1. Pentan-3-ol can be oxidized by using ordinary bleach, avoiding the use of toxic chromium-based reagents. a) Write the mechanism of the reaction of >>>pentan-3-ol<<< with bleach and acetic acid. b) As part of the work-up for the bleach oxidation, the product mixture is sequentially washed with aqueous solutions of sodium bisulfite and sodium bicarbonate. Explain why sodium bisulfite and sodium bicarbonate were used as washes in this experiment c) Imagine you successfully isolated the product the bleach oxidation of pentan-3-ol. First, (i) describe how IR spectroscopy could be used to confirm that the reaction was a success (you do not have to quote specific peak values). Then, (ii) describe how the successful interpretation of the IR spectrum would have been adversely affected if water were present in your product. d) Describe how NMR spectroscopy could be used to confirm that the oxidation of pentan-3-ol was a success (you do not have to quote specific peak values).

1. Pentan-3-ol can be oxidized by using ordinary bleach, avoiding the use of toxic chromium-based reagents. a) Write the mechanism of the reaction of >>>pentan-3-ol<<< with bleach and acetic acid. b) As part of the work-up for the bleach oxidation, the product mixture is sequentially washed with aqueous solutions of sodium bisulfite and sodium bicarbonate. Explain why sodium bisulfite and sodium bicarbonate were used as washes in this experiment c) Imagine you successfully isolated the product the bleach oxidation of pentan-3-ol. First, (i) describe how IR spectroscopy could be used to confirm that the reaction was a success (you do not have to quote specific peak values). Then, (ii) describe how the successful interpretation of the IR spectrum would have been adversely affected if water were present in your product. d) Describe how NMR spectroscopy could be used to confirm that the oxidation of pentan-3-ol was a success (you do not have to quote specific peak values).

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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Question

help

1. Pentan-3-ol can be oxidized by using ordinary bleach, avoiding the use of toxic chromium-based reagents.
a) Write the mechanism of the reaction
>>>pentan-3-ol<<< with bleach and acetic acid.
b) As part of the work-up for the bleach oxidation, the product mixture is sequentially washed with aqueous solutions
of sodium bisulfite and sodium bicarbonate. Explain why sodium bisulfite and sodium bicarbonate were used as
washes in this experiment
c) Imagine you successfully isolated the product the bleach oxidation of pentan-3-ol. First, (i) describe how IR
spectroscopy could be used to confirm that the reaction was a success (you do not have to quote specific peak
values). Then, (ii) describe how the successful interpretation of the IR spectrum would have been adversely affected
if water were present in your product.
d) Describe how NMR spectroscopy could be used to confirm that the oxidation of pentan-3-ol was a success (you
do not have to quote specific peak values).

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