Question

12 ROAD MAP: Compound A has the chemical formula CHn. Treatment of A with H,SO, and HO produces sertiary alcohol B. However, when A undergoes hvdroboration with 9-BBN followed by oxidation secondary alcohol C is formed. When Compound A is reacted with HCl alkyl halide D is produced. When D is reacted with water at room temperature alcohol B is produced. When Compound D is reacted with sodium methoxide in TH at room temperature, no reaction occurs. Upon treatment of compound C with sodium hydride followed by ethy chloride, ether E is synthesized. Treatment of E with two equivalence of HBr forms compoundF (H NMR and chemical formula provided) as one of the products. Reacting Compound C with PBr, also produces Compound F. Give the structures of A-F. [12 points] 1)9-BBN 2) H,0 OH HO HSO B C H C 1) NaH 2) CH,CH,C HCI PBry H.о, п HBr (2 eq) E D CoHBr суHо NaOCHs, THF. 23 C No Reaction H NMR for Compound F 6H Зн 1H 2H 1H, octet 2 PPM

Answer 1

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