Write down the products of ozonolysis of 1, 2-dimethylbenzene (o-xylene).

Question:

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

Solution:

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 two structures, this proves that o-xylene is a resonance hybrid of two Kekule structures (I and II).

 

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