CHAPTER 10

AMINES
• Amines: derivatives from NH3. The H atoms have been
replaced by organic gps.
NOMENCLATURE OF AMINES
• Simple amines – alkyl amines
CH3NH2 (CH3)2NH CH3CH2NH2 (CH3CH2)3N
methylamine dimethylamine ethylamine triethylamine
• Systematic nomenclature:
CH3NH2 CH3CH2CH2NH2 CH3CH(NH2)CH2CH3
methanamine 1-propanamine 2-butanamine/
isobutylamine
Unsaturated amines

CH3 NH2

C CH
H3C C CH3
H

4-methyl-3-penten-2-amine
 CH3CH2CH CHCH2NH2
(CH3)2CHC CCH2CH2NH2
CH3CH CHCH(NH2)CH3

Answer:
1) 2-pentene-1-amine
2) 5-methyl-3-hexyne-1-amine
3) 3-pentene-2-amine
PHYSICAL PROPERTIES
• Hydrogen bonding – the electronegativity
difference of the between N and H
• Partial –ve charge of N and partial +ve charge of
H
• The presence of lone pair on N allow the strong
intermolecular attraction between H and lone
pair of a second molecule.
• In water, the H on water is attracted by the
N lone pair.
• The H bonded to the N (methylamine) is
attracted to the O lone pairs.
 THE REACTION OF AMINES
Amines as Nucleophiles: Alkylation by nucleophile Substitution
 PREPARATION OF AMINES BY
REDUCTION REACTION
A) Reduction of aromatic nitro compound
Example:
B) Reduction of nitriles
c) Reduction of Amides
Aromatic Diazonium Salts
Replacement reaction
 HETEROCYCLIC AMINES

N N
benzene pyridine
H
piperidine

pyrrole H
pyrrolidine
NATURALLY OCCURING HETEROCYCLIC AMINES: ALKALOID

•Piperine: black pepper

•Lobelline : basic ingredient for smoking cessation aid , treatment of other
drug addiction such as addiction to amphetamines or cocain
•Cuscohygrine: “deadly nightshade” from atropa belladonna, etremely toxic
with hallucinogenic properties
•Nicotine: toxic alkaloid in tobacco
•Heme: hemoglobin that transport oxygen to the body, red pigment of the
blood (Fe)
•Chlorophyll a: a green material that responsible to photosynthesis in
green plants
Quinine: found in tonic water, antimalarial drugs
Tubocurarine chloride : a poison has been used on arrow and blowdarts
Morphine: pain relieving effect and generate a feeling of well-being
Dextromethorphan: control coughing like codeine but nonaddictive
Caffeine: a stimulant in coffee and tea
LSD: used as recreational drug
Strychnine: very toxic, used as a pesticide for killing small vertebrate
such as birds and rodents. Bitter taste.