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14.3: Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

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JoVE Core
Organic Chemistry

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Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
 
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14.3: Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

Naming Amides

The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.

Figure1 Figure2
IUPAC: Ethanoic acid Ethanamide
Common: Acetic acid Acetamide

Alkyl groups bonded to the nitrogen atom of amides are specified as N-alkyl or N,N-dialkyl, with the groups listed in alphabetical order.

For example, if the nitrogen atom is bonded to a methyl group, the IUPAC name is N-methylethanamide, and the common name is N-methylacetamide.

If the nitrogen atom is attached to two identical groups, like two methyl groups, the IUPAC name is N,N-dimethylethanamide, and the common name is N,N-dimethylacetamide.

However, if the two groups are different such as a methyl group and an ethyl group, the IUPAC name is N-ethyl-N-methylethanamide, and the common name is N-ethyl-N-methylacetamide.

Figure3 Figure4 Figure5
IUPAC: N-Methylethanamide N,N-Dimethylethanamide N-Ethyl-N-methylethanamide
Common: N-Methylacetamide N,N-Dimethylacetamide N-Ethyl-N-methylacetamide

When an amide group is attached to a ring the suffix “carboxylic acid” is replaced with “carboxamide.” For example, if the amide group is bonded to cyclohexane, the resulting compound is called cyclohexanecarboxamide, obtained from the parent cyclohexanecarboxylic acid.

Figure6 Figure7
IUPAC: Cyclohexanecarboxylic acid Cyclohexanecarboxamide
Common: Cyclohexanecarboxylic acid Cyclohexanecarboxamide

Cyclic amides, also called lactams, are named by substituting the suffix “ic acid” of the parent acid with “olactam.” For instance, the IUPAC name of the cyclic four-membered ester shown below is butanolactam, derived from butanoic acid, and the common name is butyrolactam, obtained from butyric acid.

For IUPAC names, the location of the oxygen atom on the ring is indicated by numbering the carbons starting from the carbonyl carbon. The number is added as a prefix, and the name butanolactam becomes 4-butanolactam.

In case of 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-butyrolactam.

Figure8 Figure9
IUPAC: Butanoic acid 4-Butanolactam
Common: Butyric acid  γ-Butyrolactam

Naming Nitriles

The IUPAC names of nitriles are derived by adding the suffix “nitrile” to the parent alkane. In the following example, the IUPAC name ethanenitrile is derived from the parent ethane.

For common names, the suffix “ic acid” of the parent acid is substituted with “onitrile.”As shown below, the common name, acetonitrile, is obtained from acetic acid.

Figure1 Figure1
IUPAC: Ethanoic acid Ethanenitrile
Common: Acetic acid      Acetonitrile

If the nitrile group is attached to a cycloalkane ring, the parent cycloalkane is named first, followed by the suffix “carbonitrile.“ For example, if the nitrile group is bonded to cyclohexane, the compound is called cyclohexanecarbonitrile, obtained from the parent cyclohexanecarboxylic acid.

Figure6 Figure11
IUPAC: Cyclohexanecarboxylic acid Cyclohexanecarbonitrile
Common: Cyclohexanecarboxylic acid Cyclohexanecarbonitrile

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Keywords: Carboxylic Acid Derivatives Amides Nitriles IUPAC Naming Common Naming N-alkyl N,N-dialkyl Cyclic Amides Lactams Nitriles

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