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Carboxylic Acids

Ch20 Carboxylic Acids (landscape).docx Page 1 Carboxylic Acids When a carbonyl carbon also bears a hydroxyl group, then these compounds are appreciably acidic, and are called Carboxylic Acids . Carboxylic Acids are classified according to the substituent that is bonded to the carboxyl carbon: Aliphatic Acids have an alkyl group bound to the carboxyl group. An aromatic acid has an aryl group bound to the carboxyl group. The simplest acid is formic acid . A Carboxylic acid donates protons by the heterolytic cleavage of the O-H bond, generating a carboxylate ion. RCOO-HRCOOHRCO2H Ch20 Carboxylic Acids (landscape).docx Page 2 Nomenclature IUPAC formulation The root name is based on the longest continuous chain of carbon atoms bearing the carboxyl group. The -e is replaced by -oic acid . The chain is numbered starting with the carboxyl carbon atom. The carboxyl group takes priority over any other functional groups previously discussed. Ch20 Carboxylic Acids (landscape).

Carboxylic acid derivatives differ in the nature of the group bound to the acyl group. -OH is an acid-Cl is the acid chloride-OCOR' is the anhydride-OR' is the ester-NR 2 is the amide Nucleophilic acyl substitution can interconvert all of these different acid derivatives.

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