Which of the following is the strongest base?

Name: Exam Paper Generator | JEE NEET Paper Generator | Vedclass
Brand: Vedclass
Rating: 5 (35 reviews)

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.

Similar Questions

Among the following isomeric amines,the amine having the highest boiling point is:

What is the product of the following reaction?

Which of the following statements is correct?

Which of the following statements is incorrect?

$R-CONH_2 \xrightarrow[\Delta]{KOBr} R-NH_2$. The correct statement about the product is:

Vedclass Test Series

Exam Paper Generator

Online Exam Module