use software to make 1H-NMR and 13C-NMR from the data in the paper and make a table with the following data1H: chemical shift , multiplet structure, integration, assignment 13C: chemical shift IntroductionEthers can be produced from two alcohols. However, unless you want to have symmetrical ethers(i.e., diethyl ether derived from ethanol), ether synthesis from different alcohols in the samereaction mixture will produce a variety of products. To produce an unsymmetrical ether(i.e., tert.-butyl methyl ether, MTBE), one component must be an alkyl halide, and the othercomponent is an alkoxide (or phenoxide) ion. The alkoxide ion can be any alkoxide but the alkylhalide is usually going to be a primary or methyl halide since the reaction usually follows anSN2 mechanism. The reason for this is that a primary halide would have less chance of undergoingelimination, hence you can end with the product you want. In this experiment, p-cresol andchloroacetic acid will be used. The phenol can easily be converted into the phenoxide ion. Thisprocedure is typical for reactions used to produce asymmetrical ethers.The Williamson ether synthesis is one of several organic chemistry reactions referred to as "NamedReactions", which employ the name of the scientist who developed it. Many of the reactions usedin organic chemistry are described as being named reactions. The Fischer Esterification reactionwas a "named reaction", referring to Emil Fischer who discovered and popularized it as a methodto produce esters. Likewise, the Grignard Reaction was similarly named after its discoverer.In today's experiment, the Williamson ether synthesis is another named reaction, developed byDr. Alexander W. Williamson who was a professor at University College in London in the latterpart of the 1800's. This reaction has been around for a long time and has been used successfully tosynthesize many different ethers. For this reaction to occur at a high yield, the alcohol portion canbe either 1°, 2°, or 3º, which can then be converted into an alkoxide nucleophile using basicconditions (i.e., NaOH can be used as the base). The alkoxide ion then reacts via an SN2 mechanismwith a primary alkyl halide (in the current experiment chloroacetic acid will be used which alsocannot undergo elimination). For example, if the alkyl halide was either 2° or 3°, an E2 eliminationreaction would likely take place instead of substitution.The simplest way to synthesize an ether is to have an alkoxide react with a primary haloalkane ora sulfonate ester under typical Sn2 conditions. The ether prepared in this experiment is amethylphenoxyacetic acid, which is a phenolic (benzene ring attached to something is a phenylgroup) ether that is prepared from p-methylphenol (p-cresol) and chloroacetic acid.The methylphenoxyacetic acid family is of interest for several reasons, including the following:1. The products are easily prepared crystalline solids, which serve as solid derivatives whosemelting points can be used to identify the phenol starting materials (o- or m- or p-cresol).2. Several well-known herbicides are members of this class of compounds, especially 2,4-dichloro-phenoxyacetic acid (2,4-D) and 2,4,5-trichlorophenoxyacetic acid (2,4,5-T). These herbicidesmimic the effect of the natural plant growth regulators, known as auxins, causing the plant to growtoo rapidly. These herbicides are selective toward broadleaf weeds, such as dandelions, velvetleaf,and plantain. Agent Orange, a mixture of the butyl esters of 2,4-D and 2,4,5-T, was used by theU.S. troops as a defoliant during the Vietnam War. НО1. Н,О, КОН+2. Н,О, НСІ+ HCІHO,Figure 1: Reaction of p-cresol with a-chloroacetic acidWe will carry out the reaction shown above to illustrate the Williamson ether synthesis and toidentify (if different isomeric cresols were used) by the melting point of the product. The reactionhas a 75 % yield.ProcedureDissolve 4.0gof KOH pellets (cannot use NaOH) in 8 mL of water in a 250-mL round bottomflask (use the flask that contains two ground-glass openings (one for the condenser unit and theother for the separatory funnel). Add 2.0 grams of p-cresol to the round bottom flask in the hood.Swirl the mixture until the solution is homogeneous. Add three boiling stones. Fit the flask with areflux condenser and heat to a gentle boil. After the mixture has started to boil, add 6 mL of a50% aqueous solution (g/mL) of chloroacetic acid dropwise using a separatory funnel placed inthe side-arm of your round-bottom flask. After the addition of the chloroacetic acid solution,continue refluxing for another 10 minutes.After reflux, transfer the solution to a small beaker while it is still hot (if you let the mixture cool,solid forms inside the flask and it is more difficult to remove). You can overcome this problem byadding about 10 mL of water to the reaction mixture, and then pour this slightly diluted mixtureinto a 100-mL beaker. After you have poured the (diluted) reaction into the 100-mL beaker, let itcool to room temperature in the beaker. Acidify the solution with drop-wise addition ofconcentrated 12 M HCI. (Monitor the pH with pH/litmus paper to be certain pH is acidic, pH=2).It might be beneficial to ensure you do not isolate the potassium salt to heat the acidified mixturewith solids until it all dissolves at a higher temperature. Then, simply cool that mixture in an icebath to attain the maximal yield of a solid product. Be sure the precipitate has formed completely,perhaps storing it on ice for about 15 min before filtering it. Filter and collect the precipitatedproduct by using a Büchner funnel vacuum filtration setup. To the collected solid product from theprevious step, you will perform a re-crystallization step by adding the entire crude product toboiling water. Do not use more than 50 mL of water to ensure you will be able to isolate crystallineproducts. Collect your re-crystallized product using vacuum filtration. Allow the solid to dry untilthe next lab period in the designated drying oven.Weigh the solid to determine the yield. Also, determine the melting point after you havedetermined your yield for recovery of your product. Acquire the 'H and the 1C-NMR spectrum(in DMSO-ds).

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Answered: use software to make 1H-NMR and 13C-NMR…

use software to make 1H-NMR and 13C-NMR from the data in the paper and make a table with the following data 1H: chemical shift , multiplet structure, integration, assignment 13C: chemical shift

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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