1,4‐Dimethoxybenzene (0.642 g) was dissolved in 2.0 mL acetic acid in a 25 mL Erlenmeyer flask using heat from a hot plate. Once the solid dissolved, 1.0 mL tert‐ butanol was added, and the reaction mixture was cooled in an ice bath. Then 2.0 mL concentrated sulfuric acid was added in 2‐3 drop portions,stirring the mixture after each aliquot. After the addition, the flask was removed from the ice bath and allowed to sit at room temperature for 15 minutes. Then 1.0 mL water was added dropwise to dilute the acid and the reaction mixture was added to 40 mL cold water in a 100 mL beaker. The solid was vacuum filtered and washed with 5 mL cold water, giving 52 g filtrate. The product wasrecrystallized from 4.5 mL methanol, yielding 0.317 g purified 1,4‐di‐tert‐butyl‐2,5‐dimethoxy benzene (27.2% yield). What is the atom economy,  e-factor, and effective mass yield?

Chemistry for Today: General, Organic, and Biochemistry
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Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
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Chapter15: Carboxylic Acids And Esters
Section: Chapter Questions
Problem 15.12E
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1,4‐Dimethoxybenzene (0.642 g) was dissolved in 2.0 mL acetic acid in a 25 mL Erlenmeyer flask using heat from a hot plate. Once the solid dissolved, 1.0 mL tert‐ butanol was added, and the reaction mixture was cooled in an ice bath. Then 2.0 mL concentrated sulfuric acid was added in 2‐3 drop portions,stirring the mixture after each aliquot. After the addition, the flask was removed from the ice bath and allowed to sit at room temperature for 15 minutes. Then 1.0 mL water was added dropwise to dilute the acid and the reaction mixture was added to 40 mL cold water in a 100 mL beaker. The solid was vacuum filtered and washed with 5 mL cold water, giving 52 g filtrate. The product wasrecrystallized from 4.5 mL methanol, yielding 0.317 g purified 1,4‐di‐tert‐butyl‐2,5‐dimethoxy benzene (27.2% yield). What is the atom economy,  e-factor, and effective mass yield?

OMe
OMe
tert-Butanol
H2SO4
Acetic acid
OMe
OMe
Transcribed Image Text:OMe OMe tert-Butanol H2SO4 Acetic acid OMe OMe
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