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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give mechanism
Transcribed Image Text:### Transcription and Explanation:
**b. Reaction Scheme**
- **Reactants:**
- A 1,3-dicarbonyl compound is depicted. It has two carbonyl groups (C=O) with a methylene (CH2) group between them. This is indicated by:
- The generic structure: R-CO-CH2-CO-R
- **Reagents:**
- The reaction takes place in the presence of hydroxylamine (\( \text{H}_2\text{NOH} \)) and a proton source (acid), denoted as \( \text{H}^+ \).
- **Product:**
- The resulting product is an isoxazole derivative, which features a five-membered ring containing nitrogen and oxygen atoms. This is indicated by the:
- Structure: A ring with N and O atoms in the 1 and 2 positions, respectively, with the carbon adjacent to oxygen having R groups attached.
**Reaction Insight:**
- This reaction illustrates the cyclization of a 1,3-dicarbonyl compound with hydroxylamine to form an isoxazole.
- The presence of the acid catalyzes the reaction, aiding in the formation of the heterocyclic ring.
**Concepts:**
- 1,3-dicarbonyl compounds can undergo cyclization reactions to form heterocycles.
- Isoxazoles are significant in medicinal chemistry due to their biological activity and are often synthesized from such reactions.
This educative illustration helps in understanding the basic principles of organic synthesis involving heterocyclic compounds.
Expert Solution
Explanation
The first is the protonation of one of the carbonyls followed by nucleophilic attack by the N-atom hydroxylamine. Secondly, the elimination of a water molecule gives the imine. Similarly, protonation, nucleophilic attack by the O-atom, dehydration leads to the product.
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