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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 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
Hydrolysis of an Ester in Acid H2SO4 / H2O H3O+ + H-OH2 proton transfers OH2 + H3O+
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 !
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
Acylation of an Enamine .. - Cl acyl group was added
Acylation of an Enamine Mechanism iminium salt slow enamine .. ….. continued
Acylation of an Enamine Mechanism (cont) +
SUMMARY OF ACYLATION enamine acyl group
MISCELLANEOUS REACTIONS OF ACID DERIVATIVES
Reaction of Esters with Organometallic Reagents cleaves the ether …. reacts twice !
NITRILES REACTIONS AND SYNTHESIS
Formation of Nitriles SN2 Reaction Addition to C=O .. + pH 6 cyanohydrin
Hydrolysis of Nitriles ACID SOLUTION BASIC SOLUTION Acid or Base
Base-Promoted Hydrolysis of a Nitrile MECHANISM NaOH 1) 2) 3) amide ….. continued
Base-Promoted Hydrolysis of a Amide MECHANISM NaOH 4) 5) 6)
Acid-catalyzed Hydrolysis of a Nitrile MECHANISM 1) 2) H2SO4 / H2O 3) H-OH2 + protonated amide ….. continued
Acid-catalyzed Hydrolysis of a Amide + .. H-OH2 .. 4) OH2 5) 6)
The Triacylglycerols glycerol fatty acid 2 fatty acid 3 fatty acid 1 Each acyl group can come from a different fatty acid chain.
SAPONIFICATION SOAP NaOH (lye) heat “SOAP”
- Na+ - Na+ - Na+ - Na+ - Na+ - Na+ - Na+ - Na+ MICELLE grease particle