Williamson ether synthesis mechanism organic chemistry. The special problems encountered in naming cyclic ethers are dis cussed in section 15 1 1a. A multioutcome experiment for the williamson ether synthesis. Williamson ether synthesis an overview sciencedirect. In addition to the expected ether product cisdimethyl 2,3diphenyloxirane2,3dicarboxylate, methyl phenylacetate and methyl phenylglyoxylate were obtained. This process is experimental and the keywords may be updated as the learning algorithm improves.
This reaction is important in the history of organic chemistry because it helped prove the structure of ethers. I tried nah method, k2co3 method for the preparation. This starting material was reacted with 4ml of a 5. With a strong base like ethoxide ion, the major reaction is elimination e2 rather than substitution s n 2, resulting in a poor yield of the desired ether. In this williamson ether synthesis, potassium tert butoxide is alkylated by methyl iodide to form methyl ter tbutyl ether mtbe. Since the reaction is s n 2, the halide should be methyl or primary. In equations like this, the reagents over the arrow are added in a sequence of separate steps, not all at once. Synthesis of alkyl aryl ethers by catalytic williamson. Many of the reactions used in organic chemistry are described as being named reactions.
Synthesize ethers through the williamson ether synthesis. The williamson ether synthesis is a reaction that converts alcohols roh into ethers ror. Hindered dialkyl ether synthesis with electrogenerated. Williamson ether synthesis is a reaction that uses deprotonated alcohol and an organohalide.
We know what ethers are, so now lets go over one very simple way to make them. Williamson ether synthesis with phenols at a tertiary stereogenic. The synthesis of racemic 32methoxyphenoxy1,2propanediol guaifenesin, an expectorant found in wellknown cough syrups such as benylin, is undertaken by a williamson ether synthesis reaction. The williamson ether synthesis is an organic reaction used to convert an alcohol and an alkyl halide to an ether using a base such as naoh. The purpose of this lab is to employ the method of williamson ether synthesis in order to produce an ether from the combination of an alkyl halide and an alcohol. In contrast, the bromine is attached to a primary carbon in this reaction. The name of the reaction was coined after alexander william williamson developed it in 1850. Several examples of the williamson ether synthesis are given in the following equations. I am trying to prepare ether from 2phenylethyl iodide with benzyl alcohol by williamson ether synthesis. Optimization of microwaveenhanced williamson ether synthesis of. Consider the williamson ether synthesis between 2naphthol and 1bromobutane in strong base.
K2o were ether and potash, the resulting mixture should consist of ether c4h10o and oxide of methyl c2h6o. Then the alkoxide negative alcohol attacks an alkyl halide in an s n 2 reaction so this problem is really asking, which step of conditions is most favorable for an s n 2 reaction recall that s n 2 reactions compete with e2. Williamson ether synthesis reaction of metal alkoxides with alkyl halides or tosylates to give ethers. The procedure stated in chem 2120 experiment 6 williamson ether synthesis of phenacetin laboratory manual was followed without any major changes. The williamson ether synthesis takes place in two steps. The williamson ether synthesis is an organic reaction, forming an ether from an organohalide. Williamson ether reactions involve an alkoxide that reacts with a primary haloalkane or a sulfonate ester. Williamson ether synthesis williamson ether synthesis. So if i start with a molecule over here on the left, and its kind of an interestinglooking molecule. Pdf williamson ether synthesis nguyen hieu academia. Williamson ether synthesis university of calgary in alberta.
Conventional means of ether synthesis are timeconsuming and. What marine recruits go through in boot camp earning the title. Williamson synthesis definition of williamson synthesis. The reaction occurs with inversion of configuration at chiral centers and can be limited by possible competing elimination. Today you are treating bromotriphenylmethane with ethanol to synthesize ethoxytriphenylmethane. Draw the electron arrow pushing mechanism for the formation of diethyl ether in the previous problem. The alcohol was converted into a nucleophile using a base and reacted via a s n 2 mechanism with an alkyl halide. Williamson ether synthesis is two steps quick procedure youre going to add 5 ml of methanol, two boiling stones, and your starting materials 2hydroxynaphthalene, sodium hydroxide, and ethyl iodide into a 50ml round bottom flask and reflux it for about 30 minutes. Inorganic chemistry organic chemistry alkyl halide ether synthesis williamson ether these keywords were added by machine and not by the authors. This video is a brief overview of the williamson ether sythesis. The most versatile method for making ethers is the williamson ether synthesis, named for english chemist alexander williamson, who devised the method in the 19th century. The detector sensitivity was determined for all the products and reactants on a pye 204 chromatograph using a 5.
Other articles where williamson ether synthesis is discussed. Calculate the number of moles of guaiacol and the number of moles of 3chloro1,2propanediol that were used in the reaction. It has been developed to a complete theory including continuum dynamics, cosmology, and links with elec. First an alcohol is deprotonated to form a strong nucleophile ro, this step isnt shown in the image below. Metalfree syntheses of aryl ethers from alcohols include the williamson ether synthesis,4 snar reactions with electrondeficient aryl fluorides,5 and reactions. One scalar model, starting from a semiheuristic view of gravity as a pressure force, is detailed. Data and results compound amount used mw gmol moles stoichiometrycomments acetaminophen 0.
