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Chapter 12 Nucleophilic Substitution: Reactions and Synthetic Applicatons

Chapter 12 Nucleophilic Substitution: Reactions and Synthetic Applicatons. Chapter 12 Problem Assignments. 1 a through f 2 a, b, c, e, f 3 4 a, b, f 5, 6, 7 12 a, b 13 a, b 15 21 b 22 a, e 23 26 a 27 a, c 30 a, b, c 32 35, 36 37 a 38 46 a 51 a, b

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Chapter 12 Nucleophilic Substitution: Reactions and Synthetic Applicatons

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  1. Chapter 12Nucleophilic Substitution:Reactions and Synthetic Applicatons

  2. Chapter 12 Problem Assignments 1 a through f 2 a, b, c, e, f 3 4 a, b, f 5, 6, 7 12 a, b 13 a, b 15 21 b 22 a, e 23 26 a 27 a, c 30 a, b, c 32 35, 36 37 a 38 46 a 51 a, b 54 62, 63 a 64 a, c 65 a, d, g 68 74

  3. Sect. 12.1: Nomenclature of alcohols alcohols are named as: alkanol you need a number to indicate where the OH group is located on the chain.

  4. Common names of alcohols(IUPAC names in parentheses) • methyl alcohol (methanol) • ethyl alcohol (ethanol) • propyl alcohol (1-propanol) • isopropyl alcohol (2-propanol) • butyl alcohol (1-butanol) • sec-butyl alcohol (2-butanol) • isobutyl alcohol (2-methyl-1-propanol) • tert-butyl alcohol (2-methyl-2-propanol)

  5. Sect. 12.2: Nomenclature of ethers • Ethers are mainly given “common” names: dimethyl ether diethyl ether ethyl methyl ether • IUPAC names use methoxy, ethoxy, etc 3-methoxyhexane 4-ethoxy-1-pentene

  6. Sect. 12.3: Nucleophilic substitution

  7. Nucleophilic Substitution (SN2)

  8. Nitrogen as a nucleophile (SN2)

  9. Carbon as a nucleophile (SN2)

  10. Sect. 12.4: Alcohols to halides with H-X; assisted ionization • R = primary; SN2 • R = secondary (both) • R = tertiary, allylic or benzylic, SN1 • Rearrangement is a serious side reaction with carbocation reactions!

  11. Assisted SN2: Mechanism

  12. Assisted SN1: Mechanism

  13. Alcohols + Phosphorus Halides

  14. Alcohol + Phosphorus Halide • This method is best for primary and secondary alcohols. • This method is generally unsuccessful with tertiary alcohols • Rearrangements do not happen with this method.

  15. HBr or PBr3??? PBr3 PBr3 H-Br will give rearrangement!

  16. Synthesis Problem #1 PBr3

  17. Chapter 12 • Sections 12.5 and 12.6: Skip!

  18. Sect 12.7: Synthesis of Ethers Williamson Ether Synthesis

  19. Synthesis Problem #2 and

  20. Synthesis Problem #3 (Methyl tert-Butyl Ether, MTBE) Do this by SN1 and SN2

  21. MTBE: Williamson Ether Synthesis: primary substrate

  22. MTBE: Williamson Ether Synthesis: tertiary substrate

  23. Sect. 12.8: Reactions of Epoxides

  24. More Reactions of Epoxides

  25. General Reaction of Epoxides: basic conditions; hits less substituted carbon

  26. Under Acidic Conditions; hits more substituted position

  27. Synthesis of Heliannuol E

  28. Synthesis of Heliannuol C

  29. Chapter 12 • These reactions have already been covered • Section 12.9: Synthesis of esters • Section 12.10: Synthesis of sulfur compounds • Section 12.11: Synthesis of amines

  30. An amine synthesis for you!

  31. Chapter 12 • These reactions have already been covered • Section 12.12: Ambident nucleophiles • Section 12.13: Synthesis of alkanes • Section 12.14: Synthesis of alkynes • Section 12.15: Synthesis of nitriles

  32. An nitrile synthesis for you!

  33. Synthesis Problem #4

  34. This problem makes use of the reactions from this chapter and Infrared spectroscopy

  35. Mary was given an unknown compound A, and told to perform the reactions listed below. She obtained the infrared spectra for each of the products. Help her to determine the structures. (Answers given 7 slides from this one!) B C A H2SO4/HgSO4 Ni / H2 C8H6 C8H8O C8H10O 2 atm H2O TsCl pyridine NaCN Spectra are on the pages that follow. acetone Ni / H2 C9H13N C9H9N D E 2 atm

  36. Compound A 2110 3310

  37. Compound B 1686

  38. Compound C 3353

  39. Compound D 2243

  40. Compound E 3374 3293

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