Dry the etoac layer with na 2so 4, filter the solution, and concentrate the. View lab report orgo 2 lab report the williamson ether synthesis. The melting point was 100c which was lower than the commercial melting point of 4c. Nucleophilic displacement formation of an ether by an sn. Conclusion the williamson ether synthesis of phenacetin was successful in producing the phenacetin. The first step in this reaction is forming the conjugate base of the alcohol called an alcoxide by reacting the alcohol with sodium metal. Why is water added after reflux to create a cloudy solution. Chemistry 3719l week 7 williamson ether synthesis on an. Week 1 synthesis of phenacetin, williamson ether synthesis reaction set up. In this williamson ether synthesis, potassium tert butoxide is alkylated by methyl iodide to form methyl ter tbutyl ether mtbe. 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.
However, the williamson synthesis may be carried out under milder conditions by employing a phasetransfer catalyst. Why must the solution be refluxed for an hour to gain the desired product. This method cannot be used with tertiary alkyl halides, because the competing elimination reaction predominates. Conclusion the williamson ether synthesis of phenacetin.
In the usual williamson synthesis of an ether, a primary alkyl halide reacts with an alkoside. Request pdf williamson ether synthesis ether from the alkylation of alkoxides by alkyl halides. Common names of symmetrical ethers add the suffix ether after naming the groups on either side of the oxygen. 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. Today you are treating bromotriphenylmethane with ethanol to synthesize ethoxytriphenylmethane. Jul 19, 2011 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. The synthesis of phenacetin from acetaminophen will be accomplished via the williamson ether synthesis. Journal of chemical education 2014, 91 10, 17201724. The williamson ether synthesis, alkoxymercuration of alkenes, and also the acid catalyzed substitution. Sn2 pathway is required for the synthesis this reaction is useful only when the alkyl halide is primary or secondary.
The synthesis of phenacetin from acetaminophen will be accomplished via the williamsonether synthesis. Exp 12 williamson ether synth get started with community. The elimination reaction occurs because the rearward approach that is needed for an s n 2 mechanism is impossible due. In an sn2 reaction mechanism there is a backside attack of an electrophile by a. Ether c from problem 26 can also be prepared from an alkene and an alcohol, draw these two. Chem m52lbh52lb experiment 2 page 1 experiment 1 williamson ether synthesis of guaifenesin and isolation of an expectorant from cough tablets reading assignment. The scientist who developed this reaction, alexander w. Williamson ether synthesis preparation of methyl p. An s n 2 reaction in which an alkoxide is alkylated by a methyl or primary alkyl halide to form an ether. Williamson ether synthesis request pdf researchgate. The williamson ether synthesis is an organic reaction, forming an ether from an alkyl halide and an alcohol.
Week 1 510512 synthesis of phenacetin, williamson ether synthesis reaction set up. Basai lab 10 williamson ether synthesis chem 233 uic. Typically it involves the reaction of an alkoxide ion with a primary alkyl halide via an s n 2 reaction. Many new bonds formed make use of this versatile reaction pathway. In williamson ether synthesis, the alkoxide ion reacts with primary alkyl halides and tosylates to form ethers. If the halides are sterically demanding and there are accessible protons in the. Pedagogical comparison of five reactions performed under microwave heating in multimode versus monomode ovens. Synthesis of alkyl aryl ethers by catalytic williamson ether. Because the reaction occurs by an sn2 mechanism, and as the carboxylate is.
