An aromatic compound ' $\mathrm{A}$ ' of molecular formula ${\mathrm{C}}_7{\mathrm{H}}_7\mathrm{ON}$ undergoes a series of reactions as shown below. Write the structures of A, B, C, D and E in the following reactions:
OR
(a) Write the structures of main products when aniline reacts with the following reagents:
(i) ${\mathrm{Br}}_2$ /water
(ii) $\mathrm{HCl}$
(iii) ${\left({\mathrm{CH}}_3\mathrm{CO}\right)}_2\mathrm{O}∕$ pyridine
(b) Arrange the following in the increasing order of their boiling point:
${\mathrm{C}}_2{\mathrm{H}}_5{\mathrm{NH}}_2,{\mathrm{C}}_2{\mathrm{H}}_5\mathrm{OH},{\left({\mathrm{CH}}_3\right)}_3\mathrm{N}$
(c) Give a simple chemical test to distinguish between the following pair of compounds:
${\left({\mathrm{CH}}_3\right)}_2\mathrm{NH}$ and ${\left({\mathrm{CH}}_3\right)}_3\mathrm{N}$