Q.

The correct order of the basic strength of methyl substituted amines in aqueous solution is

Moderate

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By Expert Faculty of Sri Chaitanya

a

CH3NH2>CH32NH>CH33 N

b

CH32NH>CH3NH2>CH33 N

c

CH33 N>CH3NH2>CH32NH

d

CH33 N>CH32NH>CH3NH2

answer is 2.

(Detailed Solution Below)

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Detailed Solution

The basicity of amines in aqueous solution depends on the stability of the ammonium cation or conjugate acid formed by accepting a proton from water which in turn depends on the +I -effect of alkyl group, extent of hydrogen bonding and steric factor. All these factors are favourable for 2° amines. Therefore, 2° amines are the strongest bases. If the alkyl group is small i.e., CH3 then there is no steric hindrance to H-bonding. Thus, the stability due to hydrogen bonding predominates over the stability due to +I -effect of CH3 group and hence primary amine is a stronger base than 3° amine. Hence, overall decreasing basic strength for methylamines in aqueous solution is CH32NH>CH3NH2>CH33 N
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