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Chapter 11: 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 in water. b. \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) is more soluble in water. c. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) is more soluble in water. d. \(\mathrm{CH}_{3} \mathrm{OH}\) is more soluble in water. e. \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}_{2} \mathrm{OH}\) is more soluble in water. f. \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\) is more soluble in water.

Step by step solution

01

Identify polar molecules

Both molecules have a polar N-H bond. \(\mathrm{NH}_{3}\) has hydrogen bonding, while \(\mathrm{CH}_{3} \mathrm{NH}_{2}\) also has it but with an additional nonpolar methyl group.
02

Predict the solubility

Both substances are polar and can hydrogen bond with water. However, \(\mathrm{CH}_{3} \mathrm{NH}_{2}\) has a nonpolar methyl group, which slightly reduces its solubility in water. Therefore, \(\mathrm{NH}_{3}\) is more soluble in water. b. \(\mathrm{CH}_{3} \mathrm{CN}\) or \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\)
03

Identify polar molecules

\(\mathrm{CH}_{3} \mathrm{CN}\) has a polar carbon-nitrogen bond. On the other hand, \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) has a polar carbon-oxygen bond and can form stronger hydrogen bonds with water.
04

Predict the solubility

As \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) can form stronger hydrogen bonds with water, it will be more soluble in water than \(\mathrm{CH}_{3} \mathrm{CN}\). c. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) or \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{3}\)
05

Identify polar molecules

\(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) has a polar oxygen-hydrogen bond and can form hydrogen bonds with water. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{3}\) is a nonpolar molecule as it only contains nonpolar C-H and C-C bonds.
06

Predict the solubility

Since \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) can form hydrogen bonds with water while \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{3}\) is nonpolar, \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) will be more soluble in water. d. \(\mathrm{CH}_{3} \mathrm{OH}\) or \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\)
07

Identify polar molecules

Both molecules have a polar oxygen-hydrogen bond and can form hydrogen bonds with water. The difference is that \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) has an additional nonpolar methyl group.
08

Predict the solubility

Both molecules can hydrogen bond with water, but \(\mathrm{CH}_{3} \mathrm{OH}\) has less nonpolar character. Therefore, \(\mathrm{CH}_{3} \mathrm{OH}\) will be more soluble in water. e. \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}_{2} \mathrm{OH}\) or \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{OH}\)
09

Identify polar molecules

Both molecules have polar oxygen-hydrogen bonds and can hydrogen bond with water. However, both substances also have large nonpolar hydrocarbon chains which decrease their solubility in water.
10

Predict the solubility

Since both molecules can hydrogen bond with water, the one with the shorter nonpolar hydrocarbon chain will be more soluble in water. Therefore, \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}_{2} \mathrm{OH}\) is more soluble in water compared to \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{OH}\). f. \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) or \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\)
11

Identify polar molecules

\(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) has a polar carbon-oxygen bond and can form hydrogen bonds with water. \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\) has a polar oxygen-hydrogen bond, and multiple polar carbon-oxygen bonds, which allows for stronger hydrogen bonding with water.
12

Predict the solubility

Since \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\) can form stronger hydrogen bonds with water due to the presence of multiple polar bonds, it will be more soluble in water compared to \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\).

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Most popular questions from this chapter

Which solvent, water or hexane \(\left(\mathrm{C}_{6} \mathrm{H}_{14}\right)\), would you choose to dissolve each of the following? a. \(\mathrm{Cu}\left(\mathrm{NO}_{3}\right)_{2}\) d. \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{16} \mathrm{CH}_{2} \mathrm{OH}\) b. \(\mathrm{CS}_{2}\) e. \(\mathrm{HCl}\) c. \(\mathrm{CH}_{3} \mathrm{OH}\) f. \(\mathrm{C}_{6} \mathrm{H}_{6}\)

An unknown compound contains only carbon, hydrogen, and oxygen. Combustion analysis of the compound gives mass percents of \(31.57 \% \mathrm{C}\) and \(5.30 \% \mathrm{H}\). The molar mass is determined by measuring the freezing- point depression of an aqueous solution. A freezing point of \(-5.20^{\circ} \mathrm{C}\) is recorded for a solution made by dissolving \(10.56 \mathrm{~g}\) of the compound in \(25.0 \mathrm{~g}\) water. Determine the empirical formula, molar mass, and molecular formula of the compound. Assume that the compound is a nonelectrolyte.

What yolume of \(0.25 M \mathrm{HCl}\) solution must be diluted to prepare \(1.00 \mathrm{~L}\) of \(0.040 \mathrm{M} \mathrm{HCl}\) ?

A solution is prepared by mixing \(1.000\) mole of methanol \(\left(\mathrm{CH}_{3} \mathrm{OH}\right)\) and \(3.18\) moles of propanol \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\right) .\) What is the composition of the vapor (in mole fractions) at \(40^{\circ} \mathrm{C}\) ? At \(40^{\circ} \mathrm{C}\), the vapor pressure of pure methanol is 303 torr, and the vapor pressure of pure propanol is \(44.6\) torr.

A \(0.500-\mathrm{g}\) sample of a compound is dissolved in enough water to form \(100.0 \mathrm{~mL}\) of solution. This solution has an osmotic pressure of \(2.50 \mathrm{~atm}\) at \(25^{\circ} \mathrm{C}\). If each molecule of the solute dissociates into two particles (in this solvent), what is the molar mass of this solute?
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