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  • Arrange the following in increasing order of their basic strength: (i) C_2 H_5 NH_2

13.4     Arrange the following in increasing order of their basic strength:

                 (i)   C_{2}H_{5}NH_{2},  C_{6}H_{5}NH_{2},  NH_{3},  C_{6}H_{5}CH_{2}NH_{2}   and   (C_{2}H_{5})_{2}NH

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Considering the inductive effect, solvation effect and steric hindrance of the alkyl group which decides the basic strength of alkylamines. order of basic strength in ethyl substituted amine is-

NH_{3}<C_{2}H_{5}NH_{2}<(C_{2}H_{5})_{2}NH

and order in benzene substituted ring-

C_{6}H_{5}NH{2}<C_{6}H_{5}CH_{2}NH_{2}

Due to the -R effect of benzene C_{6}H_{5}NH{2} has less electron density than ammonia. So, the final order is -

C_{6}H_{5}NH{2}<NH_{3}<C_{6}H_{5}CH_{2}NH_{2}<C_{2}H_{5}NH_{2}<(C_{2}H_{5})_{2}NH

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