NCERT Class XI Chemistry Hydrocarbons Solutions
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Question : 17
Total: 25
Write down the products of ozonolysis of 1,2-dimethylbenzene (o-xylene). How does the result support Kekule structure for benzene?
Solution:
The products of ozonolysis of o-xylene are:
These three products cannot be obtained if we assume a triene structure of benzene. They can be obtained only if it is assumed that the double bonds in benzene are delocalised.
If the double bonds are assumed to be betweenC 1 – C 2 , C 3 – C 4 C 5 – C 6
If the double bonds are assumed to be localized betweenC 2 – C 3 , C 4 – C 5 , C 6 – C 1
But since all the above products are obtained, it indicates that only one structure is not possible and the resonance structures proposed by Kekule are the only possibilities.
These three products cannot be obtained if we assume a triene structure of benzene. They can be obtained only if it is assumed that the double bonds in benzene are delocalised.
If the double bonds are assumed to be between
If the double bonds are assumed to be localized between
But since all the above products are obtained, it indicates that only one structure is not possible and the resonance structures proposed by Kekule are the only possibilities.
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