Which of the following compounds has the highest boiling point?Multiple Choicegraphic Butane, represented by its structural formula, has a 4-carbon chain. C1 and C4 are methyl groups. C2 and C3 are methylene groups.Expand imagegraphic Propanol has a 3-carbon chain. C1 is a methylene group and single bonded to a hydroxyl group. C2 is also methylene group. C3 is a methyl group.Expand imagegraphic The compound, represented by its structural formula, has a central oxygen atom single bonded to two methyl groups.Expand imagegraphic The compound, represented by its structural formula, has a central oxygen atom single bonded to a methyl group and an ethyl group.Expand image
Question
Which of the following compounds has the highest boiling point?Multiple Choicegraphic Butane, represented by its structural formula, has a 4-carbon chain. C1 and C4 are methyl groups. C2 and C3 are methylene groups.Expand imagegraphic Propanol has a 3-carbon chain. C1 is a methylene group and single bonded to a hydroxyl group. C2 is also methylene group. C3 is a methyl group.Expand imagegraphic The compound, represented by its structural formula, has a central oxygen atom single bonded to two methyl groups.Expand imagegraphic The compound, represented by its structural formula, has a central oxygen atom single bonded to a methyl group and an ethyl group.Expand image
Solution
The boiling point of a compound is influenced by the type and strength of the intermolecular forces present. The stronger the intermolecular forces, the higher the boiling point.
The types of intermolecular forces that exist are London dispersion forces, dipole-dipole interactions, and hydrogen bonding.
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Butane: This is a nonpolar molecule, so it only has London dispersion forces. These are the weakest type of intermolecular forces.
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Propanol: This molecule has a hydroxyl group (-OH), which means it can form hydrogen bonds, a type of dipole-dipole interaction. Hydrogen bonding is the strongest type of intermolecular force, so compounds that can form hydrogen bonds generally have higher boiling points than similar compounds that can't.
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The compound with a central oxygen atom single bonded to two methyl groups is dimethyl ether. This molecule is polar and can form dipole-dipole interactions, but it cannot form hydrogen bonds because it doesn't have a hydrogen atom bonded to a highly electronegative atom (N, O, or F).
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The compound with a central oxygen atom single bonded to a methyl group and an ethyl group is ethyl methyl ether. Like dimethyl ether, this molecule is polar and can form dipole-dipole interactions, but it cannot form hydrogen bonds.
Therefore, out of the given options, propanol would have the highest boiling point because it can form hydrogen bonds.
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