An unknown alcohol C6H14O gave a rapid Lucas Test. It could not be oxidized easily, but upon treatment with acid, the alcohol was converted to olefin, C6H12. Ozonolysis of the alkene gave two differentc arbonyls as products, both of which had the molecular formula C3H6O. What was the structure of thea lcohol, the olefin and the carbonyl compounds?

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
Section21.SE: Something Extra
Problem 75AP: One frequently used method for preparing methyl esters is by reaction of carboxylic acids with...
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An unknown alcohol C6H14O gave a rapid Lucas Test. It could not be oxidized easily, but upon treatment with acid, the alcohol was converted to olefin, C6H12. Ozonolysis of the alkene gave two differentc arbonyls as products, both of which had the molecular formula C3H6O. What was the structure of thea lcohol, the olefin and the carbonyl compounds?

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