Which of the following is the strongest base?

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Question

(D) The basicity of substituted $N,N$-dimethylanilines depends on the electron-donating or electron-withdrawing nature of the substituent and steric e

Vedclass · Accepted Answer

$4$-methyl-$N,N$-dimethylaniline

Vedclass · Answer

(D) The basicity of substituted $N,N$-dimethylanilines depends on the electron-donating or electron-withdrawing nature of the substituent and steric effects. In $4$-methyl-$N,N$-dimethylaniline,the $-CH_3$ group at the para position exerts a $+I$ effect and hyperconjugation,which increases the electron density on the nitrogen atom,making it more available for protonation. In $2$-methyl-$N,N$-dimethylaniline,the ortho-substituent causes steric hindrance,which inhibits the resonance of the lone pair of the nitrogen with the benzene ring (ortho effect),but the steric hindrance also makes it difficult for the proton to approach the nitrogen,generally reducing its basicity compared to the para-isomer. $3$-methyl-$N,N$-dimethylaniline has a $+I$ effect but lacks the strong resonance stabilization of the para-isomer. Therefore,$4$-methyl-$N,N$-dimethylaniline is the strongest base among the given options.

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