Problem: Compound X has molecular formula C8H10.  Reaction of Compound X with excess ozone, followed by reaction with dimethyl sulfide and then washing with water produces only the compounds shown below.  Draw a possibility for Compound X that is consistent with these results.

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Compound X has molecular formula C8H10.  Reaction of Compound X with excess ozone, followed by reaction with dimethyl sulfide and then washing with water produces only the compounds shown below.  Draw a possibility for Compound X that is consistent with these results.

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Based on our data, we think this problem is relevant for Professor Watson's class at UK.