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3. An alcohol containing natural product A (C10H20O) that is a common ingredient in cough drops yields two structurally isomeric alkenes, 1 and 2, on dehydration. Ozonolysis followed by an oxidative workup or a reductive workup as shown yields 3 and 4 from 1 and 2, respectively. Hydroboration of alkene 1 yields the starting alcohol A as the major product from 1. Hydroboration yields a mixture of the starting alcohol A and a diastereomer of A starting from alkene 2. Given this information deduce the structure of A, 1, and 2. Show the correct absolute and relative stereochemistry for A (the alcohol group is cis to a methyl group), 1, and 2 and correctly name these three compounds. H2SO4 heat 1) O3 2. Zn, H3O* 1 (C10H18) H. A (C10H200) нз H2SO4 1) O3 н сно heat 2 (C10H18) 2. Zn, H3O* *H 4

3. An alcohol containing natural product A (C10H20O) that is a common ingredient in cough drops yields two structurally isomeric alkenes, 1 and 2, on dehydration. Ozonolysis followed by an oxidative workup or a reductive workup as shown yields 3 and 4 from 1 and 2, respectively. Hydroboration of alkene 1 yields the starting alcohol A as the major product from 1. Hydroboration yields a mixture of the starting alcohol A and a diastereomer of A starting from alkene 2. Given this information deduce the structure of A, 1, and 2. Show the correct absolute and relative stereochemistry for A (the alcohol group is cis to a methyl group), 1, and 2 and correctly name these three compounds. H2SO4 heat 1) O3 2. Zn, H3O* 1 (C10H18) H. A (C10H200) нз H2SO4 1) O3 н сно heat 2 (C10H18) 2. Zn, H3O* *H 4

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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**Problem 3:** An alcohol containing natural product A (\(C_{10}H_{20}O\)) that is a common ingredient in cough drops yields two structurally isomeric alkenes, 1 and 2, on dehydration. Ozonolysis followed by an oxidative workup or a reductive workup yields 3 and 4 from 1 and 2, respectively. Hydroboration of alkene 1 yields the starting alcohol A as the major product. Hydroboration yields a mixture of the starting alcohol A and a diastereomer of A starting from alkene 2. Given this information, deduce the structure of A, 1, and 2. Show the correct absolute and relative stereochemistry for A (the alcohol group is cis to a methyl group), 1, and 2, and correctly name these three compounds. **Chemical Reaction Details:** - Starting compound A (\(C_{10}H_{20}O\)) undergoes dehydration in the presence of \(H_2SO_4\) and heat to form two isomeric alkenes: - Alkene 1 (\(C_{10}H_{18}\)) - Alkene 2 (\(C_{10}H_{18}\)) - Ozonolysis followed by a reductive workup (\(Zn, H_3O^+\)) from alkene 1 yields compound 3 and from alkene 2 yields compound 4. **Compounds Structures:** - Compound 3: Features an aldehyde and a ketone group. - Compound 4: Contains an aldehyde group. **Instructions:** Deduce and present the structures of A, 1, and 2, while considering the molecular formulas and the described chemical reactions. Ensure to present the correct stereochemistry where necessary.
Transcribed Image Text:**Problem 3:** An alcohol containing natural product A (\(C_{10}H_{20}O\)) that is a common ingredient in cough drops yields two structurally isomeric alkenes, 1 and 2, on dehydration. Ozonolysis followed by an oxidative workup or a reductive workup yields 3 and 4 from 1 and 2, respectively. Hydroboration of alkene 1 yields the starting alcohol A as the major product. Hydroboration yields a mixture of the starting alcohol A and a diastereomer of A starting from alkene 2. Given this information, deduce the structure of A, 1, and 2. Show the correct absolute and relative stereochemistry for A (the alcohol group is cis to a methyl group), 1, and 2, and correctly name these three compounds. **Chemical Reaction Details:** - Starting compound A (\(C_{10}H_{20}O\)) undergoes dehydration in the presence of \(H_2SO_4\) and heat to form two isomeric alkenes: - Alkene 1 (\(C_{10}H_{18}\)) - Alkene 2 (\(C_{10}H_{18}\)) - Ozonolysis followed by a reductive workup (\(Zn, H_3O^+\)) from alkene 1 yields compound 3 and from alkene 2 yields compound 4. **Compounds Structures:** - Compound 3: Features an aldehyde and a ketone group. - Compound 4: Contains an aldehyde group. **Instructions:** Deduce and present the structures of A, 1, and 2, while considering the molecular formulas and the described chemical reactions. Ensure to present the correct stereochemistry where necessary.
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