Develop a step-by-step procedure for conducting this experiment. Scenario: An or

Question

Develop a step-by-step procedure for conducting this experiment.

Scenario: An organic chemistry student was attempting to synthesize aspirin (acetyl salicylic acid) from salicylic acid and the reaction did not go to completion and the student ended up with a mixture of both compounds. Purify the salicylic acid. Provide data to show that your compound is pure.

Materials available in Lab:

Solvents: acetone, ethanol, methanol, ethyl acetate, hexanes, DCM and Pet ether.

Aqueous Solutions: 1M NaOH, 1M HCl, 3M NaOH, 3M HCl, 1M NaHCO3, saturated NaCl

Drying agent: Sodium sulfate

special glassware: TLC chambers and plates, separatory funnels

Can I add the impure compound to ethyl acetate and then add NaHCO3 to separate the asprin from the salycylic acid (in aqueous layer)?

Explanation / Answer

Aspirin, is an organic acid; therefore, it is soluble in an organic solvent DCM or diethyl ether.

Now we add a base sodium bicarbonate which will produce conjugate base of the acid. This conjugate base is a salt which is water soluble; hence it will move into aqueous layer from organic layer. Now add acid means re-acidification of this basic aqueous layer will regenerate the organic acid or aspirin.

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