Textbook Question
Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).
(c)
(d)
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Ch.10 - Structure and Synthesis of Alcohols
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 10, Problem 35b
Predict which member of each group is most soluble in water, and explain the reasons for your predictions.
b. chlorocyclohexane, cyclohexanol, or cyclohexane-1,2-diol
Verified step by step guidance1
Step 1: Analyze the functional groups present in each compound. Chlorocyclohexane contains a chlorine atom, cyclohexanol contains one hydroxyl (-OH) group, and cyclohexane-1,2-diol contains two hydroxyl (-OH) groups.
Step 2: Understand the solubility trends in water. Water is a polar solvent, and compounds with polar functional groups (such as hydroxyl groups) are more likely to form hydrogen bonds with water, increasing their solubility.
Step 3: Compare the polarity of the functional groups. The hydroxyl group (-OH) is highly polar and can form hydrogen bonds with water, whereas the chlorine atom in chlorocyclohexane is less polar and cannot form hydrogen bonds as effectively.
Step 4: Consider the number of hydroxyl groups. Cyclohexane-1,2-diol has two hydroxyl groups, which can form more hydrogen bonds with water compared to cyclohexanol, which has only one hydroxyl group.
Step 5: Predict the solubility order based on the ability to form hydrogen bonds. Cyclohexane-1,2-diol is expected to be the most soluble in water due to its two hydroxyl groups, followed by cyclohexanol with one hydroxyl group, and finally chlorocyclohexane, which has the least polar functional group.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Polarity and Solubility
Polarity refers to the distribution of electrical charge over the atoms in a molecule. Polar molecules, which have a significant difference in electronegativity between atoms, tend to dissolve well in polar solvents like water. Understanding the polarity of the compounds in question is crucial for predicting their solubility in water.
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Functional Classification
Hydrogen Bonding
Hydrogen bonding occurs when a hydrogen atom covalently bonded to a highly electronegative atom (like oxygen) interacts with another electronegative atom. Compounds capable of forming hydrogen bonds with water, such as alcohols, are generally more soluble in water. Recognizing which compounds can form these bonds is essential for solubility predictions.
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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 this case, the presence of hydroxyl (-OH) groups in cyclohexanol and cyclohexane-1,2-diol enhances their solubility in water compared to chlorocyclohexane, which lacks such groups. Identifying these functional groups helps in understanding the solubility behavior of the compounds.
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Related Practice
Textbook Question
Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).
(a)
(b)
549
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Textbook Question
Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).
(f)
(g)
654
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Textbook Question
Predict which member of each pair is more acidic, and explain the reasons for your predictions.
b. cyclohexanol or cyclohexanethiol
1005
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Textbook Question
Predict which member of each group is most soluble in water, and explain the reasons for your predictions.
a. butan-1-ol, pentan-1-ol, or propan-2-ol
619
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Textbook Question
Predict which member of each pair is more acidic, and explain the reasons for your predictions.
a. cyclopentanol or 3-chlorophenol
950
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