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What is the major product of the following reaction? -OR 1. RO 2 H,0 OR OH OR OR OR OR OR OH OR IV

What is the major product of the following reaction? -OR 1. RO 2 H,0 OR OH OR OR OR OR OR OH OR IV

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
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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**Question:** What is the major product of the following reaction? **Reaction Scheme:** A cyclic ketone with an ethoxy group and an ester group (RO, with R as a variable group) reacts sequentially with: 1. RO^- 2. H2O **Possible Products:** 1. **Compound I:** - Structure: A six-membered ring with a hydroxyl group (OH) and an ester group (OR) attached to adjacent carbon atoms. 2. **Compound II:** - Structure: A five-membered ring with a ketone and an ester group (OR) attached non-adjacently. 3. **Compound III:** - Structure: A six-membered ring with two ester groups attached non-adjacently. 4. **Compound IV:** - Structure: A seven-membered ring with a hydroxyl group and an ester group (OR) on adjacent carbon atoms, opposite each other. 5. **Compound V:** - Structure: A bicyclic compound with a ketone and an ester group (OR) attached non-adjacently. **Answer Options:** - O Compound I **Explanation:** To determine the major product, consider the mechanism of the reaction. The enolate formed after deprotonation by RO^- would favor intra- or intermolecular nucleophilic attack depending on the stability and sterics, followed by protonation to form the final product.
Transcribed Image Text:**Question:** What is the major product of the following reaction? **Reaction Scheme:** A cyclic ketone with an ethoxy group and an ester group (RO, with R as a variable group) reacts sequentially with: 1. RO^- 2. H2O **Possible Products:** 1. **Compound I:** - Structure: A six-membered ring with a hydroxyl group (OH) and an ester group (OR) attached to adjacent carbon atoms. 2. **Compound II:** - Structure: A five-membered ring with a ketone and an ester group (OR) attached non-adjacently. 3. **Compound III:** - Structure: A six-membered ring with two ester groups attached non-adjacently. 4. **Compound IV:** - Structure: A seven-membered ring with a hydroxyl group and an ester group (OR) on adjacent carbon atoms, opposite each other. 5. **Compound V:** - Structure: A bicyclic compound with a ketone and an ester group (OR) attached non-adjacently. **Answer Options:** - O Compound I **Explanation:** To determine the major product, consider the mechanism of the reaction. The enolate formed after deprotonation by RO^- would favor intra- or intermolecular nucleophilic attack depending on the stability and sterics, followed by protonation to form the final product.
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