Compound A (C9H12) absorbed 3 equivalents of H2 on

Chapter 9, Problem 9

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Compound A \(\mathrm{(C_9H_{12})}\) absorbed 3 equivalents of \(\mathrm{H_2}\) on catalytic reduction over a palladium catalyst to give B \(\mathrm{(C_9H_{18})}\). On ozonolysis, compound A gave, among other things, a ketone that was identified as cyclohexanone. On treatment with \(\mathrm{NaNH_2}\) in \(\mathrm{NH_3}\), followed by addition of iodomethane, compound A gave a new hydrocarbon, C \(\mathrm{(C_{10}H_{14})}\). What are the structures of A, B, and C?

Equation Transcription:

Text Transcription:

(C_9H_{12})

H_2

(C_9H_{18})

NaNH_2

NH_3

(C_{10}H_{14})

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