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In which of the following reactions the product is an ether?
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The correct answer is:
$\mathrm{C}_2 \mathrm{H}_5 \mathrm{Cl}+\mathrm{C}_2 \mathrm{H}_5 \mathrm{ONa}$
Alkyl halides react with sodium alkoxide to give ether. This is called Williamson's synthesis of ether.
$\mathrm{C}_2 \mathrm{H}_5 \mathrm{Cl}+\mathrm{C}_2 \mathrm{H}_5 \mathrm{ONa} \stackrel{\Delta}{\longrightarrow} \mathrm{C}_2 \mathrm{H}_5 \mathrm{OC}_2 \mathrm{H}_5+\mathrm{NaCl}$
$\mathrm{C}_2 \mathrm{H}_5 \mathrm{Cl}+\mathrm{C}_2 \mathrm{H}_5 \mathrm{ONa} \stackrel{\Delta}{\longrightarrow} \mathrm{C}_2 \mathrm{H}_5 \mathrm{OC}_2 \mathrm{H}_5+\mathrm{NaCl}$
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