Textbook Question
Predict the product of the following substitution/addition reactions involving phenoxides.
(a)
833
views
12. Alcohols, Ethers, Epoxides and Thiols
Williamson Ether Synthesis
Problem 16b
Textbook Question
Suggest a phenoxide and an alkyl halide to make the following aryl alkyl ethers.
(b) 
Verified step by step guidance1
Identify the ether linkage in the given structure. The structure is a 1,4-dioxane derivative with two ether linkages.
Recognize that the ether can be synthesized by the Williamson ether synthesis, which involves the reaction of a phenoxide ion with an alkyl halide.
Determine the phenoxide ion needed. In this case, the phenoxide ion would be derived from the aromatic ring with an oxygen atom attached, specifically a catechol derivative.
Identify the alkyl halide required. The alkyl halide should correspond to the alkyl chain that forms the ether linkage. Here, a 1,2-dibromoethane can be used to form the two ether linkages.
Propose the reaction: React catechol with 1,2-dibromoethane under basic conditions to form the desired aryl alkyl ether through a double Williamson ether synthesis.
Verified video answer for a similar problem:This video solution was recommended by our tutors as helpful for the problem above
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 formation.
Recommended video:
3:39
Metal Ion Catalysis Concept 1
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.
Recommended video:
Guided course
01:52How to name alkyl halides
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 typically proceeds via an SN2 mechanism, where the nucleophile attacks the electrophilic carbon of the alkyl halide, leading to the formation of an ether. Understanding this mechanism is essential for designing the synthesis of specific aryl alkyl ethers.
Recommended video:
Guided course
03:50The Mechanism of Williamson Ether Synthesis.
Related Videos
Related Practice