Organic Compounds that contain

Nitrogen:
N
H
H
H Nitrogen Molecule has 3 bonds that it can make as it contains a lone pair of
electrons
There are 2 main types of organic compounds that contain the Nitrogen atom, these are
amines and amides. Let look at each on, discuss how to name the compound, draw the
structure and some simple reactions.

Amine

Amines can be identified to have a nitrogen atom that is directly attached to a carbon atom.
CH2 CH3

H3C NH

Such as: N-methylethanamine

This molecule has an ethyl group attached to the nitrogen as well as a hydrogen and a
methyl group. There are 2 ways of naming an amine:
1. When naming an amine molecule, one lists the alkyl groups attached to the nitrogen
in alphabetical order.
2. Note the longest chain eg. Ethane which is attached to the nitrogen in the first
position. The methyl is attached to the nitrogen as a branch and to note that it is
attached directly to the N we use a prefix of N. Hence the name N-methylethanamine

The above molecule is thus called ethyl methyl amine. We end the name of an amine
with amine.
Let’s try a few other examples:

CH3
H3C
CH2
CH2
N

CH3

1. N,N-dimethylpropan-1-amine or ethyl dimethyl amine

 CH3
H2C
CH2
N
H3C
CH2 CH3

2. N-ethyl-N-methylpropan-1-amine or ethyl methyl propyl amine

CH2
NH CH3
H3C
CH2 CH2 CH2

3. N-ethylbutan-1-amine or butyl ethyl amine

Test your knowledge:

H3C CH3
1 NH

Name:

CH2
CH3
NH CH2
2 H3C
Name:

Draw the structure for each of the following:

1. N,N- dimethyl ethanamine
2. Butyl methyl amine

Like alcohols amines can form primary, secondary and tertiary amines.
 CH2 H
H3C N
H
1. ethanamine or ethyl amine is a primary amine

CH3
H2C

N
H3C
H
2. N-methylethanamine or ethyl methyl amine is a secondary amine

H3C

N CH3
H3C
CH2

3. N,N-dimethylethanamine or Ethyl dimethyl amine is a tertiary amine

As an aromatic compound, we do find a molecule that has a nitrogen attached to a benzene

ring:
NH2

aniline If we attach a branch to the Nitrogen on an aniline molecule:

NH
CH3

N-methylaniline The position of the methyl is noted with the prefix of a N.

CH3

NH

H3C
N,4-dimethylaniline in this example we have a methy on the benzene ring and the N
atom.
 CH3

NH

CH3
What is the name of this molecule?
Name:

Drawing a amine from the name:

1. Nethylaniline
2. Ethyl methyl amine
3. N,N-diethyl amine

Amide

An amide molecule contains both a nitrogen and an oxygen atom. Has a carbonyl group on
the carbon that is attached to the nitrogen.
An amine is formed when a carboxylic acid is reacted with an amine in the presence of heat.
O
O
H2N
+ CH3
C
CH3
H3C C Δ H3C NH
OH

Ethanoic acid methylamine N-methyl ethanamide

To name an amide the attachments to the N are treated as branches, the base name is noted by
the number of carbons from the carbonyl group. The name ends with an amide methanamide

Examples:
O
CH2
C
H3C CH2 NH2
butanamide
If there are other alkyl groups attached to the N:
O
CH2 CH3
C
H3C CH2 N
CH3
CH2
N-ethyl-N-methylbutanamide

If you have a branch on the longest chain:

H3C
O
CH2
C CH3
CH
NH

CH2
H3C
2-ethyl-N-methylbutanamide

Draw the correct structure from the following names:

1. N-ethylpropanamide
2. 3-methylbutanamide