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HYDROLYSIS REACTIONS

HYDROLYSIS REACTIONS. Hydrolysis of Esters. Basic Solution. Na +. Na +. heat. Acidic Solution. heat. excess. Hydrolysis requires strong acid or base and heating under reflux. ….. It’s not easy !. Hydrolysis of an Ester in Base. NaOH. H-OH. proton transfers. -. HO.

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HYDROLYSIS REACTIONS

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  1. HYDROLYSIS REACTIONS

  2. Hydrolysis of Esters Basic Solution Na+ Na+ heat Acidic Solution heat excess Hydrolysis requires strong acid or base and heating under reflux. ….. It’s not easy !

  3. Hydrolysis of an Ester in Base NaOH H-OH proton transfers - HO

  4. Hydrolysis of an Ester in Acid H2SO4 / H2O H3O+ + H-OH2 proton transfers OH2 + H3O+

  5. Hydrolysis of Amides Basic Solution Na+ Na+ heat Acidic Solution heat excess Hydrolysis requires strong acid or base and heating under reflux. ….. It’s not easy !

  6. Base-Promoted Hydrolysis of a Amide MECHANISM NaOH most often this step reverses because OH- is a better leaving group than NH2- once in a while stronger base than OH-, but this step doesn’t reverse because of the next one accumulates

  7. ACYLATION OF ENAMINES

  8. Acylation of an Enamine .. - Cl acyl group was added

  9. Acylation of an Enamine Mechanism iminium salt slow enamine .. ….. continued

  10. Acylation of an Enamine Mechanism (cont) +

  11. SUMMARY OF ACYLATION enamine acyl group

  12. MISCELLANEOUS REACTIONS OF ACID DERIVATIVES

  13. Reaction of Esters with Organometallic Reagents cleaves the ether …. reacts twice !

  14. Reduction of Esters

  15. Reduction of Esters to Aldehydes

  16. NITRILES REACTIONS AND SYNTHESIS

  17. Formation of Nitriles SN2 Reaction Addition to C=O .. + pH 6 cyanohydrin

  18. Hydrolysis of Nitriles ACID SOLUTION BASIC SOLUTION Acid or Base

  19. Base-Promoted Hydrolysis of a Nitrile MECHANISM NaOH 1) 2) 3) amide ….. continued

  20. Base-Promoted Hydrolysis of a Amide MECHANISM NaOH 4) 5) 6)

  21. Acid-catalyzed Hydrolysis of a Nitrile MECHANISM 1) 2) H2SO4 / H2O 3) H-OH2 + protonated amide ….. continued

  22. Acid-catalyzed Hydrolysis of a Amide + .. H-OH2 .. 4) OH2 5) 6)

  23. FATS AND OILS

  24. The Fatty Acids

  25. The Triacylglycerols glycerol fatty acid 2 fatty acid 3 fatty acid 1 Each acyl group can come from a different fatty acid chain.

  26. SAPONIFICATION SOAP NaOH (lye) heat “SOAP”

  27. - Na+ - Na+ - Na+ - Na+ - Na+ - Na+ - Na+ - Na+ MICELLE grease particle

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