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17 Nov 2019

Draw a flow chart to represent which layer (organic or water) the benzoic acid goes into during each phase of the following procedure:

-2 grams benzoic acid is combinzed with 20 mL of dietyhl either in a separatory funnel. Invert separatory funnel. While holding under fume hood, upside down, carefully open valve to release pressure in funnel. Close and vigourously shake. Using the same teachnique release pressure on seperatory fuunnel. Repeat until fully dissolved. Add 20 mL of 3M HCl to funnel. Repeat previous shaking and venting technique 5 times. After several cycles, replace the funnel in the iron ring, remove cap and allow aqueous and organic layers to separate.

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Nestor Rutherford
Nestor RutherfordLv2
8 Mar 2019

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Related questions

I am having great difficulty with the calculations! Please help! I am needing limiting reagent, moles of limiting reagent, moles of methyl benzoate isolated, theoretical yield in moles and grams and percent yield! The procedure is for Methyl Benzoate by Fischer Esterification, it is the following:

1. Place 10.0 g of benzoic acid and 25 mL of methanol in a 100-mL round bottomed flask. In the fume hood, pour 3 mL of concentrated sulfuric acid slowly and carefully down the walls of the flask, and then swirl to mix the components.

2. Attach a reflux condenser, add a boiling stone, and reflux the mixture gently for 1 hour.

3. Cool the solution and decant into a separatory funnel containing 50 mL of water, and rinse the flask with 35 mL of diethyl ether. Add this ether to the separatory funnel, shake thoroughly, and drain off the water layer, which contains the sulfuric acid and the bulk of unreacted methanol.

4. Wash the ether in the separatory funnel with 25 mL of water followed by 25 mL of 5% sodium bicarbonate to remove any remaining traces of sulfuric acid and unreacted benzoic acid. Again shake, with frequent release of pressure by inverting the separatory funnel and opening the stopcock, until no further reaction is apparent; then drain off the bicarbonate layer into a beaker. If this aqueous material is made strongly acidic with hydrochloric acid, unreacted benzoic acid may be observed.

5. Wash the ether layer in the separatory funnel with saturated sodium chloride solution and dry the solution over anhydrous magnesium sulfate so that it no longer clumps together on the bottom of the flask. After 10 minutes, decant the dry ether solution into a flask, wash the drying agent with an additional 5 mL of ether, and decant again. Remove the ether using the rotary evaporator.

Limiting reagent _______________________________

moles of limiting reagent _______________________________ moles

g of methyl benzoate isolated _______7.95______ g ______________ moles

Theoretical Yield of methyl benzoate _____________ g ______________ moles

% Yield: _____________ %

Answer the following questions regarding the preparation of a haloalkane from an alcohol and use the following information below:

A. Clearly draw the overall reaction for the preparation of a haloalkane from an alcohol, and the reaction mechanism which includes the transition state of the reaction.

B. Determine the limiting reagent and theoretical yield using the information given above. Note: The calcium chloride in this reaction was only used to promote the separation of the layers, and it is not a reactant.

Experiment: Extraction to seperate benzoic acid and naphthalene.

Procedure-

Place 2 g of a 1:1 (by weight) mixture of benzoic acid and naphthalene in a small beaker; record the exact mass of the mixture in your notebook. Add 35 mL of dichloromethane to the beaker and stir until the solid mixture has completely dissolved. Carefully pour the solution into a separatory funnel.

Add 20 mL of 3.0 M NaOH to the separatory funnel, stopper it, and shake the mixture with frequent venting. When the layers have separated, drain the bottom portion into a clean flask. Pour the aqueous layer into another clean flask labeled “aqueous layer.” Pour the organic layer back into the separatory funnel and extract with a second portion of 3.0 M NaOH. Drain the bottom layer into a clean flask labeled “organic layer” and pour the aqueous layer into the “aqueous layer” flask.

Put the organic layer back into the separatory funnel and shake with 20 mL of saturated NaCl solution. Drain the organic layer into a clean, dry flask and add a small amount of anhydrous calcium chloride to dry the solution. Allow this solution to stand for at least ten minutes, with occasional swirling, then remove the drying agent by gravity filtration; place the filtrate in a round-bottom flask and remove the solvent by simple distillation or by using the rotovap. Once the dichloromethane has been removed, scrape the crystals out of the round-bottom flask into a clean, labeled, tared vial, and determine the weight and melting point of the naphthalene crystals.

Acidify the combined aqueous layers with 6.0 M HCl until the solution tests acidic to litmus paper. A white precipitate of benzoic acid should develop as the solution is neutralized. Chill the solution in an ice bath for at least ten minutes to finish precipitating the solids, then collect the benzoic acid by vacuum filtration. Wash the crystals with a small amount of cold water; then scrape the crystals into a clean, labeled, tared vial and allow to dry. Once the crystals are dry, determine their weight and melting point.

Post-Lab Question:

Write a balanced equation (using structures) for the reaction that takes place when the aqueous layer is acidified with HCl. Why does the precipitate form when the solution is neutralized? (HINT: benzoic acid (slightly soluble in water) and sodium benzoate (soluble in water)

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