1 \(\mathrm{C}_{2} \mathrm{H}_{5}-\mathrm{O}-\mathrm{C}_{2} \mathrm{H}_{5}>\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{OH}>\)
\(\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,{\text{C}}{{\text{H}}_3} - {\text{O}} - {\text{C}}{{\text{H}}_3}\)
2 \(\mathrm{C}_{2} \mathrm{H}_{5}-\mathrm{O}-\mathrm{C}_{2} \mathrm{H}_{5} < \mathrm{C}_{4} \mathrm{H}_{9} \mathrm{OH} < \)
\(\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,{\text{C}}{{\text{H}}_3} - {\text{O}} - {\text{C}}{{\text{H}}_3}\)
3 \({\text{C}}{{\text{H}}_3} - {\text{O}} - {\text{C}}{{\text{H}}_3} < {{\text{C}}_2}{{\text{H}}_5} - {\text{O}} - {{\text{C}}_2}{{\text{H}}_5} < \)
\(\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,{{\text{C}}_4}{{\text{H}}_9}{\text{OH}}\)
4 \({\text{C}}{{\text{H}}_3} - {\text{O}} - {\text{C}}{{\text{H}}_3} < {{\text{C}}_2}{{\text{H}}_5} - {\text{O}} - {{\text{C}}_2}{{\text{H}}_5} > \)
\(\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,{{\text{C}}_4}{{\text{H}}_9}{\text{OH}}\)
Explanation:
Boiling point \(\propto\) molar mass
Boiling point \(\propto\) Hydrogen bonding. Generally, alcohols possess higher boiling point than ethers. \({{\text{C}}_{\text{2}}}{{\text{H}}_{\text{5}}} - {\text{O}} - {{\text{C}}_{\text{2}}}{{\text{H}}_{\text{5}}}\) has higher boiling point than \({\text{C}}{{\text{H}}_{\text{3}}} - {\text{O}} - {\text{C}}{{\text{H}}_{\text{3}}}\) due to more molar mass. Hence, the correct order of boiling is \({\text{C}}{{\text{H}}_{\text{3}}} - {\text{O}} - {\text{C}}{{\text{H}}_{\text{3}}} < {{\text{C}}_{\text{2}}}{{\text{H}}_{\text{5}}} - {\text{O}} - {{\text{C}}_{\text{2}}}{{\text{H}}_{\text{5}}} < {{\text{C}}_{\text{4}}}{{\text{H}}_{\text{9}}}{\text{OH}}\)