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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 .
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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 ...
As a consequence, alkoxides (and hydroxide) are powerful bases and nucleophiles (e.g., for the Williamson ether synthesis) in this solvent. In particular, RO − or HO − in DMSO can be used to generate significant equilibrium concentrations of acetylide ions through the deprotonation of alkynes (see Favorskii reaction). [36] [37]
A 1,2-Wittig rearrangement is a categorization of chemical reactions in organic chemistry, and consists of a 1,2-rearrangement of an ether with an alkyllithium compound. [1] The reaction is named for Nobel Prize winning chemist Georg Wittig. [2] [3] The intermediate is an alkoxy lithium salt, and the final product an alcohol.
Figure 6:Reaction Coordinate Diagrams showing reactions with 0, 1 and 2 intermediates: The double-headed arrow shows the first, second and third step in each reaction coordinate diagram. In all three of these reactions the first step is the slow step because the activation energy from the reactants to the transition state is the highest.
The reaction is most successful when R is aliphatic and saturated, and typically performed with a silyl chloride reactant to trap the product as a disilyl enediol ether. The reaction is performed in aprotic solvents with a high boiling point, such as benzene and toluene, in an oxygen-free atmosphere (as even traces of oxygen interfere with the ...
Elemicin has been synthesized from syringol and allyl bromide using Williamson ether synthesis and Claisen rearrangement. [5] [6] The electrophilic aromatic substitution entering the para-position was made possible by secondary Cope rearrangement. [7] This is due to syringol's allyl aromatic ether being blocked by ethers in both ortho-positions.