Amine 2ry year

HN
Amine classification NH
Cl HO
 Aryl amine : N attached to aryl group CH3 N
 Alkyl amine : N attached to alkyl group N-ethyl N-(3-chloropropyl) 5-[N-ethyl,N-methyl-amino]
 1ry amine : R—NH2 cyclohexanamine aniline heptan-3-ol
 2ry amine : R—NH—R  N with 4 bonds → +ve charge → Ammonium ion
 3ry amine : R3N CH3
Amine Nomenclature H3C
+ –
N I –
+
H NH Br
 Iupac name : Suffix “amine” & prefix “amino” H3C
+
NH3 Cl
–

CH3CH2NH2 → Ethanamine CH3NH2 → methanamine methylammonium N-ethyl-N-methylcyclopentyl N-ethyl-N-methyl propan

chloride ammonium chloride ammonium bromide
 Common name : Alkyl + amine
CH3CH2NH2 → Ethylamine CH3NH2 → methylamine
Basicity
NH2 2ry amine > 1ry amine ≥ 3ry amine > NH3 > aromatic amine “Aniline
NH2 >diphenyl amine > triphenyl amine “
HOOC NH2
 Arylamines are much weaker bases than ammonia… explain
cyclohexanamine pentan-2-amine
 Lone pair of electrons is not available by resonance with benzene
cyclohexylamine 1-methyl butylamine 4-amino-2-methylpentanoic acid
 N substituted amine
H3C
N
CH3

HOOC N  Aniline free base is more stable by resonance than the conjugate
acid of the amine (anilinium cation)
N,N-dimethyl 4-[N-ethyl,N-methyl amino] H
cycloheptanamine -2-methylpentanoic acid H+ +
NH2 NH2

Dr/Ahmed El ayde 1
 2ry year
Effect of substituents on basicity

EDG “P>O> >M” > EWG in Baicity “>M>P>O” Which N atom in chloroquinine is the strongest base?

 Nitro group decrease basicity of aniline ..explain

 [-M] pf NO2 make the lone pair of nitrogen
(NH2) less available
 NO2 destabilize
the anilinium cations

Amines isolated from plants and animals : alkaloids

 piperidine is more basic than pyridine.... explain
 piperidine has lone pair on Sp3 Nitrogen
 pyridine has lone pair on Sp2 nitrogen “more
electronegative , less basic” [2] N
 Which nitrogen is basic in imidazole?
[1] N
H
Nitrogen [2] is more basic because lone pair is more available “not enter
in resonance” & its protonation form stable ion

2 ‫أحمد العايدى‬/‫د‬ 01010288200