Textbook Question
Ethers can be converted into radicals, some more easily than others. Which of the following radicals is more stable, and thus, more likely to form?
911
views
Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
Not the one you use?Change textbookSelect a different textbook
Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
All textbooks
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 66c
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 66cChapter 12, Problem 66c
Predict the product of the following reactions. [Two of them are Williamson ether syntheses. Why isn't the other?].
(c) 
Verified step by step guidance1
Identify the reactants: Methanol (CH₃OH) and a secondary alkyl chloride (2-chlorocyclohexane).
Recognize the role of sodium (Na⁰) in the reaction. Sodium metal reacts with alcohols to form alkoxides. Here, sodium will react with methanol to form sodium methoxide (CH₃O⁻ Na⁺) and hydrogen gas.
Understand the Williamson ether synthesis mechanism: It involves the reaction of an alkoxide ion with a primary alkyl halide to form an ether. The alkoxide ion acts as a nucleophile.
Analyze the structure of the alkyl halide: 2-chlorocyclohexane is a secondary alkyl halide. Williamson ether synthesis is most effective with primary alkyl halides due to steric hindrance and potential for elimination reactions with secondary and tertiary halides.
Conclude why this reaction is not a Williamson ether synthesis: The secondary nature of the alkyl halide (2-chlorocyclohexane) makes it prone to elimination reactions rather than substitution, which is why this reaction does not proceed via the Williamson ether synthesis pathway.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Was this helpful?
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 creating ethers through the reaction of an alkoxide ion with a primary alkyl halide. This reaction typically involves an SN2 mechanism, where the nucleophile (alkoxide) attacks the electrophile (alkyl halide) to form the ether. The choice of reactants is crucial, as steric hindrance can hinder the reaction, making it less effective with secondary or tertiary alkyl halides.
Recommended video:
Guided course
03:50
The Mechanism of Williamson Ether Synthesis.
SN2 Mechanism
The SN2 mechanism is a type of nucleophilic substitution reaction characterized by a single concerted step where the nucleophile attacks the electrophile, leading to the displacement of a leaving group. This mechanism is favored by primary substrates due to less steric hindrance, allowing for a more effective attack. Understanding the SN2 mechanism is essential for predicting the outcomes of reactions in Williamson ether synthesis.
Recommended video:
Guided course
08:33Drawing the SN2 Mechanism
Reactivity of Alkyl Halides
The reactivity of alkyl halides in nucleophilic substitution reactions depends on their structure. Primary alkyl halides react readily via the SN2 mechanism, while secondary and tertiary halides are more likely to undergo elimination reactions or SN1 mechanisms due to steric hindrance. Recognizing the type of alkyl halide involved is crucial for predicting whether a reaction will proceed via Williamson ether synthesis or another pathway.
Recommended video:
Guided course
01:52How to name alkyl halides
Related Practice
Textbook Question
Why is the SN1 reaction shown an inefficient way of synthesizing ethers?
1065
views
Textbook Question
Two different Williamson ether syntheses can be used to make the compound in (a). Show them. The compound in (b), however, can only be made one way. Show it and explain why a second Williamson ether synthesis is not possible.
(a)
992
views
Textbook Question
Predict the product of the following reactions. [Two of them are Williamson ether syntheses. Why isn't the other?].
(a)
1071
views
Textbook Question
Predict the product of the following reactions. [Two of them are Williamson ether syntheses. Why isn't the other?].
(b)
683
views
Textbook Question
Starting with hydrogen sulfide, suggest a synthesis of the following thioether that makes use of two different haloalkanes.
886
views