Consider the following set of reactions,
We start with cyclobutadiene and make it react with chloroform and alkaline KOH at a low temperature to form A .
After the formation of A we heat the container mildly to form B .
B is transferred to a container filled with aqueous KOH, later PCC is added. The container is now mildly heated. This gives us the compound C .
On cooling the reaction mixture the compound C breaks to form D and E . When D and E are heated with diphenylacetylene (separately), we get the same compound X .
When X is heated in presence of Poly Phosphoric Acid, We get the final compound Z .
How many signals appear in compound Z 's H-NMR?
Inspiration :
Problem 19 in the IChO's preparatory paper.
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