Nitrogen Containing CompoundHard
Question
The correct order of the basicities of the following compounds is :
, CH3 - CH2 - NH2, (CH3)2NH, 
1 2 3 4
, CH3 - CH2 - NH2, (CH3)2NH, 1 2 3 4
Options
A.2 > 1 > 3 > 4
B.1 > 3 > 2 > 4
C.3 > 1 > 2 > 4
D.1 > 2 > 3 > 4
Solution
The correct order is :
(1) is most basic because the cation obtained by its protonation (i.e, its conjugate acid) is highly stabilized by resonance.
(4) is least baisc because lone pair of -NH2 gp. intercts with
gp. and thus less available for protonation.
(3) and (4) both are aliphatic anines but (3), a secondary amine is more basic than (2), a primary amine is more basic than (2), a primary amine, due to more + I effect in (3)
(1) is most basic because the cation obtained by its protonation (i.e, its conjugate acid) is highly stabilized by resonance.
(4) is least baisc because lone pair of -NH2 gp. intercts with
gp. and thus less available for protonation.(3) and (4) both are aliphatic anines but (3), a secondary amine is more basic than (2), a primary amine is more basic than (2), a primary amine, due to more + I effect in (3)
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