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.

Chemistry for Today: General, Organic, and Biochemistry

9th Edition

ISBN:9781305960060

Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen

Publisher:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen

Chapter14: Aldehydes And Ketones

Section: Chapter Questions

Problem 14.55E: The addition of water to aldehydes and ketones occurs rapidly, although it is not thermodynamically...

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