Compound A (C_9 H_12) absorbed 3 equivalents of H_2 on catalytic reduction over a palladium catalyst to give B (C_9 H_18). On ozonolysis, compound A gave, among other things, a ketone that was identified as cyclohexanone. On treatment with NaNH_z in NH_3, followed by addition of iodomethane, compound A gave a new hydrocarbon, C (C_10 H_14). What are the structures of A, B, and C? Hydrocarbon A has the formula C_12 H_8. It absorbs 8 equivalents of H_2 on catalytic reduction over a palladium catalyst. On ozonolysis, only two products are formed: oxalic add (HO_2 CCO_2 H) and succinic add (HO_2 CCH_2 CH_2 CO_2 H). Write the reactions, and propose a structure for A.
