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)
12. Alcohols, Ethers, Epoxides and Thiols
Williamson Ether Synthesis
Problem 16a
Textbook Question
Suggest a phenoxide and an alkyl halide to make the following aryl alkyl ethers.
(a) 
Verified step by step guidance1
Identify the ether linkage in the given structure. The ether linkage is between the oxygen atom and the two carbon-containing groups.
Determine the two parts of the ether: the aryl group (phenyl group) and the alkyl group. In this structure, the aryl group is the phenyl ring, and the alkyl group is the isopropyl group attached to the oxygen.
To synthesize this ether, you need a phenoxide ion and an alkyl halide. The phenoxide ion is derived from phenol, where the hydrogen of the hydroxyl group is replaced by a metal ion, typically sodium or potassium.
The alkyl halide should correspond to the alkyl group in the ether. In this case, the alkyl group is isopropyl, so the alkyl halide should be isopropyl bromide or isopropyl chloride.
The reaction to form the ether is a nucleophilic substitution reaction, where the phenoxide ion acts as the nucleophile and attacks the electrophilic carbon in the alkyl halide, displacing the halide ion and forming the ether bond.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Phenoxide Ion
A phenoxide ion is formed when a phenol loses a hydrogen ion (H+) from its hydroxyl group (-OH), resulting in a negatively charged oxygen atom. This ion is a strong nucleophile, making it highly reactive in nucleophilic substitution reactions. Understanding the stability and reactivity of phenoxide ions is crucial for predicting their behavior in ether synthesis.
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Alkyl Halide
An alkyl halide is a compound derived from an alkane by replacing one or more hydrogen atoms with halogen atoms (such as chlorine, bromine, or iodine). These compounds are important in organic synthesis as they can undergo nucleophilic substitution reactions, where the halogen is replaced by a nucleophile, such as a phenoxide ion, to form ethers.
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Williamson Ether Synthesis
Williamson ether synthesis is a method for producing ethers by reacting an alkoxide ion (derived from an alcohol) with a primary alkyl halide. This reaction is favored with primary halides to avoid elimination reactions. Understanding this mechanism is essential for selecting appropriate reactants to synthesize specific aryl alkyl ethers.
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