Chem 30B - Naming Amines and Amides (Rules) O

H N H R N R R N C R
Amines and amides come from ammonia (replacing the H’s).  
H R R
Ammonia Amine Amide

Classification of amines H N H R N H R N H R N R
by the number of alkyl chains:
H H R R
Ammonia Primary amine Secondary amine Tertiary amine
(one alkyl chain) (two alkyl chains) (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
CH3—CH2—NH2 CH3—NH—CH3 |
ethylamine dimethylamine CH3—N—CH2—CH3
ethyldimethylamine
Name the following amines:
CH 3
N
CH 2 NH CH2
NH 2
CH 3 CH2 CH2 CH 3 CH 3 CH NH 2

IUPAC Names of Amines

• Amines are named as alkanamines.
• The –e in the alkane name of the longest chain is changed to –amine. NH2
• The chain is numbered to locate the amine group and substituents. |
CH3—CH2—NH2 CH3—CH—CH3
ethanamine 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
HN—CH3
|
CH3—CH2—CH2—NH—CH3 CH3—CH—CH2—CH3
3 2 1 1 2 3 4
N-Methyl-1-propanamine N-Methyl-2-butanamine
CH 3
Name the following amines: CH 3 NH CH2
CH2 CH2 CH 3 CH 3 N CH 2CH 2CH3 NH 2 NHCH3

O
Amines as Branches
H2N CH2CH2CH2C OH
• When found in compounds with oxygen containing functional group:  
• -NH2 amino 4-aminobutanoic acid
(γ−aminobutyric acid)
• -NHR N-alkylamino
• -NR2 N,N-dialkylamino
N(CH3) 2
Name the following amine:
CH3CH2CH2CHCH2CH2 OH
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3-(N,N-dimethylamino)-1-hexanol
3-(N,N-dimethylamino)hexan-1-ol
Ammonium Salts R

R N 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 O O
Amides
Classification of amides R C N H R C N H R C N R

by the number of alkyl chains:

H R R

Primary amide Secondary amide Tertiary 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) || Propanamide (IUPAC)
H—C—NH2 Formamide (common) CH3—CH2—C—NH2 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 —C—N—CH3 CH3—CH2 —C—N—CH2—CH3
N-methylethanamide (IUPAC) N-ethylpropanamide (IUPAC)
N-methylacetamide (common) N-ethylpropionamide (common)

• The amide of benzene is named benzamide.

O
O

C NH 2
C NH CH 3

Benzamide N-methylbenzamide

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 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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