleavage • i. ozonolysis

  46. Alkenes & Alkynes • Reactions of alkenes & alkynes • F. Oxidations • 3. oxidative cleavage • ii. permanganate

  47. Alkenes & Alkynes • Reactions of alkenes & alkynes • F. Oxidations • 3. oxidative cleavage • iii. from diols

  48. Alkenes & Alkynes • Reactions of alkenes & alkynes • G. Conjugated Dienes • Introduction

  49. Fig. 8-12, p. 281

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