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Chapter 11: Problem 34

Based on their composition and structure, list \(\mathrm{CH}_{3} \mathrm{COOH}\), \(\mathrm{CH}_{3} \mathrm{COOCH}_{3}\), and \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) in order of (a) increasing intermolecular forces, (b) increasing viscosity, (c) increasing surface tension.

Short Answer

Expert verified
For all properties, order is methyl acetate, ethanol, acetic acid.

Step by step solution

01

Identify Molecular Structures

We begin by identifying the molecular structures and relevant groups. - \(\mathrm{CH}_{3}\mathrm{COOH}\) (Acetic Acid): Contains a carboxyl group (COOH), capable of hydrogen bonding.- \(\mathrm{CH}_{3}\mathrm{COOCH}_{3}\) (Methyl Acetate): An ester, does not easily form hydrogen bonds.- \(\mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{OH}\) (Ethanol): Contains a hydroxyl group (OH), capable of hydrogen bonding.
02

Evaluate Intermolecular Forces

Acetic acid can form strong hydrogen bonds due to its carboxyl group, providing it with strong intermolecular forces. Ethanol also forms hydrogen bonds, but generally weaker than acetic acid due to the lack of a second oxygen. Methyl acetate has only dipole-dipole interactions and Van der Waals forces, making it have the weakest intermolecular forces.
03

Rank Increasing Intermolecular Forces

The order of increasing intermolecular forces is methyl acetate (CH鈧僀OOCH鈧�), ethanol (CH鈧僀H鈧侽H), and acetic acid (CH鈧僀OOH).
04

Evaluate Viscosity

Viscosity is higher when intermolecular forces are stronger because the molecules 'stick' together more. Therefore, the rank for increasing viscosity follows the order of intermolecular forces: methyl acetate, ethanol, and acetic acid.
05

Rank Increasing Viscosity

The order of increasing viscosity is methyl acetate (CH鈧僀OOCH鈧�), ethanol (CH鈧僀H鈧侽H), and acetic acid (CH鈧僀OOH).
06

Evaluate Surface Tension

Similar to viscosity, surface tension correlates with intermolecular forces. Stronger forces lead to higher surface tension as molecules on the surface attract each other more strongly. Thus, the rank is the same as that for viscosity and intermolecular forces.
07

Rank Increasing Surface Tension

The order of increasing surface tension is methyl acetate (CH鈧僀OOCH鈧�), ethanol (CH鈧僀H鈧侽H), and acetic acid (CH鈧僀OOH).

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Intermolecular Forces
Intermolecular forces are the attractions between molecules that influence their physical properties. These forces include hydrogen bonding, dipole-dipole interactions, and Van der Waals forces. For instance, acetic acid (\(\mathrm{CH}_3\mathrm{COOH} \)) has strong hydrogen bonds due to its carboxyl group. This group can form a network of hydrogen bonds, making acetic acid's intermolecular forces the strongest among the given samples.

Ethanol (\(\mathrm{CH}_3\mathrm{CH}_2\mathrm{OH} \)), with its hydroxyl group, also engages in hydrogen bonding though less intensely than acetic acid due to its structure. Thus, it ranks second in terms of intermolecular forces.
  • Strongest: Acetic acid (\(\mathrm{CH}_3\mathrm{COOH} \))
  • Moderate: Ethanol (\(\mathrm{CH}_3\mathrm{CH}_2\mathrm{OH} \))
  • Weakest: Methyl acetate (\(\mathrm{CH}_3\mathrm{COOCH}_3 \)), which relies primarily on dipole-dipole interactions and weaker Van der Waals forces.
Viscosity
Viscosity is a measure of a fluid's resistance to flow. The stronger the intermolecular forces in a substance, the higher its viscosity becomes, as molecules are more likely to 'stick' together.

In this context, acetic acid demonstrates the highest viscosity among the substances due to its strong hydrogen bonding capability, making the fluid thicker. Ethanol, with moderately strong hydrogen bonding, exhibits medium viscosity.
  • Highest viscosity: Acetic acid (\(\mathrm{CH}_3\mathrm{COOH} \))
  • Medium viscosity: Ethanol (\(\mathrm{CH}_3\mathrm{CH}_2\mathrm{OH} \))
  • Lowest viscosity: Methyl acetate (\(\mathrm{CH}_3\mathrm{COOCH}_3 \)), as it lacks strong hydrogen bonds.
Surface Tension
Surface tension refers to the energy required to increase the surface area of a liquid due to intermolecular forces. Like viscosity, surface tension increases with stronger intermolecular forces.

Acetic acid has the highest surface tension among these substances since its molecules are strongly attracted to one another at the surface. Ethanol comes next, as its hydrogen bonds give it notable surface tension but not as high as acetic acid.
  • Highest surface tension: Acetic acid (\(\mathrm{CH}_3\mathrm{COOH} \))
  • Moderate surface tension: Ethanol (\(\mathrm{CH}_3\mathrm{CH}_2\mathrm{OH} \))
  • Lowest surface tension: Methyl acetate (\(\mathrm{CH}_3\mathrm{COOCH}_3 \)), due to its relatively weak dipole-dipole interactions.

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Most popular questions from this chapter

(a) What phase change is represented by the "heat of vaporization" of a substance? (b) Is the process of vaporization endothermic or exothermic? (c) If you compare a substance's heat of vaporization to the amount of heat released during condensation, which one is generally larger (consider the numerical value only)?

Name the phase transition in each of the following situations and indicate whether it is exothermic or endothermic: (a) lodine solid turns to iodine gas when it is heated. (b) Snowflakes turn into water when they fall on an open palm. (c) Droplets of water appear on grass in a cold humid morning. (d) Dry ice gradually disappears when left at room temperature for some period of time.

(a) What is the significance of the triple point in a phase diagram? (b) Could you measure the triple point of water by measuring the temperature in a vessel in which water vapor, liquid water, and ice are in equilibrium under \(101,32 \mathrm{kPa}\) of air? Explain.

At standard temperature and pressure, the molar volumes of \(\mathrm{Cl}_{2}\) and \(\mathrm{NH}_{3}\) gases are 22.06 and \(22.40 \mathrm{~L},\) respectively. (a) Given the different molecular weights, dipole moments, and molecular shapes, why are their molar volumes nearly the same? (b) On cooling to \(160 \mathrm{~K}\), both substances form crystalline solids. Do you expect the molar volumes to decrease or increase on cooling the gases to \(160 \mathrm{~K} ?\) (c) The densities of crystalline \(\mathrm{Cl}_{2}\) and \(\mathrm{NH}_{3}\) at \(160 \mathrm{~K}\) are 2.02 and \(0.84 \mathrm{~g} / \mathrm{cm}^{3},\) respectively. Calculate their molar volumes. (d) Are the molar volumes in the solid state as similar as they are in the gaseous state? Explain. (e) Would you expect the molar volumes in the liquid state to be closer to those in the solid or gaseous state?

(a) What atoms must a molecule contain to participate in hydrogen bonding with other molecules of the same kind? (b) Which of the following molecules can form hydrogen bonds with other molecules of the same kind: \(\mathrm{CH}_{3} \mathrm{~F}, \mathrm{CH}_{3} \mathrm{NH}_{2}, \mathrm{CH}_{3} \mathrm{OH}, \mathrm{CH}_{3} \mathrm{Br} ?\)
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