[pineapple]

*delete me*  Compound X is optically inactive and has the formula C16H16Br2.  On treatment with a strong base, X gives hydrocarbon Y, C16H14.  Compund Y absorbs 2 equivalents of hydrogen when reduced over a pallidiium catalyst and reacts with ozone to gove two fragments.  One fragment, Z is an aldehyde with the formul C7H6O.  The other fragement is glyoxal, (CHO)2.  Write the reractions involved, and suggest structures of X,Y and Z.  What is the stereochemistry of X?

[AWK]

There are two possibilities for X
(C₆H₅CHBrCH₂)₂ or (C₆H₅CH₂CHBr)₂, both gave the same hydrocarbon (C₆H₅CH=CH)₂(Y) and C₆H₅CHO (Z). Compound X should have stereochemistry meso.