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Q. The order of $S_N1$ reactivity in aqueous acetic acid solution for the compounds
1.$H_3C - \overset{\underset{||}{O}}{C}-CH_2 - Cl$
2. $H_3C - CH_2 - CH_2 - Cl$
3. $(H_3C)_3C—Cl$ is

KVPYKVPY 2013Haloalkanes and Haloarenes

Solution:

The $S_N1$ reaction depends upon the stability of carbocations. Higher is the stability of carbocation more will be the reactivity of compounds.
The carbocation of given compounds are as follows :
$CH_3 - \overset{\underset{||}{O}}{C}- CH_2 - Cl \to CH_3\overset{\underset{||}{O}}{C}-CH_2^+ + Cl^-$
$CH_3 - CH_2 - CH_2 - Cl \to CH_3CH_2CH_2^+ + Cl^-$
$(CH_3)_3CCl \to (CH_3)_3C^+ + Cl^-$
The order of stability of carbocation is
image
Thus, the order of reactivity of given compounds in $S_N1$ reaction is $3 > 2 > 1$.