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Question

What is the correct sequence of reagents used for converting nitrobenzene into m-dibromobenzene?

$\stackrel{\mathrm{NaNO}_{2}}{\longrightarrow} / \stackrel{\mathrm{HCl}}{\longrightarrow} / \stackrel{\mathrm{KBr}}{\longrightarrow} / \stackrel{\mathrm{H}^{+}}{\longrightarrow}$
$\stackrel{\mathrm{Sn} / \mathrm{HCl}}{\longrightarrow} / \stackrel{\mathrm{KBr}}{\longrightarrow} / \stackrel{\mathrm{Br}_{2}}{\longrightarrow} / \stackrel{\mathrm{H}^{+}}{\longrightarrow}$
$\stackrel{\mathrm{B} \mathrm{B}_{2} / \mathrm{Fe}}{\longrightarrow} / \stackrel{\mathrm{Sn} / \mathrm{HCl}}{\longrightarrow} / \stackrel{\mathrm{NaNO}_{2} / \mathrm{HCl}}{\longrightarrow} / \stackrel{\mathrm{CuBr} / \mathrm{HBr}}{\longrightarrow}$
$\stackrel{\mathrm{Sn} / \mathrm{HCl}}{\longrightarrow} / \stackrel{\mathrm{Br}_{2}}{\longrightarrow} / \stackrel{\mathrm{NaNO}_{2}}{\longrightarrow} / \stackrel{\mathrm{NaBr}}{\longrightarrow}$

Solution

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