hydrocarbons

Write down the products of ozonolysis of 1, 2 - dimethylbenzene (o -xylene). How does the result support Kekules structure for benzene?
15 Replies
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@Dexter
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Opt
Opt2mo ago
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Opt
Opt2mo ago
Red shows the cleaved bonds Consider, if this was say, the Dewar structure, you would not end up with these products
Opt
Opt2mo ago
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Fusion
Fusion2mo ago
Whats a dewar structure? I understood the problem easily but I don't understand this image Was this also one of the structures which was proposed for benzene? Or am I getting something wrong here
Opt
Opt2mo ago
Correct
Opt
Opt2mo ago
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Opt
Opt2mo ago
Some of these look real nonsensical now, but consider, these people did not have even the vaguest idea of what proton NMR was.
hardcoreisdead
hardcoreisdeadOP2mo ago
what will be the products in the other resonating struc of benzene
Nimboi
Nimboi2mo ago
atleast prismane is an actual compound
Opt
Opt2mo ago
Just cleave, put an O on each cleaved double bond, and you can check. It's not going to be very different You get 2 mols of one compound and 1 mol of another, always
Nimboi
Nimboi2mo ago
this raises the question, what happens when you attempt to cleave a real compound like this, i.e. a resonance hybrid its not like the compound exists in one form or the other and alternates its always the hybrid
hardcoreisdead
hardcoreisdeadOP2mo ago
thats the point of the ques ig when done irl we get 3 different compounds in a mixture its impossible to get any two thus proving benzene is always resonating +solved @Opt
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