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Chapter 7: Problem 35

Which of the molecules below would not form hydrogen bonds? (a) \(\mathrm{CH}_{3} \mathrm{OH}\) (b) \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) (c) \(\mathrm{CH}_{3} \mathrm{COOH}\) (d) \(\mathrm{NH}_{3}\) (e) None of these would form hydrogen bonds.

Short Answer

Expert verified
The correct answer is (b) \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\), as it does not meet the conditions for hydrogen bonding (no H atoms bonded to O, N, or F).

Step by step solution

01

Analyze the structure of each molecule

First, let's examine each molecule for the presence of hydrogen atoms bonded to highly electronegative atoms (O, N, or F). (a) \(\mathrm{CH}_{3} \mathrm{OH}\): There is a hydrogen atom bonded to an oxygen atom. (b) \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\): There is no hydrogen atom bonded to a highly electronegative atom (O, N, or F). (c) \(\mathrm{CH}_{3} \mathrm{COOH}\): There is a hydrogen atom bonded to an oxygen atom. (d) \(\mathrm{NH}_{3}\): There is a hydrogen atom bonded to a nitrogen atom.
02

Check for unshared electron pairs on electronegative atoms

Next, we'll verify if there are any unshared electron pairs on highly electronegative atoms in the vicinity of the hydrogen atom bonded to an electronegative atom. (a) \(\mathrm{CH}_{3} \mathrm{OH}\): The oxygen atom has two unshared electron pairs. (b) \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\): There are unshared electron pairs on the oxygen atom, but the hydrogen atoms are not bonded to an electronegative atom. (c) \(\mathrm{CH}_{3} \mathrm{COOH}\): The oxygen atom in the carboxyl group has unshared electron pairs. (d) \(\mathrm{NH}_{3}\): The nitrogen atom has one unshared electron pair.
03

Identify which molecules can form hydrogen bonds

Now we'll determine which of the molecules satisfy the conditions for hydrogen bonding: that is, a hydrogen atom bonded to a highly electronegative atom (O, N, or F) and an unshared electron pair on another highly electronegative atom. (a) \(\mathrm{CH}_{3} \mathrm{OH}\): Meets the conditions for hydrogen bonding (H-O bond and unshared electrons on O). (b) \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\): Does not meet the conditions for hydrogen bonding (no H atoms bonded to O, N, or F). (c) \(\mathrm{CH}_{3} \mathrm{COOH}\): Meets the conditions for hydrogen bonding (H-O bond and unshared electrons on O). (d) \(\mathrm{NH}_{3}\): Meets the conditions for hydrogen bonding (H-N bond and unshared electrons on N).
04

Choose the correct answer

As per our analysis, the molecule \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) is not able to form hydrogen bonds based on its structure and the absence of a hydrogen atom bonded to a highly electronegative atom. The correct answer is (b) \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\).

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Most popular questions from this chapter

All of the following are solids at room temperature. Classify them as molecular, ionic, network, or metallic. (a) Potassium \((\mathrm{K}), \mathrm{mp}=64{ }^{\circ} \mathrm{C}\) (b) Potassium chloride \((\mathrm{KCl}), \mathrm{mp}=770{ }^{\circ} \mathrm{C}\) (c) Red phosphorus \((\mathrm{P}), \mathrm{mp}=590{ }^{\circ} \mathrm{C}\) (d) Boron triiodide \(\left(\mathrm{BI}_{3}\right), \mathrm{mp}=50{ }^{\circ} \mathrm{C}\)

Elemental sulfur is a yellow solid that melts at \(113{ }^{\circ} \mathrm{C}\). Studies show sulfur to be a molecular solid consisting of \(S_{8}\) molecules held together in a lattice. What forces must be overcome to melt the solid?

\(\mathrm{SiO}_{2}\), the main component of glass, is a solid at room temperature, and \(\mathrm{CO}_{2}\) is a gas at room temperature. How do the structures of these compounds explain this fact?

Is it incorrect to say that molecules are motionless in the liquid phase? Explain.

Solid ice is less dense than liquid water. What does this say about how many water molecules there are per unit volume of ice relative to how many water molecules there are per unit volume of liquid water?
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