Chem 30B - Naming Amines and Amides (Rules)

Amines and amides come from ammonia (replacing the Hs).

Classification of amines
by the number of alkyl chains:

Ammonia

Amine

Ammonia

Amide

Primary amine
Secondary amine
(one alkyl chain) (two alkyl chains)

Tertiary amine
(three alkyl chains)

Naming Simple Amines (Common Names)

Are named as alkylamines.
List the names of the alkyl groups bonded to the N atom in alphabetical order in front of amine.
CH3
CH3CH2NH2
CH3NHCH3
|
ethylamine
dimethylamine
CH3NCH2CH3
ethyldimethylamine
Name the following amines:
CH 2
CH 3

NH
CH2

CH2

CH 3

CH2

CH 3

CH 3

CH

IUPAC Names of Amines

Amines are named as alkanamines.
The e in the alkane name of the longest chain is changed to amine.
The chain is numbered to locate the amine group and substituents.
CH3CH2NH2
ethanamine

NH 2

NH 2

NH2
|
CH3CHCH3
2-propanamine

In a secondary or tertiary amine,

The longest alkane chain is numbered.
Each alkyl group bonded to the N atom is named as a N-alkyl group
HNCH3
|
CH3CH2CH2NHCH3
CH3CHCH2CH3
3
2
1
1
2
3
4
N-Methyl-1-propanamine
N-Methyl-2-butanamine
Name the following amines:

CH 3
CH 3

NH
CH2

CH2
CH2

CH 3

CH 3

NH 2

CH 2CH 2CH3

Amines as Branches

When found in compounds with oxygen containing functional group:

-NH2
amino
-NHR
N-alkylamino
-NR2
N,N-dialkylamino
Name the following amine:

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NHCH3

H2N

CH2CH2CH2C

OH

4-aminobutanoic acid
(aminobutyric acid)
N(CH3) 2
CH3CH2CH2CHCH2CH2 OH
3-(N,N-dimethylamino)-1-hexanol
3-(N,N-dimethylamino)hexan-1-ol

Ammonium Salts

R
R

Named by naming the positive ion first and then naming the negative ion.

Pharmaceutical companies often name amine salts by naming the parent amine followed by the name of the acid
used to synthesize the salt:
HCl: amine hydrochlorides
H2SO4: amine hydrogen sulfates
O

Amides
Classification of amides
by the number of alkyl chains:

O
N

Primary amide

O
N

Tertiary amide

Propanamide (IUPAC)
Propionamide (common)

An alkyl group bonded to the N atom is named as N-alkyl in front of the amide name.
O H
O H
||
||
CH3 CNCH3
CH3CH2 CNCH2CH3
N-methylethanamide (IUPAC)
N-ethylpropanamide (IUPAC)
N-methylacetamide (common)
N-ethylpropionamide (common)

The amide of benzene is named benzamide.

O
C

O
NH 2

Benzamide

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NH

CH 3

N-methylbenzamide

Secondary amide

Amides are named as alkanamides.

IUPAC replaces oic acid ending with amide.
Common names replace -ic acid ending with amide.
O
O
||
Methanamide (IUPAC)
||
HCNH2
Formamide (common)
CH3CH2CNH2

Naming Amines and Amides Key (Rules)

Name the following amines (common names):

Name the following amines (IUPAC names):

Name the following amine:

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