Naming Amines and Amides rules PDF

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information on amino acids and nomenclature.This will help students...

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

Amines and amides come from ammonia (replacing the H’s).!

Classification of amines by the number of alkyl chains:

H

N

H

N

H

O

R

H

R

Ammonia

Amine

R

N

H

H

R

R

N

R

C

R

N

Amide

H

R

R

H

Ammonia

R

N

N

R

R

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 CH3—CH2—NH2 CH3—NH—CH3 | ethylamine dimethylamine CH3—N—CH2—CH3 ethyldimethylamine Name the following amines: CH2 CH3

CH2

CH3

CH3

CH2

CH3

N

CH2

NH

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. CH3—CH2—NH2 ethanamine

NH2

NH2

NH2 | CH3—CH—CH3 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 Name the following amines:

CH3 CH3

CH2

NH CH2

CH2

CH3

CH3

N

NH 2

CH2CH2CH3

O

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

H 2N

CH2CH2CH2C

OH

4-aminobutanoic acid (γ−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

O

Amides R

Classification of amides by the number of alkyl chains:

C

N

H

R

C

H

Primary amide

H

R

C

R

The amide of benzene is named benzamide. O C

O NH2

Benzamide

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C

NH

CH3

N-methylbenzamide

R

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 —C—N—CH3 CH3—CH2 —C—N—CH2—CH3 N-methylethanamide (IUPAC) N-ethylpropanamide (IUPAC) N-methylacetamide (common) N-ethylpropionamide (common) •

N R

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) || H—C—NH2 Formamide (common) CH3—CH2—C—NH2 •

N

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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