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Experiment 9B: Oxidation of Benzoin (Data Sheet) Running the reaction: 2.50 g of benzoin and 0.39 g of tetrabutylammonium hydrogen sulfate were dissolved in 45 mL ethyl acetate in a 125 mL Erlenmeyer flask 19 mL of bleach, 10 m of water, and 9 mL of 0.05 M disodium hydrogenphosphate buffer were added The flask was closed with parafilm and clamped The mixture was stirred vigorously for 60 minutes during which it turned bright yellow Product isolation: The mixture was transferred to a separatory funnel 8 mL of saturated sodium bicarbonate solution were added After shaking, the layers were separated (the organic layer is the top layer) The organic layer was extracted with 10 mL of water The layers were separated, and the organic layer was dried over anhydrous sodium sulfate The bright yellow solution was decanted, and the drying agent was extracted with 5 mL ethyl acetate; the wash was combined with the remaining organic layer Using the rotary evaporator, the volume of the solution was reduced to 5 mL A 5.25" Pasteur pipette was filled with alumina (until 3-4 cm from the top) After wetting the column with 2 mL ethyl acetate, the concentrated solution was added gradually; the yellow fraction was collected in a test tube The solvent was completely removed using the rotary evaporator leaving behind a dark- yellow semisolid 5 mL of 95 % ethanol were added to the crude benzil The mixture was heated to a gentle boil causing the solids to dissolve; the solution was transferred to a small beaker Upon cooling to room temperature, yellow, needle-shaped crystals formed; the mixture was place The crystals were isolated by vacuum filtration using a Hirsch funnel The crystals were washed with a small amount of ice-cold 95 % ethanol (2*1 mL) The crystals were placed in a beaker and allowed to dry in an ice bath for 15 minutes Product characterization: 1.60 g of the product М.p.: 93-95 °C

Experiment 9B: Oxidation of Benzoin (Data Sheet) Running the reaction: 2.50 g of benzoin and 0.39 g of tetrabutylammonium hydrogen sulfate were dissolved in 45 mL ethyl acetate in a 125 mL Erlenmeyer flask 19 mL of bleach, 10 m of water, and 9 mL of 0.05 M disodium hydrogenphosphate buffer were added The flask was closed with parafilm and clamped The mixture was stirred vigorously for 60 minutes during which it turned bright yellow Product isolation: The mixture was transferred to a separatory funnel 8 mL of saturated sodium bicarbonate solution were added After shaking, the layers were separated (the organic layer is the top layer) The organic layer was extracted with 10 mL of water The layers were separated, and the organic layer was dried over anhydrous sodium sulfate The bright yellow solution was decanted, and the drying agent was extracted with 5 mL ethyl acetate; the wash was combined with the remaining organic layer Using the rotary evaporator, the volume of the solution was reduced to 5 mL A 5.25" Pasteur pipette was filled with alumina (until 3-4 cm from the top) After wetting the column with 2 mL ethyl acetate, the concentrated solution was added gradually; the yellow fraction was collected in a test tube The solvent was completely removed using the rotary evaporator leaving behind a dark- yellow semisolid 5 mL of 95 % ethanol were added to the crude benzil The mixture was heated to a gentle boil causing the solids to dissolve; the solution was transferred to a small beaker Upon cooling to room temperature, yellow, needle-shaped crystals formed; the mixture was place The crystals were isolated by vacuum filtration using a Hirsch funnel The crystals were washed with a small amount of ice-cold 95 % ethanol (2*1 mL) The crystals were placed in a beaker and allowed to dry in an ice bath for 15 minutes Product characterization: 1.60 g of the product М.p.: 93-95 °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
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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 find the experimental yield and theoretical yield.

Experiment 9B: Oxidation of Benzoin (Data Sheet) Running the reaction: 2.50 g of benzoin and 0.39 g of tetrabutylammonium hydrogen sulfate were dissolved in 45 mL ethyl acetate in a 125 mL Erlenmeyer flask 19 mL of bleach, 10 m of water, and 9 mL of 0.05 M disodium hydrogenphosphate buffer were added The flask was closed with parafilm and clamped The mixture was stirred vigorously for 60 minutes during which it turned bright yellow Product isolation: The mixture was transferred to a separatory funnel 8 mL of saturated sodium bicarbonate solution were added After shaking, the layers were separated (the organic layer is the top layer) The organic layer was extracted with 10 mL of water The layers were separated, and the organic layer was dried over anhydrous sodium sulfate The bright yellow solution was decanted, and the drying agent was extracted with 5 mL ethyl acetate; the wash was combined with the remaining organic layer Using the rotary evaporator, the volume of the solution was reduced to 5 mL A 5.25" Pasteur pipette was filled with alumina (until 3-4 cm from the top) After wetting the column with 2 mL ethyl acetate, the concentrated solution was added gradually; the yellow fraction was collected in a test tube The solvent was completely removed using the rotary evaporator leaving behind a dark- yellow semisolid 5 mL of 95 % ethanol were added to the crude benzil The mixture was heated to a gentle boil causing the solids to dissolve; the solution was transferred to a small beaker Upon cooling to room temperature, yellow, needle-shaped crystals formed; the mixture was place The crystals were isolated by vacuum filtration using a Hirsch funnel The crystals were washed with a small amount of ice-cold 95 % ethanol (2*1 mL) The crystals were placed in a beaker and allowed to dry in an ice bath for 15 minutes Product characterization: 1.60 g of the product М.p.: 93-95 °C
Transcribed Image Text:Experiment 9B: Oxidation of Benzoin (Data Sheet) Running the reaction: 2.50 g of benzoin and 0.39 g of tetrabutylammonium hydrogen sulfate were dissolved in 45 mL ethyl acetate in a 125 mL Erlenmeyer flask 19 mL of bleach, 10 m of water, and 9 mL of 0.05 M disodium hydrogenphosphate buffer were added The flask was closed with parafilm and clamped The mixture was stirred vigorously for 60 minutes during which it turned bright yellow Product isolation: The mixture was transferred to a separatory funnel 8 mL of saturated sodium bicarbonate solution were added After shaking, the layers were separated (the organic layer is the top layer) The organic layer was extracted with 10 mL of water The layers were separated, and the organic layer was dried over anhydrous sodium sulfate The bright yellow solution was decanted, and the drying agent was extracted with 5 mL ethyl acetate; the wash was combined with the remaining organic layer Using the rotary evaporator, the volume of the solution was reduced to 5 mL A 5.25" Pasteur pipette was filled with alumina (until 3-4 cm from the top) After wetting the column with 2 mL ethyl acetate, the concentrated solution was added gradually; the yellow fraction was collected in a test tube The solvent was completely removed using the rotary evaporator leaving behind a dark- yellow semisolid 5 mL of 95 % ethanol were added to the crude benzil The mixture was heated to a gentle boil causing the solids to dissolve; the solution was transferred to a small beaker Upon cooling to room temperature, yellow, needle-shaped crystals formed; the mixture was place The crystals were isolated by vacuum filtration using a Hirsch funnel The crystals were washed with a small amount of ice-cold 95 % ethanol (2*1 mL) The crystals were placed in a beaker and allowed to dry in an ice bath for 15 minutes Product characterization: 1.60 g of the product М.p.: 93-95 °C
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