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Ch.14 Some Compounds with Oxygen, Sulfur, or a Halogen
McMurry - Fundamentals of General, Organic, and Biological Chemistry 8th Edition
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187Non è quello che usi tu?Cambia libro di testo
Tutti i libri di testoMcMurry 8th EditionCh.14 Some Compounds with Oxygen, Sulfur, or a HalogenProblema 55
Capitolo 14, Problema 55

Propanol is very soluble in water, but ethanethiol and chloroethane are only slightly soluble. Explain.

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1
Identify the functional groups in each compound: Propanol contains a hydroxyl group (-OH), ethanethiol contains a thiol group (-SH), and chloroethane contains a chloro group (-Cl).
Understand the concept of solubility: Solubility in water depends on the ability of a compound to form hydrogen bonds or interact favorably with water molecules, which are polar.
Analyze propanol: The hydroxyl group (-OH) in propanol is highly polar and can form hydrogen bonds with water molecules, making it very soluble in water.
Analyze ethanethiol: The thiol group (-SH) in ethanethiol is less polar than the hydroxyl group and has a weaker ability to form hydrogen bonds with water, resulting in only slight solubility.
Analyze chloroethane: The chloro group (-Cl) in chloroethane is only weakly polar and cannot form hydrogen bonds with water, leading to its slight solubility in water.

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Polarity

Polarity refers to the distribution of electrical charge over the atoms in a molecule. Molecules with a significant difference in electronegativity between their atoms, like propanol, tend to be polar, allowing them to interact favorably with water molecules. In contrast, ethanethiol and chloroethane have less polar characteristics, leading to lower solubility in water.
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Molecular Polarity (Simplified) Concept 1

Hydrogen Bonding

Hydrogen bonding is a type of strong intermolecular attraction that occurs when hydrogen is bonded to highly electronegative atoms like oxygen or nitrogen. Propanol can form hydrogen bonds with water due to its hydroxyl (-OH) group, enhancing its solubility. Conversely, ethanethiol and chloroethane lack the ability to form strong hydrogen bonds with water, resulting in their limited solubility.
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Hydrogenation Reactions Concept 1

Molecular Structure

The molecular structure of a compound, including its functional groups and overall shape, significantly influences its solubility. Propanol has a hydroxyl group that increases its affinity for water, while ethanethiol contains a thiol group, and chloroethane has a halogen, both of which do not interact as effectively with water, leading to their lower solubility.
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Molecular Models Example 1
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The boiling point of propanol is 97 °C ,much higher than that of either ethanethiol (37 °C) or chloroethane (13 °C) , even though all three compounds have similar MWs. Explain.

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Define the following terms:

b. Achiral

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What is the structural relationship between a thiol and an alcohol?

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Define the following terms:

c. Chiral carbon

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