Solve the following


Out of C6H5CH2Cl and C6H5CHClC6H5, which is more easily hydrolysed by aqueous KOH?


Hydrolysis by aqueous $\mathrm{KOH}$ proceeds through the formation of carbocation. If carbocation is stable, then the compound is easily hydrolyzed by aqueous $\mathrm{KOH}$. Now, $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{Cl}$ forms $1^{\circ}$-carbocation, while $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHClC}_{6} \mathrm{H}_{5}$ forms $2^{\circ}$-carbocation, which is more stable than $1^{\circ}$-carbocation. Hence, $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHClC}_{6} \mathrm{H}_{5}$ is hydrolyzed more easily than $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{Cl}$ by aqueous $\mathrm{KOH}$.

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