CARBOXYLIC ACIDS

 

Reference: McMurry Ch 10 George et al Ch 2.7

 

Carboxylic acids contain the functional group:

Nomenclature

 

Examples

 

 

Reactions of Carboxylic Acids

 

1. Acid Base Reaction

 

Example:

2. Esterification

Example: 

 

Some biologically active compounds containing the

carboxylic acid functional group:

 

 

 

Questions on Carboxylic Acid Nomenclature

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CARBOXYLIC ACID DERIVATIVES

 

Reference: McMurry Ch 10 George et al Ch 2.7

 

Reactions of Carboxylic Acid Derivatives

 

1. Formation of acid chlorides

Example: 

2. Interconversion of derivatives

 Example:

Acid chloride + alcohol ® ester + HCl

 

Acid chloride + amine ® amide + HCl

Ester + amine ® amide + alcohol

3. Hydrolysis of derivatives

Example:

Derivative

Relative reactivity

Conditions of hydrolysis

Products of acid hydrolysis

Products of base hydrolysis

 

high

 

 

low

 

 

H2O

 

  

 

 

 H+ /H2O/heat

or

OH- /H2O/heat

  

+ ROH

 + ROH

 H+ /H2O/heat

or

OH- /H2O/heat

  

+ R2NH2+

 + R2NH

 

 

Mechanism of reaction

 

 

Amino Acids:

 

Proteins are important natural amides. They are polymeric materials formed from amino acids. Amino acids have both an amine functional group and a carboxylic acid functional group in the same molecule and proteins are formed by linking the amine group from one molecule with the carboxylic acid group of another to form an amide bond.

Hydrolysis of a protein is typically achieved by treating it with boiling 6M hydrochloric acid. This hydrolyses all of the amide bonds and releases all of the amino acids which make up the protein.

Proteins generally consist of hundreds of amino acid residues linked together to form a single molecule with a molecular weight of >100,000.

 

Some biologically active compounds containing the

carboxylic acid derivatives:

 

Questions on Carboxylic Acid Derivatives

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