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Q.

(a) Write the reactions involved in the following:
(i) Hoffmann bromamide degradation reaction
(ii) Diazotization
(iii) Gabriel phthalimide synthesis
(b) Give reasons for the following:
(i) (CH3)2NH is more basic than (CH3)3N in an aqueous solution.
(ii) Aromatic diazonium salts are more stable than aliphatic diazonium salts.

OR

(a) Write the structures of the main products of the following reactions:
Question Image
(b) Give a simple chemical test to distinguish between Aniline and N, N-dimethylaniline.
(c) Arrange the following in the increasing order of their pKb values
C6H5NH2,C2H5NH2,C6H5NHCH3

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Detailed Solution

a. (i) Hoffmann bromamide degradation reaction
Primary amines can be prepared by Hoffmann degradation.
Question Image
(ii) Diazotization
C6H5NH2+NaNO2+2HCl273278KC6H5N2Cl+NaCl+2H2O
(iii) Gabriel phthalimide synthesis
Question Image
b.(i) Because of the Inductive effect and hydration effect
(ii) Due to resonance structures.

OR

a. (i) C6H5NHCOCH3
(ii) C6H5SO2NCH32
(III) C6H6
(b) When chloroform in the presence of KOH and heat, Aniline gives an offensive smell while
N, N-dimethylaniline does not.
(c) C2H5NH2<C6H5NHCH3<C6H5NH2

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