In which of the following reactions the product is an ether?

In which of the following reactions the product is an ether?
  1. $\mathrm{C}_6 \mathrm{H}_6+\mathrm{CH}_3 \mathrm{COCl} /$ anhydrous $\mathrm{AlCl}_3$
  2. $\mathrm{C}_2 \mathrm{H}_5 \mathrm{Cl}+\mathrm{aq} . \mathrm{KOH}$
  3. $\mathrm{C}_6 \mathrm{H}_6+\mathrm{C}_6 \mathrm{H}_5 \mathrm{COCl} /$ anhydrous $\mathrm{AlCl}_3$
  4. $\mathrm{C}_2 \mathrm{H}_5 \mathrm{Cl}+\mathrm{C}_2 \mathrm{H}_5 \mathrm{ONa}$

Solution

Alkyl halides react with sodium alkoxide to give ether. This is called Williamson's synthesis of ether. $\mathrm{C}_2 \mathrm{H}_5 \mathrm{Cl}+\mathrm{C}_2 \mathrm{H}_5 \mathrm{ONa} \stackrel{\Delta}{\longrightarrow} \mathrm{C}_2 \mathrm{H}_5 \mathrm{OC}_2 \mathrm{H}_5+\mathrm{NaCl}$

Asked in: AP EAMCET 2005

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