Textbook Question
Draw the condensed structural formula, or line-angle formula if cyclic, for each of the following: (12.1)
d. 2,4-dibromophenol
Ch.12 Alcohols, Thiols, Ethers, Aldehydes, and Ketones
Timberlake14th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9781292472249
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Table of contents
- Ch.1 Chemistry in Our Lives19
- Ch.2 Chemistry and Measurements80
- Ch.3 Matter and Energy53
- Ch.4 Atoms and Elements58
- Ch.5 Nuclear Chemistry42
- Ch.6 Ionic and Molecular Compounds57
- Ch.7 Chemical Quantities and Reactions38
- Ch.8 Gases30
- Ch.9 Solutions50
- Ch.10 Acids and Bases and Equilibrium64
- Ch.11 Introduction to Organic Chemistry: Hydrocarbons77
- Ch.12 Alcohols, Thiols, Ethers, Aldehydes, and Ketones82
- Ch.13 Carbohydrates54
- Ch.14 Carboxylic Acids, Esters, Amines, and Amides91
- Ch.15 Lipids61
- Ch.16 Amino Acids, Proteins, and Enzymes84
- Ch.17 Nucleic Acids and Protein Synthesis86
- Ch.18 Metabolic Pathways and ATP Production73
Timberlake14th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9781292472249Not the one you use?Change textbook
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Timberlake 14th EditionCh.12 Alcohols, Thiols, Ethers, Aldehydes, and KetonesProblem 50c
Timberlake 14th EditionCh.12 Alcohols, Thiols, Ethers, Aldehydes, and KetonesProblem 50cChapter 12, Problem 50c
Which compound in each pair would be more soluble in water? Explain.
c. methyl propyl ether or 1-butanol
Verified step by step guidance1
Identify the key factors that influence solubility in water: Water is a polar solvent, so compounds that can form hydrogen bonds with water or have polar functional groups are generally more soluble.
Analyze the structure of methyl propyl ether: This compound contains an ether functional group (-O-) but lacks hydroxyl (-OH) groups, which limits its ability to form hydrogen bonds with water. Its solubility in water is primarily due to the oxygen atom's lone pairs, which can weakly interact with water molecules.
Analyze the structure of 1-butanol: This compound contains a hydroxyl (-OH) group, which can form strong hydrogen bonds with water molecules. This significantly enhances its solubility in water compared to compounds without hydroxyl groups.
Compare the two compounds: While both compounds have some ability to interact with water, 1-butanol's hydroxyl group allows it to form stronger and more extensive hydrogen bonding with water than the ether group in methyl propyl ether.
Conclude: Based on the ability to form hydrogen bonds, 1-butanol would be more soluble in water than methyl propyl ether.
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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 interact well with water, a polar solvent. In contrast, nonpolar molecules do not dissolve well in water due to their lack of charge separation.
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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. In the context of solubility, compounds that can form hydrogen bonds with water, such as alcohols, are generally more soluble than those that cannot, as these interactions help to stabilize the solute in the solvent.
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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 the compounds in the question, the presence of the hydroxyl (-OH) group in 1-butanol enhances its solubility in water compared to methyl propyl ether, which lacks this polar functional group.
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Related Practice
Textbook Question
Which compound in each pair would be more soluble in water? Explain.
a. butane or 1-propanol
Textbook Question
Which compound in each pair would be more soluble in water? Explain.
b. 2-propanol or 2-pentanol
Textbook Question
Draw the condensed structural or line-angle formula for the alkene, aldehyde, or ketone product of each of the following reactions:
a.
Textbook Question
Draw the condensed structural or line-angle formula for the alkene, aldehyde, or ketone product of each of the following reactions:
a.
Textbook Question
Draw the condensed structural or line-angle formula for the alkene, aldehyde, or ketone product of each of the following reactions:
c.