A compound X of formula C7H8O liberates H2 with sodium, is insoluble in aqueous NaOH, gives no colour with neutral FeCl3, and is oxidised by PCC to a compound that gives a silver mirror with Tollens' reagent. X is

JEE Advanced levelSingle correct optionDifficulty 3 of 3ap048

A compound X of formula $C X_{7} H X_{8} O$ liberates $H X_{2}$ with sodium, is insoluble in aqueous $NaOH$ , gives no colour with neutral $FeCl X_{3}$ , and is oxidised by $PCC$ to a compound that gives a silver mirror with Tollens' reagent. X is

Liberation of

H X_{2}

shows an O-H, but insolubility in alkali and no

FeCl X_{3}

colour rule out phenols (cresols). Methoxybenzene has no O-H. Benzyl alcohol,

C X_{6} H X_{5} CH X_{2} OH

, is oxidised by PCC to benzaldehyde, which gives the silver mirror.