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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 Hydrohalogenation i. alkenes ii. alkynes 2. Halogenation i. alkenes ii. alkynes Halohydrins i. alkenes

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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 • Hydrohalogenation • i. alkenes • ii. alkynes • 2. Halogenation • i. alkenes • ii. alkynes • Halohydrins • i. alkenes • ii. alkynes • 4. Hydration • i. alkenes • ii. alkynes

  4. Alkenes & Alkynes • Reactions of alkenes & alkynes • A. Electrophilic Additions • Hydrohalogenation • i. alkenes • ii. alkynes

  5. Electrophilic addition of Br2 to an alkene

  6. p. 217

  7. p. 218

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

  9. Alkenes & Alkynes • Reactions of alkenes & alkynes • A. Electrophilic Additions • Halohydrins • i. alkenes

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

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

  12. Alkenes & Alkynes • Reactions of alkenes & alkynes • A. Electrophilic Additions • 4. Hydration • i. alkenes • a. hydroboration & oxidation

  13. p. 223

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

  15. Jmol

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

  17. Alkenes & Alkynes • Reactions of alkenes & alkynes • A. Electrophilic Additions • 4. Hydration • i. alkynes • b. oxymercuration

  18. Alkenes & Alkynes • Reactions of alkenes & alkynes • A. Electrophilic Additions • 4. Hydration • i. alkynes • a. hydroboration & oxidation

  19. Alkenes & Alkynes • Reactions of alkenes & alkynes • B. Reductions • 1. Alkenes • i. Catalytic hydrogenation

  20. Alkenes & Alkynes • Reactions of alkenes & alkynes • B. Reductions • 1. Alkynes • i. Catalytic hydrogenation • a. Complete reduction

  21. Alkenes & Alkynes • Reactions of alkenes & alkynes • B. Reductions • 1. Alkynes • i. Catalytic hydrogenation • b. Lindlar’s catalyst (partial reduction)

  22. Alkenes & Alkynes • Reactions of alkenes & alkynes • C. Reductions • 1. Alkynes • ii. Dissolving metal reduction (partial reduction)

  23. epep !

  24. Alkenes & Alkynes • Reactions of alkenes & alkynes • C. Alkyne alkylation

  25. Fig. 8-19, p. 292

  26. Alkenes & Alkynes • Reactions of alkenes & alkynes • D. Carbene addition

  27. Fig. 7-6, p. 228

  28. Carbenes

  29. Alkenes & Alkynes • Reactions of alkenes & alkynes • E. Oxidations • Introduction

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

  31. Epoxide formation through reaction of peracids

  32. Alkenes & Alkynes • Reactions of alkenes & alkynes • E. Oxidations • 1. epoxidation • ii. via halohydrins

  33. 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

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

  35. Sharpless epoxidation (CH3)3COOH

  36. Knowles Asymmetric Reduction

  37. Alkenes & Alkynes • Reactions of alkenes & alkynes • E. Oxidations • 2. dihydroxylation • i. osmium tetraoxide

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

  39. Alkenes & Alkynes • Reactions of alkenes & alkynes • E. Oxidations • 2. Dihydroxylation • Application : Synthesis

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

  41. p. 237

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

  43. Alkenes & Alkynes • Reactions of alkenes & alkynes • E. Oxidations • 3. oxidative cleavage • ii. permanganate

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

  45. Alkenes & Alkynes • Reactions of alkenes & alkynes • F. Conjugated Dienes • Introduction

  46. Fig. 8-12, p. 281

  47. Fig. 8-13, p. 282

  48. Fig. 8-14, p. 282

  49. Alkenes & Alkynes • Reactions of alkenes & alkynes • F. Conjugated Dienes • 1. Addition of HX

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