Z →HCl R-Cl;  Identify Z in the reaction

This is a reaction involving  C- O cleavage;  Reactivity order-  30 alcohol>20 alcohol>10 alcohol.Primary and secondary alcohols require anhydrous Zinc chloride as a catalyst.Tertiary alcohols being highly reactive can give the product even with HCl.Phenols due to double bond character in  C-O bond( resonance ) cannot involve in nucleophilic substitution.