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

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

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:
$(1)$ $CH_3-CO-CH_2-Cl$
$(2)$ $CH_3-CH_2-CH_2-Cl$
$(3)$ $(CH_3)_3C-Cl$

Similar Questions

Which among the following is most reactive via $S_N2$ mechanism?

$KCN$ reacts readily to give a cyanide with:

Which one of the following is used to obtain the maximum percentage of terminal alkene by dehydrohalogenation of $CH_3CH_2C(CH_3)_2Br$?

Select the incorrect order among the following:

Sodium ethoxide is a specific reagent for

Vedclass Test Series

Exam Paper Generator

Online Exam Module

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)$ $(CH_3)_3C-Cl$