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Question

(a) Illustrate the following reaction giving suitable example in each case:

(i) Hoffmann bromamide degradation reaction

(ii) Diazotisation

(iii) Gabriel phthalimide synthesis

(b) Distinguish between the following pairs of compounds:

(i) Aniline and N-methylaniline

(ii) (CH3)2NH and (CH3)3N

OR

(a) Write the structures of main products when benzene diazonium chloride (C6H5N2+Cl) reacts with the following reagents:

(i) CuCN/KCN

(ii) H2O

(iii) CH3CH2OH

(b) Arrange the following:

(i) C2H5NH2, C2H5OH, (CH3)3N – in the increasing order of their boiling point

(ii) Aniline, p-nitroaniline, p-methylaniline - in the increasing order of their basic strength

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Solution

(a)

(i)CH3O||CNH2+Br2+4NaOHCH3NH2+Na2CO3+2NaBr+2H2O

(ii)C6H5NH2+NaNO2+2HCl273278 k−−−−−C6H5N+2Cl+NaCl+2H2O

(iii)

(b) (i) Aniline is a primary amine and N-methylaniline is a secondary amine.

(i) (CH3)2 NH is a secondary amine and (CH3)3N is a tertiary amine.

OR

(a)

(i)

(ii)

(iii)

(b)

(i) (CH3)3N<C2H5NH2<C2H5OH

(ii) p-nitroaniline< Aniline < p-methylaniline


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