14.2:
Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides
The IUPAC and common names of acid halides are derived from the parent carboxylic acids by replacing "-ic acid" with "-yl halide."
For cyclic acid halides, the suffix "-carboxylic acid" is changed to "-carbonyl halide."
In esters, the alkyl group attached to the oxygen atom is named first, followed by the acid, where the suffix "-ic acid" is replaced with "-ate."
Cyclic esters, also called lactones, are named by substituting the suffix "-oic acid" or "-ic acid" with "-olactone."
Here, the ring size is added as a prefix. For IUPAC names, the ring size is indicated by a number, whereas for common names, it is designated by a Greek letter.
In symmetrical anhydrides, the suffix "-acid" is changed to "-anhydride." In unsymmetrical anhydrides, the names of both carboxylic acids are listed alphabetically, followed by the suffix "anhydride."
Cyclic anhydrides derived from dicarboxylic acids are named by replacing the suffix "acid" with "anhydride."
14.2:
Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides
Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
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| IUPAC: | Ethanoic acid | Ethanoyl chloride |
| Common: | Acetic acid | Acetyl chloride |
Cyclic acid halides are named by replacing the suffix “carboxylic acid” with “carbonyl halide.” For instance, if the acetyl chloride group is bonded to a cyclohexane ring, the resulting compound is called cyclohexanecarbonyl chloride, derived from the parent cyclohexanecarboxylic acid.
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| IUPAC: | Cyclohexanecarboxylic acid | Cyclohexanecarbonyl chloride |
| Common: | Cyclohexanecarboxylic acid | Cyclohexanecarbonyl chloride |
Naming Esters
Esters are named by citing the alkyl group attached to the oxygen atom first, and then adding the name of the acid, where the suffix “ic acid” is substituted with “ate.” In this example, the IUPAC name of the ester is methyl ethanoate derived from ethanoic acid, and the common name, methyl acetate, is obtained from acetic acid.
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| IUPAC: | Ethanoic acid | Methyl ethanoate |
| Common: | Acetic acid | Methyl acetate |
Cyclic esters, also referred to as lactones, are named by replacing the suffix “ic acid” of the parent acid with “olactone.” The following example is that of a cyclic four-membered ester where the IUPAC and common names are butanolactone and butyrolactone, respectively.
For IUPAC names, the location of the oxygen atom on the ring is deduced by numbering the carbons starting from the carbonyl carbon, and adding it as a prefix. Thus, butanolactone becomes 4-butanolactone. In common names, the number is replaced by a Greek letter; however, the carbon atom adjacent to the carbonyl carbon is labelled first, giving the name γ-⁠butyrolactone.
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| IUPAC: | Butanoic acid | 4-Butanolactone |
| Common: | Butyric acid | γ-Butyrolactone |
Naming Acid Anhydrides
Acid anhydrides can be symmetrical or unsymmetrical. Symmetrical anhydrides are formed from a mixture of two identical carboxylic acids and are named by changing the suffix “acid” with “anhydride”. For example, the IUPAC name ethanoic anhydride is derived from ethanoic acid, and the common name, acetic anhydride, is obtained from acetic acid.
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| IUPAC: | Ethanoic acid | Ethanoic anhydride |
| Common: | Acetic acid | Acetic anhydride |
In contrast, unsymmetrical anhydrides are formed from a mixture of two different acids and are named by citing both acids in alphabetical order, followed by the suffix “anhydride.” In the following example, the IUPAC and common names are ethanoic propanoic anhydride and acetic propionic anhydride, respectively.
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| IUPAC: | Ethanoic acid | Propanoic acid | Ethanoic propanoic anhydride |
| Common: | Acetic acid | Propionic acid | Acetic propionic anhydride |
Unlike acyclic acid anhydrides, cyclic anhydrides are synthesized from dicarboxylic acids. However, the nomenclature follows the same rules, and the compounds are named by replacing the suffix “acid” with “anhydride.” As shown below, the IUPAC name butanedioic anhydride is derived from butanedioic acid, and the common name, succinic anhydride, is obtained from succinic acid.
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| IUPAC: | Butanedioic acid | Butanedioic anhydride |
| Common: | Succinic acid | Succinic anhydride |