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

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter18: Ethers And Epoxides; Thiols And Sulfides

Section18.SE: Something Extra

Problem 36MP: Aldehydes and ketones undergo acid-catalyzed reaction with alcohols to yield hemiacetals, compounds...

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