Ethylene glycol 1HOCH2CH2OH2, the major substance in

Chapter , Problem 11.27

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Ethylene glycol 1HOCH2CH2OH2, the major substance in antifreeze, has a normal boiling point of 198 C. By comparison, ethyl alcohol 1CH3CH2OH2 boils at 78 C at atmospheric pressure. Ethylene glycol dimethyl ether 1CH3OCH2CH2OCH32 has a normal boiling point of 83 C, and ethyl methyl ether 1CH3CH2OCH32 has a normal boiling point of 11 C. (a) Explain why replacement of a hydrogen on the oxygen by a CH3 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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