Williamson Ether SynthesisOne of the side reactions in this reaction is the C-alkylation. How does this product look like? Why is it formed? How does the student remove this product from the target compound? Experiment 3: Williamson Ether SynthesisIntroductionEthers 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 ethersynthesis is oneofseveral-organie chemistry reactions referred to as "NamedReactions", which employ-the name-of the seientist-who-developed it. Manyof the reactions usedin organie chemistry-are deseribed as-being named reaetions. The Fischer Esterifieation reaetionwas a "named reaction", referring to Emi-Fischer who discovered and popułarized it as a methodto produce esters: Likewise, the Grignard-Reaction was simitarly-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 Łondon 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 3°, 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 Sy2 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). ОНHO1. Н,О, КОН+ Cl-2. Н2О, НСІ+ HCIОНFigure 1: Reaction of p-cresol with a-chloroacetic acid

Here we have to say how C-alkylation product is formed in williamson's synthesis and poduct look…

Williamson Ether Synthesis One of the side reactions in this reaction is the C-alkylation. How does this product look like? Why is it formed? How does the student remove this product from the target compound?

Williamson Ether Synthesis One of the side reactions in this reaction is the C-alkylation. How does this product look like? Why is it formed? How does the student remove this product from the target compound?

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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