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Provide mechanism with curved arrows for Part C: Synthesis of tetraphenylcyclopentadienone

Provide mechanism with curved arrows for Part C: Synthesis of tetraphenylcyclopentadienone

Organic Chemistry
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
Chapter23: Amines
Section23.6: Reactions With Acids
Problem 23.9P
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Provide mechanism with curved arrows for

Part C: Synthesis 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
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
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