C. An organic compound A with molecular formula C:Hs0 shows a major peak at 1710 cm-‘shows…

C. An organic compound A with molecular formula C:Hs0 shows a major peak at 1710 cm-‘shows a positive Tollen’s reagent test. When treated with NaBH. in THF, a compound B was obtained that showed IR peaks at 2920, 2850 cm-1 and a broad peak at 3300 cm and gave a negative Lucas test. Partial NMR data (not all peaks shown) of both A and B shows consistently 8 1.1(d, 6H) and 81.5 (m, 1H). Compound B when subjected to treatment with POCIS, Py at 0°C generated compound C which shows an IR peak at 1640 cm–and 3050 cm. Compound C when treated with bromine water followed by NaH yielded compound D. Dupon treatment with CH S Nat in CHSH afforded a S-containing compound E. Deduce the structure of the organic compounds A through E. Show your work. (2 pts)