Convert aniline to fluorobenzene.

An organic compound (A) of molecular formula ${\mathrm{C}}_7{\mathrm{H}}_5\mathrm{N}$ on reaction with alkaline ${\mathrm{H}}_2{\mathrm{O}}_2$ furnishes (B). Acid hydrolysis of both (A) and (B) produces the same aromatic acid (C) of molecular formula ${\mathrm{C}}_7{\mathrm{H}}_6{\mathrm{O}}_2$. Reaction of both (A) and (B) with ${\mathrm{LiAlH}}_4$ gives a primary amine (D) of molecular formula ${\mathrm{C}}_7{\mathrm{H}}_9\mathrm{N}$. Identify (A), (B), (C) and (D). Write arrowhead equations for the formation of (B) from (A) and (D) from (A).

Distinguish between the following two compounds by a chemical reaction:

${\mathrm{C}}_6{\mathrm{H}}_5{\mathrm{NH}}_2$ and ${\mathrm{C}}_6{\mathrm{H}}_5{\mathrm{NHCH}}_3$.

Write structural formula of the compounds $\mathrm{A}$ to $\mathrm{D}$.

${\mathrm{C}}_6{\mathrm{H}}_5{\mathrm{NO}}_2\underset{\mathrm{conc}. {\mathrm{H}}_2{\mathrm{SO}}_4}{\overset{\mathrm{conc}. {\mathrm{HNO}}_3}{\to }}\mathrm{A}\stackrel{\mathrm{NaSH}}{\to }\mathrm{B}\underset{50\% \mathrm{Ethanol},∆}{\overset{\mathrm{Zn}+{\mathrm{NH}}_4\mathrm{Cl}}{\to }}\mathrm{C}\stackrel{\mathrm{Tollen}\text{'}\mathrm{s} \mathrm{reagent}}{\to }\mathrm{D}$

Write structural formula of the compounds $\mathrm{A}$ to $\mathrm{F}$.

(m) ${\mathrm{C}}_6{\mathrm{H}}_5{\mathrm{CONH}}_2\stackrel{{\mathrm{Br}}_2/\mathrm{KOH}}{\to }\mathrm{A}\stackrel{{\mathrm{Br}}_2/{\mathrm{H}}_2\mathrm{O}}{\to }\mathrm{B}$

(n) ${\mathrm{C}}_6{\mathrm{H}}_5\mathrm{Cl}\underset{\mathrm{dry} \mathrm{Ether}}{\overset{\mathrm{Mg}}{\to }}\mathrm{C}\underset{\mathrm{ii}) {\mathrm{H}}_3{\mathrm{O}}^{+}}{\overset{\mathrm{i}) {\mathrm{CO}}_2/ \mathrm{dry} \mathrm{Ether}}{\to }}\mathrm{D}$

(o) ${\left({\mathrm{CH}}_3\right)}_3\mathrm{C}-\mathrm{CHO}\underset{∆}{\overset{\mathrm{conc}. \mathrm{NaOH}}{\to }}\mathrm{E}+\mathrm{F}$