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Chapter 10: Problem 112

For each of the following pairs, predict which substance is more soluble in water. a. \(\mathrm{CH}_{3} \mathrm{NH}_{2}\) or \(\mathrm{NH}_{3}\) b. \(\mathrm{CH}_{3} \mathrm{CN}\) or \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) c. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) or \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{3}\) d. \(\mathrm{CH}_{3} \mathrm{OH}\) or \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) e. \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}_{2} \mathrm{OH}\) or \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{OH}\) f. \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) or \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\)

Short Answer

Expert verified
a. \(\mathrm{NH}_{3}\) is more soluble. b. \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) is more soluble. c. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) is more soluble. d. \(\mathrm{CH}_{3} \mathrm{OH}\) is more soluble. e. \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{OH}\) is more soluble. f. \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\) is more soluble.

Step by step solution

01

a. Comparing \(\mathrm{CH}_{3} \mathrm{NH}_{2}\) and \(\mathrm{NH}_{3}\)

Both of these substances are polar and will engage in hydrogen bonding with water. While both will be soluble, \(\mathrm{CH}_{3} \mathrm{NH}_{2}\) has an additional methyl group which is nonpolar and may cause a slight decrease in solubility. Therefore, \(\mathrm{NH}_{3}\) is more soluble in water.
02

b. Comparing \(\mathrm{CH}_{3} \mathrm{CN}\) and \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\)

The polarity of \(\mathrm{CH}_{3} \mathrm{CN}\) is due to the cyano group, while the polarity of \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) is due to hydrogen bonding with the oxygen. In this case, \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) is more soluble in water due to stronger hydrogen bonding.
03

c. Comparing \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) and \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{3}\)

\(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) is polar due to the hydroxyl group, which can engage in hydrogen bonding with water. On the other hand, \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{3}\) is nonpolar and has only weak van der Waals forces. Therefore, \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) is more soluble in water.
04

d. Comparing \(\mathrm{CH}_{3} \mathrm{OH}\) and \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\)

Both of these substances are polar due to the hydroxyl group. However, \(\mathrm{CH}_{3} \mathrm{OH}\) has a smaller nonpolar region than \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\), making it slightly more soluble in water.
05

e. Comparing \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}_{2} \mathrm{OH}\) and \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{OH}\)

Both of these substances have a polar hydroxyl group capable of hydrogen bonding. However, \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}_{2} \mathrm{OH}\) has a larger nonpolar region than \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{OH}\), which decreases its solubility in water. Therefore, \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{OH}\) is more soluble in water.
06

f. Comparing \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) and \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\)

Both of these substances are polar. \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) engages in hydrogen bonding with water, while \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\) can form hydrogen bonds and also dissociate into ions. In this case, \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\) is more soluble in water due to its ability to dissociate into ions, which further increases the solubility.

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Most popular questions from this chapter

You make \(20.0 \mathrm{g}\) of a sucrose \(\left(\mathrm{C}_{12} \mathrm{H}_{22} \mathrm{O}_{11}\right)\) and NaCl mixture and dissolve it in \(1.00 \mathrm{kg}\) water. The freezing point of this solution is found to be \(-0.426^{\circ} \mathrm{C}\). Assuming ideal behavior, calculate the mass percent composition of the original mixture, and the mole fraction of sucrose in the original mixture.

The freezing-point depression of a 0.091-m solution of CsCl is \(0.320^{\circ} \mathrm{C} .\) The freezing-point depression of a \(0.091-m\) solution of \(\mathrm{CaCl}_{2}\) is \(0.440^{\circ} \mathrm{C}\). In which solution does ion association appear to be greater? Explain.

What is ion pairing?

The vapor pressures of several solutions of water-propanol \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\right)\) were determined at various compositions, with the following data collected at \(45^{\circ} \mathrm{C}:\) $$\begin{array}{|lc|} \hline & \text { Vapor Pressure } \\ \chi_{\mathrm{H}_{2} \mathrm{O}} & \text { (torr) } \\ 0 & 74.0 \\ 0.15 & 77.3 \\ 0.37 & 80.2 \\ 0.54 & 81.6 \\ 0.69 & 80.6 \\ 0.83 & 78.2 \\ 1.00 & 71.9 \\ \hline \end{array}$$a. Are solutions of water and propanol ideal? Explain. b. Predict the sign of \(\Delta H_{\text {soln }}\) for water-propanol solutions. c. Are the interactive forces between propanol and water molecules weaker than, stronger than, or equal to the interactive forces between the pure substances? Explain. d. Which of the solutions in the data would have the lowest normal boiling point?

For an acid or a base, when is the normality of a solution equal to the molarity of the solution and when are the two concentration units different?
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