Compound A (C9H12) absorbed 3 equivalents of H2 on catalytic reduction over a palladium catalyst to give B (C9H18). On ozonolysis, compound A produced 3 products, C, D and E which was a ketone identified as cyclohexanone. On treatment with NaNH2 in NH3, followed by addition of iodomethane, compound A gave new hydrocarbon, F (C10H14). Draw structures of A, B, C, D and F.

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Compound A (C9H12) absorbed 3 equivalents of H2 on catalytic reduction over a
palladium catalyst to give B (C9H18). On ozonolysis, compound A produced 3 products, C, D
and E which was a ketone identified as cyclohexanone. On treatment with NaNH2 in NH3,
followed by addition of iodomethane, compound A gave new hydrocarbon, F (C10H14). Draw
structures of A, B, C, D and F.

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