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ROAD MAP. Compound A has the chemical formula CHio. Treatment of A with HS0, and H:0 produces ohol B However, when A undergoes hydroboration with 9-BBN followed by oxidation, secondary alcohol C with chemical formula CsHi20 is formed (H NMR provided below). If either Compound A or Compound B is alkyl halide D. When Compound D is reacted with sodium in THF at room temperature, no reaction occurs. Upon treatment of compound C with sodium hydride pound 12.. alc followed by ethyl chloride, ether E is synthesized. Treatment of E with two equivalence of HBr forms com F. Reacting Compound C with PBrs also produces Compound F. Give the structures of A-F. [12 points) 1) 9-BBN 2) H2O2, OH HSO4 CsH1 H NMR provided 1) NaH HCl HCI HBr (2 eq) NaOCHs. THF, 23°C No Reaction | H NMR Compound C Doublet, 6H Doublet, 3H Pentet, 1H Multiplet, 1H 1H PPM
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9BBN 13 ßY ta. PIH MC 丹

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