Academic Calendar; College Documentation Week 1 (5/10-5/12) – Synthesis of Phenacetin, Williamson Ether Synthesis Reaction Set Up. This reaction consists of two steps. 34 x 10-3limiting reagent ethyl iodide0. Potassium carbonate is used to deprotonate the alcohol in the first step of the Williamson ether synthesis, and since NaOH is a stronger base than K 2 CO 3, the substitution will allow the reaction to proceed. In your report, don't forget to include a percent yield and comments in the conclusion section regarding potential sources of reduced yield/recovery. Williamson Ether Synthesis of Phenacetin 1 answer below » Draw and describe the mechanism of reaction (using arrows for electron pushing), is it SN1, SN2, E1 or E2? 2. Williamson Ether Synthesis of Phenacetin Essay Example Yield for recrystallized phenacetin = *100% = 38. 6mL 68. 973. 354 g151. Williamson Ether Synthesis Displacement of a halide by an alkoxide to form an ether is called Williamson Ether Synthesis. The procedure stated in Chem 2120 experiment 6 Williamson Ether Synthesis of Phenacetin laboratory manual was followed without any major changes. This makes either solvent alone unsuitable for recrystallization. Attach a microscale water-cooled condenser and, It is an analgesic (a medication that reduces or eliminates pain) and antipyretic (a medication that reduces fever) and is found in many over-the-counter drugs. Week 1 – Synthesis of Phenacetin, Williamson Ether Synthesis Reaction Set Up. The ether group was observed to be at 1241.58 and the amide group (N-H bond) was observed at 3280. Like aspirin, phenacetin was also an effective antipyretic, (fever reducer) which you should be able to pick out from the Greek name. Typically it involves the reaction of an alkoxide ion with a primary alkyl halide via an S N 2 reaction.This reaction is important in the history of organic chemistry because it helped prove the structure of ethers. Typically it involves the reaction of an alkoxide ion with a primary alkyl halide via an SN2 reaction. The reaction conditions must be rigorous, paying special attention to the anhydrous solvent. When applied to an unsymmetrical ether, as in this case, there are two different combinations of reactants are possible. OH N H O K. 2. What are the two components (reactants) of a Williamson-Ether Synthesis. The reaction occurs with inversion of configuration at chiral centers and can be limited by possible competing elimination reactions. The princi- pal starting material of this reaction is N-(4-hydroxyphenyl)-acetamide, a compound also known as acetaminophen. Conclusion The Williamson Ether synthesis of Phenacetin was successful in producing the Phenacetin. Conclusion The Williamson Ether synthesis of Phenacetin was successful in producing the Phenacetin. 12%. In a Williamson ether synthesis, you start by adding a base like methoxide to deprotonate a phenol so the deprotonated phenolate can act as a nucleophile. However, the Williamson synthesis may be carried out under milder conditions by employing a phase-transfer catalyst. This project was created with Explain Everything™ Interactive Whiteboard for iPad. or, if your crystals are adhered to the inside surface of the flask, by simply decanting the liquid into a beaker in your hood marked as waste. Do not remove waste is material containing iodoethane from a fume hood without a cover to contain the vapors. Lab 10: Williamson Ether Synthesis: Preparation of Phenacetin from Acetaminophen Erica Li (Lab Partner: Sankhya A.) Data and results Compound Amount used MW (g/mol) Moles Stoichiometry/Comments acetaminophen 0.354 g 151.16 2.34 x 10-3 limiting reagent K2CO3, KOH or an alkali metal are able to react with an alcohol to produce an alkoxide. Scheme 1. Of Bromoethane, Which Has A Density Of 1.47 G/mL. The Williamson Ether Synthesis A. In the usual Williamson synthesis of an ether, a primary alkyl halide reacts with an alkoside. The first step in this reaction is forming the conjugate base of the alcohol (called an alcoxide) by reacting the alcohol with sodium metal. Overall, phenacetin was prepared by the Williamson ether synthesis using acetaminophen and iodoethane in the presence of a base. In this experiment, you will synthesize phenacetin from 4-acetamidophenol and iodoethane via a facile Williamson ether synthesis, after which the solid product will be purified by recrystallization. 