Question & Answer: Based on the following information in the paragraph, determine the structure of each unknown…..

Compound A, C10H16, gave a precipitate if treated with ammoniacal silver nitrate. If compound A is reacted under mild conditions with a limited amount of hydrogen gas and Raney nickel, com- pound B, Ci0H18, can be isolated. Ozonolysis of compound B gave compound C, CsH1o0 (see IR and NMR spectra of compound S C), and compound D, as velil as an unidentified compound. Com- pound D had two peaks in the mass spectrum of approximately the same relative abundance at m/e 29 and 30 plus another weaker peak at m/e 28. Compound B reacted with nascent hydrogen to give compound E, C1oH20- Reaction of compound hydrolysis of the reaction mixture, compound F, C6H140, which is converted predominantly into compound G, CoH1 compound and 58. d E, C10H20 Reaction of compound C with methylmagnesium iodide formed, after 2, with concentrated H2S04. Vigorous oxidation of compound G gave only H as product. Compound H displayed prominant mass spectrum peaks at m/e 15, 43