Editing Williamson ether synthesis (section)

{{Short description|Method for preparing ethers}}
{{Reactionbox
| Name = Williamson Ether Synthesis
| Type = Coupling reaction
| NamedAfter = [[Alexander William Williamson]]
| Section3 = {{Reactionbox Identifiers
   | OrganicChemistryNamed = williamson-synthesis
   | RSC_ontology_id = 0000090
 }}
}}
[[Image:WilliamsonEtherSynthPhenoxyaceticacid.svg|thumb|400px|right|Ether synthesis by reaction of [[salicylaldehyde]] with [[chloroacetic acid]] and [[sodium hydroxide]]<ref>{{OrgSynth|collvol = 5|collvolpages = 251|year = 1966|volume = 46|pages = 28|prep = CV5P0251|title = Coumarone|doi = 10.15227/orgsyn.046.0028|first1 = Albert W.|last1 = Burgstahler|first2 = Leonard R.|last2 = Worden}}</ref>]]The '''Williamson ether synthesis''' is an [[organic reaction]],  forming an [[ether]] from an [[organohalide]] and a deprotonated alcohol ([[alkoxide]]). This reaction was developed by [[Alexander William Williamson|Alexander Williamson]] in 1850.<ref>{{cite journal|first = Alexander|last = Williamson|author-link = Alexander William Williamson|title = Theory of Ætherification|journal = [[Philosophical Magazine]]|volume = 37|issue = 251|pages = 350–356|year = 1850|doi=10.1080/14786445008646627|url = https://zenodo.org/record/1431121}} ([http://web.lemoyne.edu/~giunta/williamson.html Link to excerpt.])</ref> Typically it involves the reaction of an [[alkoxide ion]] with a primary alkyl [[halide]] via an [[SN2 reaction|S<sub>N</sub>2 reaction]]. This reaction is important in the history of organic chemistry because it helped prove the structure of [[ether]]s.

The general reaction mechanism is as follows:<ref name = morrison>{{cite book|last1=Boyd|first1 = Robert Neilson|last2 = Morrison|first2 = Robert Thornton|title = Organic Chemistry|publisher = [[Prentice Hall]]|location = Englewood Cliffs, N.J.|edition = 6th|year = 1992|pages = 241–242|isbn = 9780136436690}}</ref>

[[Image:Williamson-ether-synthesis-2D.svg|400px|Williamson ether synthesis mechanism]]

An example is the reaction of [[sodium ethoxide]] with [[chloroethane]] to form [[diethyl ether]] and sodium chloride:

:{{chem2|C2H5Cl + C2H5ONa -> C2H5OC2H5 + NaCl }}