2. Because phenacetin could possibly be a carcinogen, it is important to wear gloves and goggles at all times when working with this substance. Acetaminophen is treated . What precautions should one use when working with phenacetin? View desktop site, can i have help answering 3, and 4? Phenacetin has been implicated in the renal failure and concomitant death of the rather remarkable Howard Hughes in 1976. CO. 3, CH. Lab 7 Williamson Ether Synthesis Objectives • Synthesize phenacetin by the formation of an ether functional group • Identify the product of the ether synthesis by various methods Background Williamson Ether Synthesis The formation of an ether by reacting an alkyl halide with the conjugate base of an alcohol or phenol is called a Williamson ether synthesis. Dec 14 2020 06:34 AM. Either of those groups can be added last in the synthesis of phenacetin. The phenolic hydrogen is sufficiently acidic to be deprotonated by … lodoethane is very toxic and it is both an allergen and a teratogen. Be sure to show the role of the base. Even a trace of water can spoil the reaction. How many molar equivalents of ethyl iodide did we use? © 2003-2021 Chegg Inc. All rights reserved. Reactions 1 and 2 below are two examples of this procedure. Using different alcohols and alkylating reagents, both symmetrical and asymmetrical ethers can be prepared by this reaction. The moles of base should be _____ the moles of the phenol. CH. b) Propanol for 2&butanone is not an appropriate substitution. 3. F MW[g/mol): m used (9): V used[mu): equiv: mpC: BPCA HAZARDSI NOTES From Page No. | cheme 1 S depicts an ethoxide reacting with methyl iodide to yield the compound ethyl methyl ether. The Williamson Ether Synthesis can specifically be found in sections 17-2 and 18-2. You will find that a final waterlethanol ratio of 5:1 to 10:1 by volume works well. That's the Williamson Ether Synthesis. a discrete layer on the bottom of the reaction vessel. The percent yield was 201.2& which was extremely high because the product was very wet and not set out long enough to dry. Figure 1: Acetaminophen to Phenacetin Reaction. williamson ether synthesis: preparation of phenacetin from acetaminophen partners: victor, zahra april 12, 2016 methods and background the goal of this lab is This reaction was developed by Alexander Williamson in 1850. What are two disadvantages of using more? The ether group was observed to be at 1241.58 and the amide group (N-H bond) was observed at 3280. Attach a total condenser to the 100 ml round bottom flask and set up a simple reflux using an electric heating mantle. Phenacetin synthesized from acetaminophen using potassium carbonate . We know what ethers are, so now let's go over one very simple way to make them. Solution for 2. The principal starting material for this reaction is an alcohol or a phenol, in this case acetaminophen. Want to see the step-by-step answer? See Answer. 3:37. This reaction forms hydrogen gas (H 2) as a biproduct, so if you perform this reaction take caution to keep all flame sources away during sodium addition. The phenolic hydrogen is sufficiently acidic to be deprotonated by potassium carbonate to allow the reaction to occur. when an alkyl halide and the conjugate base of an alcohol react to form an ether. Anamika Kalam 14,056 views. Obtain 360 mg of acetaminophen and transfer into a dry 25-mL round-bottom flask (RBF). Aspirin, the wonder drug, is an analgesic, anticoagulant, antiinflammatory, and antipyretic. © 2003-2021 Chegg Inc. All rights reserved. Start studying Experiment 6A: Williamson Ether Synthesis of Phenacetin. Williamson Ether Synthesis: In a Williamson ether synthesis, an alcohol is reacted with a base to give an alkoxide followed by addition of an alkyl halide. Be sure that the ground glass joints have a thin layer of silicone vacuum grease on them to prevent the joints from becoming fused, commonly called frozen, such that they become stuck and cannot be taken apart. The use of phenacetin has largely been replaced by the use of, you guessed it, 4-acetamidophenol, which is more commonly known by the name acetaminophen. Williamson ether synthesis - phenacetin - Duration: 3:37. check_circle Expert Answer. odotto phenacetin ETI CH, NO₂ Cio His Na 4-portamdoptent Na,Co, H2O PRECAUTIONS wote Always handle iodoethane in a fume hood with gloves using extreme caution. & Obtain the mass of an Extra-Strength Tylenol tablet. 1 Approved Answer. This reaction is important in the history of organic chemistry because it helped prove the … This reaction consists of two steps. Experiment 12 – The Williamson Ether Synthesis pg. Scheme 2 shows the reaction that will be performed i n this experiment . Return all equipment, including ring stands and heating mantles, to their storage places. | Acetaminophen was converted to phenacetin by reflux. This is Ch. Does the acetaminophen have to deprotonate to the phenolate before reacting? Below is the overall reaction for the synthesis OH K.CO This reaction is run in an organic solvent and refluwed for an hour to produce crude phenacetin, which is mostly pure. 3. The procedure stated in Chem 2120 experiment 6 Williamson