Benzene in a Kaleidoscope

Chemistry Level pending

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?


Problem 19 in the IChO's preparatory paper.


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