1. When butan-1-ol, A, is oxidized using PCC under rigorously anhydrous conditions, an aldehyde, B, is easily obtained as the product. However, if water is present during the oxidation, a carboxylic acid, C, is produced instead. When butan-2- ol, D, is oxidized with PCC, a ketone, E, is produced, regardless of whether or not water is present. Finally, 2- methylbutan-2-ol, F, cannot be oxidized using PCC under any conditions. () Explain why water affects the oxidation of a primary alcohol using PCC but net affect the oxidation of a secondary alcohol. Then, () explain why a tertiary alcohol cannot be oxidized using PCC regardless of conditions. You do not need to show any mechanisms, but be sure to draw the structures of any important intermediates discussed in your answer. :ÖH A D.

1. When butan-1-ol, A, is oxidized using PCC under rigorously anhydrous conditions, an aldehyde, B, is easily obtained as the product. However, if water is present during the oxidation, a carboxylic acid, C, is produced instead. When butan-2- ol, D, is oxidized with PCC, a ketone, E, is produced, regardless of whether or not water is present. Finally, 2- methylbutan-2-ol, F, cannot be oxidized using PCC under any conditions. () Explain why water affects the oxidation of a primary alcohol using PCC but net affect the oxidation of a secondary alcohol. Then, () explain why a tertiary alcohol cannot be oxidized using PCC regardless of conditions. You do not need to show any mechanisms, but be sure to draw the structures of any important intermediates discussed in your answer. :ÖH A D.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter10: Organohalides

Section10.SE: Something Extra

Problem 19MP: The formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol...

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