Ether Synthesis of Phenacetin laboratory manual was followed without any major changes. Because of its widespread use during the war, a number of serious side effects were noticed. Williamson Ether Synthesis of Acetaminophen to Phenacetin with the use of 2-Butanone and Potassium The percent yield was 201.2& which was extremely high because the product was very wet and not set out long enough to dry. Add a stir bar, 0.28 g of K 2CO Experts are waiting 24/7 to provide step-by-step solutions in as fast as 30 minutes! how is an alkoxide formed. Consult the instructor if you suspect that you added too much ethanol, or if your product has "oiled out." Why is it important for the number of moles of methoxide ion to be equal to the number of moles of p-acetamidophenol? 4. The principal product phenacetin was once the active ingredient of several analgesic and antipyretic Excedrin medications but has been banned in the U.S. since 1931 due to serious health concerns. Solved: williamson ether synthesis i have this assignment chegg com lab report diigo groups three reactions are depicted below indicate which propose a mechanism for the synth 10 preparation of phenacetin from acetaminophen studocu lodoethane is sufficiently nonpolar to be immiscible with water, and the high MW of iodine makes it very dense, so it is visible as sodium Potassium carbonate works because it is basic enough to cause a reaction with the alcohol to synthesize an ether. The phenolic hydrogen is sufficiently acidic to be deprotonated by potassium carbonate to allow the reaction to occur. The phenoxide anion then displaces iodide via backside attack in a one-step process. Which are stronger--phenols or alcohols? OH WILLIAMSON ETHER SYNTHESIS INTRODUCTION Near the close of the nineteenth century, phenacetin, an unsymmetrical ether, was developed as an effective analgesic (pain reliever). However, the Williamson synthesis may be carried out under milder conditions by employing a phase-transfer catalyst. What would be the undesirable result of adding too much ethanol during the recrystallization? Lab 10: Williamson Ether Synthesis: Preparation of Phenacetin from Acetaminophen Erica Li (Lab Partner: Sankhya A.) Name: Paul Smith Chem 254-006 TA: Brooklynn Venteicher Experiment 2: Williamson Ether Synthesis Date: 2/2/21 Purpose The purpose of this lab is to perform a SN2 Williamson ether synthesis reaction using microwave synthesis and to isolate the product by extraction and purify it by recrystallization. A base of potassium carbonate was used in order to deprotonate the phenolic hydrogen which will allow for the reaction to occur. That's the Williamson Ether Synthesis. 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. The Williamson ether synthesis is a reaction that converts alcohols (R-OH) into ethers (R-O-R). P-Acetamidophenol :1.510 G Molar Mass: 151.17g/mol Bromoethane: 1.6 G Molar Mass: 108.97 G/mol Final Product: Phenacetin 0.904 G … The Williamson ether synthesis is an organic reaction, forming an ether from an organohalide and a deprotonated alcohol. & Williamson ether synthesis. This new species is called a phenoxide anion, and it serves as a more potent nucleophile than the starting alcohol. 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. Sodium carbonate (washing soda) is a stronger base than sodium bicarbonate (baking soda), and as such is injurious to the eyes. Privacy It was later banned because it caused cancer and kidney diseases. The synthesis of an ether via the Williamson-ether reaction . The synthesis of an ether via the Williamson-ether reaction . However, the presence of the base (potassium carbonate) causes the generation of the conjugate base of acetaminophen. * It may be practical for one tablet to be shared between two students. Calculate The Theoretical Yield For The Williamson Ether Synthesis From 0.151g. It's called beta-naphthol. Question: Calculate The Percent Yield Of Phenacetin Obtained From The Williamson Ether Synthesis. So that's beta-naphthol. Less base might result in the phenol _____. 1 12. The product will be analyzed by melting point, chemical tests, TLC, and IR and 1H NMR spectroscopy. Additionally, it is important not to inhale the substance. 