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Carboxylic Acids: Properties and Synthesis

Carboxylic Acids: Properties and Synthesis. Chapter 18. Assignments. In-text problems: 18-1 and 18-2 18-4 (IUPAC only!!) 18-6 to 18-10 18-14 to 18-20 End-of-chapter problems: 1 3 to 9 11 to 16 . Sect. 18.1: IUPAC Nomenclature. -oic acid IUPAC ending

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Carboxylic Acids: Properties and Synthesis

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  1. Carboxylic Acids:Properties and Synthesis Chapter 18 WWU- Chemistry

  2. Assignments • In-text problems: • 18-1 and 18-2 • 18-4 (IUPAC only!!) • 18-6 to 18-10 18-14 to 18-20 • End-of-chapter problems: • 1 • 3 to 9 • 11 to 16 WWU- Chemistry

  3. Sect. 18.1: IUPAC Nomenclature • -oic acid IUPAC ending • -carboxylic acid IUPAC ending for ring compounds WWU- Chemistry

  4. 3-Methylbutanoic acid WWU- Chemistry

  5. 2-Chloropentanoic acid WWU- Chemistry

  6. 4-methoxy-3,5-hexadienoic acid WWU- Chemistry

  7. Cyclohexanecarboxylic acid WWU- Chemistry

  8. 3-methylcyclohexanecarboxylic acid WWU- Chemistry

  9. Benzoic acid or Benzenecarboxylic acid WWU- Chemistry

  10. Numbering system WWU- Chemistry

  11. 2-chlorobenzoic acid or 2-chlorobenzenecarboxylic acid WWU- Chemistry

  12. Common names for benzoic acids WWU- Chemistry

  13. Common names! ortho-chlorobenzoic acid o-chlorobenzoic acid WWU- Chemistry

  14. IUPAC only 3-chloro-2-nitrobenzoic acid or 3-chloro-2-nitrobenzenecarboxylic acid WWU- Chemistry

  15. IUPAC only 3-(3-nitrophenyl)propanoic acid WWU- Chemistry

  16. Common Names WWU- Chemistry

  17. Some more common names • butyric acidand isobutyric acid • valeric acid and isovaleric acid • Fatty acids: myristic, palmitic and stearic acids WWU- Chemistry

  18. 2-Methylpropanoic acid Isobutyric acid WWU- Chemistry

  19. Fatty acids WWU- Chemistry

  20. Sect. 18.2: carboxylate salts • endings: oate • combine with sodium, potassium etc. • Example: sodium butanoate (IUPAC) or sodium butyrate (common) WWU- Chemistry

  21. Carboxylate Ion Formation WWU- Chemistry

  22. Sect. 18.3: hydrogen bonding Carboxylic acids are very high boiling! Low MW acids are water soluble and High MW acids are water insoluble! WWU- Chemistry

  23. Sections 18.4, 18.5, 18.6 • Much of this material is review! • Key table: Table 18-18 on page 62!! • Skip Section 18.7. WWU- Chemistry

  24. Resonance Effects Effect Acid Base Examples Electron withdrawing by resonance (-R) weaken strengthen releasing by Resonance (+R) Electron weaken strengthen WWU- Chemistry

  25. Electron-withdrawing effects involving resonance (-R)These substituents strengthen acids and weaken bases on the benzene ring WWU- Chemistry

  26. Substituents with Electron-Withdrawing Resonance Effects WWU- Chemistry

  27. Electron-withdrawing Effects: strengthen acids weaken bases WWU- Chemistry

  28. A substituted benzoic acid WWU- Chemistry

  29. Electron releasing effect by resonance (+R)These substituents weaken acids and strengthen bases on the benzene ring WWU- Chemistry

  30. Substituents with Electron-Releasing Resonance Effects WWU- Chemistry

  31. Electron-releasing Effects: • - weaken acids • - strengthen bases WWU- Chemistry

  32. Substituted benzoic acid WWU- Chemistry

  33. Benzoic Acid: pKa = 4.19 WWU- Chemistry

  34. Inductive Effect Effect Acid Base Examples weaken Electron withdrawing by inductive effect (-I) strengthen electron releasing by inductive effect (+I) weaken strengthen WWU- Chemistry

  35. Electron withdrawing by inductive effects (-I)These substituents strengthen acids and weaken bases WWU- Chemistry

  36. Substituents with Electron-Withdrawing Inductive Effects on substituted acetic acids WWU- Chemistry

  37. WWU- Chemistry

  38. Inductive and resonance Inductive, only Resonance and weak inductive Benzoic Acid: pKa = 4.19 WWU- Chemistry

  39. Another substituted benzoic acid • 4-chlorobenzoic acid is weird!! Resonance effect will decrease acidity, but inductive effect wins out. WWU- Chemistry

  40. Electron releasing effect by inductive effect (+I)These substituents weaken acids and strengthen bases WWU- Chemistry

  41. Substituents with Electron-Releasing Inductive Effects WWU- Chemistry

  42. WWU- Chemistry

  43. Benzoic Acid: pKa = 4.19 WWU- Chemistry

  44. Sect. 18.8: Carbonation of Grignard Reagents WWU- Chemistry

  45. Sect. 18.9: Formation of Nitriles WWU- Chemistry

  46. Hydrolysis of Nitriles WWU- Chemistry

  47. Sect. 18.10: Oxidation of Primary Alcohols WWU- Chemistry

  48. Oxidation of Side Chains WWU- Chemistry

  49. WWU- Chemistry

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