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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.
Aliphatic hypoiodites can be synthesized through a variant on the Williamson ether synthesis: an alkoxide reacts with iodine monochloride, releasing the alkyl hypoiodite and chloride. [11] Alternatively, the Meyer-Hartmann reaction applies: a silver alkoxide reacts with elemental iodine to give the hypoiodite and silver iodide.
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 ...
The primary alcohols have general formulas RCH 2 OH. The simplest primary alcohol is methanol (CH 3 OH), for which R = H, and the next is ethanol, for which R = CH 3, the methyl group. Secondary alcohols are those of the form RR'CHOH, the simplest of which is 2-propanol (R = R' = CH 3). For the tertiary alcohols, the general form is RR'R"COH.
Primary alkyl halides work best, as secondary and tertiary alkyl halides prefer the E2 elimination product. [6] This ether synthesis removes the risk of self-condensation, and yields can be as high as 95% in the laboratory. A Williamson ether synthesis between p-ethylphenolate and bromoethane to form 4-ethyl-1-ethoxybenzene.
For example, the synthesis of macrocidin A, a fungal metabolite, involves an intramolecular ring closing step via an S N 2 reaction with a phenoxide group as the nucleophile and a halide as the leaving group, forming an ether. [2] Reactions such as this, with an alkoxide as the nucleophile, are known as the Williamson ether synthesis.
Stages in the oxidation of primary alcohols to carboxylic acids via aldehydes and aldehyde hydrates. Almost all industrial scale oxidations use oxygen or air as the oxidant. [2] Through a variety of mechanisms, the removal of a hydride equivalent converts a primary or secondary alcohol to an aldehyde or ketone, respectively.
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.