(a) An amide 'A' with molecular formula C₇>H₇ON undergoes Hoffmann Bromamide degradation reaction to give amine 'B'. 'B' on treatment with nitrous acid at 273-278 K form 'C' and on treatment with chloroform and ethanolic potassium hydroxide forms 'D'. 'C' on treatment, with ethanol gives 'E'. Identify 'A','B', 'C','D' and 'E' and write the sequence of chemical equations.

(b) (i) (1) What is Hinsberg's reagent ?
(2) Arrange the following compounds in the increasing order of their basic strength in gaseous phase:

C₂H₅NH₂, (C₂H₅)₃N, (C₂H₅)₂NH (ii) Give reasons for the following :

(1) Methyl amine is more basic than aniline.
(2) Aniline readily reacts with bromine water to give 2, 4, 6- tribromoaniline.
(3) Primary amines have higher boiling points than tertiary amines.

Solution

,,,,,