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).

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter19: Eas: Electrophilic Aromatic Substitution

Section: Chapter Questions

Problem 10E

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