An alkene (A) C_(16)H_(16) on ozonolysis gives only one product (B) (C_(8)H_(8)O). Compound (B) on reaction with NaOH//I_(2) yields sodium benzoate. Compound (B) reacts with KOH//NH_(2) yielding a hydrocarbon (C_(8)H_(10)). Write the structures of compounds (B) and (C ). Based on this information, two isomeric structures can be proposed for alkene (A). write thair structures and identify the isomer which on catalytic hydrogenation (H_(2)+Pd+C) gives a recemic mixture.

An alkene (A) C_(16)H_(16) on ozonolysis gives only one product (B) (C

1.	An alkene (A) C_(16)H_(16) on ozonolysis gives only one product (B) (C_(8)H_(8)O). Compound (B) on reaction with NaOH//I_(2) yields sodium benzoate. Compound (B) reacts with KOH//NH_(2) yielding a hydrocarbon (C_(8)H_(10)). Write the structures of compounds (B) and (C ). Based on this information, two isomeric structures can be proposed for alkene (A). write thair structures and identify the isomer which on catalytic hydrogenation (H_(2)+Pd+C) gives a recemic mixture.
Answer» Solution :Alkene `(A)` is symmetrical since on ozonolysis gives `2 mol` of `(B)` `(C_(8)H_(8)O)`. `DU` in `B=((2n_(C )+2)-n_(H))/2=((2xx8+2)-8)/2=5^(@)` Since, `C:H~~1:1`, B contains benzene ring. Moreover, `B` gives iodoform test, it must contain `(MeCO-)` group). So the STRUCTURE of B may be `(PhCOMe)` (acetophenone). Reactions: