Which of the following is likely to undergo r | vedclass

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(B) Racemization occurs in $SN^1$ reactions when the substrate forms a stable,planar carbocation intermediate that is chiral. Among the given options,

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$CH_3-CH_2-CH(Cl)-CH_3$

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(B) Racemization occurs in $SN^1$ reactions when the substrate forms a stable,planar carbocation intermediate that is chiral. Among the given options,$CH_3-CH_2-CH(Cl)-CH_3$ ($2$-chlorobutane) is a secondary alkyl halide that can form a planar carbocation $(CH_3-CH_2-CH^+-CH_3)$ upon the loss of the chloride ion. This carbocation is prochiral and can be attacked by the nucleophile from either side,leading to a racemic mixture. $CH_3-CH(Cl)-CH_3$ (isopropyl chloride) forms a less stable secondary carbocation and is less prone to $SN^1$ compared to $2-$chlorobutane. $CH_3-CH_2-CH(Cl)-CH_2-CH_3$ ($3$-chloropentane) forms a carbocation that is achiral due to symmetry,so it does not result in a racemic mixture. $(CH_3)_3C-CH_2-Cl$ is a primary alkyl halide and typically undergoes $SN^2$ reactions.

Which of the following is likely to undergo racemization during alkaline hydrolysis by $SN^1$ mechanism?

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