Chem 30B - Naming Amines and Amides (Rules) Amines and amides come from ammonia (replacing the

Hs).!
H N H H R N R R R N R

O C R

Ammonia

Amine

Amide

Classification of amines by the number of alkyl chains:

N H

N H

N R

N R

Ammonia

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 CH2 NH CH2 CH2 CH 3 N CH 3 CH 3 CH NH 2

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

Tertiary amine (three alkyl chains)

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. The chain is numbered to locate the amine group and substituents. CH3CH2NH2 ethanamine 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 CH2 NH CH2 CH2 CH 3 CH 3 N CH 2CH 2CH3

NH2 | CH3CHCH3 2-propanamine

NH 2

NHCH3

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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O 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 N 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 O N H H R C N R H R O C N R R

Amides
Classification of amides by the number of alkyl chains:
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) || HCNH2 Formamide (common) CH3CH2CNH2

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 NH 2 O 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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