An organic compound $A$ contains nitrogen and chlorine. It dissolves readily in water to give a solution that turns litmus red. Titration of compound $A$ with standard base indicates that the molecular weight of $A$ is $131 \pm 2$. When a sample of $A$ is treated with aqueous $NaOH$,a liquid separates which contains $N$ but not $Cl$. Treatment of the obtained liquid with nitrous acid followed by phenol gives an orange precipitate. The compound $A$ is:

  • A
    $C_6H_5NH_3Cl$
  • B
    $C_6H_5CH_2NH_2 \cdot HCl$
  • C
    $o-Cl-C_6H_4NH_2$
  • D
    $p-Cl-C_6H_4NH_3Cl$

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$E \xleftarrow{KOH/Br_2} D \xleftarrow{H_2O_2/OH^{-} \atop (Partial \ Hydrolysis)} C \xleftarrow{NaCN} C_2H_5-Cl$ $\xrightarrow{AgCN} A$ $\xrightarrow{LiAlH_4} B$
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Identify the product $B$ in the following reaction:
$C_6H_5NH_2$ $\xrightarrow[0^\circ-5^\circ C]{NaNO_2/HCl} A$ $\xrightarrow{Ph-N(CH_3)_2} B$

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