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| List-$I$ | List-$II$ |
|---|---|
| $A$. Phenol $\rightarrow$ Salicylaldehyde | $I$. $Br_2$ in $CS_2$ |
| $B$. Phenol $\rightarrow$ Benzene | $II$. $Na_2Cr_2O_7/H_2SO_4$ |
| $C$. Phenol $\rightarrow$ $p$-Benzoquinone | $III$. $Zn$ |
| $D$. Phenol $\rightarrow$ $p$-Bromophenol | $IV$. $CHCl_3/NaOH$ |
| Column-$I$ (Reaction) | Column-$II$ (Bond broken) |
|---|---|
| $(A)$ $RCH_2OH \xrightarrow{CrO_3} RCHO$ | $(i)$ $C-O$ bond breaks. |
| $(B)$ Phenol $\xrightarrow{HNO_3}$ $p$-Nitrophenol + $o$-Nitrophenol | (ii) $O-H$ bond breaks. |
| $(C)$ Phenol + $NaOH \rightarrow$ Sodium phenoxide + $H_2O$ | (iii) $O-H$ and $C-H$ bonds break. |
| $(D)$ $CH_3CH_2CH_2OH \xrightarrow{H_2SO_4, \Delta} CH_3CH=CH_2$ | (iv) $C-H$ bond breaks. |
| Column-$I$ | Column-$II$ |
|---|---|
| $(i)$ $2-$methylphenol | $(a)$ Hydroquinone |
| $(ii)$ Benzene$-1,2-$diol | $(b)$ Phenetole |
| $(iii)$ Benzene$-1,3-$diol | $(c)$ Catechol |
| $(iv)$ Benzene$-1,4-$diol | $(d)$ $o$-Cresol |
| $(v)$ Methoxybenzene | $(e)$ Quinone |
| $(vi)$ Ethoxybenzene | $(f)$ Resorcinol |
| $(g)$ Anisole |
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