Problem: Ethylene glycol (HOCH2CH2OH), the major substance in antifreeze, has a normal boiling point of 198 oC. By comparison, ethyl alcohol (CH3CH2OH) boils at 78 oC at atmospheric pressure. Ethylene glycol dimethyl ether (CH3OCH2CH2OCH3) has a normal boiling point of 83 oC, and ethyl methyl ether (CH3CH2OCH3) has a normal boiling point of 11 oC.Explain why replacement of a hydrogen on the oxygen by CH3 generally results in a lower boiling point.

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  • According to their molecular formula, structure of ethyl alcohol and ethyl methyl ether appears as:

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Problem Details

Ethylene glycol (HOCH2CH2OH), the major substance in antifreeze, has a normal boiling point of 198 oC. By comparison, ethyl alcohol (CH3CH2OH) boils at 78 oC at atmospheric pressure. Ethylene glycol dimethyl ether (CH3OCH2CH2OCH3) has a normal boiling point of 83 oC, and ethyl methyl ether (CH3CH2OCH3) has a normal boiling point of 11 oC.

Explain why replacement of a hydrogen on the oxygen by CH3 generally results in a lower boiling point.

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