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Question

Explain the following reaction:
(a) Sandmeyer reaction 
(b) Wurtz's Fitting reaction


Solution

  • (a) Sandmeyer reaction $$\rightarrow$$
It is used to synthesize aryl halides from aryl diazonium salts. It is an example of a radical-nucleophilic aromatic substitution.
When a primary aromatic amine, dissolved or suspended in cold aqueous mineral acid, is treated with sodium nitrite, a diazonium salt is formed. Mixing the solution of freshly prepared diazonium salt with cuprous chloride or cuprous bromide results in the replacement of the diazonium group by $$-Cl$$ or $$-Br$$.
$${C}_{6}{H}_{5}-N{H}_{2} \xrightarrow[273-278 \; K]{NaN{O}_{2} + HX} {{C}_{6}{H}_{5}-{N}_{2}}^{+}{X}^{-} \begin{cases} \xrightarrow{CuCl} & {C}_{6}{H}_{5}-Cl \\ \xrightarrow{CuBr} & {C}_{6}{H}_{5}-Br \\ \xrightarrow{CuCN} & {C}_{6}{H}_{5}-CN \end{cases}$$
  • b) Wurtz's Fittig reaction $$\rightarrow$$
A mixture of an alkyl halide and aryl halide gives an alkylarene when treated with sodium in dry ether and is called Wurtz-Fittig reaction.
$${C}_{6}{H}_{5}-X + Na + R-X \xrightarrow{Ether} {C}_{6}{H}_{5}-R + NaX$$

Chemistry

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