| Column-$(I)$ (Reactants) | Column-$(II)$ (Major Products) |
|---|---|
| $(A)$ $C_6H_5CH_3 + X_2 \xrightarrow{Fe, \text{dark}}$ | $(i)$ $C_6H_5CH(Br)CH_3$ |
| $(B)$ $C_6H_5NH_2 \xrightarrow{NaNO_2, HX, 273-278 \ K}$ | $(ii)$ $C_6H_5N_2^+X^-$ |
| $(C)$ $C_6H_5N_2^+X^- \xrightarrow{Cu_2X_2}$ | $(iii)$ $p-X-C_6H_4CH_3 + o-X-C_6H_4CH_3$ |
| $(D)$ $C_6H_5CH_2CH_3 \xrightarrow{Br_2, \Delta \text{ or } UV \text{ light}}$ | $(iv)$ $C_6H_5X$ |
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| Column-$I$ (Reaction) | Column-$II$ (Mechanism) |
| $(A)$ $OH^- + CH_3Cl \to HOCH_3 + Cl^-$ | $(1)$ $S_N2$ mechanism |
| $(B)$ $(CH_3)_3CBr + OH^- \to (CH_3)_3COH + Br^-$ | $(2)$ $S_E2$ aromatic |
| $(C)$ $CH_3CH_2Br \xrightarrow[ethanol]{KOH} CH_2 = CH_2$ | $(3)$ $S_N1$ mechanism |
| $(D)$ $C_6H_6 + Br_2 \xrightarrow{Fe} C_6H_5Br + HBr$ | $(4)$ $\beta$-elimination (dehydrohalogenation) |
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