Naming Amides

Definition of Primary Amides:

Primary amides are organic chemical compounds that include the functional group: Amide Group

That is, primary amides are a class or category of organic chemical compounds that include a part consisting of a carbon atom connected to both:

  • a nitrogen atom connected to two hydrogen atoms by single covalent bonds between the nitrogen and each of the hydrogen atoms (that is an -amine group).
    AND
  • an oxygen atom (connected to the carbon atom by a double covalent bond).

These molecules can vary in size up to very long molecules most of which consist of carbon atoms attached to each other and also to hydrogen atoms.

Primary, Secondary and Tertiary Amides:

In general, amides are organic chemicals whose molecules include a carbon atom (C) attached to both an oxygen atom (O) and a nitrogen atom (N). In the cases of primary amides, that N is also attached to two hydrogen (H) atoms, which together are written NH2. There are also more complicated amides called secondary amides and tertiary amides. In the case of secondary amides one of the hydrogen atoms attached to the nitrogen is replaced by another group or carbon chain e.g. by a methyl group, as in methylbutanamide. Many introductory texts only describe primary amides which are described as simply including the group -CONH2.

As shown, the difference between primary, secondary and tertiary amides is the number of C atoms attached to the N. In all cases, one of the C attached to the N is also attached to an O.

Above (Top): Simple examples of types of amides
(Lower): More general representations

In the cases of ...

  • Primary amides, only one cardon atom is attached to the N. In that case the N is also attached to two Hs.
  • Secondary amides, two carbon atoms are attached to the N. In that case the N is also attached to one H.
  • Tertiary amides, three carbon atoms are attached to the N.

An alternative group-name for amides is carboxamides, i.e. the carboxamide group (of chemicals).

Amides are named according to the same system as other organic compounds, with the suffix -amide used to designate the presence in the molecule of an amide group.

The first step is to consider the number of carbon atoms forming a chain. If they are in an unbranched configuration then the number of carbon atoms is indicated according to the same system as used for linear alkanes and as shown in the table below.

If the carbon atoms do not form a single chain but include branches, the longest chain of carbon atoms within the molecule determines the base of the name of the compound onto which is added information about the branches incl. their lengths in terms of the number of carbon atoms in each branch (i.e. methyl- indicates a branch consisting of just one carbon atom attached to the main chain, ethyl- indicates a branch of two carbon atoms in length, etc.). and their positions along the longest linear carbon chain.

Names and Structures of simple Linear Primary Amides

The first 10 members of the homologous series of linear primary amides, i.e. with the -amide group attached to the first (= last) carbon atom is:

  • Formamide (CH3NO)
    Simple Formula:
    HCONH2
    Simple Structure:
    structure of formamide
    *Examples of other / previous names:
    • Methanamide
    • 1-Methanamide
    • Methanamid
    • Carbamaldehyde
    • Formimidic acid
    • Formic acid, amide
    • Formamid
    • Formic amide
  • Ethanamide (C2H5NO)
    Simple Formula:
    CH3CONH2
    Simple Structure:
    structure of ethanamide
    *Examples of other / previous names:
    • Acetamide
    • Acetic acid amide
    • Acetimidic acid
    • Methanecarboxamide
    • Ethanimidic acid
    • Acetamid
    • Ethionamide
    • Ethanamid
    • Acetimidic acid
  • Propanamide (C3H7NO)
    Simple Formula:
    CH3CH2CONH2
    Simple Structure:
    structure of propanamide
    *Examples of other / previous names:
    • n-Propanamide
    • Propylamide
    • n-Propylamide
    • Propionamide
    • Propionic amide
    • Propanimidic acid
    • Propionimidic acid
    • Propionic acid
    • Propionic acid amide
    • Propyzamide
    • Protionamide
  • Butanamide (C4H9NO)
    Simple Formula:
    CH3CH2CH2CONH2
    Simple Structure:
    structure of butanamide
    *Examples of other / previous names:
    • n-Butanamide
    • Butyramide
    • n-Butyramide
    • n-Butylamide
    • Butanimidic acid
  • Pentanamide (C5H11NO)
    Simple Formula:
    CH3CH2CH2CH2CONH2
    Simple Structure:
    structure of pentanamide
    *Examples of other / previous names:
    • n-Pentanamide
    • Valeramide
    • n-Valeramide
    • Pentanimidic acid
  • Hexanamide (C6H13NO)
    Simple Formula:
    CH3CH2CH2CH2CH2CONH2
    Simple Structure:
    structure of hexanamide
    *Examples of other / previous names:
    • n-Hexanamide
    • Caproamide
    • n-Caproamide
    • Capronamide
    • Hexylamide
    • Hexamide
    • Hexanoamide
    • Policapram
    • n-Capronamide
    • n-Caproic amide
  • Heptanamide (C7H15NO)
    Simple Formula:
    CH3CH2CH2CH2CH2CH2CONH2
    Simple Structure:
    structure of heptanamide
    *Examples of other / previous names:
    • n-Heptanamide
    • Enanthamide
    • Octanoylamide
    • Heptamide
    • Enanthic acid amide
  • Octanamide (C8H17NO)
    Simple Formula:
    CH3CH2CH2CH2CH2CH2CH2CONH2
    Simple Structure:
    structure of octanamide
    *Examples of other / previous names:
    • n-Octanamide
    • Caprylamide
  • Nonanamide (C9H19NO)
    Simple Formula:
    CH3CH2CH2CH2CH2CH2CH2CH2CONH2
    Simple Structure:
    structure of nonanamide
    *Examples of other / previous names:
    • n-Nonanamide
    • Nonamide
    • Pelargonamide
    • Nonan-1-amide
    • Nonanoic acid amide
    • Nonan-1-amide
  • Decanamide (C10H21NO)
    Simple Formula:
    CH3CH2CH2CH2CH2CH2CH2CH2CH2CONH2
    Simple Structure:
    structure of decanamide
    *Examples of other / previous names:
    • n-Decanamide
    • Decylamide
    • Capramide
    • Decanamide-
    • Decanoic acid amide
    • Decan-1-amide

Note: *The synonyms indicated for compounds listed above are just some examples of alternative names found online and believed to have been used to refer to the substance indicated. They have not all been verified and may include common (non-scientific) names and trade names specific to particular suppliers. The purpose of these lists is to give a general indication of the range of names by which these amides are, or have been, known.

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