Question

Compound X, C14H12Br2, is optically inactive. On treatment with strong base, X gives hydrocarbon Y, C14H10. Compound Y absorbs 2 equivalents of hydrogen when reduced over a palladium catalyst to give Z (C14H14) and reacts with ozone to give one product, benzoic acid (C7H6O2). Draw the structure of compound Y. Use the wedge/hash bond tools to indicate stereochemistry. Ignore alkene stereochemistry. If more than one structure fits the description, draw them all. Draw one structure per sketcher. Add additional sketchers using the dropdown menu in the bottom right corner. Separate structures with + signs from the dropdown menu.

Answer 1

Since the final product after reaction with ozone is benzoic acid, this means the compound X have 2 benzene rings. Also it is given that the compound X is optically inactive. So the compound X will be meso -1,2-Dibromo-1,2-diphenylethane.

Now the compound X on reaction with strong base gives alkyne (compound Y). Alkyne on reduction with 2 equivalents of H2 in presence of Pd catalyst gives respective alkane (compound Z).