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 halid…
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."
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Q1: How are acid halides named in IUPAC and common nomenclature?
Acid halide names derive from parent carboxylic acids by replacing the suffix "-ic acid" with "-yl halide." For example, ethanoic acid becomes ethanoyl chloride in IUPAC nomenclature, while acetic acid becomes acetyl chloride in common nomenclature. For cyclic acid halides, the suffix "-carboxylic acid" changes to "-carbonyl halide."
Q2: What is the naming convention for esters and lactones?
Esters are named by citing the alkyl group attached to oxygen first, then the acid name with "-ic acid" replaced by "-ate." Cyclic esters, called lactones, use "-olactone" instead. Ring size is indicated by a number in IUPAC names or a Greek letter in common names, such as γ-butyrolactone for the common name.
Q3: How do you distinguish between symmetrical and unsymmetrical acid anhydrides?
Symmetrical anhydrides form from two identical carboxylic acids and are named by replacing "-acid" with "-anhydride," such as acetic anhydride. Unsymmetrical anhydrides form from two different acids and list both acid names alphabetically before adding "-anhydride," for example, acetic propionic anhydride.
Q4: What suffix changes occur when naming cyclic anhydrides from dicarboxylic acids?
Cyclic anhydrides derived from dicarboxylic acids follow the same naming rules as acyclic anhydrides. The suffix "-acid" is replaced with "-anhydride." For instance, butanedioic acid becomes butanedioic anhydride in IUPAC nomenclature, while succinic acid becomes succinic anhydride in common nomenclature.
Q5: Why is numbering important when naming lactones?
Numbering identifies the oxygen atom's position on the lactone ring. In IUPAC names, carbons are numbered starting from the carbonyl carbon, and this number is added as a prefix, such as 4-butanolactone. In common names, a Greek letter replaces the number, with the carbon adjacent to the carbonyl carbon labeled first.
Q6: How does the parent carboxylic acid structure determine acid halide nomenclature?
The parent carboxylic acid name directly determines the acid halide name through systematic suffix replacement. Both IUPAC and common names follow this pattern: the acid's base name is retained, and only the acid suffix changes to the halide suffix. This approach ensures consistency and clarity in nomenclature of carboxylic acid derivatives.
Q7: What is the relationship between ester nomenclature and the alkyl group attached to oxygen?
The alkyl group bonded to the oxygen atom is named first in ester nomenclature, followed by the carboxylic acid name with its suffix modified. For example, methyl ethanoate has methyl as the alkyl group and ethanoate as the acid portion, derived from ethanoic acid.