Q.

The order of basic strength of the following in aqueous solution is
NH3, C2H5NH2, (C2H5)2NH, (C2H5)3N

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a

(C2H5)3N > C2H5NH2 > (C2H5)2NH > NH3

b

NH3 > H2NC2H5 > N(C2H5)3 > HN(C2H5)2

c

(C2H5)3N > (C2H5)2NH > C2H5NH2 > NH3

d

(C2H5)2NH > (C2H5)3N > C2H5NH2 > NH3

answer is B.

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Detailed Solution

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  • Basicity of aliphatic amines should be: primary>secondary>tertiary, which is opposite to the inductive effect based order.
  • Secondly, when the alkyl group is small, like -CH3 group, there will be steric hindrance.
  • Therefore, the change of the nature of alkyl group, i.e. from -CH3 to -C2H5 results in change in the order of basic strength.
  • Thus, there is a subtle interplay of inductive effect, solvation effect and steric hindrance of alkyl group, which decides the basic strength of alkyl amines.
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