Procedure Dissolve 4.0 g of KOH pellets (cannot use NaOH) in 8 mL of water in a 250-mL round bottom flask (use the flask that contains two ground-glass openings (one for the condenser unit and the other for the separatory funnel). Add 2.0 grams of p-cresol to the round bottom flask in the hood. Swirl the mixture until the solution is homogeneous. Add three boiling stones. Fit the flask with a reflux condenser and heat to a gentle boil. After the mixture has started to boil, add 6 mL of a 50% aqueous solution (g/mL) of chloroacetic acid dropwise using a separatory funnel placed in the side-arm of your round-bottom flask. After the addition of the chloroacetic acid solution, continue refluxing for another 10 minutes. After reflux, transfer the solution to a small beaker while it is still hot (if you let the mixture cool, solid forms inside the flask and it is more difficult to remove). You can overcome this problem by adding about 10 mL of water to the reaction mixture, and then pour this slightly diluted mixture into a 100-mL beaker. After you have poured the (diluted) reaction into the 100-mL beaker, let it cool to room temperature in the beaker. Acidify the solution with drop-wise addition of concentrated 12 M HCI. (Monitor the pH with pH/litmus paper to be certain pH is acidic, pH=2). It might be beneficial to ensure you do not isolate the potassium salt to heat the acidified mixture with solids until it all dissolves at a higher temperature. Then, simply cool that mixture in an ice bath to attain the maximal yield of a solid product. Be sure the precipitate has formed completely, perhaps storing it on ice for about 15 min before filtering it. Filter and collect the precipitated product by using a Büchner funnel vacuum filtration setup. To the collected solid product from the previous step, you will perform a re-crystallization step by adding the entire crude product to boiling water. Do not use more than 50 mL of water to ensure you will be able to isolate crystalline products. Collect your re-crystallized product using vacuum filtration. Allow the solid to dry until the next lab period in the designated drying oven. Weigh the solid to determine the yield. Also, determine the melting point after you have determined your yield for recovery of your product. Acquire the 'H and the BC-NMR spectrum (in DMSO-ds).
Procedure Dissolve 4.0 g of KOH pellets (cannot use NaOH) in 8 mL of water in a 250-mL round bottom flask (use the flask that contains two ground-glass openings (one for the condenser unit and the other for the separatory funnel). Add 2.0 grams of p-cresol to the round bottom flask in the hood. Swirl the mixture until the solution is homogeneous. Add three boiling stones. Fit the flask with a reflux condenser and heat to a gentle boil. After the mixture has started to boil, add 6 mL of a 50% aqueous solution (g/mL) of chloroacetic acid dropwise using a separatory funnel placed in the side-arm of your round-bottom flask. After the addition of the chloroacetic acid solution, continue refluxing for another 10 minutes. After reflux, transfer the solution to a small beaker while it is still hot (if you let the mixture cool, solid forms inside the flask and it is more difficult to remove). You can overcome this problem by adding about 10 mL of water to the reaction mixture, and then pour this slightly diluted mixture into a 100-mL beaker. After you have poured the (diluted) reaction into the 100-mL beaker, let it cool to room temperature in the beaker. Acidify the solution with drop-wise addition of concentrated 12 M HCI. (Monitor the pH with pH/litmus paper to be certain pH is acidic, pH=2). It might be beneficial to ensure you do not isolate the potassium salt to heat the acidified mixture with solids until it all dissolves at a higher temperature. Then, simply cool that mixture in an ice bath to attain the maximal yield of a solid product. Be sure the precipitate has formed completely, perhaps storing it on ice for about 15 min before filtering it. Filter and collect the precipitated product by using a Büchner funnel vacuum filtration setup. To the collected solid product from the previous step, you will perform a re-crystallization step by adding the entire crude product to boiling water. Do not use more than 50 mL of water to ensure you will be able to isolate crystalline products. Collect your re-crystallized product using vacuum filtration. Allow the solid to dry until the next lab period in the designated drying oven. Weigh the solid to determine the yield. Also, determine the melting point after you have determined your yield for recovery of your product. Acquire the 'H and the BC-NMR spectrum (in DMSO-ds).
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.63P
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