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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 .
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 ...
Thus, elimination by E2 limits the scope of the Williamson ether synthesis (an S N 2 reaction) to essentially only 1° haloalkanes; 2° haloalkanes generally do not give synthetically useful yields, while 3° haloalkanes fail completely. With strong base, 3° haloalkanes give elimination by E2.
15-Crown-5 is a crown ether with the formula (C 2 H 4 O) 5. It is a cyclic pentamer of ethylene oxide that forms complex with various cations , including sodium (Na + ) [ 2 ] and potassium (K + ); [ 3 ] however, it is complementary to Na + and thus has a higher selectivity for Na + ions.
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 ...
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.
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Morse's cited article describes the synthesis of paracetamol from 4-aminophenol and acetic acid. [6] Phenacetin may be synthesized as an example of the Williamson ether synthesis: ethyl iodide, paracetamol, and anhydrous potassium carbonate are heated in 2-butanone to give the crude product, which is recrystallized from water. [7]