Amines Amines are nitrogencontaining compounds Structure and Classification Amines are classified as 1 2 or 3 depending on the number of carbon groups bonded to nitrogen Aliphatic amine ID: 914265
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Slide1
Chemistry 2100
Chapter 16
Slide2Amines
Amines are nitrogen-containing compounds
Slide3Structure and Classification
Amines are classified as 1°, 2°, or 3° depending on the number of carbon groups bonded to nitrogen.
Aliphatic amine:
All carbons bonded to nitrogen are derived from alkyl groups. See the three above.
Aromatic amine:
One or more of the groups bonded to nitrogen are aryl groups.
Slide4Structure and Classification
Heterocyclic amine:
An amine in which the nitrogen atom is part of a ring.
Heterocyclic aliphatic amine:
A heterocyclic amine in which the ring is saturated (has no C=C bonds).
Heterocyclic aromatic amine:
The amine nitrogen is part of an aromatic ring.
Slide5Nomenclature
IUPAC names
We derive IUPAC names for aliphatic amines just as we did for alcohols.
Drop the final
-e
of the parent alkane and replace it by
-amine.Use a number to locate the amino group on the parent chain.
Slide6Physical Properties
Amines are polar compounds:
Both 1° and 2° amines have N-H bonds, and can form hydrogen bonds with one another.
3° Amines have no N-H bond and cannot form hydrogen bonds with one another.
Slide7CH
3
CH
2
CH
2
N
H
2
(bp 48°C)
CH
3
CH
2
N
H
CH
3 (bp 35°C) (CH3)3N (bp 3°C)
CH3CH3 (bp -88°C) CH3NH2 (bp -7°C) CH3OH (bp +65°C)
NH3 (bp -33°C) H2O (bp +100°C)
Boiling Points
Slide8Odor
Like ammonia, low-molecular-weight amines have very sharp, penetrating odors.
Trimethylamine, for example, is the pungent principle in the smell of rotting fish.
Two other particularly pungent amines are 1,4-butanediamine (putrescine) and 1,5-pentanediamine (cadaverine).
Slide9Basicity of Amines
Slide10free base
ammonium salt
(hydrochloride)
Ammonium Salts
Slide11(S)-
(+)-coniine
(S)-
(–)-nicotine
(–)-strychnine
(–)-cocaine hydrochloride
Alkaloids
Slide12Nitrosation
Slide13Slide14Slide15Slide16Slide17Slide18Slide19Slide20Azo Dyes
Slide21Slide22Slide23Slide24Orange II
Slide25Orange II
Slide26Orange II
Slide27Orange II
American Flag Red
Slide28Slide29Slide30Heterocyclic Amines
Slide31Slide32nicotinamide / niacin (B
3
)
Slide33Morphine
Codeine
Heroin
Slide34Poison Dart Frogs