Module 6.

2 Nitrogen compounds, polymers and synthesis 10/04/23

6.2.3 Amides
Amides are compounds that contain the
amide functional group.
Related to COOH group

Related to amine group

In chemical formulae, this is often written as
CONH.
Primary amides have an organic group, such as a
methyl group or benzene ring,
attached to the carbon atom in the functional group.
Secondary amides have an additional
organic group attached to the nitrogen
atom in the functional group. R and R' can be
identical to or different from each other.
Quick check
 Naming primary amides

First carbon - methan

• The suffix is ‘amide’.

• The root is generated by the number of
carbon atoms on the parent
hydrocarbon chain which has the
functional group.
 Naming primary amides
Draw the displayed formula and name each amide
Naming primary amides
 Naming secondary amides
• Second part of the name is the same as
naming primary amides
 Making
amides
Primary amides can be formed by the reaction
between an acyl chloride and
ammonia.
 Making
amides

One of the products of the reaction is hydrogen chloride.

 Making
amides

One of the products of the reaction is hydrogen chloride.

 Making
amides
The other product is a primary amide.
 Acid hydrolysis

The C–N bond in amides can be broken by acid hydrolysis.

The amide is heated under reflux with aqueous acid.

A carboxylic acid and ammonia are produced.

 Acid hydrolysis

The ammonia reacts with the acid to produce

ammonium ions.
 Acid hydrolysis
If the acid used is hydrochloric acid,
ammonium chloride is produced.
 Alkaline hydrolysis
The C–N bond in amides can be broken by alkaline hydrolysis.
The amide is heated under reflux with aqueous alkali.

Same
products
as acid
hydrolysis
 Alkaline hydrolysis

The carboxylic acid loses a hydrogen ion in alkaline

hydrolysis, forming a carboxylate ion.
 Alkaline hydrolysis

If the alkali used is sodium hydroxide, a sodium salt of

the carboxylic acid is produced.
 Questions
1. State the formula of an acyl group
2. Describe the similarities and differences
between primary and secondary amides
3. Draw the displayed formula of butanamide
and classify it as either a primary or a
secondary amide
4. Define the term polyamide
5. What does the ‘N’ signify in the name N-
ethylethanamide