For the reaction CH_3Br + Nu^{-} rightarrow C | vedclass

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Question

(A) The rate of an $S_N2$ reaction is directly proportional to the nucleophilicity of the attacking species. Nucleophilicity is related to the basicit

Vedclass · Accepted Answer

$4 > 3 > 1 > 2$

Vedclass · Answer

(A) The rate of an $S_N2$ reaction is directly proportional to the nucleophilicity of the attacking species. Nucleophilicity is related to the basicity of the nucleophile. Stronger bases are generally better nucleophiles. The basicity order of the given species is: $CH_3O^{-} > HO^{-} > PhO^{-} > AcO^{-}$. $CH_3O^{-}$ is the strongest base due to the $+I$ effect of the $CH_3$ group. $HO^{-}$ is a strong base. $PhO^{-}$ is less basic than $HO^{-}$ due to resonance stabilization of the phenoxide ion. $AcO^{-}$ is the least basic among these due to the resonance stabilization of the carboxylate ion by two oxygen atoms. Therefore,the order of nucleophilicity and reaction rate is: $(4) CH_3O^{-} > (3) HO^{-} > (1) PhO^{-} > (2) AcO^{-}$. Thus,the correct order is $4 > 3 > 1 > 2$.

For the reaction $CH_3Br + Nu^{-} \rightarrow CH_3 - Nu + Br^{-}$,arrange the following nucleophiles $(Nu^{-})$ in the decreasing order of their reaction rate: $(1) PhO^{-}, (2) AcO^{-}, (3) HO^{-}, (4) CH_3O^{-}$.

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