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11 Dec 2019

Alcohol Fermentation Lab

Question 2

Approximately how long did it take to convert all the startingmaterial to product?

a.
~30 minutes

b.
~40 minutes

c.
~50 minutes

d.
~60 minutes

1 points

Question 3

During the liquid-liquid extraction with water, which layer wasyour final product in?

a.
Upper organic layer

b.
Lower organic layer

c.
Upper aqueous layer

d.
Lower aqueous layer

1 points

Question 4

What was the boiling point of your final product?

a.
35.6

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Reid WolffLv2

13 Dec 2019

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This is my lab procedure... please answer the following

1. Describe how the extraction is used to isolate the camphor.

2. Describe the reaction occurring and explain the catalytic cycle involving NaClO.

2. Add 1.0 g (6.5 mmol) of borneol, then 4 mL of ethyl acetate and a magnetic stir bar to the round bottom flask. 3. Stir the mixture until the solid dissolves using the stir bar. While stiring, add 0.08 g sodium chloride and 1.5 mL of distilled water to the flask 4. Add 20 ml of bleach to the separatory funnel. Make sure the stop cock is closed to start with 5. Next add the bleach solution to the reaction mixture in small portions with while stirring for a period of 10 minutes or more Monitor the temperature to control the rate of addition so that the temperature remains below 50Â°C. Have an ice water bath nearby to cool the reaction mixture if it begins to approach 50Â°C. When the addition is complete, seal the flask with Paraflim and stir for 30 minutes or more 6. Continue to stir the mixture for 50 minutes at room temperature, then add another 0.03 g sodium chloride 7. Stir for a further 10 minutes, then add 15 mL distilled water 8. Add a "spatula tip of sodium bisulfite to reduce any unreacted NaCIO, then test the aqueous layer with starch-iodide paper: a blue-black color indicates that more sodium bisulfite is needed 9. Separate the layers using a separatory funnel. Drain the lower (aqueous) layer into a 50 mL Erlenmeyer and label it as flask A this is to be extracted further. Pour out the upper layer (ethyl acetate) into another 50 mL Erlenmeyer and label as flask B; this 10. Return the aqueous layer (from flask A) to the separatory funnel and extract three more times with 5 mL of ethyl acetate. Each 11. Now return the organic layer (in flask B) to the separatory funnel and extract this organic solution with 5 mL saturated sodium 12. Dry the organic layer in flask B further by adding some crystals of using sodium sulfate. Transfer the dried solution (by will be used to hold the organic extracts time put the upper organic layer into flask B, until you end up with one big organic extract chloride solution, placing the lower layer into flask A and the upper organic layer into flask B decanting) into a pre-weighed (labeled) 50 mL beaker and let it dry in the fume hood for 30 minutes. You should be left with a final white powder product of camphor. Weigh the flask to determine the amount of crude wet product. 13. Allow your product to dry (preferable in a desiccator) overnight and reweigh it the next day. Use the weight of the dried/purified product to determine the % yield 14. Assess the purity of the final product using FTIR spectroscopy

Organic chemistry question about extraction lab...?
Procedure:
Place 2.0 g of the mixture of sucrose, acetylsalicylic acid and acetanilide into a 125 mL Erlenmeyer flask.
Add 50 mL of methylene chloride (dichloromethane) and dissolve as much of the solid as possible.
Remove the insoluble sucrose via gravity filtration using fluted filter paper. Allow to dry until the next lab period.
Add the methylene chloride solution to the separatory funnel and extract it with two 25 mL portions of 5 % sodium bicarbonate (aqueous).
Place the combined aqueous layers into a 400 mL beaker and add enough concentrated hydrochloric acid to make it very acidic (less than pH of 2) â approximately 10 mL
Allow the solid to crystallize from the aqueous layer. Chilling in an ice bath may be required.
When lots of solid has been formed, collect the solid by vacuum filtration. Wash the solid with approximately 5 mL of cold water
Allow the solid to dry open until the next lab period.
Dry the organic layer (methylene chloride) over anhydrous sodium sulfate.
Decant the solvent from the drying agent (or gravity filter through fluted filter paper) into a clean, dry a pre-weighed 100 mL round-bottom flask.
Evaporate the solvent using rotary evaporation and allow the residue to dry open over the week.
The following lab period, weigh all 3 solids, take the melting points of all 3 solids and calculate the percent composition of the original solid.

Drying agents:
Equations for drying agents:
MgSO4 (s) + 7 H2O(l) ï MgSO4.7H2O(s)
CaSO4(s) + 2 H2O(l) ï CaSO4.2H2O(s)
CaCl2(s) + 6 H2O(l) ï CaCl2.6H2O(s)
Na2SO4(s) + 7 H2O(l) ï Na2SO4.7H2O(s)

1. The original organic solution was extracted two times with aqueous sodium bicarbonate. After the extraction, what compound(s) were in the organic layer? What compound(s) were in the aqueous layer?

