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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 Amines • Amines are derivatives of ammonia, NH3, in which one or more hydrogens have been replaced by organic groups.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