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Ch.12 Alcohols, Thiols, Ethers, Aldehydes, and Ketones
Timberlake - Chemistry: An Introduction to General, Organic, and Biological Chemistry 13th Edition
Timberlake13th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9780134421353Not the one you use?Change textbook
Chapter 12, Problem 49a

Which compound in each pair would be more soluble in water? Explain.
a. butane or 1-propanol

Verified step by step guidance
1
Identify the key property that affects solubility in water: Water is a polar solvent, so compounds with polar functional groups (e.g., -OH) or the ability to form hydrogen bonds are generally more soluble in water than nonpolar compounds.
Analyze the structure of butane: Butane is a hydrocarbon with the formula C4H10. It is nonpolar because it consists only of carbon and hydrogen atoms, which share electrons almost equally, and it lacks any polar functional groups.
Analyze the structure of 1-propanol: 1-Propanol has the formula C3H7OH. It contains a hydroxyl (-OH) group, which is highly polar and capable of forming hydrogen bonds with water molecules, making it more compatible with water.
Compare the solubility of the two compounds: Since 1-propanol has a polar -OH group and can form hydrogen bonds, it is more soluble in water than butane, which is nonpolar and cannot form hydrogen bonds.
Conclude: 1-Propanol is more soluble in water than butane due to its polar hydroxyl group and ability to form hydrogen bonds with water molecules.

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Key Concepts

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

Polarity

Polarity refers to the distribution of electrical charge over the atoms in a molecule. Polar molecules, which have a significant difference in electronegativity between their atoms, tend to dissolve well in water due to hydrogen bonding. In contrast, nonpolar molecules, like butane, do not interact favorably with water, making them less soluble.
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Hydrogen Bonding

Hydrogen bonding is a type of strong intermolecular attraction that occurs when a hydrogen atom covalently bonded to a highly electronegative atom, such as oxygen, interacts with another electronegative atom. This interaction significantly increases the solubility of compounds like 1-propanol in water, as it allows for effective interactions with water molecules.
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Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the case of 1-propanol, the hydroxyl (-OH) functional group enhances its solubility in water, while butane, lacking such a group, remains largely hydrophobic and insoluble.
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