FIND PERCENT YIELD OF CRUDE AND FINAL PRODUCT OF tetraphenylnaphthalene

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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FIND PERCENT YIELD OF CRUDE AND FINAL PRODUCT OF 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
Product characterization
0.35 g of the crude product
of the final product
M.p.: 192-196 °C (first melting point), 199-202 °C (second melting point)
0.21
g
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 Product characterization 0.35 g of the crude product of the final product M.p.: 192-196 °C (first melting point), 199-202 °C (second melting point) 0.21 g
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