Question

An alkene (A) C16H16 on ozonolysis gives only one product (B) C8H8O. Compound (B) on reaction with NgOH/l2 yields-sodium benzoate. Compound (B) reacts with KOH/ NH2M2, yielding a hydrocarbon (C2H10. Write the structures of compounds (B) and (C). Based on this information two isomeric structures can be proposed for alkene (A). Write their structures and identify the isomer which on catalytic hydrogenation (H2 / Pd-C) gives a racemic mixture.

Answer 1

Alkene A is symmetric because it given a carbonyl compound (C8H8O) on ozonolysis.

As,it gives iodoform test with a mixture of NaOH and I2, so it must have CH3CO- group. Thus, the possible structure of compound B is C6H5-CO-CH3

On the basis of structure of compound B, the compound A is

Symmetric alkenes show the properties of geometrical isomerism. Hence, its cis and ,trans isomers are possible. In these isomers trans isomer gives racemic mixture on hydrogenation (H2 / Pd-C)