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Magazine Chapter 11: Q64P (page 591)
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 H2under 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.
Short Answer
Step by step solution
About the given information
The molecular formula of the compound is C6H12O. The compound Q has one element of unsaturation. There may be a ring or C=C or C=O. There is no asymmetric carbon in Q and cannot be separated into enantiomers.
About the given information
Compound Q has no reaction with Br2 , KMnO4, H2 . Thus, Q is not an alcohol, not C=O, and C=C. Q undergoes a reaction with H2SO4and loses H2O. Thus, Q has a ring.
About the reaction
The compound R has a C=C, that is, it ozonolyses to give one acyclic product. The transformation from S to R has a C=C in the ring. R has enantiomers and the dehydration produces C=C creating an asymmetric carbon. S is a ketoaldehyde that gives a 4-membered ring.
Thus, the reaction is as follows:
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