Textbook Question
Show how you would accomplish the following synthetic conversions.
(d)
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Ch.11 - Reactions 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 11, Problem 42a,b
Show how you would accomplish the following synthetic conversions.
(a) 
(b) 
Verified step by step guidance1
Step 1: For part (a), identify the functional group transformation. The starting material is cyclohexanol (an alcohol), and the product is cyclohexyl ethyl ether. This indicates that the reaction involves ether formation, likely through Williamson ether synthesis.
Step 2: In Williamson ether synthesis, the alcohol is first converted into an alkoxide ion by reacting it with a strong base such as sodium hydride (NaH) or potassium hydroxide (KOH). This deprotonates the alcohol to form the cyclohexoxide ion.
Step 3: The alkoxide ion then reacts with an alkyl halide, such as ethyl bromide (CH3CH2Br), in an SN2 reaction. This results in the formation of the ether bond, yielding cyclohexyl ethyl ether.
Step 4: For part (b), identify the functional group transformation. The starting material is benzyl bromide (C6H5CH2Br), and the product is stilbene (C6H5CH=CHC6H5). This indicates that the reaction involves coupling and elimination to form a double bond.
Step 5: Benzyl bromide undergoes a coupling reaction, likely through a Wurtz reaction mechanism. In the presence of sodium metal (Na), two benzyl bromide molecules react to form a stilbene structure via elimination of bromine and formation of a carbon-carbon double bond.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophile, replacing a leaving group. In the context of the provided reaction, the hydroxyl group (OH) acts as a leaving group, and the alkyl group (OCH2CH3) is introduced through this substitution process, resulting in the formation of an ether.
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Nucleophiles and Electrophiles can react in Substitution Reactions.
Reactivity of Alcohols
Alcohols are versatile compounds that can undergo various reactions due to the presence of the hydroxyl (-OH) group. In this case, the alcohol is converted into an ether, which typically requires activation of the alcohol to enhance its reactivity, often through protonation or conversion to a better leaving group, facilitating the nucleophilic attack.
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Mechanism of Ether Formation
The formation of ethers from alcohols can occur via several mechanisms, including the Williamson ether synthesis. This involves the reaction of an alkoxide ion with a primary alkyl halide or a suitable electrophile. Understanding the mechanism is crucial for predicting the outcome of the reaction and ensuring the correct conditions are applied for successful ether synthesis.
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Related Practice
Textbook Question
In each case, show how you would synthesize the chloride, bromide, and iodide from the corresponding alcohol.
(a) 1-halobutane (halo = chloro, bromo, iodo)
(b) halocyclopentane
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Textbook Question
Show how you would convert 2-methylcyclopentanol to the following products. Any of these products may be used as the reactant in any subsequent part of this problem.
(g) 2-methylcyclopentyl acetate
(h) 1-bromo-1-methylcyclopentane
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Textbook Question
Show how you would convert 2-methylcyclopentanol to the following products. Any of these products may be used as the reactant in any subsequent part of this problem.
d. 1-methylcyclopentanol
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Textbook Question
Predict the major products of dehydration catalyzed by sulfuric acid.
(a) hexan-1-ol
(b) hexan-2-ol
(c) pentan-3-ol
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Textbook Question
Show how you would accomplish the following synthetic conversions.
(c)
1
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