What is the correct order of basicity for the | vedclass

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(D) The basicity of substituted anilines depends on the electron-donating or electron-withdrawing nature of the substituent attached to the benzene ri

Vedclass · Accepted Answer

$III < IV < I < II$

Vedclass · Answer

(D) The basicity of substituted anilines depends on the electron-donating or electron-withdrawing nature of the substituent attached to the benzene ring.Electron-donating groups $(EDG)$ increase the electron density on the nitrogen atom,thereby increasing basicity.Electron-withdrawing groups $(EWG)$ decrease the electron density on the nitrogen atom,thereby decreasing basicity.In the given structures:$(I)$ $p$-toluidine: $-CH_3$ is an $EDG$ (+$I$ effect).$(II)$ $p$-anisidine: $-OCH_3$ is a strong $EDG$ (+$M$ effect).$(III)$ $p$-nitroaniline: $-NO_2$ is a strong $EWG$ (-$M$ and -$I$ effect).$(IV)$ $p$-chloroaniline: $-Cl$ is an $EWG$ (-$I$ effect,but +$M$ effect is weak).Comparing the effects: The strongest $EDG$ is $-OCH_3$ $(II)$,followed by $-CH_3$ $(I)$. The EWGs are $-Cl$ $(IV)$ and $-NO_2$ $(III)$. Since $-NO_2$ is a much stronger $EWG$ than $-Cl$,it will make the aniline the least basic.Thus,the order of basicity is: $III < IV < I < II$.

What is the correct order of basicity for the substituted anilines ($I$ to $IV$)?

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