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Chapter 8

Chapter 8. Alkyne. Properties. C n H 2n-2 Reactions of alkyne that are common to alkene are additions and oxidations. Reactions that are specific to alkyne involve acidity of  C  H (acetylenic) hydrogen. sp hybridization - linear. Alkyne. Naming Synthesis Reactions. Naming.

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Chapter 8

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  1. Chapter 8 Alkyne Chapter 8 - Alkyne

  2. Properties • CnH2n-2 • Reactions of alkyne that are common to alkene are additions and oxidations. • Reactions that are specific to alkyne involve acidity of  C  H (acetylenic) hydrogen. • sp hybridization - linear. Chapter 8 - Alkyne

  3. Alkyne • Naming • Synthesis • Reactions Chapter 8 - Alkyne

  4. Naming 2,5-Dimethyl-3-hexyne Chapter 8 - Alkyne

  5. Naming 3,3-Dimethyl-1-butyne Chapter 8 - Alkyne

  6. Naming 3,3-Dimethyl-4-Octyne Chapter 8 - Alkyne

  7. Naming 2,5,5-Trimethyl-3-heptyne Chapter 8 - Alkyne

  8. Naming 2,4-octadien-6-yne Chapter 8 - Alkyne

  9. Naming 6-Isopropylcyclodecyne Chapter 8 - Alkyne

  10. Naming 3-Chloro-1-propyne 5-Hexyne-1-ol 3-butyn-2-ol Chapter 8 - Alkyne

  11. Alkyne • Naming • Synthesis • Reactions Chapter 8 - Alkyne

  12. Addition Elimination Alkyne Synthesis Dehydrohalogenation of halides Halogenation of alkene: Halogenation/dehydrohalogenation Chapter 8 - Alkyne

  13. allylic vinylic alkyl Alkyne Synthesis vinylic halides Chapter 8 - Alkyne

  14. Alkyne • Naming • Synthesis • Reactions Chapter 8 - Alkyne

  15. Reactions • Addition of HX and X2 • Hydration - mercuration and hydroboration • Reduction • Oxidation • Alkylation Chapter 8 - Alkyne

  16. Bond Energies Alkyne reactions are similar to alkenes - center around the pi bond. Chapter 8 - Alkyne

  17. Addition of HX and X2 Follow Markovnikov’s rule & trans addition. Chapter 8 - Alkyne

  18. Reactions • Addition of HX and X2 • Hydration - mercuration and hydroboration • Reduction • Oxidation • Alkylation Chapter 8 - Alkyne

  19. Mercuration Oxymercuration alkene alcohol enol alkyne vinyl alcohol keto tautomerism isomerization Chapter 8 - Alkyne

  20. Resonance stabilized intermediate enol keto Chapter 8 - Alkyne

  21. - ol -al Note! Chapter 8 - Alkyne

  22. Mercuration Chapter 8 - Alkyne

  23. Answer Key Chapter 8 - Alkyne

  24. Mercuration Chapter 8 - Alkyne

  25. Answer Key Chapter 8 - Alkyne

  26. Mercuration Summary • Alkyne  Ketone. • Tautomerism enol  keto. • Follow Markovnikov rule. • Acid catalyzed. Chapter 8 - Alkyne

  27. Reactions • Addition of HX and X2 • Hydration - mercuration and hydroboration • Reduction • Oxidation • Alkylation Chapter 8 - Alkyne

  28. Hydroboration alkene alcohol Chapter 8 - Alkyne

  29. enol keto Resonance stabilized intermediate Chapter 8 - Alkyne

  30. Acid enol is protonated first then loses a proton. Base enol loses a proton then regains it. Chapter 8 - Alkyne

  31. Hydroboration Chapter 8 - Alkyne

  32. Answer Key Chapter 8 - Alkyne

  33. Hydroboration Summary • Alkyne  Ketone (internal ) or aldehyde (terminal ). • Tautomerism enol  keto. • Follow non-Markovnikov rule. • Base catalyzed. Chapter 8 - Alkyne

  34. Hydroboration - Mercuration Chapter 8 - Alkyne

  35. Answer Key Chapter 8 - Alkyne

  36. Reactions • Addition of HX and X2 • Hydration - mercuration and hydroboration • Reduction • Oxidation • Alkylation Chapter 8 - Alkyne

  37. Reduction alkene alkane Chapter 8 - Alkyne

  38. Reduction Chapter 8 - Alkyne

  39. Answer Key Chapter 8 - Alkyne

  40. Reactions • Addition of HX and X2 • Hydration - mercuration and hydroboration • Reduction • Oxidation • Alkylation Chapter 8 - Alkyne

  41. Oxidation aldehyde alkene acid Chapter 8 - Alkyne

  42. Oxidation Chapter 8 - Alkyne

  43. Answer Key Chapter 8 - Alkyne

  44. Oxidation Summary • Alkyne  caboxylic acid and CO2. • Shortening the chain. Chapter 8 - Alkyne

  45. Reactions • Addition of HX and X2 • Hydration - mercuration and hydroboration • Reduction • Oxidation • Alkylation Chapter 8 - Alkyne

  46. Alkylation deprotonated acetylide anion sodium amide carbanion powerful nucleophile acidic reaction center Chapter 8 - Alkyne

  47. Alkylation Chapter 8 - Alkyne

  48. Alkylation Chapter 8 - Alkyne

  49. Answer Key Chapter 8 - Alkyne

  50. Chapter 8 - Alkyne

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