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Chapter 26: Problem 110

For each of the following pairs, indicate which substance has (a) the higher boiling point, \(\mathrm{C}_{6} \mathrm{H}_{12}\) or \(\mathrm{C}_{6} \mathrm{H}_{6}\) (b) the greater solubility in water, \(\bar{C}_{3} H_{7} O H\) or \(\mathrm{C}_{7} \mathrm{H}_{15} \mathrm{OH}\) (c) the greater acidity in aqueous solution, \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHO}\) or \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COOH}\).

Short Answer

Expert verified
The higher boiling point is benzene, \(\mathrm{C}_{6} \mathrm{H}_{6}\). The greater solubility in water is propyl alcohol, \(\mathrm{C}_{3} \mathrm{H}_{7} \mathrm{OH}\). The greater acidity in aqueous solution is benzoic acid, \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COOH}\).

Step by step solution

01

Analyze the Boiling Point

Determine the type of intermolecular forces present in the molecules. The molecule with stronger forces will have a higher boiling point. Cyclohexane \(\mathrm{C}_{6} \mathrm{H}_{12}\) is a nonpolar molecule with London dispersion forces while benzene \(\mathrm{C}_{6} \mathrm{H}_{6}\) is a polar molecule with enhanced London dispersion forces due to a delocalized electron cloud. Therefore, benzene would have a higher boiling point.
02

Determine Solubility in Water

According to the 'like dissolves like' concept, polar molecules dissolve in polar solvents and nonpolar molecules dissolve in nonpolar solvents. Water is a polar solvent. Propyl alcohol \(\mathrm{C}_{3} \mathrm{H}_{7} \mathrm{OH}\) is shorter and has a higher proportion of polar (O-H) bonds compared to heptanol \(\mathrm{C}_{7} \mathrm{H}_{15} \mathrm{OH}\), thus will be more soluble in water.
03

Determine Acidity in Solution

An acid is a substance that can donate a proton (H+ ion) in a solution. In the case of benzaldehyde \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHO}\) and benzoic acid $\mathrm{C}_{6} \mathrm{H}_{5}\mathrm{COOH}$, benzoic acid can lose a proton from its carboxyl group (COOH), thus it is the stronger acid in aqueous solution.

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Most popular questions from this chapter

Supply condensed structural formulas for the following substances. (a) 2,4,6 -trinitrotoluene (TNT-an explosive) (b) methyl salicylate (oil of wintergreen) [Hint: Salicylic acid is \(o \text { -hydroxybenzoic acid. }]\) (c) 2 -hydroxy-1,2,3-propanetricarboxylic acid (citric \(\left.\operatorname{acid}, \mathrm{C}_{6} \mathrm{H}_{8} \mathrm{O}_{7}\right)\).

Draw Lewis structures of the following simple organic molecules: (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH} ;\) (b) \(\mathrm{H}_{3} \mathrm{CCN}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}\).

Identify the functional group in each compound (i.e., alcohol, amine, etc.). (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH}\) (b) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}_{2} \mathrm{OCH}_{3}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}\left(\mathrm{NH}_{2}\right) \mathrm{CH}_{2} \mathrm{CH}_{3}\) (d) \(\mathrm{CH}_{3} \mathrm{COOCH}_{3}\).

Write structural formulas corresponding to these condensed formulas. (a) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (b) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}_{2} \mathrm{Br}\) (c) \(\mathrm{Cl}_{3} \mathrm{CCH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{CH}_{2} \mathrm{Cl}\).

Write structural formulas for all the isomers of \(\mathrm{C}_{4} \mathrm{H}_{7} \mathrm{Cl}\). Indicate any enantiomers or diastereomers that occur.
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