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Chapter 22: Problem 24

Arrange these compounds in order of increasing boiling point. (a) 1 -butanol, butane, diethylether (b) hexane, 1 -hexanol, dipropylether

Short Answer

Expert verified
Question: Arrange the given compounds in the two sets in order of increasing boiling point and justify your answer. Answer: The order of increasing boiling point for set (a) is: butane < diethylether < 1-butanol, and for set (b): hexane < dipropylether < 1-hexanol. This order is determined by comparing the intermolecular forces present in each compound, with stronger forces leading to a higher boiling point. Hydrogen bonding has the strongest influence on boiling points, followed by dipole-dipole interactions and London dispersion forces.

Step by step solution

01

Comparing Intermolecular Forces in Set (a) Compounds

First, we need to determine the types of intermolecular forces present in each compound in set (a): 1. 1-butanol: Due to the presence of an -OH group, 1-butanol has hydrogen bonding, dipole-dipole interactions, and London dispersion forces. 2. Butane: Being a nonpolar molecule, butane only has London dispersion forces. 3. Diethylether: Due to the presence of a polarized C-O bond, diethylether has dipole-dipole interactions and London dispersion forces, but no hydrogen bonding.
02

Ordering Set (a) Compounds by Boiling Point

Now that we know the types of intermolecular forces in each compound, let's arrange them in order of increasing boiling point: 1. Butane (only London dispersion forces) 2. Diethylether (dipole-dipole interactions and London dispersion forces) 3. 1-butanol (hydrogen bonding, dipole-dipole interactions, and London dispersion forces) Hence, the order of increasing boiling point for set (a) is: butane < diethylether < 1-butanol.
03

Comparing Intermolecular Forces in Set (b) Compounds

Moving on to set (b), we need to determine the types of intermolecular forces present in each compound: 1. Hexane: Being a nonpolar molecule, hexane only has London dispersion forces. 2. 1-hexanol: Due to the presence of an -OH group, 1-hexanol has hydrogen bonding, dipole-dipole interactions, and London dispersion forces. 3. Dipropylether: Due to the presence of a polarized C-O bond, dipropylether has dipole-dipole interactions and London dispersion forces, but no hydrogen bonding.
04

Ordering Set (b) Compounds by Boiling Point

Now that we know the types of intermolecular forces in each compound, let's arrange them in order of increasing boiling point: 1. Hexane (only London dispersion forces) 2. Dipropylether (dipole-dipole interactions and London dispersion forces) 3. 1-hexanol (hydrogen bonding, dipole-dipole interactions, and London dispersion forces) Hence, the order of increasing boiling point for set (b) is: hexane < dipropylether < 1-hexanol.

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Most popular questions from this chapter

Write the structural formula of the ester formed by methyl alcohol with (a) formic acid. (b) acetic acid. (c) \(\mathrm{CH}_{3}-\left(\mathrm{CH}_{2}\right)_{6}-\mathrm{COOH}\).

Give the structure of (a) a four-carbon straight-chain alcohol with an - OH group not at the end of the chain. (b) a five-carbon straight-chain carboxylic acid. (c) the ester formed when these two compounds react.

The general formula of an alkane is \(\mathrm{C}_{n} \mathrm{H}_{2 n+2}\). What is the general formula of an (a) alkene? (b) alkyne? (c) alcohol derived from an alkane?

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