Which of the following would show hydrogen bonding? (a) \(\mathrm{CH}_{3} \mathrm{~F}\) (b) \(\mathrm{HO}-\mathrm{OH}\) (c) \(\mathrm{NH}_{3}\) (d) \(\mathrm{H}_{3} \mathrm{C}-\mathrm{O}-\mathrm{CH}_{3}\)

Short Answer

Expert verified
(a) \(\mathrm{CH}_{3} \mathrm{F}\) (b) \(\mathrm{HO}-\mathrm{OH}\) (c) \(\mathrm{NH}_{3}\) (d) \(\mathrm{H}_{3} \mathrm{C}-\mathrm{O}-\mathrm{CH}_{3}\) Answer: (b) \(\mathrm{HO}-\mathrm{OH}\) and (c) \(\mathrm{NH}_{3}\)

Step by step solution

01

Analyze Molecule (a) - \(\mathrm{CH}_{3} \mathrm{F}\)

The first molecule features a covalent bond between carbon and fluorine, with three hydrogen atoms bonded to the carbon. However, none of the hydrogen atoms are attached to a highly electronegative atom such as nitrogen, oxygen, or fluorine. Therefore, hydrogen bonding cannot occur in this molecule.
02

Analyze Molecule (b) - \(\mathrm{HO}-\mathrm{OH}\)

The second molecule is water, with an oxygen atom sharing covalent bonds with two hydrogen atoms. Oxygen is a highly electronegative atom, and hydrogen bonding can occur between water molecules. The hydrogens covalently bonded to oxygen will also be attracted to the oxygen atoms of other nearby water molecules, creating hydrogen bonds. So, this molecule can show hydrogen bonding.
03

Analyze Molecule (c) - \(\mathrm{NH}_{3}\)

In this molecule, a nitrogen atom shares covalent bonds with three hydrogen atoms. Nitrogen is also a highly electronegative atom, resulting in hydrogen bonding between different ammonia molecules. The hydrogens covalently bonded to nitrogen will be attracted to the nitrogen atoms of other nearby ammonia molecules, establishing hydrogen bonds. Therefore, this molecule can also show hydrogen bonding.
04

Analyze Molecule (d) - \(\mathrm{H}_{3} \mathrm{C}-\mathrm{O}-\mathrm{CH}_{3}\)

This molecule has an oxygen atom sharing covalent bonds with two carbon atoms. The two \(\mathrm{H}_{3} \mathrm{C}\) groups on either side of the oxygen cannot form hydrogen bonds because they are bonded to carbon, not a highly electronegative atom. Consequently, this molecule cannot show hydrogen bonding as there are no suitable hydrogen donors or acceptors within the molecule.
05

Conclusion

Based on the analysis of the four molecules, the ones that can show hydrogen bonding are: (b) \(\mathrm{HO}-\mathrm{OH}\) (c) \(\mathrm{NH}_{3}\)

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Most popular questions from this chapter

Classify each of the following solids as metallic, network covalent, ionic, or molecular. (a) It is insoluble in water, melts above \(500^{\circ} \mathrm{C}\), and does not conduct electricity either as a solid, dissolved in water, or molten. (b) It dissolves in water but does not conduct electricity as an aqueous solution, as a solid, or when molten. (c) It dissolves in water, melts above \(100^{\circ} \mathrm{C}\), and conducts electricity when present in an aqueous solution.

Explain in terms of forces between structural units why (a) HI has a higher boiling point than \(\mathrm{HBr}\). (b) \(\mathrm{GeH}_{4}\) has a higher boiling point than \(\mathrm{SiH}_{4}\). (c) \(\mathrm{H}_{2} \mathrm{O}_{2}\) has a higher melting point than \(\mathrm{C}_{3} \mathrm{H}_{8}\). (d) \(\mathrm{NaCl}\) has a higher boiling point than \(\mathrm{CH}_{3} \mathrm{OH}\).

The normal boiling point for methyl hydrazine \(\left(\mathrm{CH}_{3} \mathrm{~N}_{2} \mathrm{H}_{3}\right)\) is \(87^{\circ} \mathrm{C}\). It has a vapor pressure of \(37.0 \mathrm{~mm} \mathrm{Hg}\) at \(20^{\circ} \mathrm{C}\). What is the concentration (in \(\mathrm{g} / \mathrm{L}\) ) of methyl hydrazine if it saturates the air at \(25^{\circ} \mathrm{C}\) ?

An experiment is performed to determine the vapor pressure of formic acid. A 30.0-L volume of helium gas at \(20.0^{\circ} \mathrm{C}\) is passed through \(10.00 \mathrm{~g}\) of liquid formic acid \((\mathrm{HCOOH})\) at \(20.0^{\circ} \mathrm{C}\). After the experiment, \(7.50 \mathrm{~g}\) of liquid formic acid remains. Assume that the helium gas becomes saturated with formic acid vapor and the total gas volume and temperature remain constant. What is the vapor pressure of formic acid at \(20.0^{\circ} \mathrm{C} ?\)

The data below give the vapor pressure of octane, a major component of gasoline. \(\begin{array}{lllcl}\text { vp }(\mathrm{mm} \mathrm{Hg}) & 10 & 40 & 100 & 400 \\ t\left({ }^{\circ} \mathrm{C}\right) & 19.2 & 45.1 & 65.7 & 104.0\end{array}\) Plot ln vp versus \(1 / T\). Use your graph to estimate the heat of vaporization of octane. \(\left(\ln P=A-\frac{\Delta H_{\mathrm{vap}}}{R}\left(\frac{1}{T}\right)\right.\), where \(A\) is the \(y\) -intercept and \(\Delta H_{\mathrm{vap}}\) is the slope.)

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