A Compound was converted readily into B when it was treated with concentrated sulfuric acid. A stream of hydrogen gas bubbles was observed when a small piece of sodium metal was added to a solution of A in ether solvent. However, when A was reacted with a chromic acid solution, the orange solution persisted. Compound B, which readily reacted with bromine, was ozonolyzed to produce C and D. Compound C reacted readily with Ag(NH3)2+OH- to produce a silver mirror, but D did not. When a solution containing B was hydroborated, E was produced that was shown to have zero elements of unsaturation (DI = 0). When potassium permanganate was added to E the purple solution suddenly became brown. Treatment of E with benzoyl chloride led to F, which showed the principal stretches indicated in its' IR spectrum. Conversely, when E was treated with pyridinium chlorochromate (PCC), G was produced whose IR spectrum only showed one prominent peak at 1710 cm-1, and whose non proton-decoupled carbon NMR spectrum displayed five the sets of peaks indicated. Finally, reaction of diethylamine with G followed by reduction with sodium borohydride yielded H that displayed a strong parent ion peak in its' mass spectrum at 171 m/z. Draw the structures of compounds A - H in the boxes provided and provide any relevant information about the structures beside the boxes.
concentrated H2SO4
1. O3 2. CH3SCH3
Compound C positive Tollen's test (silver mirror)
Compound A IR: 3400 cm-1 (br) negative Jone's test 1H NMR: 3.51 (br s, 1H), 1.74 (q, 2H), 1.01 (t, 3H) ppm
Compound B Decolourized a drop of bromine when it was ad...