Search results
Results from the WOW.Com Content Network
The Williamson ether synthesis is an organic reaction, forming an ether from an organohalide and a deprotonated alcohol . This reaction was developed by Alexander Williamson in 1850. [ 2 ] Typically it involves the reaction of an alkoxide ion with a primary alkyl halide via an S N 2 reaction .
Bis-aryl ethers (such as diphenyl ether) cannot be synthesized through the Williamson ether synthesis, however, as aryl halides cannot undergo nucleophilic substitution. As such, an Ullmann condensation can be employed: an aryl halide is able to react with phenol (or its derivatives) to form a bis-aryl ether in the presence of a copper-based ...
Alexander Williamson. Williamson is credited for his research on the formation of unsymmetrical ethers by the interaction of an alkoxide with a haloalkane, known as the Williamson ether synthesis. He regarded ethers and alcohols as substances analogous to and built up on the same type as water, and he further introduced the water-type as a ...
Diphenyl ether is the organic ... a modification of the Williamson ether synthesis, ... pressure hydrolysis of chlorobenzene in the production of phenol. [7]
Alkyl aryl ethers can be synthesized through the Williamson ether synthesis by treating sodium phenolate with an alkyl halide: [5] C 6 H 5 ONa + CH 3 I → C 6 H 5 OCH 3 + NaI C 6 H 5 ONa + (CH 3 O) 2 SO 2 → C 6 H 5 OCH 3 + (CH 3 O)SO 3 Na
The acid-base behavior is complicated by homoassociation, reflecting the association of phenol and phenoxide. [6] Sodium phenoxide reacts with alkylating agents to afford alkyl phenyl ethers: [2] NaOC 6 H 5 + RBr → ROC 6 H 5 + NaBr. The conversion is an extension of the Williamson ether synthesis.
Alcohols alkylate to give ethers: + ′ ′ When the alkylating agent is an alkyl halide, the conversion is called the Williamson ether synthesis. Alcohols are also good alkylating agents in the presence of suitable acid catalysts.
Alkoxides, although generally not stable in protic solvents such as water, occur widely as intermediates in various reactions, including the Williamson ether synthesis. [1] [2] Transition metal alkoxides are widely used for coatings and as catalysts. [3] [4]