An alkane (A) `C_(16)H_(16)` on ozonolysisi gives only one products (B) `C_(8)H_(8)O`. Compound (B) or reaction with `NaOH//I_(2)` yields sodium benzoate. Comopund (B) reacts with `KOH//NH_(2)NH_(2)` yielding a hydrogen (C) `C_(8) H(10)^(.)` Write the structures of compounds (B) and (C). Based on this infromation two their structures and identify the isomer which on catalytic hydrpgenation `(H_(2)//Pd-C)` gives a racemic mixture.

Explanation

Since, (A) on ozonolysis gives only one product (B), the alkene must be a symmetrical one. This reactions may be written as,

Further, (B) on treatment with `I_(2)//"NaOH"` (iodoform test) gives sodium benzoate, one of the group (a) and (b) may be identified with `C_(6)H_(5)` and hence the other one may be `CH_(3)` group. The gives reactions are as follows.

The alkenes (A) will have two isomers, cis-trans. The catalyst huydrogenation `H_(2)//Pd-C` involves syn-addition of hydrogen. The trans-isomer gives racemic mixture while cis-isomer gives a meso compound.