Question 15 Marks
Arrange the following compounds in a decreasing order of basic strength in their aqueous solutions.
$NH_3, CH_3NH_2, (CH_3)_2NH, (CH_3)_3N$
$NH_3, CH_3NH_2, (CH_3)_2NH, (CH_3)_3N$
Answer
View full question & answer→The relative strength of $CH _3 NH _2$, $\left( CH _3\right)_2 NH$ and $\left( CH _3\right)_3 N$ depends upon the stabilisation of their conjugate acids which depend on the number of factors like $H -$bonding, steric hindrance and $+ I -$effect of the alkyl groups. All these factors are favourable for $2^0$ amines, therefore $\left( CH _3\right)_2 NH$ is a stronger base than $CH _3 NH _2$ and $\left( CH _3\right)_3 N$. Since, $\left( CH _3\right)_3 N$ does not have $H -$atom linked to N atom, therefore, the stabilisation of the conjugate acid$-$derived from $CH _3 NH _2$ due to $H -$bonding is greater than that of the conjugate acid derived from $\left( CH _3\right)_3 N$.

Further, in $NH _3$ $no + I - $group is linked to $N -$atom thus, it is least basic among all the given amines. Hence, the order would be:$ \left(CH_3\right)_2 NH>CH_3 NH_2>\left(CH_3\right)_3 N>NH_3.$

Further, in $NH _3$ $no + I - $group is linked to $N -$atom thus, it is least basic among all the given amines. Hence, the order would be:$ \left(CH_3\right)_2 NH>CH_3 NH_2>\left(CH_3\right)_3 N>NH_3.$
