In 1932, A. A. Levine and A. G. Cole studied the ozonolysis of o-xylene and isolated three products: glyoxal, 2, 3-butanedione, and pyruvaldehyde: In what ratio would you expect the three products to be formed if o-xylene is a resonance hybrid of two structures? The actual ratio found was 3 parts glyoxal, 1 part 2, 3-butanedione, and 2 parts pyruvaldehyde. What conclusions can you draw about the structure ofo-xylene?

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Cнз CHз 1. Оз 2. Zn CHз—С—с—снз н-с—с—н CH3—С—с—н Glyoxal 2,3-Butanedione Pyruvaldehyde