In 1932, A. A. Levine and A. G. Cole studied the ozonolysis of o-xylene and isolated
Chapter 15, Problem 15.28(choose chapter or problem)
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: Glyoxal 1. O3 2. Zn 2,3-Butanedione Pyruvaldehyde CH3 CH3 H C C H + + O O CH3 C C CH3 O O CH3 C C H In what ratio would you expect the three products to be formed if o-xylene isa resonance hybrid of two structures? The actual ratio found was 3 parts glyoxal,1 part 2,3-butanedione, and 2 parts pyruvaldehyde. What conclusionscan you draw about the structure of o-xylene?
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