Based on the procedure provided, how much acetic acid (in mL) should Ashe use when setting up the reaction at this new scale (to make 0.750 g of benzopinacolone)?
Based on the procedure provided, how much acetic acid (in mL) should Ashe use when setting up the reaction at this new scale (to make 0.750 g of benzopinacolone)?
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter18: Functional Derivatives Of Carboxylic Acids
Section: Chapter Questions
Problem 18.59P
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Question 4: Based on the procedure provided, how much acetic acid (in mL) should Ashe use when setting up the reaction at this new scale (to make 0.750 g of benzopinacolone)?
![Ashe went into the lab to set up the following reaction:
OH
strong acid
OH
heat
benzopinacol
molar mass = 366.46 g/mol
benzopinacolone
molar mass = 348.45 g/mol
They found a procedure ahead of time that says the following:
"Combine 100 mg of benzopinacol and 1 mL of acetic acid in a test tube. Add a small crystal of iodine (the solution should brown), and warm the test tube gently. Follow the
reaction by TLC. When it is complete (just a few minutes), chill the reaction mixture and filter the resulting crystals. You may have to add some cold ethanol to have enough
liquid to filter. Wash the crystals with a little cold ethanol, then record a melting point and yield." (From Bell, Clark, and Taber)](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F87311036-785b-48b7-ad0a-ffb7f8402d00%2F2b1a21e8-e79e-4afd-8f4c-92e52ef26db2%2Fcuxecd_processed.png&w=3840&q=75)
Transcribed Image Text:Ashe went into the lab to set up the following reaction:
OH
strong acid
OH
heat
benzopinacol
molar mass = 366.46 g/mol
benzopinacolone
molar mass = 348.45 g/mol
They found a procedure ahead of time that says the following:
"Combine 100 mg of benzopinacol and 1 mL of acetic acid in a test tube. Add a small crystal of iodine (the solution should brown), and warm the test tube gently. Follow the
reaction by TLC. When it is complete (just a few minutes), chill the reaction mixture and filter the resulting crystals. You may have to add some cold ethanol to have enough
liquid to filter. Wash the crystals with a little cold ethanol, then record a melting point and yield." (From Bell, Clark, and Taber)
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