Outline the SN2 mechanism for this reaction. for the Williamson Ether Synthesis OH1) Н-О, КОНOHCI.HO.2) H2O, HC1+HC1chloroacetic acidH3Cpcresolpmethylphenoxyacetic acidThe 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 liquid phenol starting materials (o- or m- or p-cresol).2. Several well-known herbicides are members of this class of compounds, especially 2,4-dichlorophenoxyacetic acid (2,4-D) and 2,4,5-trichlorophenoxyacetic acid (2,4,5-T). Theseherbicides mimic the effect of the natural plant growth regulators, known as auxins, causing theplant to grow too rapidly. These herbicides are fairly selective toward broadleaf weeds, such asdandelions, velvetleaf and plantain. Agent Orange, a mixture of the butyl esters of 2,4-D and2,4,5-T, was used by the U.S. troops as a defoliant during the Vietnam War.We will carry out the reaction shown above to illustrate the Williamson ether synthesis and to identify(if different isomeric cresols were used) by the melting point of the product.To perform this synthesis, do the following:1. Dissolve 4 g of 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).2. Add 2 grams of your cresol to the round bottom flask in the hood.3. Swirl the mixture until a homogeneous solution results.4. Add 3 boiling stones.5. Fit the flask with a reflux condenser and heat to a gentle boil.6. After the mixture has started to boil, add 6 mL of a 50% aqueous solution (g/mL) of chloroaceticacid drop-wise using a Separatory funnel placed in the side-arm of your round-bottom flask.7. After addition of the chloroacetic acid solution, continue continue refluxing for another 10minutes.8. After reflux, transfer the solution to a small beaker while it is still hot (if you let the mixturecool, solid forms inside the flask and it is more difficult to remove). You can overcome thisproblem by adding about 10 mL of DI water to the reaction mixture, and then pour this slightlydiluted mixture into a 100-mL beaker..9. After you have poured the (diluted) reaction into the 100-mL beacker, let it cool to roomtemperature in the beaker.10. Acidify the solution with drop-wise addition of concentrated 12 M HC1. (Monitor the pH withpH/litmus paper to be certain pH is acidic).11. It might be beneficial to ensure you do not isolate the potassium salt to heat the acidified mixturewith solids until it all dissolves at the higher temperature. Then, simply cool that mixture in anice bath to attain maximal yield of solid product. Be sure the precipitate has formed completely,perhaps storing on ice for about 15 min before filtering it.

Question

Outline the SN2 mechanism for this reaction. for the Williamson Ether Synthesis OH1) Н-О, КОНOHCI.HO.2) H2O, HC1+HC1chloroacetic acidH3Cpcresolpmethylphenoxyacetic acidThe 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 liquid phenol starting materials (o- or m- or p-cresol).2. Several well-known herbicides are members of this class of compounds, especially 2,4-dichlorophenoxyacetic acid (2,4-D) and 2,4,5-trichlorophenoxyacetic acid (2,4,5-T). Theseherbicides mimic the effect of the natural plant growth regulators, known as auxins, causing theplant to grow too rapidly. These herbicides are fairly selective toward broadleaf weeds, such asdandelions, velvetleaf and plantain. Agent Orange, a mixture of the butyl esters of 2,4-D and2,4,5-T, was used by the U.S. troops as a defoliant during the Vietnam War.We will carry out the reaction shown above to illustrate the Williamson ether synthesis and to identify(if different isomeric cresols were used) by the melting point of the product.To perform this synthesis, do the following:1. Dissolve 4 g of 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).2. Add 2 grams of your cresol to the round bottom flask in the hood.3. Swirl the mixture until a homogeneous solution results.4. Add 3 boiling stones.5. Fit the flask with a reflux condenser and heat to a gentle boil.6. After the mixture has started to boil, add 6 mL of a 50% aqueous solution (g/mL) of chloroaceticacid drop-wise using a Separatory funnel placed in the side-arm of your round-bottom flask.7. After addition of the chloroacetic acid solution, continue continue refluxing for another 10minutes.8. After reflux, transfer the solution to a small beaker while it is still hot (if you let the mixturecool, solid forms inside the flask and it is more difficult to remove). You can overcome thisproblem by adding about 10 mL of DI water to the reaction mixture, and then pour this slightlydiluted mixture into a 100-mL beaker..9. After you have poured the (diluted) reaction into the 100-mL beacker, let it cool to roomtemperature in the beaker.10. Acidify the solution with drop-wise addition of concentrated 12 M HC1. (Monitor the pH withpH/litmus paper to be certain pH is acidic).11. It might be beneficial to ensure you do not isolate the potassium salt to heat the acidified mixturewith solids until it all dissolves at the higher temperature. Then, simply cool that mixture in anice bath to attain maximal yield of solid product. Be sure the precipitate has formed completely,perhaps storing on ice for about 15 min before filtering it.

Accepted Answer

In this question we will give the SN2 mechanism of the Williamson ether synthesis of p-cresol +…