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Acid Chlorides Preparation and Reactions

Acid Chlorides Preparation and Reactions. Preparation of an Acid Chloride (“A” Method). Example. Example #2. Preparation of Acid Chlorides (“C+” Method). Preparation of an Acid Chloride (“C-” Method).

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Acid Chlorides Preparation and Reactions

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  1. Acid ChloridesPreparation and Reactions WWU-Chemistry

  2. Preparation of an Acid Chloride(“A” Method) WWU-Chemistry

  3. Example WWU-Chemistry

  4. Example #2 WWU-Chemistry

  5. Preparation of Acid Chlorides(“C+” Method) WWU-Chemistry

  6. Preparation of an Acid Chloride(“C-” Method) The single advantage to this method is that it does not produce HCl as a product. Use this method when your molecule can’t stand HCl. WWU-Chemistry

  7. Hydrolysis of an Acid Chloride • Notice the direction of the equilibrium arrow. • Explain why you can’t make an acid chloride by reacting a carboxylic acid with hydrogen chloride. • This explains why acid chlorides are very moisture-sensitive and why it is difficult to store them. WWU-Chemistry

  8. Preparation of an Ester(“A” Method) Because the ester is so much more stable than the acid chloride, this reaction proceeds at a rapid rate and in high yield. WWU-Chemistry

  9. Example WWU-Chemistry

  10. Preparation of an Amide(“A” Method) • Two equivalents of amine are required. • The first equivalent acts as nucleophile to form the amide • The second equivalent acts as a base and reacts with the HCl that is formed. WWU-Chemistry

  11. Example #1(Ammonia is the Nucleophile) Because the amide is so much more stable than the acid chloride, this reaction proceeds rapidly and in high yield. WWU-Chemistry

  12. Example #2(Primary Amine is the Nucleophile) WWU-Chemistry

  13. Example #3(Secondary Amine is the Nucleophile) WWU-Chemistry

  14. Preparation of an Acid Anhydride • This will also work with an acid chloride and a carboxylate anion. • Because the acid chloride is less stable than the acid anhydride, this reaction proceeds rapidly and in good yield. WWU-Chemistry

  15. Example WWU-Chemistry

  16. Rosenmund Reduction Recall this from Chapter 17, Section 17.17 WWU-Chemistry

  17. Example WWU-Chemistry

  18. Also... WWU-Chemistry

  19. By contrast, lithium aluminum hydride reduces acid chlorides all the way to alchols. WWU-Chemistry

  20. Example WWU-Chemistry

  21. Acid chlorides react with enamines to yield 1,3-dicarbonyl compounds • In this reaction, the first step involves formation of the enamine • see Chapter 16, Section 16.13 • The enamine, being highly nucleophilic, reacts with the acid chloride in a nucleophilic acyl substitution process. • Hydrolysis of the resulting iminium salt yields the final product. WWU-Chemistry

  22. Acylation of an Enamine WWU-Chemistry

  23. Acylation of an Enamine -- Mechanism (Part 1) WWU-Chemistry

  24. Acylation of an Enamine -- Mechanism -- Part 2 WWU-Chemistry

  25. Acylation of an Enamine -- Mechanism -- Part 3 WWU-Chemistry

  26. Overall Sequence WWU-Chemistry

  27. Example WWU-Chemistry

  28. Example #2 WWU-Chemistry

  29. Also review... • Conversion of acid chlorides to ketones • review material in Chapter 17, Section 17.18 WWU-Chemistry

  30. Using Dialkylcadmium Reagents WWU-Chemistry

  31. Using Lithium Dialkylcuprates WWU-Chemistry

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