ОН ОН HCI на сто p-benzoquinone (1) Na2Cr2O7 H₂SO4 ОН ОН (2)

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...
icon
Related questions
Question
100%

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!

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.
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.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 3 steps with 2 images

Blurred answer
Knowledge Booster
Stereochemistry in Organic Reactions
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY