For a practical we will be given a variety of situations relating to the labs we

Question

For a practical we will be given a variety of situations relating to the labs we have done over the semester. I am unsure what procedure to carry out in this situation.

Materials Available to Students in Lab: Solvents: acetone, ethanol, methanol, ethyl acetate, hexanes, dichloromethane and petroleum ether. Aqueous Solutions: 1 M NaOH, 1 M HCl, 3 M NaOH, 3 M HCl, 1 M NaHCO3, saturated NaCl. Drying Agent: sodium sulfate Special Glassware: TLC chambers and plates, separatory funnels

"An organic chemistry student attempted to synthesize o-toluic acid from o-chlorotoluene via a Grignard reaction and dry ice. The reaction did not go to completion and the student ended up with a mixture of o-toluic acid and o-chlorotoluene. Purify the o-toluic acid. Provide data to show that your compound is pure."

Explanation / Answer

First you have to add NaHCO3 solution to the mixture. Toluic acid will react with NaHCo3 to form a salt and will dissolve in aqueous solution. Next you have t add ether to it which will dissolve the nonpolar o chloro toluene. Then tke the whole ether-water mixture to a seperatory funnel. two layers will form inside the separatory funnel : one for aqueous phase and another of organic phase. water is heavier than ether . so, it will be at the bottom. Take out the aquous layer and add NaOH to it, to neutralize the solution. The neutralize solution is then evaporated to get the solid toluic acid.

Ether layer is dried over anhydrous sdium sulphate and removed the solvent by heating to get the o chloro toluene.

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