Aside from the standard lab report items, your report should include the following items in the. Williamson ether synthesis of guaifenesin to 25 ml roundbottom flask containing a magnetic stir bar, dissolve guaiacol 2. The synthesis of phenacetin from acetaminophen introduction. Williamson ether synthesis of an expectorant guaifenesin and. Chemistry 381 williamson ether synthesis 1 williamson. Other articles where williamson ether synthesis is discussed. The mechanism begins with the base abstracting the proton from the alcohol to form an alkoxide intermediate. It uses an alkoxide ion to attack an alkyl halide, substituting the alkoxy. The williamson ether synthesis is an sn2 reaction in which an alkoxide ion is a. The reaction conditions must be rigorous, paying special attention to the anhydrous solvent. 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 williamson ether synthesis is an organic reaction, forming an ether from an organohalide and a deprotonated alcohol. This was also because the product was wet and gave an incorrect reading as well as. In the previous laboratory experiment a variety of substitution reactions both sn1 and sn2. Use a small amount of etoac to rinse out the reaction vial as necessary. In todays experiment, the williamson ether synthesis is another named reaction, developed by dr. Let us find you another lab report on topic williamson ether synthesis preparation of.
Synthesis of ethyl nbutyl ether chem undergrad courses. In this experiment, guaifenesin will be simultaneously synthesized in the laboratory and isolated from a guai aid cough tablet. Williamson ether synthesis usually takes place as an s n 2 reaction of a primary alkyl halide with an alkoxide ion. Williamson ether synthesis mechanism organic chemistry. Generally the williamson synthesis utilizes a phenoxide or alkoxide nucleophile oxygen is small, and has a full negative charge acting on a usually primary alkyl halide cl, br or i leaving groups substrate. Preparation of phenacetin from acetaminophen partners. Williamson ether synthesis an overview sciencedirect. Despite its simplicity and wide applicability, this method fails to yield desirable products whenever a parent alcohol is treated with a secondary or tertiary halide. Williamson ether synthesis of an expectorant guaifenesin. Apr 03, 2015 williamson ether synthesis organic chemistry lab lecture. The same material will also be isolated from over the counter tablets via a simple extraction. Add a stir bar, 560 mg of k 2co 3 ground if necessary, 6.
David rawn, in organic chemistry study guide, 2015. The reaction occurs with inversion of configuration at chiral centers and can be limited by possible competing elimination. Inorganic chemistry organic chemistry alkyl halide ether synthesis williamson ether these keywords were added by machine and not by the authors. The williamson ether synthesis master organic chemistry. Although the williamson ether synthesis is a general method for the laboratory production of ethers, there are some limitations to its use. An ether synthesis using phase transfer catalysis journal. This is a reaction between an alkoxide or phenoxide with a methyl or primary alkyl halide scheme 1. Williamson ether synthesis organic chemistry lab lecture. Williamson ether synthesis is the most widely and simplest method in ether synthesis. Williamson synthesis definition of williamson synthesis.
Synthesis of alkyl aryl ethers by catalytic williamson. The williamson ether synthesis is the easiest, and perhaps the fastest, way to create ethers. Chemistry 381 williamson ether synthesis 1 williamson ether. Draw the complete electron pushing mechanism for reaction that you are performing. Trick to write the product of williamsons ether synthesis. Pdf zinccatalyzed williamson ether synthesis in the absence of. The williamson ether synthesis is a reaction that converts alcohols roh into ethers ror. Victor, zahra april 12, 2016 methods and background the goal of this lab is to use the williamson ether synthesis and prepare a phenacetin. Williamson ether synthesis report chem 233 uic studocu. The structure of ethers was proved due to this chemical reaction. In this lab, the williamson ether synthesis was used to convert acetaminophen to phenacetin. Likewise, the grignard reaction was similarly named after its discoverer. Pdf zinccatalyzed williamson ether synthesis in the.
This method is suitable for the preparation of a wide variety of unsymmetric ethers. Obtain the mass of an extrastrength tylenol tablet. 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 preparation of phenacetin from. The nucleophilic substitution of halides with alkoxides leads to the desired products. With the theoretical and experimental yield obtained, the percent yield was calculated and found to be 36. Williamson ether synthesis is a reaction that uses deprotonated alcohol and an organohalide. Williamson who was a professor at university college in london in the latter part of the 1800s. 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. Twostep synthesis of an ether from an alcohol, a strong base is a dded to deprotonate the alcohol, which then attacks an alkyl halide. 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. Grab the best paper we use cookies to create the best experience for you. Williamson ether synthesis is a reaction that uses deprotonated alcohol and an organohalide to form an ether. The name of the reaction was coined after alexander william williamson developed it in 1850.
