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Ch. 14 - Ethers, Epoxides, and Thioethers
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh. 14 - Ethers, Epoxides, and ThioethersProblem 1
Chapter 14, Problem 1

Rank the given solvents in decreasing order of their ability to dissolve each compound.
Solutes:
(a) NaOAc
(b)
(c)


Solvents:
ethyl ether
water
ethanol
dichloromethane

Verified step by step guidance
1
Step 1: Understand the solubility principles. Solubility depends on the polarity of the solvent and solute. Polar solvents dissolve polar solutes, and non-polar solvents dissolve non-polar solutes. This is often summarized by the phrase 'like dissolves like'.
Step 2: Analyze the polarity of the solvents. Water is highly polar due to its hydrogen bonding capabilities. Ethanol is also polar but less so than water, as it has both a polar hydroxyl group and a non-polar ethyl group. Ethyl ether is less polar, and dichloromethane is moderately polar.
Step 3: Consider the solute NaOAc (sodium acetate). NaOAc is an ionic compound, which means it is highly polar. Ionic compounds generally dissolve well in polar solvents.
Step 4: Rank the solvents based on their ability to dissolve NaOAc. Since NaOAc is ionic, it will dissolve best in the most polar solvent. Therefore, water will be the best solvent, followed by ethanol, dichloromethane, and ethyl ether.
Step 5: Apply the same analysis to other solutes (b) and (c) if they are provided. Determine their polarity and match them with the solvents using the 'like dissolves like' principle.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Polarity of Solvents

Polarity is a key factor in determining a solvent's ability to dissolve a solute. Polar solvents, like water, can dissolve ionic compounds and polar solutes due to their ability to form hydrogen bonds and dipole-dipole interactions. Non-polar solvents, such as ethyl ether, are better suited for dissolving non-polar solutes through van der Waals forces.
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Solubility Principles

The principle 'like dissolves like' is fundamental in organic chemistry, indicating that polar solutes dissolve well in polar solvents, while non-polar solutes dissolve in non-polar solvents. This concept helps predict solubility based on the chemical nature of both the solvent and solute, guiding the ranking of solvents for each compound.
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Ionic vs. Covalent Compounds

Understanding the nature of the solute, whether ionic or covalent, is crucial for predicting solubility. Ionic compounds, like NaOAc, typically dissolve in polar solvents due to ion-dipole interactions. Covalent compounds may require specific solvent characteristics, such as polarity or hydrogen bonding capability, to dissolve effectively.
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Related Practice
Textbook Question

In the presence of 18-crown-6, potassium permanganate dissolves in benzene to give "purple benzene," a useful reagent for oxidizing alkenes in an aprotic environment. Use a drawing of the complex to show why KMnO4 dissolves in benzene and why the reactivity of the permanganate ion is enhanced.

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Textbook Question

Give a common name (when possible) and a systematic name for each compound.

(a) CH3OCH=CH2

(b) CH3CH2OCH(CH3)2

(c) ClCH2CH2OCH3

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Textbook Question

Aluminum trichloride (AlCl3) dissolves in ether with the evolution of a large amount of heat. (In fact, this reaction can become rather violent if it gets too warm.) Show the structure of the resulting aluminum chloride etherate complex.

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