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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 .
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.
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 ...
Williamson ether synthesis; R−Br + OR' − → R−OR' + Br − (S N 2) The Wenker synthesis, a ring-closing reaction of aminoalcohols. The Finkelstein reaction, a halide exchange reaction. Phosphorus nucleophiles appear in the Perkow reaction and the Michaelis–Arbuzov reaction. The Kolbe nitrile synthesis, the reaction of alkyl halides ...
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.
18-Crown-6 can be synthesized by the Williamson ether synthesis using potassium ion as the template cation. Structure of nickel-aquo nitrate complex of the ligand derived from the templated trimerization of 2-aminobenzaldehyde. [5] The phosphorus analogue of an aza crown can be prepared by a template reaction. [6]
The leaving group X in the organic partner is usually a halide, although triflate, tosylate, pivalate esters, and other pseudohalides have been used. [15] Chloride is an ideal group due to the low cost of organochlorine compounds. Frequently, however, C–Cl bonds are too inert, and bromide or iodide leaving groups are required for acceptable ...
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.