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Experiment 9C: Aldol Condensation (Data Sheet) Running the reaction 0.44 g of dibenzyl ketone and 0.43 g of benzil were dissolved in 3 mL of absolute ethanol in a 10 mL round-bottom flask After adding a spin bar and an air condenser, the mixture was heated to a gentle reflux 0.50 mL of ethanolic potassium hydroxide was added dropwise The color changed immediately from bright yellow to dark brown During the 10 min of reflux, a very dark precipitate formed Product isolation The mixture was allowed to cool down to room temperature before being placed in an ice- bath The solids were isolated by vacuum filtration using a Hirsch funnel The solids were washed with 1 mL of ice-cold 95 % ethanol being air was sucked through the crystals for 10 minutes (=crude) The crude was recrystallized from 15 mL of 95 % ethanol: toluene (1:1) The hot, saturated solution was allowed to cool down slowly using a hot water bath After 30 minutes, the mixture cooled to room temperature and was placed in an ice-bath The crystals were isolated by vacuum filtration using a Hirsch funnel The crystals were air-dried before characterization TLC data: mobile phase: hexane: ethyl acetate (3:1), stationary phase: SiO2, dibenzyl ketone: 11 mm, benzil: 35 mm, product: 71 mm (only one spot in the lane), solvent front: 88 mm Product characterization 0.74 g of the crude product 0.68 g of the final product M.p.: 216.3-217.8 °C

Experiment 9C: Aldol Condensation (Data Sheet) Running the reaction 0.44 g of dibenzyl ketone and 0.43 g of benzil were dissolved in 3 mL of absolute ethanol in a 10 mL round-bottom flask After adding a spin bar and an air condenser, the mixture was heated to a gentle reflux 0.50 mL of ethanolic potassium hydroxide was added dropwise The color changed immediately from bright yellow to dark brown During the 10 min of reflux, a very dark precipitate formed Product isolation The mixture was allowed to cool down to room temperature before being placed in an ice- bath The solids were isolated by vacuum filtration using a Hirsch funnel The solids were washed with 1 mL of ice-cold 95 % ethanol being air was sucked through the crystals for 10 minutes (=crude) The crude was recrystallized from 15 mL of 95 % ethanol: toluene (1:1) The hot, saturated solution was allowed to cool down slowly using a hot water bath After 30 minutes, the mixture cooled to room temperature and was placed in an ice-bath The crystals were isolated by vacuum filtration using a Hirsch funnel The crystals were air-dried before characterization TLC data: mobile phase: hexane: ethyl acetate (3:1), stationary phase: SiO2, dibenzyl ketone: 11 mm, benzil: 35 mm, product: 71 mm (only one spot in the lane), solvent front: 88 mm Product characterization 0.74 g of the crude product 0.68 g of the final product M.p.: 216.3-217.8 °C

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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FIND PERCENT YIELD FOR CRUDE AND FINAL PRODUCT OF tetraphenylcyclopentadienone 

Experiment 9C: Aldol Condensation (Data Sheet) Running the reaction 0.44 g of dibenzyl ketone and 0.43 g of benzil were dissolved in 3 mL of absolute ethanol in a 10 mL round-bottom flask After adding a spin bar and an air condenser, the mixture was heated to a gentle reflux 0.50 mL of ethanolic potassium hydroxide was added dropwise The color changed immediately from bright yellow to dark brown During the 10 min of reflux, a very dark precipitate formed Product isolation The mixture was allowed to cool down to room temperature before being placed in an ice- bath The solids were isolated by vacuum filtration using a Hirsch funnel The solids were washed with 1 mL of ice-cold 95 % ethanol being air was sucked through the crystals for 10 minutes (=crude) The crude was recrystallized from 15 mL of 95 % ethanol: toluene (1:1) The hot, saturated solution was allowed to cool down slowly using a hot water bath After 30 minutes, the mixture cooled to room temperature and was placed in an ice-bath The crystals were isolated by vacuum filtration using a Hirsch funnel The crystals were air-dried before characterization TLC data: mobile phase: hexane: ethyl acetate (3:1), stationary phase: SiO2, dibenzyl ketone: 11 mm, benzil: 35 mm, product: 71 mm (only one spot in the lane), solvent front: 88 mm Product characterization 0.74 g of the crude product 0.68 g of the final product M.p.: 216.3-217.8 °C
Transcribed Image Text:Experiment 9C: Aldol Condensation (Data Sheet) Running the reaction 0.44 g of dibenzyl ketone and 0.43 g of benzil were dissolved in 3 mL of absolute ethanol in a 10 mL round-bottom flask After adding a spin bar and an air condenser, the mixture was heated to a gentle reflux 0.50 mL of ethanolic potassium hydroxide was added dropwise The color changed immediately from bright yellow to dark brown During the 10 min of reflux, a very dark precipitate formed Product isolation The mixture was allowed to cool down to room temperature before being placed in an ice- bath The solids were isolated by vacuum filtration using a Hirsch funnel The solids were washed with 1 mL of ice-cold 95 % ethanol being air was sucked through the crystals for 10 minutes (=crude) The crude was recrystallized from 15 mL of 95 % ethanol: toluene (1:1) The hot, saturated solution was allowed to cool down slowly using a hot water bath After 30 minutes, the mixture cooled to room temperature and was placed in an ice-bath The crystals were isolated by vacuum filtration using a Hirsch funnel The crystals were air-dried before characterization TLC data: mobile phase: hexane: ethyl acetate (3:1), stationary phase: SiO2, dibenzyl ketone: 11 mm, benzil: 35 mm, product: 71 mm (only one spot in the lane), solvent front: 88 mm Product characterization 0.74 g of the crude product 0.68 g of the final product M.p.: 216.3-217.8 °C
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