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1HNMR spectrum from the literature table labeled diagram chemical shift (literature), multiplet structure, integration, assignment please all in table based on the data in the lab FOR EXAMPLE NO Chemical shift experimental  multiplet Integration Assignment  1 7.45 ppm  Triplet 1 Para to Cl 2 7.55 ppm Triplet 1 Meta to Cl 3 7.56 ppm Doublet 1 Ortho to Cl 4 7.81 ppm Doublet 1 Ortho to Cl 5 13.43 ppm  Singlet 1 -COOH

1HNMR spectrum from the literature table labeled diagram chemical shift (literature), multiplet structure, integration, assignment please all in table based on the data in the lab FOR EXAMPLE NO Chemical shift experimental  multiplet Integration Assignment  1 7.45 ppm  Triplet 1 Para to Cl 2 7.55 ppm Triplet 1 Meta to Cl 3 7.56 ppm Doublet 1 Ortho to Cl 4 7.81 ppm Doublet 1 Ortho to Cl 5 13.43 ppm  Singlet 1 -COOH

Organic Chemistry
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter31: Synthetic Polymers
Section31.SE: Something Extra
Problem 28AP
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1HNMR spectrum from the literature table

labeled diagram chemical shift (literature), multiplet structure, integration, assignment please all in table based on the data in the lab

FOR EXAMPLE

NO

Chemical shift experimental 

multiplet

Integration

Assignment 

1

7.45 ppm 

Triplet

1

Para to Cl

2

7.55 ppm

Triplet

1

Meta to Cl

3

7.56 ppm

Doublet

1

Ortho to Cl

4

7.81 ppm

Doublet

1

Ortho to Cl

5

13.43 ppm 

Singlet

1

-COOH

 

