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Provide mechanism with curved arrows for Part D: Synthesis of 1,2,3,4-tetraphenylnaphthalene

Provide mechanism with curved arrows for Part D: Synthesis of 1,2,3,4-tetraphenylnaphthalene

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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Provide mechanism with curved arrows for 

Part D: Synthesis of 1,2,3,4-tetraphenylnaphthalene

Experiment 9D: Diels-Alder Reaction (Data Sheet) Running the reaction 0.21 g of tetraphenylcyclopentadienone, 0.105 g of anthranilic acid. and 1.2 mL of 1,2-dimethoxyethane are placed in a 25-mL round-bottom flask equipped with an air condenser The mixture was brought to a gentle boil A solution of 0.40 mL of isopentyl nitrite in 1.0 mL of 1,2-dimethoxyethane was added dropwise in 60 seconds; the evolution of gas was observed and a gradual change on color towards brown The mixture was refluxed for 15 minutes leading to an orange color Product isolation: The mixture was allowed to cool down to room temperature The solution was poured into a beaker containing 10 mL of water and 5 mL of methanol A yellow-orange, powdery solid formed that was isolated by vacuum filtration on a Büchner funnel; after washing a solid with 2 mL of methanol, air was sucked through the solids The solids were recrystallized from 12 mL of hot isopropanol After being placed in an ice-bath for 30 minutes, the fine, white crystal were isolated by vacuum filtration on a Hirsch funnel
Transcribed Image Text:Experiment 9D: Diels-Alder Reaction (Data Sheet) Running the reaction 0.21 g of tetraphenylcyclopentadienone, 0.105 g of anthranilic acid. and 1.2 mL of 1,2-dimethoxyethane are placed in a 25-mL round-bottom flask equipped with an air condenser The mixture was brought to a gentle boil A solution of 0.40 mL of isopentyl nitrite in 1.0 mL of 1,2-dimethoxyethane was added dropwise in 60 seconds; the evolution of gas was observed and a gradual change on color towards brown The mixture was refluxed for 15 minutes leading to an orange color Product isolation: The mixture was allowed to cool down to room temperature The solution was poured into a beaker containing 10 mL of water and 5 mL of methanol A yellow-orange, powdery solid formed that was isolated by vacuum filtration on a Büchner funnel; after washing a solid with 2 mL of methanol, air was sucked through the solids The solids were recrystallized from 12 mL of hot isopropanol After being placed in an ice-bath for 30 minutes, the fine, white crystal were isolated by vacuum filtration on a Hirsch funnel
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