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This is Mixed Aldol condensations of benzaldehyde and acetone. What are products

ID: 989698 • Letter: T

Question

This is Mixed Aldol condensations of benzaldehyde and acetone. What are products A, B, and C. Please find the procedure(s) below. Any help would be appreciated.

Part A:

           One gram of NaOH, a magnetic stir bar, and 10mL deionized water were placed in an Erlenmeyer flask and stirred on a hot plate then cooled to room temperature. Six mL 95% ethanol was added. 1.0mL benzaldehyde, 0.36mL acetone, and 3mL 95% ethanol were mixed in a test tube. Mixed with a vortex mixture. This was then added dropwise to the NaOH solution and rinsed with 1mL 95% ethanol and added to the mixture. After two minutes, the reaction mixture was stirred vigorously for 20minutes. 5mL 95% ethanol was added to the reaction and then filtered using a Hirsch funnel. The crystals were washed with 5mL 50% ethanol, 10mL deionized water, 5mL 50% ethanol, and 2 1-mLportions of 95% ethanol. The product was air dried and yield and IR were obtained. What's product A?

Part B:

           0.25g of NaOH, a stir bar, and ½ mL deionized water was placed in an Erlenmeyer flask and stirred. The reaction was cooled to room temperature and 2.5mL 95% ethanol was added. 0.5mLbenzaldehyde and 3mL acetone in a test tube were mixed and added dropwise to the mixture. The test tube was rinsed with 1mL 95%ethanol and added to the mixture. The contents were stirred for 15minutes. 8mL deionized water was added and placed in a separatory funnel. 5mL dichloromethane was added and the aqueous layer was extracted. This was repeated one more time. The organic extracts were combined in an Erlenmeyer flask and dried over anhydrous NaSO4.The solution was heated in a sand bath with a boiling chip.Potassium permanganate, 2,4-dinitrophenyl hydrazine, and sodium bicarbonate classification tests were performed. What is product B.

Part C:

           The remainder of the product from part B was dissolved in 6mLmethanol. The mixture was stirred and 22mL 6% sodium hypochlorite was added in small portions over ice. The mixture was stirred for 15 minutes.½ mL acetone was added and then transferred to a separatory funnel. 5mL saturated NaCL was added and the solution was extracted three times with 3mL portions of dichloromethane. The aqueous layer was placed in an Erlenmeyer flask. The pH was checked after acidifying the aqueous solution. The acidified mixture was heated in a sand bath in the hood for 10 minutes. The mixture was then cooled in ice-inducing crystallization. The crystals were collected and washed with cold deionized water and air dried. What's product C ?

Explanation / Answer

Cross Aldol Condensation between Benzaldehyde and Acetone.
In this experiment, dibenzalacetone, or 1,5-diphenyl-1, 4-pentadien-3-one, will be prepared
by the crossed aldol condensation of acetone with two equivalents of benzaldehyde. The base is
sodium hydroxide and the solvent is a mixture of ethanol and water. This reaction does not
produce a mixture of products since benzaldehyde does not contain any -hydrogens.

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