a) Identify the reactant $A$ in the following reaction:
$A + 2 R - X ⟶ R_{4} N^{+} X^{-}$
b) Explain Hoffmann's bromamide degradation reaction for the preparation of methanamine.
c) Which is more basic among aqueous solutions of aniline and ammonia? Give one reason.

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Solution

a) The reactant (A) is $R_{3} N$
$R_{3} N A + R - X \to R_{4} N^{+} X^{-}$
b) Hoffmann's bromamide degradation reaction for the preparation of methanamine
$C H_{3} - C O N H_{2} + B r_{2} + 4 N a O H \to C H_{3} - N H_{2} + N a_{2} C O_{3} + 2 N a B r + 2 H_{2} O$
Acetamide is treated with bromine and $N a O H$ in aqueous medium to form methanamine
c) Among aqueous solutions of aniline and ammonia, ammonia is more basic. In aniline, the lone pair of $N$ atom is involved in resonance with benzene ring.

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