Unknown Q is determined to have a molecular formula of C6H12O. Q is not opticall

Question

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 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 a structure for compounds Q,R, and S and show how your structures would react appropriately to give these results.

Explanation / Answer

These links will be helpful to your answers http://www.preterhuman.net/texts/science_and_technology/chemistry/Lange's%20Handbook%20of%20Chemistry%20(15th%20Edition)%20(pdf)/63847_1a.pdf http://www.cytss.edu.hk/chem/f67res/o10.pdf

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