4) Hydrogenation of A with a Pd/C catalyst at low pressure produces, B, C,H₁2. Reaction of A with KMnO4/NaOH, H₂O produces C, C₂H₁2O₂. Upon chromic acid oxidation, A, B, or C each produce the same acidic product D, CH₁O4. When D is strongly heated it is transformed into a neutral compound E, C8H4O3. When E is exposed to moist air it slowly converts back to D. What are the structures of A, B, C, D, and E? Explain why the conversion of D to E is crucial to assigning the correct structures?

4) Hydrogenation of A with a Pd/C catalyst at low pressure produces, B, C,H₁2. Reaction of A with KMnO4/NaOH, H₂O produces C, C₂H₁2O₂. Upon chromic acid oxidation, A, B, or C each produce the same acidic product D, CH₁O4. When D is strongly heated it is transformed into a neutral compound E, C8H4O3. When E is exposed to moist air it slowly converts back to D. What are the structures of A, B, C, D, and E? Explain why the conversion of D to E is crucial to assigning the correct structures?

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter6: Reactions Of Alkenes

Section: Chapter Questions

Problem 6.23P: Account for the fact that treating propenoic acid (acrylic acid) with HCl gives only...

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