Textbook Question
Which reaction in each of the following pairs takes place more rapidly? (EtOH is ethyl alcohol; Et2O is diethyl ether.)
d.
e.
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Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 9 - Substitution and Elimination Reactions of Alkyl HalidesProblem 61a,b
Bruice 8th EditionCh. 9 - Substitution and Elimination Reactions of Alkyl HalidesProblem 61a,bChapter 10, Problem 61a,b
What is the best way to prepare the following ethers using an alkyl halide and an alkoxide ion?
a. 
b. 
Verified step by step guidance1
Step 1: Recognize that the synthesis of ethers using an alkyl halide and an alkoxide ion is typically achieved through the Williamson Ether Synthesis. This reaction involves an SN2 mechanism, where the alkoxide ion acts as a nucleophile and the alkyl halide acts as an electrophile.
Step 2: Analyze the ether structure provided. The ether has two alkyl groups attached to the oxygen atom. One group is a tert-butyl group (on the left), and the other is a 2,2-dimethylpropyl group (on the right). Decide which part will come from the alkoxide ion and which from the alkyl halide.
Step 3: Consider steric hindrance. The SN2 mechanism requires a less sterically hindered alkyl halide for the reaction to proceed efficiently. The 2,2-dimethylpropyl group is highly hindered, so it is better to use the tert-butoxide ion (tert-butyl group) as the alkoxide and the 2,2-dimethylpropyl group as the alkyl halide.
Step 4: Write the reaction. Use tert-butoxide ion (\( \text{(CH}_3\text{)}_3\text{CO}^- \)) as the nucleophile and 2,2-dimethylpropyl bromide (\( \text{(CH}_3\text{)}_3\text{CCH}_2\text{Br} \)) as the electrophile. The reaction proceeds via an SN2 mechanism to form the desired ether.
Step 5: Ensure the reaction conditions are suitable. Use a polar aprotic solvent (e.g., DMSO or acetone) to facilitate the SN2 reaction and avoid side reactions. Heat may be applied if necessary to drive the reaction to completion.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Williamson Ether Synthesis
Williamson Ether Synthesis is a method for preparing ethers by reacting an alkoxide ion with a primary alkyl halide. The alkoxide acts as a nucleophile, attacking the electrophilic carbon of the alkyl halide, leading to the formation of an ether. This reaction is particularly effective with primary halides to minimize steric hindrance and avoid elimination reactions.
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The Mechanism of Williamson Ether Synthesis.
Alkoxide Ion
An alkoxide ion is a deprotonated alcohol, represented as R-O⁻, where R is an alkyl group. Alkoxides are strong nucleophiles and are commonly used in ether synthesis due to their ability to effectively attack electrophiles. They can be generated by treating alcohols with strong bases, such as sodium hydride or sodium metal.
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Nucleophilicity and Electrophilicity
Nucleophilicity refers to the ability of a species to donate an electron pair to form a chemical bond, while electrophilicity is the ability of a species to accept an electron pair. In the context of ether synthesis, the alkoxide ion is the nucleophile that attacks the electrophilic carbon of the alkyl halide, facilitating the formation of the ether product.
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Related Practice
Textbook Question
Would you expect acetate ion (CH3CO2−) to be a better nucleophile in an SN2 reaction with an alkyl halide carried out in methanol or in dimethyl sulfoxide?
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Textbook Question
Under which of the following reaction conditions will (R)-1-chloro-1-phenylethane form the most (R)-1-phenyl-1-ethanol: in water or in 1.0 M HO−?
1
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Textbook Question
What products (including stereoisomers, if applicable) are formed from the reaction of 3-bromo-3-methylpentane:
b. with H2O?
2
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Textbook Question
Identify the three products formed when 2-bromo-2-methylpropane is dissolved in a mixture of 80% ethanol and 20% water.
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Textbook Question
What is the best way to prepare the following ethers using an alkyl halide and an alkoxide ion?
c.
d.
2
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