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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Upon oxidation, phenols are transformed to p-benzoquinone, which can undergo a cycloaddition reaction with a diene to make (1). After acidic workup with HCl, a tautomerization transforms the product back to a phenol derivative (2). Draw the complete, detailed mechanism of p-benzoquinone to (1) and the mechanism from (1) to (2).
please explain!
Transcribed Image Text:This diagram illustrates a chemical synthesis pathway involving the conversion of a dihydroxybenzene (hydroquinone) to a naphthol compound. The process is shown in three steps:
1. **Oxidation of Hydroquinone to p-Benzoquinone:**
- Starting Material: A benzene ring with two hydroxyl groups (OH) attached at para positions.
- Reagents: Sodium dichromate (Na₂Cr₂O₇) and sulfuric acid (H₂SO₄).
- Product: p-Benzoquinone, a benzene ring with two ketone groups (C=O) at the para positions, indicated by the name "p-benzoquinone" beneath the structure.
2. **Cyclization with an Alkene:**
- Intermediate: p-Benzoquinone undergoes a cyclization reaction with an alkene.
- Product: A bicyclic structure with two ketone groups (labeled as compound (1)).
3. **Reduction to a Dihydroxynaphthalene:**
- Reagents: Hydrochloric acid (HCl) with heat (indicated by the delta symbol, ∆).
- Product: A naphthol structure with two hydroxyl groups at the 1,4-positions (labeled as compound (2)).
This sequence demonstrates the transformation of a simple aromatic compound into a more complex fused ring system.
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