Williamson ether synthesis lab chem 2 spring 20 lab. The first step in this reaction is forming the conjugate base of the alcohol called an alcoxide by reacting the alcohol with sodium metal. Ethers are a class of organic compounds that contain an ether groupan oxygen atom connected to two alkyl or aryl groups. Lets look at an example of the williamson ether synthesis. Hey, i opened a post two days ago asking for help searching for a procedure on the next step of my synthesis, but it seems that i got stuck on the step before. Alexander william williamson 18241904 discovered this reaction in 1850 at university college, london. View lab report williamson ether synthesis lab from chem 2 at denison university.
The mechanism begins with the base abstracting the proton from the alcohol to form an alkoxide intermediate. The williamson ether synthesis is an s n 2 reaction in which an alkoxide ion is a nucleophile that displaces a halide ion from an alkyl halide to give an ether. The transfer properties of the ionic species involved in the williamson ether synthesis by phase. The general method for the synthesis of ether is williamson ether synthesis, involves nucleophilic displacement of a halide ion or other good leaving group by an alkoxide ion. Sy nth e icu of b ad l m r o w ch 3chch 3 ch 3ch 2o this reaction has the bromine attached to a secondary carbon. The alkoxide then attacks the alkyl halide in a nucleophilic substitution reaction sn 2. Abstract the enantioselective formation of aryloxyketo esters is described for the first time. These attempts to produce a green version of williamson ether synthesis have been based on the use of weak alkylating agents such as carboxylic acid esters at relatively high temperatures.
Dubois the dow chemical company, new england laboratory, box 400, wayland, mass. Microwaves reduce reaction time by directly transferring heat to the interior of the. The williamson ether synthesis formally forms an ether from an alkoxide, and an hydrocarbyl halidethe alkoxide is often added as the parent alcohol in the presence of stoichiometric or excess metal hydroxide, i. Now this substance was actually obtained, and neither ether nor oxide of methyl. The williamson ether synthesis, alkoxymercuration of alkenes, and also the acid catalyzed substitution. Hindered ether 1, a key intermediate for the synthesis of an aurora. Before turning to the specific chemistry of alcohols and ethers, we re mind you that the naming of these compounds is summarized in sections 72 and 73. Typically it involves the reaction of an alkoxide ion with a primary alkyl halide via an s n 2 reaction. For almost 70 years, there have been attempts to advance the williamson ether synthesis process to allow the use of lowcost, noncarcinogenic, weak alkylating agents and avoid salt production. Williamson ether synthesis reaction mechanism duration. An improved williamson ether synthesis using phase. Williamson ether synthesis of phenacetin essay sample. Illustrated glossary of organic chemistry williamson.
R3hba can be esterified with butanol or ethanol or converted to ethers by reaction with alcohols using the catalytic williamson ether synthesis fuhrmann and talbiersky, 2005 or dehydrated to. The williamson ether synthesis is the easiest, and perhaps the fastest, way to create ethers. Williamson synthesis is a reaction forming an ether by reaction of organic halide and deprotonated alcohol. David rawn, in organic chemistry study guide, 2015. The fischer esterification reaction was a named reaction, referring to emil. Hindered dialkyl ether synthesis via electrogenerated. The williamson ether synthesis is one of several organic chemistry reactions referred to as named reactions, which employ the name of the scientist who developed it. The williamson ether synthesis can specifically be found in sections 172 and 182. The williamson ether synthesis is an organic reaction, forming an ether from an organohalide and a deprotonated alcohol. Procedure the procedure stated in chem 2120 experiment 6 williamson ether synthesis of phenacetin laboratory manual was followed without any major changes. Williamson synthesis definition is a method of synthesizing ethers by reaction of a sodium alkoxide with a halogen derivative of a hydrocarbon as an alkyl halide.
Alkoxides consist of the conjugate base of an alcohol and are comprised of an r group bonded to an oxygen atom. Ether c from problem 26 can also be prepared from an alkene and an alcohol, draw these two. Williamson ether synthesis jacob jones april 16, 2015 introduction. Symmetrical ethers can be prepared by treating the corresponding alcohol with a strong acid limitations. An s n 2 reaction in which an alkoxide is alkylated by a methyl or primary alkyl halide to form an ether. Hindered dialkyl ether synthesis with electrogenerated carbocations. Data and results compoundamount used mw gmol moles stoichiometrycomments acetaminophen0. Microwaves are a prominent tool in organic synthesis. The williamson ether synthesis chemistry 2 spring 20 background the williamson ether synthesis yields an ether by the reaction of an alkyl halide with an alkoxide or alcohol. Williamson ether synthesis mechanism, uses, limitations. Optimization of microwaveenhanced williamson ether.
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