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Chapter 22: Problem 119

Consider the compounds butanoic acid, pentanal, \(n\) -hexane, and 1 -pentanol. The boiling points of these compounds (in no specific order) are \(69^{\circ} \mathrm{C}, 103^{\circ} \mathrm{C}, 137^{\circ} \mathrm{C}\), and \(164^{\circ} \mathrm{C}\). Match the boiling points to the correct compound.

Short Answer

Expert verified
The correct boiling points for the given compounds are: Butanoic acid: \(164^{\circ}\mathrm{C}\), Pentanal: \(103^{\circ}\mathrm{C}\), n-Hexane: \(69^{\circ}\mathrm{C}\), and 1-Pentanol: \(137^{\circ}\mathrm{C}\).

Step by step solution

01

Identify intermolecular forces in each compound

* Butanoic acid (C4H8O2): Since it is an acid (COOH group), it can form hydrogen bonds, dipole-dipole interactions, and van der Waals forces (London dispersion forces). * Pentanal (C5H10O): It has an aldehyde group (H-C=O), so it features dipole-dipole interactions and van der Waals forces. * n-Hexane (C6H14): It is an alkane, so it only has weak van der Waals forces. * 1-Pentanol (C5H12O): Since it is an alcohol (OH group), it can form hydrogen bonds, dipole-dipole interactions, and van der Waals forces.
02

Rank the compounds by intermolecular force strength

We know that hydrogen bonding is the strongest intermolecular force, then comes dipole-dipole interaction, and then van der Waals forces. With this information, we can rank the compounds from strongest intermolecular forces to weakest: 1. Butanoic acid (Hydrogen bonding; strongest) 2. 1-Pentanol (Hydrogen bonding) 3. Pentanal (Dipole-dipole interaction) 4. n-Hexane (Van der Waals forces; weakest)
03

Match boiling points based on intermolecular force strength

Now let's match the boiling points (in ascending order) to the compounds according to their intermolecular force strength: 1. n-Hexane: \(69^{\circ}\mathrm{C}\) (weakest intermolecular forces) 2. Pentanal: \(103^{\circ}\mathrm{C}\) (dipole-dipole interaction) 3. 1-Pentanol: \(137^{\circ}\mathrm{C}\) (hydrogen bonding) 4. Butanoic acid: \(164^{\circ}\mathrm{C}\) (strongest intermolecular forces) So, the correct boiling points are as follows: * Butanoic acid: \(164^{\circ}\mathrm{C}\) * Pentanal: \(103^{\circ}\mathrm{C}\) * n-Hexane: \(69^{\circ}\mathrm{C}\) * 1-Pentanol: \(137^{\circ}\mathrm{C}\)

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Most popular questions from this chapter

Polycarbonates are a class of thermoplastic polymers that are used in the plastic lenses of eyeglasses and in the shells of bicycle helmets. A polycarbonate is made from the reaction of bisphenol A (BPA) with phosgene \(\left(\mathrm{COCl}_{2}\right)\) : Phenol \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}\right)\) is used to terminate the polymer (stop its growth). a. Draw the structure of the polycarbonate chain formed from the above reaction. b. Is this reaction a condensation or an addition polymerization?

Give the structure for each of the following. a. 4 -methyl-1-pentyne b. \(2,3,3\) -trimethyl- 1 -hexene c. 3 -ethyl- 4 -decene

If you had a group of hydrocarbons, what structural features would you look at to rank the hydrocarbons in order of increasing boiling point?

Draw the structures for two examples of unsaturated hydrocarbons. What structural feature makes a hydrocarbon unsaturated?

Give two examples of saturated hydrocarbons. How many other atoms are bonded to each carbon in a saturated hydrocarbon?
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