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Question:

Write down the products of ozonolysis of 1,2-dimethylbenzene (o-xylene). How does the result support Kekule structure for benzene?

Answer:

o-xylene has two resonance structures:

All three products, i.e., methyl glyoxal, 1, 2-dimethylglyoxal, and glyoxal are obtained from two Kekule structures. Since all three products cannot be obtained from any one of the structures, this proves that o-xylene is a resonance hybrid of two Kekule structures (I and II).


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