Amides
- Amides are formed from the condensation reaction of carboxylic acids or acyl chlorides with ammonia or amines
- Amides are common in nature such as in proteins where the amine and carboxylic acid groups of amino acids bond together
- Amides have a general structure of RCONR2
The general structure of an amide
- Amides can be classified as primary, secondary or tertiary amides
- Like amines, this is done as a comparison to ammonia, depending on the number of substitutions on the amide nitrogen
- Primary amide - one carbon bonded to the amide nitrogen
- R' and R'' are both hydrogen atoms so one "ammonia" hydrogen has been substituted with the carbonyl group from the RCO portion of the molecule
- Secondary amide - two carbons bonded to the amide nitrogen (one MUST be the carbonyl carbon)
- Tertiary amide - three carbons bonded to the amide nitrogen (one MUST be the carbonyl carbon)
- Primary amide - one carbon bonded to the amide nitrogen
Naming primary amides
- For primary amides, we simply add -amide to the stem name
- e.g. CH3CONH2
- Contains two carbons with a C-C (ethan-) and an amide group (-amide)
- This gives us ethanamide
- e.g. CH3CONH2
Naming secondary amides
- For secondary amides, the alkyl chain attached to the nitrogen is added at the start of the chemical name
- This alkyl chain is prefixed with N-
- The chain containing the carbonyl group is named the same as a primary amide
- e.g. CH3CONH(C3H7)
- Contains a propyl group on the nitrogen (N-propyl)
- Contains two carbons with a C-C (ethan-) and an amide group (-amide)
- This gives us N-propylethanamide
- e.g. CH3CONH(C3H7)
Naming tertiary amides
- For tertiary amides, there are two alkyl chains attached to the nitrogen
- The naming of these chains is the same as secondary amides
- As with standard nomenclature, these chains are listed in alphabetical order and the prefix 'di-' is used if necessary
- e.g. CH3CONCH3(C3H7)
- Contains a methyl group on the nitrogen (N-methyl)
- Contains a propyl group on the nitrogen (N-propyl)
- Contains two carbons with a C-C (ethan-) and an amide group (-amide)
- This gives us N-methyl-N-propylethanamide
- e.g. CH3CONCH3(C3H7)