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Propose a complete mechanism for the following reaction. 요 + 1. NaOEt 2. H3O+

Propose a complete mechanism for the following reaction. 요 + 1. NaOEt 2. H3O+

Chemistry
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
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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PROPOSE a complete mechanism for the following reaction with details please. 

**Propose a complete mechanism for the following reaction.** **Reactants:** 1. An epoxide with a three-membered ring containing an oxygen atom. 2. A diester compound with two ester groups separated by a methylene (-CH2-) link. The ester groups are ethyl esters. **Reagents:** 1. Sodium ethoxide (NaOEt) 2. Hydronium ion (H3O⁺) **Product:** - A cyclized compound with a five-membered lactone ring adjacent to a ketone group, along with an ethyl ester. **Reaction Overview:** The reaction involves the opening of an epoxide ring and subsequent cyclization facilitated by a base (sodium ethoxide) followed by an acid work-up (hydronium ion) to form the final lactone product. **Steps:** 1. **Epoxide Ring Opening:** - Sodium ethoxide acts as a nucleophile, attacking the less hindered carbon of the epoxide, leading to its opening. 2. **Intramolecular Cyclization:** - The deprotonated intermediate can undergo intramolecular attack on the carbonyl carbon of the ester, resulting in the formation of a five-membered ring. 3. **Acid Work-up:** - The intermediate formed is protonated by hydronium ion to yield the final lactone product, stabilizing the structure and ensuring the completion of the cyclization. This mechanism illustrates a typical example of nucleophilic ring opening and cyclization reactions in organic synthesis.
Transcribed Image Text:**Propose a complete mechanism for the following reaction.** **Reactants:** 1. An epoxide with a three-membered ring containing an oxygen atom. 2. A diester compound with two ester groups separated by a methylene (-CH2-) link. The ester groups are ethyl esters. **Reagents:** 1. Sodium ethoxide (NaOEt) 2. Hydronium ion (H3O⁺) **Product:** - A cyclized compound with a five-membered lactone ring adjacent to a ketone group, along with an ethyl ester. **Reaction Overview:** The reaction involves the opening of an epoxide ring and subsequent cyclization facilitated by a base (sodium ethoxide) followed by an acid work-up (hydronium ion) to form the final lactone product. **Steps:** 1. **Epoxide Ring Opening:** - Sodium ethoxide acts as a nucleophile, attacking the less hindered carbon of the epoxide, leading to its opening. 2. **Intramolecular Cyclization:** - The deprotonated intermediate can undergo intramolecular attack on the carbonyl carbon of the ester, resulting in the formation of a five-membered ring. 3. **Acid Work-up:** - The intermediate formed is protonated by hydronium ion to yield the final lactone product, stabilizing the structure and ensuring the completion of the cyclization. This mechanism illustrates a typical example of nucleophilic ring opening and cyclization reactions in organic synthesis.
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