Carboxylic acids and their derivatives. Required background: Aldehydes, ketones Acidity of alcohols Reaction mechanisms Essential for: Aminoacids, peptides.

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Presentation transcript:

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 3. Decarboxylation 4. Acyl substitution 5. Reduction of carboxylic acid derivatives 6. Condensation polymers 7. Overview of lipids 8. Claisen condensation

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.

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

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

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

Examples of carboxylic acid derivatives

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

Reactions of carboxylic acid derivatives with nucleophiles Reactions of acid chlorides

Reactions of anhydrides

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

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

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

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

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

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

Claisen condensation

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