I need a little help in ORGANIC chem PLZZZZZZ?

Question

Suggest how the behaviour of the compound C6H5CH2Cl with hot KOH differs from that of C6H5Cl and from that of C6H5CH2CH2Cl. In each case, state the type of reaction undergone (if any) and write the formula of the product.

Answer 1

C6H5-CH2-Cl would ionize to C6H5-CH2+, SN1 mechanism, which would then react with H2O to form C6H5-CH2-OH. C6H5-Cl might not react. However, if the KOH were concentrated enough and hot enough, then C6H5Cl might lose HCl to form benzyne. Benzyne might then react with H2O to form C6H5-OH. C6H5-CH2-CH2-Cl would react via an E2 mechanism to eliminate HCl and form C6H5-CH=CH2.