ure showing formal charges and all valence electrons for the anion radical of maleic acid (first intermediate of the mechanism)

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
icon
Concept explainers
Question

Draw an important Lewis Structure showing formal charges and all valence electrons for the anion radical of maleic acid (first intermediate of the mechanism). 

### Chemical Conversion Process

This image illustrates a chemical conversion sequence starting from maleic anhydride, proceeding through maleic acid, and culminating in succinic acid. The process involves the following steps:

1. **Maleic Anhydride to Maleic Acid:**
   - **Reactant:** Maleic Anhydride
   - **Addition of Water (H₂O):** The double-bonded oxygen on the five-membered ring acts as an electrophile. Water (H₂O) reacts with maleic anhydride to form maleic acid. This reaction involves the hydrolysis of the anhydride group, leading to the formation of two -OH groups.

2. **Maleic Acid to Succinic Acid:**
   - **Reactants:** Maleic Acid, Zinc (Zn), and Hydrochloric Acid (HCl)
   - **Transformation:** In the presence of zinc and hydrochloric acid, maleic acid is converted to succinic acid. This reduction involves the hydrogenation of the double bond, saturating the structure and leading to the formation of a fully saturated six-membered ring of succinic acid.

### Chemical Structures

- **Maleic Anhydride:** Contains a five-membered ring with two adjacent carbonyl groups (C=O).
- **Maleic Acid:** Features a similar five-membered ring structure, now with two carboxylic acid groups (-COOH).
- **Succinic Acid:** A similar structure to maleic acid but with a saturated six-membered ring, also containing two carboxylic acid groups.

This series of reactions demonstrates a typical organic chemistry process involving hydrolysis and reduction.
Transcribed Image Text:### Chemical Conversion Process This image illustrates a chemical conversion sequence starting from maleic anhydride, proceeding through maleic acid, and culminating in succinic acid. The process involves the following steps: 1. **Maleic Anhydride to Maleic Acid:** - **Reactant:** Maleic Anhydride - **Addition of Water (H₂O):** The double-bonded oxygen on the five-membered ring acts as an electrophile. Water (H₂O) reacts with maleic anhydride to form maleic acid. This reaction involves the hydrolysis of the anhydride group, leading to the formation of two -OH groups. 2. **Maleic Acid to Succinic Acid:** - **Reactants:** Maleic Acid, Zinc (Zn), and Hydrochloric Acid (HCl) - **Transformation:** In the presence of zinc and hydrochloric acid, maleic acid is converted to succinic acid. This reduction involves the hydrogenation of the double bond, saturating the structure and leading to the formation of a fully saturated six-membered ring of succinic acid. ### Chemical Structures - **Maleic Anhydride:** Contains a five-membered ring with two adjacent carbonyl groups (C=O). - **Maleic Acid:** Features a similar five-membered ring structure, now with two carboxylic acid groups (-COOH). - **Succinic Acid:** A similar structure to maleic acid but with a saturated six-membered ring, also containing two carboxylic acid groups. This series of reactions demonstrates a typical organic chemistry process involving hydrolysis and reduction.
The image illustrates a chemical reaction sequence involving the reduction and oxidation of a benzoquinone derivative using zinc and hydronium ions (H₃O⁺). Here's a step-by-step explanation of the process shown:

1. **Starting Compound:**
   - The compound is 2,5-dihydroxybenzoquinone, with the chemical structure featuring a six-membered aromatic ring with two hydroxyl (OH) groups and two ketone (C=O) groups.

2. **First Reaction with Zinc:**
   - Zinc (Zn) is used to reduce the compound. The result is the removal of one of the ketone groups, forming a hydroquinone derivative with a negative charge (anion) on the oxygen atom.

3. **Hydronium Ion Addition:**
   - Upon treatment with hydronium ions (H₃O⁺), the anion is protonated. The ketone group is retained as an alcohol (OH), resulting in a diol with an aromatic ring.

4. **Second Reaction with Zinc:**
   - The compound undergoes a second reduction with zinc, further altering the structure by reducing another ketone group to an alcohol.

5. **Second Hydronium Ion Addition:**
   - Again, hydronium ions are introduced, leading to the final product of a fully reduced aromatic ring with three hydroxyl groups.

6. **Equilibrium Formation:**
   - The final structure is in equilibrium with a keto form, showing a tautomerization between the hydroquinone and benzoquinone structures.

This sequence highlights a redox process in organic chemistry where zinc acts as the reducing agent, and hydronium ions facilitate protonation.
Transcribed Image Text:The image illustrates a chemical reaction sequence involving the reduction and oxidation of a benzoquinone derivative using zinc and hydronium ions (H₃O⁺). Here's a step-by-step explanation of the process shown: 1. **Starting Compound:** - The compound is 2,5-dihydroxybenzoquinone, with the chemical structure featuring a six-membered aromatic ring with two hydroxyl (OH) groups and two ketone (C=O) groups. 2. **First Reaction with Zinc:** - Zinc (Zn) is used to reduce the compound. The result is the removal of one of the ketone groups, forming a hydroquinone derivative with a negative charge (anion) on the oxygen atom. 3. **Hydronium Ion Addition:** - Upon treatment with hydronium ions (H₃O⁺), the anion is protonated. The ketone group is retained as an alcohol (OH), resulting in a diol with an aromatic ring. 4. **Second Reaction with Zinc:** - The compound undergoes a second reduction with zinc, further altering the structure by reducing another ketone group to an alcohol. 5. **Second Hydronium Ion Addition:** - Again, hydronium ions are introduced, leading to the final product of a fully reduced aromatic ring with three hydroxyl groups. 6. **Equilibrium Formation:** - The final structure is in equilibrium with a keto form, showing a tautomerization between the hydroquinone and benzoquinone structures. This sequence highlights a redox process in organic chemistry where zinc acts as the reducing agent, and hydronium ions facilitate protonation.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Electronic Effects
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
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