Q.How will you prepare benzyl alcohol from toluene ?

Toluene is first chlorinated at its methyl (side-chain) hydrogen using $Cl_2$/sunlight to give benzyl chloride, which is then hydrolysed with aqueous NaOH to give benzyl alcohol.

Step 1 — Free-radical side-chain chlorination:

When toluene is treated with chlorine gas in the presence of sunlight or UV light (photochemical conditions, no catalyst like $FeCl_3$/$AlCl_3$ which would instead direct ring substitution), chlorination occurs selectively at the benzylic (side-chain) $CH_3$ group via a free-radical mechanism, giving benzyl chloride:

$C_6H_5-CH_3 + Cl_2 \xrightarrow{h\nu\,(\text{sunlight})} C_6H_5-CH_2Cl + HCl$

(Note: with excess $Cl_2$/sunlight, further chlorination can give benzal chloride $C_6H_5CHCl_2$ and benzotrichloride $C_6H_5CCl_3$; controlled, limited chlorination is used to stop at the mono-chloro stage, benzyl chloride.)

Step 2 — Alkaline hydrolysis: …