Textbook Question
Identify the alkene and alcohol partners that could be used to make the following ethers.
(a)
12. Alcohols, Ethers, Epoxides and Thiols
Williamson Ether Synthesis
4:02 minutesProblem 103
Textbook Question
In contrast to Assessment 13.102, only one combination of haloalkane and alkoxide can be used in the Williamson ether synthesis to make the ether shown. Identify the combination and explain why it is the only combination that works.
Verified step by step guidance1
Identify the ether product: The ether shown is isopropyl phenyl ether, which consists of an isopropyl group and a phenyl group connected by an oxygen atom.
Understand the Williamson ether synthesis: This reaction involves the reaction of an alkoxide ion with a haloalkane to form an ether. The alkoxide ion acts as a nucleophile, attacking the electrophilic carbon in the haloalkane.
Determine the possible alkoxide: The alkoxide must correspond to the part of the ether that is less hindered. In this case, the phenoxide ion (C6H5O-) is less hindered compared to the isopropyl group.
Select the appropriate haloalkane: The haloalkane should be the more hindered part of the ether, which is the isopropyl group. Therefore, the haloalkane should be isopropyl bromide (or chloride).
Explain why this combination works: The phenoxide ion is a strong nucleophile and can effectively attack the less hindered primary carbon in isopropyl bromide, leading to the formation of isopropyl phenyl ether. Other combinations would lead to steric hindrance or less favorable reactions.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Williamson Ether Synthesis
The Williamson ether synthesis is a method for creating ethers by reacting an alkoxide ion with a haloalkane. This reaction typically involves a nucleophilic substitution mechanism, where the alkoxide acts as a nucleophile and attacks the electrophilic carbon in the haloalkane, displacing the halide ion. The choice of haloalkane and alkoxide is crucial, as steric hindrance and the nature of the leaving group can significantly affect the reaction's success.
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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 the Williamson ether synthesis, the alkoxide is a strong nucleophile due to its negative charge, and the haloalkane must be a suitable electrophile, typically a primary or methyl halide, to facilitate the reaction without steric hindrance that would impede nucleophilic attack.
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03:Nucleophile or Electrophile
Steric Hindrance
Steric hindrance is the prevention of chemical reactions due to the spatial arrangement of atoms within a molecule. In the Williamson ether synthesis, using a bulky haloalkane can hinder the approach of the nucleophile, making the reaction less favorable or impossible. Therefore, the selection of a primary haloalkane is often necessary to ensure that steric factors do not obstruct the nucleophilic attack by the alkoxide.
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