How to calculate theoretical and percent yield. My values are: .152 g magnesium turnings, 1.10 g of bromobenze, 5 g of dry ice. mass of obtained product = .515 g

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How to calculate theoretical and percent yield. My values are: .152 g magnesium turnings, 1.10 g of bromobenze, 5 g of dry ice. mass of obtained product = .515 g 

Page < 3
a by-product. Separation of benzoic acid from biphenyl can be done by treatment with a base
such as sodium hydroxide, which neutralizes the acid to form a water-soluble salt, whereas
biphenyl remains in the ether layer and can be discarded.
11. Add to the separatory funnel 4 mL of 5% sodium hydroxide solution, shake contents with
occasional venting, allow layers to separate and collect into a labeled Erlenmeyer flask the
bottom aqueous layer containing the sodium salt of the product.
12. The upper ether layer remaining in the conical vial still contains benzoic acid that needs to be
extracted. Repeat step 11 twice with 4 mL portions of sodium hydroxide solution for a total of
three extractions and combine the bottom aqueous layers in the labeled Erlenmeyer flask.
13. Discard the ether layer obtained after the third treatment/extraction with sodium hydroxide.
14. Heat on a hot plate the Erlenmeyer flask containing the combined aqueous layers. Five minutes of
boiling will be sufficient to remove traces of ether dissolved in the aqueous layer.
15. Remove the flask from the hot plate and let the contents cool for 5 minutes. Add dropwise with
stirring 5 mL HCl and cool the content in an ice bath. Benzoic acid is freed from its salt and
precipitates as a white solid.
16. Filter the solid product on a Hirsch funnel under vacuum and wash away traces of HCl by adding
small portions of cold water totaling 4 mL. Dry the solid by keeping it under vacuum on the
Hirsch funnel for 20 minutes.
17. Weigh the solid and calculate the percent yield of the crude benzoic acid obtained. Measure the
melting point and compare it with literature value. Based on the melting point obtained, the
instructor will indicate if purification is necessary. Show product to the instructor before
discarding it.
Results to report
- Percent yield of crude product and its melting point, including comparison with the literature value.
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Transcribed Image Text:Page < 3 a by-product. Separation of benzoic acid from biphenyl can be done by treatment with a base such as sodium hydroxide, which neutralizes the acid to form a water-soluble salt, whereas biphenyl remains in the ether layer and can be discarded. 11. Add to the separatory funnel 4 mL of 5% sodium hydroxide solution, shake contents with occasional venting, allow layers to separate and collect into a labeled Erlenmeyer flask the bottom aqueous layer containing the sodium salt of the product. 12. The upper ether layer remaining in the conical vial still contains benzoic acid that needs to be extracted. Repeat step 11 twice with 4 mL portions of sodium hydroxide solution for a total of three extractions and combine the bottom aqueous layers in the labeled Erlenmeyer flask. 13. Discard the ether layer obtained after the third treatment/extraction with sodium hydroxide. 14. Heat on a hot plate the Erlenmeyer flask containing the combined aqueous layers. Five minutes of boiling will be sufficient to remove traces of ether dissolved in the aqueous layer. 15. Remove the flask from the hot plate and let the contents cool for 5 minutes. Add dropwise with stirring 5 mL HCl and cool the content in an ice bath. Benzoic acid is freed from its salt and precipitates as a white solid. 16. Filter the solid product on a Hirsch funnel under vacuum and wash away traces of HCl by adding small portions of cold water totaling 4 mL. Dry the solid by keeping it under vacuum on the Hirsch funnel for 20 minutes. 17. Weigh the solid and calculate the percent yield of the crude benzoic acid obtained. Measure the melting point and compare it with literature value. Based on the melting point obtained, the instructor will indicate if purification is necessary. Show product to the instructor before discarding it. Results to report - Percent yield of crude product and its melting point, including comparison with the literature value. of 3 ZOOM +
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>
Procedure
1. Add 0.15 g magnesium turnings in a dry 25 mL round bottom flask. If the turnings are not shiny
scrape the surface with a spatula to remove the oxide layer that prevents the reaction to occur.
Add a stir bar and attach a Claisen head provided with a drying tube filled with Dryrite™ and a
rubber septum on the open end.
2. Approximately 10 mL of anhydrous diethyl ether is stored in a dry 10 mL volumetric flask
covered with a rubber septum (an Erlenmeyer flask can be used). Portions of diethyl ether will be
taken out of the flask throughout the experiment, preferably with a syringe and needle through the
septum. You will need to tilt the flask in order to get the liquid into the syringe.
3. Place 0.70 mL bromobenzene into a preweighed conical vial and determine its weight. Add 4.0
mL anhydrous diethyl ether from the volumetric flask using a syringe with needle and swirl
gently. Take approximately 1.0 mL of solution using a syringe with needle and cap back the vial.
The rest of the solution will be added in portions to the magnesium turnings.
