8. The published procedure called for the solution to be heated at reflux for 90

Question

8. The published procedure called for the solution to be heated at reflux for 90 minutes, which would take up half of a 3-hour lab period. If this were shortened, conversion of starting material might not be complete, and all of the compounds shown below may be present in the crude product 0OCH OH 0 0 acetylsalicylic acid salicylic acid salicylic acicd methyl acetylsalicylate a) (15 points) Assume that you have dissolved your crude product in dichloromethane. Propose a series of extractions that would successfully separate the desired methyl salicylate from these other three components. Be specific about what aqueous solutions you would use, the order that you perform the extractions in, which component is dissolved in each layer, and how the pure (i.e. no remaining solvent or water) methyl salicylate is finally isolated.

Explanation / Answer

8(a) we can separate acetyl salicylic acid with methyl acetyl salicylate by adding NaOH which will dissolve sodium salt of acids. The salt is soluble in water and can be extracted by addition of HCl to give bak the acid.

2) It may hydrolyze the ester to acid

3) Molecular weight = 152.15

Density = 1.174

25% yield

25% yield means that if we start with 1 mole then we will obtain only 0.25 moles of prouduct

0.25 moles = 152.15 x 0.25 = 38.04 grams

Volume = Mass / Density = 38.04 / 1.174 = 32.402 mL

10) acetyl salicylic acid will give brisk effervesence with NaHCO3 due to evolution of CO2 when reacted with it.

The test will not be given by methyl salicylate

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