The order of S_{N^1} reactivity in aqueous ac | vedclass

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Question

(C) $S_{N^1}$ reactivity depends on the stability of the carbocation intermediate formed after the departure of the leaving group $(Cl^-)$.$(1)$ $CH_3

Vedclass · Accepted Answer

$3 > 2 > 1$

Vedclass · Answer

(C) $S_{N^1}$ reactivity depends on the stability of the carbocation intermediate formed after the departure of the leaving group $(Cl^-)$.$(1)$ $CH_3-CO-CH_2-Cl$ forms $CH_3-CO-CH_2^+$,which is destabilized by the electron-withdrawing carbonyl group ($-I$ effect).$(2)$ $CH_3-CH_2-CH_2-Cl$ forms a primary carbocation $(CH_3-CH_2-CH_2^+)$,which is unstable.$(3)$ $(CH_3)_3C-Cl$ forms a tertiary carbocation $((CH_3)_3C^+)$,which is highly stable due to hyperconjugation and inductive effects.Comparing the stability: $(3)$ (tertiary) is the most stable. Between $(1)$ and $(2)$,$(2)$ is more stable than $(1)$ because the carbonyl group in $(1)$ strongly destabilizes the adjacent positive charge. Thus,the order is $3 > 2 > 1$.

The order of $S_{N^1}$ reactivity in aqueous acetic acid solution for the compounds:
$(1)$ $CH_3-CO-CH_2-Cl$
$(2)$ $CH_3-CH_2-CH_2-Cl$
$(3)$ $(CH_3)_3C-Cl$

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The order of $S_{N^1}$ reactivity in aqueous acetic acid solution for the compounds:$(1)$ $CH_3-CO-CH_2-Cl$$(2)$ $CH_3-CH_2-CH_2-Cl$$(3)$ $(CH_3)_3C-Cl$