Nomenclature of Carboxylic Acid Derivatives

The following page contains a detailed description of the IUPAC rules for the naming of common carboxylic acid derivatives; a summary of these rules is given in the figure below.

Simple carboxylic acids are named as derivatives of the parent alkane, using the suffix -oic acid

  1. Select the longest continuous carbon chain containing the carboxylic acid group, and derive the parent name by replacing the -e ending with -oic acid.
  2. Number the carbon chain, beginning at the end nearest to the carboxylic acid group.
  3. Number the substituents and write the name, listing substituents alphabetically.
  4. Carboxylic acid substituents attached to rings are named using the suffix -carboxylic acid.

Several simple examples are shown below:

In the first example, the parent chain is a pentane and the carboxylic acid group is assigned as carbon #1. On the pentane parent there is an ethyl group in position #2; hence the name, 2-ethylpentanoic acid.

In the second example, there are two potential four-carbon chains; in this case, the chain with the most substituents is selected as parent (a butanoic acid). Attached to the butanoic acid at carbon #2 is an ethyl group and at carbon #3, a bromine; hence the name 3-bromo-2-ethylbutanoic acid.

In the third example, the carboxylic acid is attached to a cycloalkene ring and will therefore be named as a "carboxylic acid" substituent (rule #4). The parent ring is a cyclohexene; letting the carboxylic acid be carbon #1, the name is 2-cyclohexenecarboxylic acid.

In the last example, the name is based on benzoic acid as the parent. In this case, we simply number the substituents to give the lowest number sequence at the first point of difference and arrange alphabetically; 5-bromo-2-methylbenzoic acid.

Simple acid halides are named by identifying the acyl group, using the suffix -oyl followed by the halogen.

  1. Select the longest continuous carbon chain containing the acyl group, and derive the parent name by replacing the -e ending with -oyl, then append the halogen.
  2. Number the carbon chain, beginning at the end nearest to the acyl group.
  3. Number the substituents and write the name, listing substituents alphabetically.
  4. Acid halide substituents attached to rings are named using the suffix -carbonyl.

Several simple examples are shown below:

In the first example, the parent chain is a pentane and the acyl group is assigned as carbon #1. On the pentane parent there is an ethyl group in position #2; hence the name, 2-ethylpentanoyl chloride.

In the second example, there are two potential four-carbon chains; in this case, the chain with the most substituents is selected as parent (a butanoyl bromide). Attached to the chain at carbon #2 is an ethyl group and at carbon #3, a bromine; hence the name 3-bromo-2-ethylbutanoyl bromide.

In the third example, the acyl group is attached to a cycloalkene ring and will therefore be named as a "carbonyl chloride" substituent (rule #4). The parent ring is a cyclohexene; letting the acyl group be carbon #1, the name is 2-cyclohexenecarbonyl chloride.

In the last example, the name is based on benzoic acid as the parent. In this case, we simply number the substituents to give the lowest number sequence at the first point of difference and arrange alphabetically; 5-bromo-2-methylbenzoyl fluoride.

Simple acid anhydrides are named by replacing the ending "acid" with "anhydride".

  1. Select the longest continuous carbon chain containing the carboxylic acid group, and derive the parent name by replacing the -e ending with -oic anhydride.
  2. Number the carbon chain, beginning at the end nearest to the acyl group.
  3. Number the substituents and write the name, listing substituents alphabetically.

Several simple examples are shown below:

In the first example, the parent chains are both pentane; hence the name, pentanoic anhydride (also as bis-pentanoic anhydride).

In the second example, there are two parent chains; ethanoic acid and butanoic acid; hence the name butanoic ethanoic anhydride (acetic can be used in place of ethanoic).

In the third example, the name is based on benzoic acid as the parent and the name is simply benzoic anhydride.

In the last example, the name is based on phthalic acid and the name is simply phthalic anhydride.

Simple amides are named by replacing the ending -oic acid with -amide .

