Tandem Reaction Pathway: OH no heat {}=&_ no solvent CH3 CH3 + enantiomer

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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Experiment 12: Fischer Esterification and Green Diels-Alder
Tandem Reaction Pathway:
no heat
{{ = &-
no solvent
+ enantiomer
CO₂H
CH3
proton transfer
CH3
OH
CH3
H
O
Transcribed Image Text:Experiment 12: Fischer Esterification and Green Diels-Alder Tandem Reaction Pathway: no heat {{ = &- no solvent + enantiomer CO₂H CH3 proton transfer CH3 OH CH3 H O
2. A reaction like this is normally performed in refluxing toluene. Why might the
modified procedure that you will perform be considered a "greener, more
sustainable" method? Give at least two reasons.
Experimental Procedure: Using the appropriate pipet, carefully transfer 50 µL of (E,E)-
2,4-hexadien-1-ol into the bottom of a clean, dry, tared small beaker (<100 mL, the
smaller the better!). After the transfer, weigh your beaker. Add an equimolar amount of
finely powdered, solid maleic anhydride (~44 mg) to the same beaker. Use the small end
of a clean, dry metal spatula to vigorously and continuously stir the mixture as it liquefies
and resolidifies (10-15 minutes). After solidification is complete, weigh the beaker and
calculate the mass of product and yield. Analyze your product by IR (solid) and melting
point (lit value reported to be 159-161°C).
Transcribed Image Text:2. A reaction like this is normally performed in refluxing toluene. Why might the modified procedure that you will perform be considered a "greener, more sustainable" method? Give at least two reasons. Experimental Procedure: Using the appropriate pipet, carefully transfer 50 µL of (E,E)- 2,4-hexadien-1-ol into the bottom of a clean, dry, tared small beaker (<100 mL, the smaller the better!). After the transfer, weigh your beaker. Add an equimolar amount of finely powdered, solid maleic anhydride (~44 mg) to the same beaker. Use the small end of a clean, dry metal spatula to vigorously and continuously stir the mixture as it liquefies and resolidifies (10-15 minutes). After solidification is complete, weigh the beaker and calculate the mass of product and yield. Analyze your product by IR (solid) and melting point (lit value reported to be 159-161°C).
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