Textbook Question
Predict which member of each pair is more soluble in water. Explain your prediction.
(e)
(f)
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Ch. 2 - Acids and Bases; Functional Groups
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 2, Problem 32a,b
Predict which member of each pair is more soluble in water. Explain your prediction.
(a) 
(b) 
Verified step by step guidance1
Identify the functional groups present in each compound. In pair (a), the first compound is cyclopentane, which is a hydrocarbon with no polar functional groups. The second compound is tetrahydrofuran, which contains an ether group (an oxygen atom bonded to two carbon atoms).
Consider the polarity of the compounds. Cyclopentane is nonpolar, while tetrahydrofuran is polar due to the presence of the oxygen atom, which can form hydrogen bonds with water.
Predict the solubility in water for pair (a). Tetrahydrofuran is more soluble in water than cyclopentane because it can engage in hydrogen bonding with water molecules, increasing its solubility.
For pair (b), identify the functional groups. The first compound is tetrahydro-2H-pyran, which contains one ether group. The second compound is 1,3-dioxolane, which contains two ether groups.
Predict the solubility in water for pair (b). 1,3-dioxolane is more soluble in water than tetrahydro-2H-pyran because it has two oxygen atoms that can form hydrogen bonds with water, enhancing its solubility compared to the single oxygen in tetrahydro-2H-pyran.
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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 have a significant difference in electronegativity between atoms, leading to partial positive and negative charges. This property affects solubility, as polar substances tend to dissolve well in polar solvents like water, while nonpolar substances do not.
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2:04
Molecular Polarity
Hydrogen Bonding
Hydrogen bonding is a strong type of dipole-dipole interaction that occurs when hydrogen is bonded to highly electronegative atoms like oxygen, nitrogen, or fluorine. Molecules capable of hydrogen bonding can interact favorably with water, enhancing their solubility. For example, alcohols and carboxylic acids are more soluble in water due to their ability to form hydrogen bonds.
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00:48The definition of hydrogenation.
Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The presence of functional groups such as hydroxyl (-OH) or carbonyl (C=O) can significantly influence a compound's solubility in water. Compounds with polar functional groups are generally more soluble in water compared to those with nonpolar groups.
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02:36Identifying Functional Groups
Related Practice
Textbook Question
Which of the following pure compounds can form hydrogen bonds? Which can form hydrogen bonds with water? Which ones do you expect to be soluble in water?
a. (CH3CH2)2NH
b. (CH3CH2)3N
c. CH3CH2CH2OH
d. (CH3CH2CH2)2OH
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Textbook Question
Predict which member of each pair is more soluble in water. Explain your prediction.
(c)
(d)
Textbook Question
Diethyl ether and butan-1-ol are isomers, and they have similar solubilities in water. Their boiling points are very different, however. Explain why these two compounds have similar solubility properties but dramatically different boiling points.
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Textbook Question
Which of the following pure compounds can form hydrogen bonds? Which can form hydrogen bonds with water? Which ones do you expect to be soluble in water?
e. CH3(CH2)3CH3
f. CH2=CH—CH2CH3
g. CH3COCH3
h. CH3CH2COOH
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Textbook Question
Sulfur dioxide has a dipole moment of 1.60 D. Carbon dioxide has a dipole moment of zero, even though C―O bonds are more polar than S―O bonds. Explain this apparent contradiction.
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