Day 2: Recrystallization and analysis of the o-chlorobenzoic acid Recrystallize the product using hot toluene. Be sure to add enough toluene so that the solid dissolves at a higher temperature, but some of the solid stays undissolved at room temperature. Do not add too much toluene, as you may not be able to crystallize your product. If you believe you added too much toluene, or if o-chlorobenzoic acid crystals do not appear upon cooling the solution on ice, you will need to evaporate some of the toluene in the hood. The crystals should be suspended fully in toluene before filtration. After drying the solids, determine the melting point of the product. Acquire the infrared spectrum and the 'H-NMR spectrum in DMSO-d6. Cleanup Notes: Solid MnO2 often sticks to the glassware and is difficult to remove, even with soapy water and scrubbing. You can easily clean your glassware, however, by using 12 M HCI. In order not to waste the concentrated acid, transfer your concentrated HCl washings into a large beaker which can be used many times by other students. Clean your ground-glass joints by dipping them into the acid wash solution. To clean your flask, pour the concentrated acid into your flask and swirl. The MnO2 should be easily removed using these procedures. The acid wash solution can be re-used several times by pouring it back into the collection beaker so that it is available to other students. Cleanup Caution: Before you use the concentrated HCl, be sure your flask is rinsed and free of any solid material. Do not leave excess water in the flask. Once your flask is clean and free of loose residue, you can then remove the bound MnO2 which stains your flask by adding the concentrated HCl.
Transcribed Image Text:Day 2: Recrystallization and analysis of the o-chlorobenzoic acid Recrystallize the product using hot toluene. Be sure to add enough toluene so that the solid dissolves at a higher temperature, but some of the solid stays undissolved at room temperature. Do not add too much toluene, as you may not be able to crystallize your product. If you believe you added too much toluene, or if o-chlorobenzoic acid crystals do not appear upon cooling the solution on ice, you will need to evaporate some of the toluene in the hood. The crystals should be suspended fully in toluene before filtration. After drying the solids, determine the melting point of the product. Acquire the infrared spectrum and the 'H-NMR spectrum in DMSO-d6. Cleanup Notes: Solid MnO2 often sticks to the glassware and is difficult to remove, even with soapy water and scrubbing. You can easily clean your glassware, however, by using 12 M HCI. In order not to waste the concentrated acid, transfer your concentrated HCl washings into a large beaker which can be used many times by other students. Clean your ground-glass joints by dipping them into the acid wash solution. To clean your flask, pour the concentrated acid into your flask and swirl. The MnO2 should be easily removed using these procedures. The acid wash solution can be re-used several times by pouring it back into the collection beaker so that it is available to other students. Cleanup Caution: Before you use the concentrated HCl, be sure your flask is rinsed and free of any solid material. Do not leave excess water in the flask. Once your flask is clean and free of loose residue, you can then remove the bound MnO2 which stains your flask by adding the concentrated HCl.
Day 1: Preparation of o-chlorobenzoic acid Dissolve 3.0 g of KMNO4 (Use caution not to get on the skin) in 35 mL of water in a 250-mL round-bottomed flask. Add about 1.0 g of 2-chlorotoluene (use about 1.00 mL liquid and determine its mass and moles based on density). Attach a water-jacketed condenser and reflux (with a few added boiling stones) the reaction mixture for about 1.5 hours. After the reflux is completed, collect the filtrate by using vacuum filtration in a Büchner funnel using the procedure described below (filter the hot solution, but do not wash with hot or cold water). Note: The insoluble MnO2, which is a byproduct of this reaction, will be removed from the soluble organic product by vacuum filtration. However, if the liquid is still purple (indicating MnO4 ion is still present), you will need to react to the remaining MnO4 ion with sodium bisulfite (NaHSO3). Remember that the reaction mixture will not be clear, but you should be able to detect the purple color. Slowly add small amounts of solid sodium bisulfite (NaHSO3) to reduce any remaining permanganate ion (how do you know if you need to do this step, and how much sodium bisulfite to add?). When no more purple color is present (the mixture will still contain the brownish-black solid suspension), you have added enough sodium bisulfite. Be careful because the reaction between sodium bisulfite and potassium permanganate is highly exothermic (heat released). After you have added enough sodium bisulfite to remove the purple color in the reaction flask, you will collect the filtrate using vacuum filtration and a Büchner funnel. The filtrate may not be colorless, but it cannot be purple. After this initial filtration of the reaction contents to which sodium bisulfite has been added, the filtrate is used to isolate the benzoic acid derivative (i.e., be sure the filtrate is not purple). If the filtrate contains any purple color you will need to reclaim the filtrate and add more sodium bisulfite and repeat the filtration to produce a clear filtrate (a slight brownish hue to the filtrate is acceptable, but it must not be purple) for isolation of the aromatic acid. Remember, at this step it is the liquid filtrate you must keep, discarding the brownish-black precipitate. Put the clear and mostly colorless solution (remember that a slight brownish color is acceptable) in the ice bath. Acidify the mixture by adding about 2.5 mL of concentrated HCl. Add the acid drop by drop and mix by swirling the mixture. Check the pH with Litmus paper to ensure that the solution is acidic (pH<3). (As little as 4-5 drops may be enough to make the solution acidic and initiate the formation of solid material.) Collect the precipitated organic product using vacuum filtration and a Büchner funnel. You can use small amounts of water to wash the solid material in the filter to remove any remaining solids from the crystallization container, before drying. The solid product will be stored in the drying oven until the next lab period for recrystallization. STOP, and store your solid material until the next lab period for recrystallization. (If you were not able to produce solid material during the first lab period, you can store your liquid until the next lab period.)
Transcribed Image Text:Day 1: Preparation of o-chlorobenzoic acid Dissolve 3.0 g of KMNO4 (Use caution not to get on the skin) in 35 mL of water in a 250-mL round-bottomed flask. Add about 1.0 g of 2-chlorotoluene (use about 1.00 mL liquid and determine its mass and moles based on density). Attach a water-jacketed condenser and reflux (with a few added boiling stones) the reaction mixture for about 1.5 hours. After the reflux is completed, collect the filtrate by using vacuum filtration in a Büchner funnel using the procedure described below (filter the hot solution, but do not wash with hot or cold water). Note: The insoluble MnO2, which is a byproduct of this reaction, will be removed from the soluble organic product by vacuum filtration. However, if the liquid is still purple (indicating MnO4 ion is still present), you will need to react to the remaining MnO4 ion with sodium bisulfite (NaHSO3). Remember that the reaction mixture will not be clear, but you should be able to detect the purple color. Slowly add small amounts of solid sodium bisulfite (NaHSO3) to reduce any remaining permanganate ion (how do you know if you need to do this step, and how much sodium bisulfite to add?). When no more purple color is present (the mixture will still contain the brownish-black solid suspension), you have added enough sodium bisulfite. Be careful because the reaction between sodium bisulfite and potassium permanganate is highly exothermic (heat released). After you have added enough sodium bisulfite to remove the purple color in the reaction flask, you will collect the filtrate using vacuum filtration and a Büchner funnel. The filtrate may not be colorless, but it cannot be purple. After this initial filtration of the reaction contents to which sodium bisulfite has been added, the filtrate is used to isolate the benzoic acid derivative (i.e., be sure the filtrate is not purple). If the filtrate contains any purple color you will need to reclaim the filtrate and add more sodium bisulfite and repeat the filtration to produce a clear filtrate (a slight brownish hue to the filtrate is acceptable, but it must not be purple) for isolation of the aromatic acid. Remember, at this step it is the liquid filtrate you must keep, discarding the brownish-black precipitate. Put the clear and mostly colorless solution (remember that a slight brownish color is acceptable) in the ice bath. Acidify the mixture by adding about 2.5 mL of concentrated HCl. Add the acid drop by drop and mix by swirling the mixture. Check the pH with Litmus paper to ensure that the solution is acidic (pH<3). (As little as 4-5 drops may be enough to make the solution acidic and initiate the formation of solid material.) Collect the precipitated organic product using vacuum filtration and a Büchner funnel. You can use small amounts of water to wash the solid material in the filter to remove any remaining solids from the crystallization container, before drying. The solid product will be stored in the drying oven until the next lab period for recrystallization. STOP, and store your solid material until the next lab period for recrystallization. (If you were not able to produce solid material during the first lab period, you can store your liquid until the next lab period.)
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