Two isomeric cyclic dienes X and Y having molecular formula C6H8 on hydrogenation give cyclohexane as the only product. A mixture of these two dienes on reductive ozonolysis gives succinaldehyde, propane –1,3–dial and glyoxal. Deduce the structures of dienes X and Y.

Engineering

Chemistry

Test of Alkenes and alkynes

Question

Two isomeric cyclic dienes X and Y having molecular formula C₆H₈ on hydrogenation give cyclohexane as the only product. A mixture of these two dienes on reductive ozonolysis gives succinaldehyde, propane –1,3–dial and glyoxal. Deduce the structures of dienes X and Y.

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Since X and Y on hydrogenation give cyclohexane as the only product, therefore, X and Y must be cyclohexadienes. The two possible cyclohexadienes are shown in the figure.

Reductive ozonolysis of X will two molecules of propane –1,3– dial whereas reductive ozonolysis of Y will give succinaldehyde and glyoxal as shown below :

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