Unknown Q is determined to have a molecular formula of C6H12O. Q is not optically active, and passing it through achiral column does not separate it into enantiomers. Q does not react with Br2, nor with cold, dilute KMnO4, nor doesit take up H2 under catalytic hydrogenation. Heating of Q with H2SO4 gives product R, of formula C6H10, which canbe separated into enantiomers. Ozonolysis of a single enantiomer of R produces S, an acyclic, optically active ketoaldehyde of formula C6H10O2. Propose structures for compounds Q, R, and S, and show how your structures would reactappropriately to give these results.

Unknown Q is determined to have a molecular formula of C6H12O. Q is not optically active, and passing it through achiral column does not separate it into enantiomers. Q does not react with Br2, nor with cold, dilute KMnO4, nor doesit take up H2 under catalytic hydrogenation. Heating of Q with H2SO4 gives product R, of formula C6H10, which canbe separated into enantiomers. Ozonolysis of a single enantiomer of R produces S, an acyclic, optically active ketoaldehyde of formula C6H10O2. Propose structures for compounds Q, R, and S, and show how your structures would reactappropriately to give these results.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter4: Organic Compounds: Cycloalkanes And Their Stereochemistry

Section4.SE: Something Extra

Problem 61AP: Ketones react with alcohols to yield products called acetals. Why does the all-cis isomer of...

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