Which compound undergoes nucleophilic substit | vedclass

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Question

(A) The reaction with $NaCN$ typically proceeds via the $S_N2$ mechanism,as $CN^-$ is a strong nucleophile.The rate of $S_N2$ reaction is inversely pr

Vedclass · Accepted Answer

$CH_3CH_2CH_2CH_2Br$

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(A) The reaction with $NaCN$ typically proceeds via the $S_N2$ mechanism,as $CN^-$ is a strong nucleophile.The rate of $S_N2$ reaction is inversely proportional to the steric hindrance at the reaction center.The order of reactivity for $S_N2$ is: primary $(1^\circ)$ > secondary $(2^\circ)$ > tertiary $(3^\circ)$.Comparing the given compounds:$(A)$ $CH_3CH_2CH_2CH_2Br$ is a primary alkyl halide $(1^\circ)$.$(B)$ $CH_3CH_2CH(CH_3)Br$ is a secondary alkyl halide $(2^\circ)$.$(C)$ $(CH_3)_2CHCH_2Br$ is a primary alkyl halide $(1^\circ)$,but it has steric hindrance at the $\beta$-carbon.$(D)$ $CH_3CH_2C(CH_3)_2Br$ is a tertiary alkyl halide $(3^\circ)$.Among the primary halides,$CH_3CH_2CH_2CH_2Br$ has the least steric hindrance at the reaction center,making it the fastest to undergo $S_N2$ substitution.

Which compound undergoes nucleophilic substitution with $NaCN$ at the fastest rate?

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