(a) Write the reactions involved in the following:

(i) Hoffmann bromamide degradation reaction

(ii) Diazotisation

(iii) Gabriel phthalimide synthesis

(b) Give reasons :

(i) $(C H_{3})_{2} N H$ is more basic than $(C H_{3})_{3} N$ in an aqueous solution.

(ii) Aromatic diazonium salts are more stable than aliphatic diazonium salts.

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Solution

(a) (i) $R C O N H_{2} + B r_{2} + 4 N a O H \to R N H_{2} + 2 N a B r + N a_{2} C O_{3} + 2 H_{2} O$

(b) (i) Because of the combined effect of inductive effect of inductive effect and solvation effect.

(ii) Due to resonance stablisation of aromatic diazonium salts.

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Similar questions

(i i) (C H_{3})_{2} N H

(C H_{3})_{3} N

(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) $(C H_{3})_{2} N H a n d (C H_{3})_{3} N$

(a) Write the structures of main products when benzene diazonium chloride $(C_{6} H_{5} {N_{2}}^{+} C l^{-})$ reacts with the following reagents:

(i) CuCN/KCN

(ii) $H_{2} O$

(iii) $C H_{3} C H_{2} O H$

(b) Arrange the following:

(i) $C_{2} H_{5} N H_{2}$ , $C_{2} H_{5} O H$ , $(C H_{3})_{3} N$ – 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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