Order of basic strength: (A) Ph-NH_2,(B) Ph-N | vedclass

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Question

(C) The basic strength of aromatic amines is influenced by the electron-donating $+I$ effect of alkyl groups and the steric inhibition of protonation

Vedclass · Accepted Answer

$C > B > A > D$

Vedclass · Answer

(C) The basic strength of aromatic amines is influenced by the electron-donating $+I$ effect of alkyl groups and the steric inhibition of protonation $(SIP)$ effect.$(1)$ The $+I$ effect of methyl groups increases the electron density on the nitrogen atom,making it more available for donation. Thus,the basicity order for $N$-substituted anilines is: $N,N$-dimethylaniline $(C) > N$-methylaniline $(B) > 	ext{Aniline} (A)$.$(2)$ In $o$-toluidine $(D)$,the ortho-methyl group causes steric hindrance to the protonation of the amino group,a phenomenon known as the Steric Inhibition of Protonation $(SIP)$ effect. This significantly reduces its basicity compared to aniline $(A)$.$(3)$ Combining these factors,the overall order of basic strength is: $C > B > A > D$.

Order of basic strength: $(A) Ph-NH_2$,$(B) Ph-NH-CH_3$,$(C) Ph-N(CH_3)_2$,$(D) \text{o-toluidine (2-methylaniline)}$

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