4. Insert the syringe needle through the rubber septum and add to magnesium dropwise and with
stirring the bromobenzene solution, while keeping the round bottom flask on a hot plate at 60C°.
Evolution of bubbles is expected as a sign that an exothermic reaction starts to take place after the
initial gentle heating of the mixture.
5.
If it fails to initiate the reaction, add a small crystal of iodine to the flask, under gentle heating
(consult instructor).
6.
When reaction starts and bubbles are observed, some cloudiness can be seen developing in the
solution, and the mixture will boil without using the hot plate. Take another portion of 1.0 mL
solution prepared at step 3 and add it dropwise to the reaction mixture. Add the remaining
solution of bromobenzene slowly in 1 mL portions within 15 minutes. If bubble formation ceases,
reheat the flask with a hot plate at about 60 C°, and if boiling becomes too vigorous, remove the
hot plate and/or stop the dropwise addition of bromobenzene.
7. Rinse the empty conical vial used for bromobenzene with 2.0 mL anhydrous diethyl ether and add
it to the reaction mixture using the same syringe. Overall, the complete addition should take
approximately 30-40 minutes and should lead to the consumption of magnesium and formation of
some gray residue.
8. In a 150 mL beaker, add very quickly about 5 g of crushed dry ice (no precise weighing is
necessary and use gloves). With a Pasteur pipette, add the reaction mixture cooled to room
temperature and transfer it to the beaker containing dry ice. Cover the beaker with a watch glass
and let it stand until the dry ice sublimes. What is left is a glassy material (frozen due to the low
temperature of dry ice) containing the precursor of benzoic acid, a Grignard adduct.
9. Grignard adduct is decomposed by treatment with 1 mL concentrated HCl (dropwise addition to
the beaker, with a stir bar). Unreacted magnesium is consumed by HCl and if there is solid
undissolved, add 40 mL of ether. If solid is still undissolved, add 10 mL of water. The goal is to
obtain two layers without any solids. If there is not enough time to finish, the experiment can be
floakr
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Transcribed Image Text:Page < 2 > Procedure 1. Add 0.15 g magnesium turnings in a dry 25 mL round bottom flask. If the turnings are not shiny scrape the surface with a spatula to remove the oxide layer that prevents the reaction to occur. Add a stir bar and attach a Claisen head provided with a drying tube filled with Dryrite™ and a rubber septum on the open end. 2. Approximately 10 mL of anhydrous diethyl ether is stored in a dry 10 mL volumetric flask covered with a rubber septum (an Erlenmeyer flask can be used). Portions of diethyl ether will be taken out of the flask throughout the experiment, preferably with a syringe and needle through the septum. You will need to tilt the flask in order to get the liquid into the syringe. 3. Place 0.70 mL bromobenzene into a preweighed conical vial and determine its weight. Add 4.0 mL anhydrous diethyl ether from the volumetric flask using a syringe with needle and swirl gently. Take approximately 1.0 mL of solution using a syringe with needle and cap back the vial. The rest of the solution will be added in portions to the magnesium turnings. 4. Insert the syringe needle through the rubber septum and add to magnesium dropwise and with stirring the bromobenzene solution, while keeping the round bottom flask on a hot plate at 60C°. Evolution of bubbles is expected as a sign that an exothermic reaction starts to take place after the initial gentle heating of the mixture. 5. If it fails to initiate the reaction, add a small crystal of iodine to the flask, under gentle heating (consult instructor). 6. When reaction starts and bubbles are observed, some cloudiness can be seen developing in the solution, and the mixture will boil without using the hot plate. Take another portion of 1.0 mL solution prepared at step 3 and add it dropwise to the reaction mixture. Add the remaining solution of bromobenzene slowly in 1 mL portions within 15 minutes. If bubble formation ceases, reheat the flask with a hot plate at about 60 C°, and if boiling becomes too vigorous, remove the hot plate and/or stop the dropwise addition of bromobenzene. 7. Rinse the empty conical vial used for bromobenzene with 2.0 mL anhydrous diethyl ether and add it to the reaction mixture using the same syringe. Overall, the complete addition should take approximately 30-40 minutes and should lead to the consumption of magnesium and formation of some gray residue. 8. In a 150 mL beaker, add very quickly about 5 g of crushed dry ice (no precise weighing is necessary and use gloves). With a Pasteur pipette, add the reaction mixture cooled to room temperature and transfer it to the beaker containing dry ice. Cover the beaker with a watch glass and let it stand until the dry ice sublimes. What is left is a glassy material (frozen due to the low temperature of dry ice) containing the precursor of benzoic acid, a Grignard adduct. 9. Grignard adduct is decomposed by treatment with 1 mL concentrated HCl (dropwise addition to the beaker, with a stir bar). Unreacted magnesium is consumed by HCl and if there is solid undissolved, add 40 mL of ether. If solid is still undissolved, add 10 mL of water. The goal is to obtain two layers without any solids. If there is not enough time to finish, the experiment can be floakr of 3 ZOOM +
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