  1. Select the longest continuous carbon chain containing the acyl group, and derive the parent name by replacing the -e ending with -amide.
  2. Number the carbon chain, beginning at the end nearest to the acyl group.
  3. Number the substituents and write the name, listing substituents alphabetically.
  4. Acid halide substituents attached to rings are named using the suffix -carboxamide.
  5. If the nitrogen atom is further substituted, the substituents are preceded by N- to indicate that they are attached to the nitrogen.

Several simple examples are shown below:

In the first example, the parent chain is a pentane and the acyl group is assigned as carbon #1. On the pentane parent there is an ethyl group in position #2; hence the name, 2-ethylpentanamide.

In the second example, there are two potential four-carbon chains; in this case, the chain with the most substituents is selected as parent (a butane). Attached to the chain at carbon #2 is an ethyl group and at carbon #3, a bromine; hence the name 3-bromo-2-ethylbutanamide.

In the third example, the acyl group is attached to a cycloalkene ring and will therefore be named as a "carboxamide" substituent (rule #4). The parent ring is a cyclohexene; letting the acyl group be carbon #1, the name is 2-cyclohexenecarboxamide.

In the last example, the name is based on benzoic acid as the parent and the nitrogen has a methyl substituent. In this case, we simply number the substituents to give the lowest number sequence at the first point of difference and arrange alphabetically; N-methyl-5-bromo-2-methylbenzamide.

Simple carboxylate esters are named as derivatives of the carboxylic acid, by changing the suffix -oic acid to -oate, and naming the alcohol portion first.

  1. Select the longest continuous carbon chain containing the acyl group, and derive the parent name by replacing the -e ending with -oate, then append the the alcohol to the front of the name.
  2. Number the carbon chain, beginning at the end nearest to the acyl group.
  3. Number the substituents and write the name, listing substituents alphabetically.
  4. Acid halide substituents attached to rings are named using the suffix -carboxylate.

Several simple examples are shown below:

In the first example, the alcohol is methanol the parent chain is a pentane and the acyl group is assigned as carbon #1. On the pentane parent there is an ethyl group in position #2; hence the name, methyl 2-ethylpentanoate.

In the second example, the alcohol is ethanol and there are two potential four-carbon chains; in this case, the chain with the most substituents is selected as parent (a butanoyl bromide). Attached to the chain at carbon #2 is an ethyl group and at carbon #3, a bromine; hence the name ethyl 3-bromo-2-ethylbutanoate.

In the third example, the alcohol is cyclopentanol and the acyl group is attached to a cycloalkene ring and will therefore be named as a "carboxylate" substituent (rule #4). The parent ring is a cyclohexene; letting the acyl group be carbon #1, the name is cyclopentyl 2-cyclohexenecarboxylate.

In the last example, the alcohol is methanol and the name is based on benzoic acid as the parent. In this case, we simply number the substituents to give the lowest number sequence at the first point of difference and arrange alphabetically; methyl 5-bromo-2-methylbenzoate.

Simple nitriles are named as derivatives of the parent alkane, using the suffix -nitrile to -oate, and naming the alcohol portion first.

  1. Select the longest continuous carbon chain containing the nitrile, and derive the parent name by appending -nitrile.
  2. Number the carbon chain, beginning at the end nearest to the nitrile group.
  3. Number the substituents and write the name, listing substituents alphabetically.
  4. Acid halide substituents attached to rings are named using the suffix -carbonitrile.

Several simple examples are shown below:

In the first example, the parent chain is a pentane and the nitrile group is assigned as carbon #1. On the pentane parent there is an ethyl group in position #2; hence the name, 2-ethylpentanenitrile.

In the second example, there are two potential four-carbon chains; in this case, the chain with the most substituents is selected as parent (a butanenitrile). Attached to the chain at carbon #2 is an ethyl group and at carbon #3, a bromine; hence the name 3-bromo-2-ethylbutanenitrile.

In the third example the nitrile group is attached to a cycloalkene ring and will therefore be named as a "carbonitrile" substituent (rule #4). The parent ring is a cyclohexene; letting the acyl group be carbon #1, the name is 2-cyclohexenecarbonitrile.

In the last example the name is based on benzonitrile as the parent. In this case, we simply number the substituents to give the lowest number sequence at the first point of difference and arrange alphabetically; .