$A$ colourless substance $'A'$ $(C_6H_7N)$ is sparingly soluble in water and gives a water-soluble compound $'B'$ on treating with mineral acid. On reacting with $CHCl_3$ and alcoholic potash,$'A'$ produces an obnoxious smell due to the formation of compound $'C'$. Reaction of $'A'$ with benzenesulphonyl chloride gives compound $'D'$ which is soluble in alkali. With $NaNO_2$ and $HCl$,$'A'$ forms compound $'E'$ which reacts with phenol in an alkaline medium to give an orange dye $'F'$. Identify compounds $'A'$ to $'F'$.

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(A) The substance $'A'$ is $C_6H_5NH_2$ (Aniline).
$1$. $C_6H_5NH_2 + HCl \rightarrow C_6H_5NH_3^+Cl^-$ (Anilinium chloride,$'B'$).
$2$. $C_6H_5NH_2 + CHCl_3 + 3KOH \rightarrow C_6H_5NC + 3KCl + 3H_2O$ (Phenyl isocyanide,$'C'$).
$3$. $C_6H_5NH_2 + C_6H_5SO_2Cl \rightarrow C_6H_5NHSO_2C_6H_5 + HCl$ ($N$-phenylbenzenesulphonamide,$'D'$).
$4$. $C_6H_5NH_2 + NaNO_2 + 2HCl \xrightarrow{273-278 \ K} C_6H_5N_2^+Cl^- + NaCl + 2H_2O$ (Benzenediazonium chloride,$'E'$).
$5$. $C_6H_5N_2^+Cl^- + C_6H_5OH \xrightarrow{OH^-} C_6H_5-N=N-C_6H_4OH$ ($p$-hydroxyazobenzene,orange dye,$'F'$).

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Match the following:
List-$I$ (Amine)List-$II$ ($pK_b$ value)
$A$. $N,N$-Dimethylaniline$I$. $9.30$
$B$. Aniline$II$. $8.92$
$C$. $N$-Ethylethanamine$III$. $9.38$
$D$. $N$-Methylaniline$IV$. $3.00$

The correct answer is

An organic compound $A$ on reduction gives compound $B$,which on reaction with trichloromethane and caustic potash forms $C$. The compound $C$ on catalytic reduction gives $N$-methylbenzenamine. The compound $A$ is,

Complete the following reactions:
$(i)$ $C_{6}H_{5}NH_{2} + CHCl_{3} +$ alc. $KOH \rightarrow$
$(ii)$ $C_{6}H_{5}N_{2}Cl + H_{3}PO_{2} + H_{2}O \rightarrow$
$(iii)$ $C_{6}H_{5}NH_{2} + H_{2}SO_{4}$ (conc.) $\rightarrow$
$(iv)$ $C_{6}H_{5}N_{2}Cl + C_{2}H_{5}OH \rightarrow$
$(v)$ $C_{6}H_{5}NH_{2} + Br_{2(aq)} \rightarrow$
$(vi)$ $C_{6}H_{5}NH_{2} + (CH_{3}CO)_{2}O \rightarrow$
$(vii)$ $C_{6}H_{5}N_{2}Cl \xrightarrow[(ii) NaNO_{2}/Cu, \Delta ]{(i) HBF_{4}}$

Which of the following statements is incorrect?

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Product $(E)$ is

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