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 of the following is not true for $S_{N}1$ reaction?

The major product of the following reaction is:

Phosgene is formed slowly from which one of the following on exposure to air and sunlight?

What is the major product of the following reaction?
$CH_2=CH-CH_2-CH(Br)-CH_3 + KOH \xrightarrow[\text{heat}]{\text{alcohol}} \dots$

The following reaction is described as:
$CH_3(CH_2)_5-CH(CH_3)-Br + OH^- \rightarrow HO-CH(CH_3)(CH_2)_5CH_3 + Br^-$

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)$ $(CH_3)_3C-Cl$