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. ethyl iodide K CO, OH acetominophen phenacetin. Williamson ether synthesis mechanism and example Synthesis of phenacetin (common ochem lab reaction) The Williamson ether synthesis is a reaction that converts alcohols (R-OH) into ethers (R-O-R). After the 100 ml round bottom flask is cool enough to handle, add 25 ml of the purified water that has been thoroughly chilled in an ice bath. williamson ether synthesis: preparation of phenacetin from acetaminophen partners: victor, zahra april 12, 2016 methods and background the goal of this lab is This was also because the product was wet and gave … O CH. The Williamson Ether synthesis is the simplest and most popular method to prepare both symmetrical and unsymmetrical ethers. Rcsm Mahavidhalay | Home; About us. 12% For this experiment, acetaminophen was the limiting reagent; hence the crude product gave a yield of 76. However, a suitable mixture can easily be obtained by dissolving the phenacetin in a minimal amount of ethanol (using this to facilitate transfer into a weighed recrystallization vessel - a 50 mL Erlenmeyer flask or larger) and then adding water while maintaining a temperature near the boiling point (just put your recrystallization vessel on the hot plate) until a saturated solution is achieved with all solid remaining dissolved. In the Williamson ether systhesis the generation of an alkoxide is necessary for the reaction to occur. The melting point was 100C which was lower than the commercial melting point of 134C. Scheme 1. Why is sodium hydroxide not used instead of sodium carbonate? Subsequently, phenacetin was banned from common use in the United States by the Food and Drug Administration in 1983. No reaction via Williamson-Ether synthesis However will swing SN1 because of stable carbocation formed. O CH. The goal of this lab was to produce phenacetin by using Williamson ether synthesis by utilizing the starting components of acetaminophen, iodomethane and potassium carbonate as shown in figure one. Add a stir bar, 560 mg of K 2CO 3 (ground if necessary), 6.0 mL of acetonitrile (CH 3CN), and lastly 0.56 mL of ethyl iodide. Draw the electron arrow pushing mechanism for the formation of diethyl ether in the previous problem. Solved: williamson ether synthesis i have this assignment chegg com lab report diigo groups three reactions are depicted below indicate which propose a mechanism for the synth 10 preparation of phenacetin from acetaminophen studocu O NaOME + H3C Br + Br- CH3 CH3 HO H3C p-acetamidophenol bromoethane phenacetin Figure 2 Overall reaction to produce phenacetin using Williamson ether synthesis Phenacetin, p-ethoxyacetanilide, contains an ether group and an amide group para to each other on a benzene ring. Ether C from problem 26 can also be prepared from an alkene and an alcohol, draw these two. The reason potassium carbonate is used is to be able to deprotonate the phenols hydrogen. Phenacetin will then be subjected to an electrophilic aromatic substitution (EArS) reaction to introduce a bromine into the ring at a yet to be determined position. This reaction is a nucleophilic substitution of an alkali alkoxide on an alkylating reagent to form an ether and an inorganic salt and is generally referred to as the Williamson ether synthesis. Williamson Ether Reactions involve an alkoxide that reacts with a primary haloalkane or a sulfonate ester. alkoxide and alkyl halide. ABSTRACT In this experiment the experimenter performed a Williamson ether synthesis, which forms ether from an alkyl halide and an alcohol. Isolate the crude product via vacuum filtration in the hood! Introduction It would be beneficial if you review the chapter on substitution reactions in your textbook prior to lab. The synthesis of phenacetin from acetaminophen will be accomplished via the Williamsonether - synthesis. Tylenol) into phenacetin to exemplify a Williamson ether synthesis. Scheme 2. Two examples of the Williamson ether synthesis and its mechanism - an easy but useful reaction. Data and results CompoundAmount used MW (g/mol) Moles Stoichiometry/Comments acetaminophen0. Lab 8: Williamson Ether Synthesis of Phenacetin Ethan Gorman, Kyle; 8/12/16 Abstract This experiment is designed to illustrate the reaction and mechanism of an SN2 reaction known as a Williamson Ether Synthesis. In the usual Williamson synthesis of an ether, a primary alkyl halide reacts with an alkoside. In a Williamson Ether Synthesis of Phenacetin When the reaction is complete, water will be added to the reaction mixture. Abstract. The phenol of acetaminophen is a relatively poor nucleophile. Grind to a fine powder and transfer 0.22 g of Tylenol into a dry 15-mL round-bottom flask (RBF). Terms Figure 1 Carbonate. The reaction occurs with inversion of configuration at chiral centers and can be limited by possible competing … 3. Of P-acetamidophenol And 0.12 ML. Call Us-+91-9457657942, +91-9917344428. Phenacetin is an older analgesic first used for pain relief, like Acetaminophen, and to reduce fevers. Privacy Check out a sample Q&A here. Want to see this answer and more? 2&Butanone is the solvent, and since the second step of the W.E. 05 3. The rate of the reaction depends on the concentration of both the phenoxide anion and the iodoethane; so the reaction is described as S 