Organic chemistry laboratory i chem 233 uploaded by. The phenolic hydrogen is sufficiently acidic to be deprotonated by potassium carbonate to allow. Williamson, was a professor at university college in london in the latter part of the 1800s. Basai lab 10 williamson ether synthesis chem 233 uic studocu. Illustrated glossary of organic chemistry williamson. Conclusion the williamson ether synthesis of phenacetin was. Let us write or edit the lab report on your topic williamson ether synthesis preparation of methyl pethylphenyl ether with a personal 20% discount. The alkoxide then attacks the alkyl halide in a nucleophilic substitution reaction sn 2. The williamson ether synthesis is an organic reaction, forming an ether from an organohalide. 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. Alexander william williamson 18241904 discovered this reaction in 1850 at university college, london. This process is experimental and the keywords may be updated as the learning algorithm improves.
Williamson ether synthesis usually takes place as an sn2 reaction of a primary alkyl halide with an alkoxide ion. Cyclic ethers naming these heterocyclic compounds depends on the ring size and number of oxygens. Williamson ether synthesis mechanism, uses, limitations. Dielsalder cycloaddition, wittig salt formation, e2 dehydrohalogenation to form an alkyne, williamson ether synthesis, and fischer esterification. Guaifenesin tablets warning causes skin and eye irritation. Lab 10 lab report lab 10 williamson ether synthesis. Williamson ether synthesis on an acetamidophenol prelab reading from zubrick. Depicted in scheme 1 is ethoxide reacting with methyl iodide to yield the compound ethyl methyl ether. Jul 14, 2015 the williamson ether synthesis, alkoxymercuration of alkenes, and also the acid catalyzed substitution. Cyclic ethers naming these heterocyclic compounds depends on the ring size and. July 25, 2016 methods and background the purpose of this experiment is to prepare phenacetin by williamson ether synthesis of acetaminophen using iodoethane and potassium carbonate. The reaction occurs with inversion of configuration at chiral centers and can be limited by possible competing elimination reactions. The williamson ether synthesis proceeds via an s n 2 mechanism, in which an alkoxide ion displaces a halogen ion.
Pdf a zinccatalyzed williamson ether synthesis is described with microwave heating in. The williamson reaction is widely used in both laboratory and industrial synthesis, and remains the simplest and most popular method of preparing ethers. It may be practical for one tablet to be shared between two students. Draw the electron arrow pushing mechanism for the formation of diethyl ether in the previous problem. What is the name of the mechanism that this undergoes. Hanna thomson lab 10 erica tuesday 8am williamson ether synthesis. Williamson ether synthesis an overview sciencedirect topics. Iupac names ethers by taking the more complex alkyl group as the root name, and naming the remaining part as an alkoxy group. Preparation of phenacetin from acetaminophen erica li lab partner.
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. Obtain 360 mg of acetaminophen and transfer into a dry 25ml roundbottom flask rbf. 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. 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. Nucleophilic displacement formation of an ether by an sn2 reaction the williamsonether synthesis bond formation by use of an sn2 reaction is very important for organic and biological synthesis. Chemistry 381 williamson ether synthesis 3 into a 250 ml separatory funnel containing etoac 100 ml. Since the alkoxide ion is a strong base, their use is limited to primary unhindered alkylating agents. This reaction was developed by alexander williamson in 1850. A zinccatalyzed williamson ether synthesis is described with microwave heating in the presence of dmf or stirring in an oilbath using thf as solvent and in the absence of base. Otherwise, elimination competes strongly with the nucleophilic substitution for the reactant molecules. Williamson ether synthesis lab simplest way to synthesize an ether is to have an alkoxide react with a primary haloalkane or a sulfonate ester under typical sn2 conditions. Alkoxides consist of the conjugate base of an alcohol and are comprised of an r group bonded to an oxygen atom.