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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![**Title: Propose a Mechanism for the Following Transformation**
**Transformation Reaction:**
- **Initial Compound:** A cyclopropanone structure where the carbonyl group (C=O) is part of a three-membered ring.
- **Reagents Used:** Sulfuric acid (\[H₂SO₄\]) and methanol (MeOH).
**Product Formed:**
- The structure is transformed into a molecule containing a four-membered ring with the addition of a hydroxyl group (OH) and a methoxy group (MeO) in a trans arrangement.
**Reaction Explanation:**
In this reaction, the small, strained cyclopropanone ring is opened by the action of sulfuric acid and methanol. This leads to the formation of a larger, more stable ring structure containing functional groups. The mechanism likely involves the following steps:
1. **Protonation:** The carbonyl oxygen of the cyclopropanone is protonated by sulfuric acid, increasing the electrophilicity of the carbonyl carbon.
2. **Nucleophilic Attack:** Methanol acts as a nucleophile and attacks the electrophilic carbon of the carbonyl group, opening the strained cyclopropanone ring.
3. **Formation of a Stable Intermediate:** The ring-opening results in the formation of a larger ring with both hydroxyl and methoxy substituents.
4. **Final Deprotonation:** Subsequent deprotonation yields the final product.
This reaction demonstrates principles of ring strain relief and nucleophilic attack on activated carbonyl compounds.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fa6fdb913-5513-48f0-8c37-c1f95f49bc32%2Fb22afe75-f054-4628-b429-54fc858a0319%2Fuuehphf_processed.png&w=3840&q=75)
Transcribed Image Text:**Title: Propose a Mechanism for the Following Transformation**
**Transformation Reaction:**
- **Initial Compound:** A cyclopropanone structure where the carbonyl group (C=O) is part of a three-membered ring.
- **Reagents Used:** Sulfuric acid (\[H₂SO₄\]) and methanol (MeOH).
**Product Formed:**
- The structure is transformed into a molecule containing a four-membered ring with the addition of a hydroxyl group (OH) and a methoxy group (MeO) in a trans arrangement.
**Reaction Explanation:**
In this reaction, the small, strained cyclopropanone ring is opened by the action of sulfuric acid and methanol. This leads to the formation of a larger, more stable ring structure containing functional groups. The mechanism likely involves the following steps:
1. **Protonation:** The carbonyl oxygen of the cyclopropanone is protonated by sulfuric acid, increasing the electrophilicity of the carbonyl carbon.
2. **Nucleophilic Attack:** Methanol acts as a nucleophile and attacks the electrophilic carbon of the carbonyl group, opening the strained cyclopropanone ring.
3. **Formation of a Stable Intermediate:** The ring-opening results in the formation of a larger ring with both hydroxyl and methoxy substituents.
4. **Final Deprotonation:** Subsequent deprotonation yields the final product.
This reaction demonstrates principles of ring strain relief and nucleophilic attack on activated carbonyl compounds.
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