Write the structures of A, B, C, D and E in the following reactions:

OR
(a) Write the structures of the main products when benzene diazonium chloride reacts with the following reagents:
(i) KI
(ii) CH3CH2OH
(iii) Cu/HCl
(b) Arrange the following in the increasing order of their basic character in an aqueous solution:
CH3NH2, (CH3)2NH, (CH3)3N
(c) Give a simple chemical test to distinguish between the following pair of compounds:
C6H5NH2 and CH3-NH2
A = Acetanilide (protection of –NH2 group)

B = 4- Bromoacetanilide (attack of Br at para position)

C = 4- Bromoaniline (de-protection of –NH2 group)

D = Phenyl isonitrile

E = 4- Nitroacetanilide

OR
(a)
(i)

(ii)

(iii)

(b) For methyl substituted amines, the order of basicity is 2°>1°>3°. This order is concluded from considering a subtle interplay of inductive effect, solvation effect and steric hinderance of alkyl group. Therefore, increasing order of their basic character in an aqueous solution is (CH3)2NH > CH3NH2 > (CH3)3N.
(c) Chemical test to distinguish between Aniline (aromatic amine) and Methyl amine (aliphatic amine) is azo dye test.
A dye is produced when aniline is treated with HONO whereas brisk effervescence of N2 gas is obtained when methyl amine is treated under same conditions.
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