Unknown Q is determined to have a molecular formula of C6H12O. Q is not optically active, and passing it through a chiral column does not separate it into enantiomers. Q does not react with Br2, nor with cold, dilute KMnO4, nor does it take up H2 under catalytic hydrogenation. Heating of Q with H2SO4 gives product R, of formula C6H10, which can be 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 react appropriately to give these results.
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