Provide mechanism with curved arrows for Part D: Synthesis of 1,2,3,4-tetraphenylnaphthalene Experiment 9D: Diels-Alder Reaction (Data Sheet)Running the reaction0.21 g of tetraphenylcyclopentadienone, 0.105 g of anthranilic acid. and 1.2 mL of1,2-dimethoxyethane are placed in a 25-mL round-bottom flask equipped with an aircondenserThe mixture was brought to a gentle boilA solution of 0.40 mL of isopentyl nitrite in 1.0 mL of 1,2-dimethoxyethane was addeddropwise in 60 seconds; the evolution of gas was observed and a gradual change on colortowards brownThe mixture was refluxed for 15 minutes leading to an orange colorProduct isolation:The mixture was allowed to cool down to room temperatureThe solution was poured into a beaker containing 10 mL of water and 5 mL of methanolA yellow-orange, powdery solid formed that was isolated by vacuum filtration on aBüchner funnel; after washing a solid with 2 mL of methanol, air was sucked through thesolidsThe solids were recrystallized from 12 mL of hot isopropanolAfter being placed in an ice-bath for 30 minutes, the fine, white crystal were isolated byvacuum filtration on a Hirsch funnel

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

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy

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Problem 56GP: Long-range coupling between protons more than two carbon atoms apart is sometimes observed when ...

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Concept explainers

Diol

In chemistry there are so many chemical compounds that have a hydroxyl group but a chemical compound having two hydroxyl groups (-OH) is termed as a diol. It also implies the presence of two alcohols whereas polyols contain two or more than two hydroxyl groups (-OH). Glycol or 1,2-diol is an aliphatic diol that has two alcohol groups on adjacent carbon atoms. In industries, the most commonly used diol is ethylene glycol.

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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

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