Derivatives of Carboxylic Acids

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Presentation transcript:

Derivatives of Carboxylic Acids

formulas Carboxylic acids and their derivatives can be expressed as variation of a single formula in which electronegative atom (O, N, or halogen) is bonded to an acyl group (RC=O) Carboxylic acid -OH is attached to acyl group. Ester -OR, alkoxy is attaches to acyl group

Amide -NH2 is attached to acyl group Acid chloride -Cl is attached to acyl group Acid anhydride RCO || O is bonded to the group of another (2 acids minus one molecule of H2O

Uses Acids, esters and amides are abundant in nature Proteins are amides (amino acids connect by amide linkage) Ester linkages are found in fats, oils, and natural waxes. Their pleasant odors are responsible for the taste and fragrance of fruits and flowers.

Nomenclature of Acid derivatives Esters: Change –oic acid to –ate and precede the name with alkyl group. (alcohol + acid) Amides: Change –oic acid to amide

Preparation of Esters and Amides Preparation of Esters : condensation reaction between alcohol and acid O || ROH + R’COH  ROCR’ + H2O

Amides: condensation reaction between an acid and NH3 or an amine. O O || || RCOH + HNR’  RCNR’ + H2O

Aspirin and other Analgesics Pain relievers are among the most important medicinal application of carboxylic acid derivatives. Aspirin is acetyl salicylic acid, salicylate ester of acetic acid. Salicylic acid is a bifunctional molecule (acid and phenol) which is itself a disinfectant. Aspirin comes from the willow bark which was used in the Middle Ages by Jesuit missionaries.

Amines Amines are derivatives of ammonia, NH3, in which one or more hydrogens have been replaced by organic groups. If one H is replaced it is primary If two H are replaced, it is secondary If three H are replaced, it is tertiary. Aromatic groups make it an arylamine.

Nomenclature Simple amines can be named acceptably by common nomenclature as alkyl amine in which amine is added to the name of the organic group. If IUPAC nomenclature, the suffix –amine is added to the name of the longest continuous carbon chains possessing the functional group. Change the –e to amine. Phenylalkyamines have benzene ring, alkyl group and amine