Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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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).

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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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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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