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Nucleophilic Substitution Reactions: Reactions and Synthetic Applications

Nucleophilic Substitution Reactions: Reactions and Synthetic Applications. Assignment for Chapter 12. Read Sections 12.0 through 12.4 SKIP Pages 1108 (bottom) through 1112 (Sect. 12.4) New material on N-bromosuccinimide reactions SKIP Sections 12.5 through 12.6

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Nucleophilic Substitution Reactions: Reactions and Synthetic Applications

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  1. Nucleophilic Substitution Reactions:Reactions and Synthetic Applications WWU -- Chemistry

  2. Assignment for Chapter 12 • Read Sections 12.0 through 12.4 • SKIP Pages 1108 (bottom) through 1112 (Sect. 12.4) • New material on N-bromosuccinimide reactions • SKIP Sections 12.5 through 12.6 • Read Sections 12.7 through 12.8 • SKIP Section 12.9 • Read Sections 12.10 through 12.11 • SKIP Section 12.12 • Read Sections 12.13 through end of chapter • ORGANIC NOMENCLATURE: Alcohols and Ethers WWU -- Chemistry

  3. Problem Assignment • In-Text Problems • 12-1 through 12-8 • 12-12 through 12-24 • 12-27 through 12-32 • 12-34 through 12-39 • End-of-Chapter Problems • 40 through 42 • 46 through 54 • 57 through 61 • 63 through 75 WWU -- Chemistry

  4. General Rules for Nomenclature • Choose the longest continuous chain of carbon atoms which includes the carbon atom bearing the functional group. This chain will identify the parent hydrocarbon. • Number the parent carbon chain from the end nearest the functional group, irrespective of other substitution. • Indicate the substituents by name and number. Assign a number to the carbon atom bearing the functional group. • Combine all parts into one word, using correct punctuation. WWU -- Chemistry

  5. General Rules for Nomenclature (continued) • Show the presence of the functional group by replacing the -e of the alkane ending (sometimes the -ane) with the appropriate ending for the functional group. Show the position of the functional group by inserting a number into the name immediately before the name of the parent chain. WWU -- Chemistry

  6. Block Diagram for Nomenclature WWU -- Chemistry

  7. Nucleophilic Substitution WWU -- Chemistry

  8. Nucleophilic Substitution WWU -- Chemistry

  9. Assisted Nucleophilic Substitution WWU -- Chemistry

  10. Assisted SN2: Mechanism WWU -- Chemistry

  11. Assisted SN1: Mechanism WWU -- Chemistry

  12. Alcohol + Hydrogen Halide • This method is best with tertiary alcohols • This reaction works very slowly with primary and secondary alcohols. • Rearrangements are possible! WWU -- Chemistry

  13. Neopentyl Alcohol + Lucas Reagent WWU -- Chemistry

  14. Alcohols + Phosphorus Halides WWU -- Chemistry

  15. 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. WWU -- Chemistry

  16. Preparation of Tosylates TsCl R-OTs WWU -- Chemistry

  17. Which Alkyl Halide Should I Use? • If the halide is a better leaving group, the reaction will go in higher yield. I- > Br- > Cl- • If the halide is cheaper, the reaction will be more economical. Cl- > Br- > I- WWU -- Chemistry

  18. Best compromise… Alkyl bromides! Exception: For CH3—X, use Methyl iodide Which Alkyl Halide Should I Use? (Part Two) WWU -- Chemistry

  19. Addition of Hydrogen Halides to Double Bonds This reaction follows Markovnikov’s Rule Chapter 8, Section 8.4 WWU -- Chemistry

  20. Free Radical Halogenation of Alkanes Chapter 3, Section 3.17 WWU -- Chemistry

  21. Allylic Halogenation with N-Bromosuccinimide WWU -- Chemistry

  22. Mechanism – Step 1 WWU -- Chemistry

  23. Mechanism – Step 2 WWU -- Chemistry

  24. Mechanism – Step 3 WWU -- Chemistry

  25. Mechanism – Step 4 WWU -- Chemistry

  26. Halogenation at a Benzylic Position WWU -- Chemistry

  27. Benzylic Substitution – Mechanism Step 2 WWU -- Chemistry

  28. Conversion of Alkyl Halides to Alcohols SN1 SN2 WWU -- Chemistry

  29. Synthesis of Ethers WWU -- Chemistry

  30. Williamson Ether Synthesis SN2 WWU -- Chemistry

  31. General Reaction of Epoxides WWU -- Chemistry

  32. Under Acidic Conditions… WWU -- Chemistry

  33. Reactions of Epoxides WWU -- Chemistry

  34. More Reactions of Epoxides WWU -- Chemistry

  35. Reactions of Epoxides in Basic Medium WWU -- Chemistry

  36. Reactions of Epoxides in Acidic Medium WWU -- Chemistry

  37. Synthesis of Heliannuol E Hydrolyze to remove methyl group. WWU -- Chemistry

  38. Synthesis of Heliannuol C Hydrolyze to remove methyl group. WWU -- Chemistry

  39. Synthesis Problem #1 WWU -- Chemistry

  40. Outline the Mechanism WWU -- Chemistry

  41. HBr or PBr3??? WWU -- Chemistry

  42. Synthesis Problem #2 WWU -- Chemistry

  43. Synthesis of MTBE(Methyl tert-Butyl Ether) WWU -- Chemistry

  44. Synthesis Problem #3 WWU -- Chemistry

  45. Reactions of Epoxides WWU -- Chemistry

  46. More Reactions of Epoxides WWU -- Chemistry

  47. What are the Products? WWU -- Chemistry

  48. Synthesis Problem #4 WWU -- Chemistry

  49. The Synthesis Problem from Hell! WWU -- Chemistry

  50. Try this! Plus any additional needed reagents and solvents WWU -- Chemistry

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