Ethylene glycol (HOCH2CH2OH), the major substance in antifreeze, has a normal boiling

Chapter 18, Problem 11.27

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Ethylene glycol \((HOCH_2 CH_2OH)\), the major substance in antifreeze, has a normal boiling point of \(198 ^{\circ}C\). By comparison, ethyl alcohol \((CH_3 CH_2 OH)\) boils at \(78 ^{\circ}C\) at atmospheric pressure. Ethylene glycol dimethyl ether \((CH_3 OCH_2 CH_2 OCH_3)\) has a normal boiling point of \(83 ^{\circ}C\), and ethyl methyl ether \((CH_3 CH_2 OCH_3)\) has a normal boiling point of \(11 ^{\circ}C\).

(a) Explain why replacement of a hydrogen on the oxygen by a \(CH_3\) group generally results in a lower boiling point.

(b) What are the major factors responsible for the difference in boiling points of the two ethers?

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