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Carboxylic acids and their derivatives

Carboxylic acids and their derivatives. Required background: Aldehydes, ketones Acidity of alcohols Reaction mechanisms Essential for: Aminoacids, peptides. Outline 1. Acidity and basicity of carboxylic acids 2. Fischer esterification

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Carboxylic acids and their derivatives

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  1. Carboxylic acids and their derivatives

  2. Required background: Aldehydes, ketones Acidity of alcohols Reaction mechanisms Essential for: Aminoacids, peptides

  3. Outline 1. Acidity and basicity of carboxylic acids 2. Fischer esterification 3. Decarboxylation 4. Acyl substitution 5. Reduction of carboxylic acid derivatives 6. Condensation polymers 7. Overview of lipids 8. Claisen condensation

  4. Carboxylic acids are stronger acids, than phenol, because the conjugate base (carboxylate) is stabilized by the delocalization of the negative charge between two electronegative oxygens.

  5. Outline 1. Acidity and basicity of carboxylic acids 2. Fischer esterification 3. Decarboxylation 4. Acyl substitution 5. Reduction of carboxylic acid derivatives 6. Condensation polymers 7. Overview of lipids 8. Claisen condensation

  6. Outline 1. Acidity and basicity of carboxylic acids 2. Fischer esterification 3. Decarboxylation 4. Acyl substitution 5. Reduction of carboxylic acid derivatives 6. Condensation polymers 7. Overview of lipids 8. Claisen condensation

  7. Outline 1. Acidity and basicity of carboxylic acids 2. Fischer esterification 3. Decarboxylation 4. Acyl substitution 5. Reduction of carboxylic acid derivatives 6. Condensation polymers 7. Overview of lipids 8. Claisen condensation

  8. Examples of carboxylic acid derivatives

  9. Reactivity with nucleophiles is decreased by the stabilizing conjugation, which depends on the electron donating ability of X Acid chlorides > anhydrides > esters, acids > amides > nitriles > salts

  10. Reactions of carboxylic acid derivatives with nucleophiles Reactions of acid chlorides

  11. Reactions of anhydrides

  12. Reactions of esters Hydrolysis of carboxylic acid derivatives Acid-catalyzed hydrolysis of esters is the reaction of esterification, going backwards.

  13. Outline 1. Acidity and basicity of carboxylic acids 2. Fischer esterification 3. Decarboxylation 4. Acyl substitution 5. Reduction of carboxylic acid derivatives 6. Condensation polymers 7. Overview of lipids 8. Claisen condensation

  14. Outline 1. Acidity and basicity of carboxylic acids 2. Fischer esterification 3. Decarboxylation 4. Acyl substitution 5. Reduction of carboxylic acid derivatives 6. Condensation polymers 7. Overview of lipids 8. Claisen condensation

  15. Outline 1. Acidity and basicity of carboxylic acids 2. Fischer esterification 3. Decarboxylation 4. Acyl substitution 5. Reduction of carboxylic acid derivatives 6. Condensation polymers 7. Overview of lipids 8. Claisen condensation

  16. Lipids are compounds of biological origin that dissolve in nonpolar solvents, such as chloroform and diethyl ether. The name lipid comes from the Greek word lipos, for fat. Unlike carbohydrates and proteins, which are defined in terms of their structures, lipids are defined by the physical operation that we use to isolate them. Not surprisingly, then, lipids include a variety of structural types. Examples are the following

  17. Outline 1. Acidity and basicity of carboxylic acids 2. Fischer esterification 3. Decarboxylation 4. Acyl substitution 5. Reduction of carboxylic acid derivatives 6. Condensation polymers 7. Overview of lipids 8. Claisen condensation

  18. Claisen condensation

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