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Ch.11 - Liquids & Phase Changes
Chapter 11, Problem 95

Dimethyl ether has the following structure. Illustration A shows hydrogen bonding between dimethyl ether and water.
(b) Which of the following illustrations depicts the hydrogen bonding that occurs between dimethyl ether and water? (i) Illustration B depicts the structure of dimethyl ether.
(ii)

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1
Identify the structure of dimethyl ether. It has the formula CH3-O-CH3.
Understand that hydrogen bonding occurs between a hydrogen atom attached to a highly electronegative atom (like O, N, or F) and another electronegative atom with a lone pair of electrons.
Analyze the given illustrations. Illustration A shows a hydrogen bond between the oxygen of dimethyl ether and a hydrogen atom of water.
Illustration B shows a hydrogen bond between the hydrogen of dimethyl ether and the oxygen atom of water.
Determine which illustration correctly depicts the hydrogen bonding. Since hydrogen bonding involves the lone pair on the oxygen of dimethyl ether and the hydrogen of water, Illustration A is correct.

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Key Concepts

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

Hydrogen Bonding

Hydrogen bonding is a type of intermolecular force that occurs when a hydrogen atom covalently bonded to a highly electronegative atom, such as oxygen or nitrogen, experiences an attraction to another electronegative atom. This interaction is crucial in determining the physical properties of substances, such as boiling and melting points. In the context of dimethyl ether and water, hydrogen bonds form between the hydrogen atoms of water and the oxygen atom of dimethyl ether.
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Molecular Structure of Dimethyl Ether

Dimethyl ether (C2H6O) is an organic compound with a simple structure consisting of two methyl groups (–CH3) attached to an oxygen atom. Its molecular geometry is bent due to the presence of lone pairs on the oxygen, which influences its polarity and ability to engage in hydrogen bonding. Understanding its structure is essential for predicting how it interacts with water and other polar solvents.
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Polarity and Solubility

Polarity refers to the distribution of electrical charge over the atoms in a molecule, which affects how molecules interact with each other. Polar molecules, like water and dimethyl ether, can dissolve in each other due to their ability to form hydrogen bonds. This concept is vital for understanding why dimethyl ether can mix with water and how the hydrogen bonding illustrated in the question occurs.
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