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Predict which compound in each pair has the higher boiling point. Explain your

Chapter 2, Problem 2-35

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QUESTION:

Predict which compound in each pair has the higher boiling point. Explain your prediction. (a) CH3CH2OCH3 or CH3CH(OH)CH3 (b) CH3CH2CH2CH3 or CH3CH2CH2CH2CH3 (c) CH3CH2CH2CH2CH3 or (CH3)2CHCH2CH3 (d) CH3CH2CH2CH2CH3 or CH3CH2CH2CH2CH2Cl (e) (e) or NH CH3 N (f) (f) or O NH CH3 NH

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QUESTION:

Predict which compound in each pair has the higher boiling point. Explain your prediction. (a) CH3CH2OCH3 or CH3CH(OH)CH3 (b) CH3CH2CH2CH3 or CH3CH2CH2CH2CH3 (c) CH3CH2CH2CH2CH3 or (CH3)2CHCH2CH3 (d) CH3CH2CH2CH2CH3 or CH3CH2CH2CH2CH2Cl (e) (e) or NH CH3 N (f) (f) or O NH CH3 NH

ANSWER:

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The boiling point of organic compounds

A liquid boils or converts into a gaseous state when its vapor pressure equals the atmospheric pressure. It represents the energy required to overcome all the intermolecular forces that exist in a molecule to be converted to a gaseous state.

All the physical properties of an organic compound depend on the intermolecular forces between the molecules of the substance. If the intermolecular forces are strong, more energy will be required to overcome these forces, increasing the boiling point.

The intermolecular force common to all organic compounds is the dispersion force. It is the weakest force. Polar molecules experience dipole-dipole interaction, which is stronger than dispersion forces. The strongest intermolecular force among organic compounds is hydrogen bonds, and molecules with hydrogen bonds have the highest boiling point.

 

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