Question

2 isomeric dienes x and y having molecular formula c6h8 on hydrogenation give cyclo hexane as the only product .A nixture of this 2 dienes on reductive Ozonolysis give auccinaldehyde,prropan 1,3 dial and glyoxal deduse the structure of x and y​

Answer 1

X and Y are 1,3-cyclohexadiene and 1,4-cyclohexadiene.

• Since both x and Y on hydrogenation gives cyclohexane and contains 6 carbons, all the 6 carbons must be bonded in a cyclic manner.
• Since the products of ozonolysis of the mixture of X and Y are (glyoxal , popan-1,3-dial,butan-1,4-dial) ,we can deduce that (glyoxal and butan-1,4-dial) would be obtained by ozonolysis of one diene while the other diene will produce (2 molecules of propan-1,3-dial) as the total number of carbons on either side of the reaction does not change during ozonolysis.
• So, as we know the product side of the ozonolysis of X and Y we can easily get X and Y thinking of possible cyclohexan-dienes.