2 (substitution nucleophilic bimolecular). The main route is oxidative de-ethylation, giving rise to n-acetyl-para-aminophenol, which is excreted in the urine as the sulphate or as the glucuronide. * See Answer *Response times vary by subject and question complexity. The principal product is an ether, in this case phenacetin (see Figure 1 below). Draw the complete mechanism of the reaction. Subsequent recrystallization (especially slow recrystallization) will increase the purity. The basic reaction is an alcohol (as an alkoxide) with an alkyl halide to synthesize ether. The Williamson ether synthesis, alkoxymercuration of alkenes, and also the acid catalyzed substitution. Harvest the crystals by decanting (if they have adhered to the glass) or by vacuum filtration (if a significant amount are floating freely). Overall, phenacetin was prepared by the Williamson ether synthesis using acetaminophen and iodoethane in the presence of a base. 06% while the recrystallized product gave a yield of 38. Williamson Ether Synthesis: In a Williamson ether synthesis, an alcohol is reacted with a base to give an alkoxide followed by addition of an alkyl halide. CLEANUP Filtrates and washings containing ethyl iodide must go in the marked waste container. Metabolic pathways for phenacetin involve de-ethylation, N-deacetylation and ring hydroxylation. OH WILLIAMSON ETHER SYNTHESIS INTRODUCTION Near the close of the nineteenth century, phenacetin, an unsymmetrical ether, was developed as an effective analgesic (pain reliever). TABLE OF REAGENTS: C TYPE: (mol) 0.0198 168-172 387 - NAME(S) (tyleno) 4-acetamidophenol Storting material ACETAMINOPHEN 151.16 3.0 LOOF LR] 1.8 155.47 1.126 REAGENT -(11.97 71.5-73.3 See Safety pg. p-Acetamidophenol :1.510 g molar mass: 151.17g/mol Bromoethane: 1.6 … The melting point was 100C which was lower than the commercial melting point of 134C. 162. phenols. Place them in a tared container, labeled with your name and the identity of the substance, in the bottom drawer to dry over the week before you record a final mass. While the solution is refluxing, put a wash bottle with purified water in an ice bath to cool for later use. So if I start with a molecule over here on the left, and it's kind of an interesting-looking molecule. Like aspirin, phenacetin was also an effective antipyretic, (fever reducer) which you should be able to pick out from the Greek name. Terms During World War II, phenacetin was commonly distributed to military personnel as A.P.C., which stood for aspirin, phenacetin, and caffeine. What is a williamson ether synthesis? Handcrafted S1 • E1 How To Butcher An Entire Cow: Every Cut Of Meat Explained | Bon Appetit - … Among these side effects were renal disease and certain unusual cancers of the urinary tract. 75 x 10-31. 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 Williamson Ether Synthesis. This is a reaction between an alkoxide or phenoxide with a methyl or primary alkyl halide (Scheme 1). (a) (b) (c) (d) (e) Q18.2.3. Table 1 displays the reaction table of the compounds used. Reflux until the iodoethane is nearly all consumed (no more than one hour) as judged by visual inspection. Rani J answered on December 16, 2020. In this experiment, (±)-3-chloro-1,2-propane-diol will be allowed to react with the conjugate base of Guaicol (2-methoxyphenol) via an S N2 reaction to provide guaifenesin as a racemic mixture. I, DMSO ethoxide ethyl methyl ether. Acetaminophen itself is a poor nucleophile. Let's look at an example of the Williamson ether synthesis. Williamson Ether Synthesis of Phenacetin Purpose To synthesize phenacetin through the Williamson ether synthesis method Theory and Background The process of displacing a halide (R-X where X = Cl, Br, 1) by an alkoxide anion (R-0-) to form an ether is called a Williamson ether synthesis. Calculate the percent yield of phenacetin obtained from the Williamson ether synthesis. Q18.2.4. View desktop site, Williamson Ether Synthesis of Phenacetin Purpose To synthesize phenacetin through the Williamson ether synthesis method Theory and Background The process of displacing a halide (R-X where X = Cl, Br, 1) by an alkoxide anion (R-0-) to form an ether is called a Williamson ether synthesis. This reaction is a nucleophilic substitution of an alkali alkoxide on an alkylating reagent to form an ether and an inorganic salt and is generally referred to as the Williamson ether synthesis. Two layers will form:… In this experiment, (±)-3-chloro-1,2-propane-diol will be allowed to react with the conjugate base of Guaicol (2-methoxyphenol) via an S N2 reaction to provide guaifenesin as a racemic mixture. Discovered in 1850, the Williamson ether synthesis is still today one of the most …

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