Textbook Question
Predict which member of each pair is more soluble in water. Explain your prediction.
(e)
(f)
1
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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 32c,d
Predict which member of each pair is more soluble in water. Explain your prediction.
(c) 
(d) 
Verified step by step guidance1
Step 1: Understand the concept of solubility in water. Solubility is influenced by the ability of a compound to interact with water molecules. Polar compounds and those capable of hydrogen bonding are generally more soluble in water.
Step 2: Identify the functional groups present in each compound of the pair. Functional groups such as hydroxyl (-OH), amino (-NH2), and carboxyl (-COOH) can enhance solubility due to their ability to form hydrogen bonds with water.
Step 3: Compare the polarity of the compounds. Polar compounds have an uneven distribution of electron density, which allows them to interact more effectively with the polar water molecules.
Step 4: Consider the molecular size and structure. Smaller molecules or those with more branching may be more soluble due to increased surface area for interaction with water.
Step 5: Evaluate the overall ability of each compound to form hydrogen bonds with water. The compound with more hydrogen bonding sites or stronger polar interactions will likely be more soluble.
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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. Molecules with polar bonds have a significant difference in electronegativity between the bonded atoms, leading to a dipole moment. Polar molecules tend to be more soluble in water, a polar solvent, due to the attraction between the dipoles of the solute and solvent.
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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. These bonds significantly increase solubility in water because water molecules can form hydrogen bonds with the solute, enhancing the interaction and dissolution process.
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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. Groups like hydroxyl (-OH) and amino (-NH2) are polar and can form hydrogen bonds, increasing solubility in water. The presence and type of functional groups in a molecule are crucial in predicting its solubility.
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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
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
Predict which member of each pair is more soluble in water. Explain your prediction.
(a)
(b)
2
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Textbook Question
N-Methylpyrrolidine has a boiling point of 81 °C, and piperidine has a boiling point of 106 °C.
b. Tetrahydropyran has a boiling point of 88 °C, and cyclopentanol has a boiling point of 141 °C. These two isomers have a boiling point difference of 53 °C. Explain why the two oxygen-containing isomers have a much larger boiling point difference than the two amine isomers.
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