Which of the following sets of reagents, used in the order shown, would enable the preparation of $p$-chlorophenol from $p$-chloronitrobenzene?

  • A
    $1. Fe, HCl; 2. NaOH; 3. NaNO_2, H_2SO_4; 4. H_3PO_2$
  • B
    $1. Fe, HCl; 2. NaOH; 3. NaNO_2, H_2SO_4; 4. H_2O, \Delta$
  • C
    $1. Fe, HCl; 2. NaOH; 3. NaNO_2, H_2SO_4; 4. \text{ethanol}$
  • D
    $1. NaOH, \Delta; 2. HCl$

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An aromatic compound $A$ on treatment with aqueous ammonia and heating forms compound $B$,which on heating with $Br_2$ and $KOH$ forms a compound $C$ of molecular formula $C_6H_7N$. Write the structures and $IUPAC$ names of compounds $A, B$,and $C$.

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The product $(A)$ of the given reaction is:

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In a reaction of aniline,a coloured product $C$ was obtained as shown below:
$A$ $\xrightarrow{NaNO_2/HCl} B$ $\xrightarrow{N,N-dimethylaniline, \text{cold}} C$
The structure of $C$ would be:

$A$ is a neutral organic compound $(M.F.: C_8H_9ON)$. On treatment with aqueous $Br_2 / HO^{(-)}$, $A$ forms a compound $B$ which is soluble in dilute acid. $B$ on treatment with aqueous $NaNO_2 / HCl$ $(0-5^{\circ}C)$ produces a compound $C$ which on treatment with $CuCN / NaCN$ produces $D$. Hydrolysis of $D$ produces $E$ which is also obtainable from the hydrolysis of $A$. $E$ on treatment with acidified $KMnO_4$ produces $F$. $F$ contains two different types of hydrogen atoms. The structure of $A$ 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.) $\rightarrow$
$(iv)$ $C_{6}H_{5}N_{2}Cl + C_{2}H_{5}OH \rightarrow$
$(v)$ $C_{6}H_{5}NH_{2} + Br_{2(aq)} \rightarrow$
$(vi)$ $C_{6}H_{5}NH_{2} + (CH_{3}CO)_{2}O \rightarrow$
$(vii)$ $C_{6}H_{5}N_{2}Cl \xrightarrow[(ii) NaNO_{2}/Cu, \Delta ]{(i) HBF_{4}}$

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