________________________________________________________________________________________________________________________________________________________________________________________________________________________

2. Assume that both acetylsalicylic acid and acetanilide are soluble in diethyl ether, and that diethyl ether was used in place of the methylene chloride. Would the ether layer be the bottom layer in the separatory funnel or the top layer? Explain your answer.

3. Assume that both acetylsalicylic acid and acetanilide are soluble in methanol, and that methanol was used in place of the methylene chloride. What problem(s) might occur during the extractions? (Careful, this is a trick question.)

4. Historically, the solid residue that is left after the methylene chloride solution is evaporated has a lower melting point that its literature value, due to impurities. Explain what impurities are present and why.

I need to know the procedures of the experiment below :

Separation of a Three-Component Mixture by Extraction â

benzoic acid ethyl 4-hydroxybenzoate diphenyl sulfone

A 1.5-gram sample of a 1:1:1 (by weight) mixture of benzoic acid, ethyl 4-hydroxybenzoate and diphenyl sulfone was added to a 125 mL separatory funnel. Isopropyl acetate (20 mL) was added to the separatory funnel and the mixture swirled until all solids had dissolved. The solution was sequentially extracted with saturated aqueous NaHCO3 solution (4 X 5 mL), then with water (1 X 5 mL); with the aqueous extracts from each extraction being added to a 50 mL beaker (beaker 1). [The separatory funnel should be shaken for at least 1 minute during each of the four NaHCO3 extractions. Venting of the funnel should be done every 20-25 seconds during each extraction. When draining off the aqueous layer in these and all subsequent extractions leave a two mm tall layer of aqueous solution in the separatory funnel. This greatly reduces the amount of organic layer that contaminates the aqueous extracts.] Next the organic layer was extracted sequentially with 5% aqueous NaOH solution (3 X 5 mL) then with water (1 X 5 mL). Each aqueous extract was collected in a 50 mL beaker (beaker 2). [The separatory funnel should be shaken for at least 1.0 minute during each NaOH extraction..] The remaining organic layer is extracted with saturated aqueous NaCl solution (5 mL) and the aqueous layer is discarded [Do not leave any water in the funnel after this extraction]. The organic layer is transferred to a 50 mL erlenmeyer flask (flask 3). The separatory funnel is washed with isopropyl acetate (2 X 2 mL) with each washing being added to flask 3. The organic solution in flask 3 is dried (Na2SO4) then decanted into a tared 50 mL Erlenmeyer flask (flask 4). The drying agent is washed with isopropyl acetate (2 X 1 mL) with each rinse being added to flask 4. The solvent in flask 4 is evaporated to give crude diphenyl sulfone as a white solid: .416 g, 83.2%, M. pt.=121-127oC. [Evaporate the solvent using a hot plate sat on a moderate (4) setting. You must be very careful not to overheat the product when all the solvent has boiled away. The only way to actually know when all of the solvent has been removed is to weight the flask at the point of â presumed drynessâ, then reheat for a few seconds and re-weigh the flask. If the weight does not change, the product is solvent free. An alternative, and probably better, procedure is to evaporate the isopropyl acetate until only 3-5 mL of solution remains, cool, add hexane (10 mL), chill in an ice bath then filter. Both procedures work well. If insufficient time remains to isolate this material on day 1, then store the dried isopropyl acetate solution in your drawer until the next lab period. The solvent will have evaporated by then. Optional: tlc (alumina,

70/30 hexane/ethyl acetate) showed a single spot, Rf = .58. The crude product is recrystallized from toluene to give the crude product; M. pt.= 125-127ï° C.]

The aqueous solution in beaker 1 was acidified (acid to litmus paper) by the addition of 6 M HCl solution to give a white precipitate. [Caution! Foaming will occur due to liberation of CO2] After cooling the resulting mixture in an ice bath for 10 minutes, the solid was isolated by vacuum filtration, washed with ice water (3 X 1ml), and air dried to give crude benzoic acid as a white solid: .358 g, 71.6%, M. pt.= 115-120oC. [OPTIONAL: tlc (alumina, 70/30 hexane/ethyl acetate) showed a single spot (Rf = .03). This material was recrystallized from water to give pure benzoic acid; M. pt. = 118- 120ï°C.]

The aqueous solution in beaker 2 was acidified (acid to litmus paper) by the addition of 6 M HCl to give a white precipitate. The resulting aqueous mixture was cooled in an ice bath for 10 minutes. The resulting white solid was isolated by vacuum filtration, washed with ice water (3 X 1 mL), and air dried to give the crude ethyl 4-hydroxybenzoae: .353 g, 70.6%, M.pt.= 113-117oC. [Optional: tlc (alumina, 70/30 hexane/ethyl acetate) showed a single spot (Rf = .42). The crude material was recrystallized from 1/1 toluene/hexane to give the pure ethyl 4-hydroxybenzoate as a white solid; M. pt.= 115- 117ï°C.]

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	a.	Upper organic layer
	b.	Lower organic layer
	c.	Upper aqueous layer
	d.	Lower aqueous layer